mat]ial f ! ,google ,pr9t project47 ,,"s ,,con/itu5ts ,,( ,,! ,,poison ,,ivy ,,plant 7,,rhus ,,toxicod5dron7 ,,diss]tation ,,submitt$ ,,to ,,! ,,bo>d ,,( ,,univ]sity ,,/udies ,,( ,,! ,,johns ,,hopk9s ,,univ]sity ,,9 ,,con=mity ,,) ,,! ,,requirem5ts ,,= ,,! ,,degree ,,( ,,doctor ,,( ,,philosophy ,,by ,,william ,,&]son ,,syme #aijf #aijf ,,! ,,sun ,,job ,,pr9t+ ,,(fice ,,baltimore ,transcrib]'s ,note3 ,und]scores ar\nd words indicates italics :ile an und]score & curly brackets 9 an equation indicates a subscript4 ,,cont5ts4 ,ackn[l$gm5ts #d ,lit]ature #e ,introduction #g ,"w ( ,khittel #aa ,"w ( ,mais* #ab ,"w ( ,pfaff #ac ,exp]im5tal #ad ,gallic ,acid #ah ,fiset9 #bj ,rhamnose #bc ,! ,poison #bh ,potassium ,p]manganate z a ,rem$y = ,rhus ,poison+ #ce ,summ>y #cg ,biography #ch ,,ackn[l$gm5ts4 ,! au?or desires to avail himself ( ?is opportunity to t5d] 8 ?anks to ^? "u ^: guidance he has work$ :ile a /ud5t at ! ,johns ,hopk9s ,univ]sity1 namely to ,pr(essors ,rems51 ,morse1 ,jones1 & ,&rews1 & to ,doctors ,acree & ,t+le = in/ruction 9 lecture room & laboratory4 ,he is especially indebt$ to ,dr4 ,s4 ,f4 ,acree1 at ^: sugge/ion ?is rese>* "w 0 und]tak51 = c\nsel & assi/ance 9 its prosecution4 ,he w\ld also ?ank ,messrs4 ,p>ke1 ,davis & ,co41 ( ,detroit1 ,mi*41 = ! prep>ation ( ! crude mat]ial us$ 9 ?is inve/igation1 & ! ,u4 ,s4 ,dep>tm5t ( ,agriculture1 ,wa%+ton1 ,d4 ,c41 = electrotypes ( figures #ag1 #ah1 & #ai 9 ,bullet9 ,no4 #bj1 ,division ( ,botany4 ,,lit]ature4 ,acides ,gummiques1 ,g>ros 7,diss]tation7 #ahie4 ,am]ican ,*emical ,j\rnal4 ,am]ican ,j\rnal ( ! ,m$ical ,sci5ces4 ,am]ican ,j\rnal ( ,ph>macy4 ,annal5 d] ,*emie und d] ,ph>macie 7,liebig74 ,annales de ,*imie et de ,physique4 ,b]i*te d] deuts*5 *emis*5 ,gesells*aft4 ,bio*emie d] ,pflanz5 7,czapek7 #aije4 ,brooklyn ,m$ical ,j\rnal4 ,bullet9 de la ,societe ,*imique4 ,bullet9s #bj & #bf ,u4 ,s4 ,dep>tm5t ( ,agriculture1 ,division ( ,botany4 ,*emie d] ,zuck]>t51 ,von ,lippmann1 #aijd4 ,*emik]-,zeitung4 ,comptes r5dus4 ,indu/ries ( ,japan1 ,j4 ,j4 ,re94 ,j\rnal ( ! ,*emical ,society4 ,j\rnal ( ,exp]im5tal ,m$ic9e4 ,les ,sucres1 ,maqu5ne1 #aijj4 ,manual ( ,botany1 #f? ,edition1 ,gray4 ,m$ical & ,surgical ,report]4 ,new ,york ,m$ical ,record4 ,proce$+s ( ! ,am]ican ,ph>maceutical ,association4 ,treatise on ,*emi/ry1 ,roscoe & ,s*orlemm]4 ,ueb] ,mateg]b/(f1 ,reu*l9 7,diss]tation7 #aijd4 ,,"s ,,con/itu5ts ,,( ,,! ,,poison ,,ivy ,,plant4 7,,rhus ,,toxicod5dron7 ,,introduction4 ,plants belong+ to ! natural ord] ,anac>diaciae 7,ca%ew family or ,suma* family7 are f\nd 9 all ! temp]ate climates ( ! _w & q frequ5tly 9 semi-tropical climates4 ,_m ( ^! plants play important p>ts 9 economic botany1 yield+ dye-/uffs1 tann+ mat]ial1 wax1 v>ni%1 & drugs4 ,sev]al species are poison\s4 ,at lea/ ?ree poison\s species ( ! g5us ,rhus are f\nd 9 ! ,unit$ ,/ates4 ,^! ?ree are all common & well-kn[n plants1 b confusion frequ5tly arises conc]n+ !m on acc\nt ( ! diff]5t names by :i* !y are kn[n 9 diff]5t localities4 ,= example1 poison ivy 7,rhus toxicod5dron or ,rhus radicans7 probably ! be/ kn[n poison\s plant 9 ,am]ica1 be+ f\nd 9 all ! ,/ates except ^? 9 ! extreme ,we/1 is (t5 conf\nd$ ) & popul>ly call$ poison oak4 ,! true poison oak is ! ,rhus div]siloba ( ! ,we/]n ,/ates4#a ,! ?ird & mo/ poison\s species ( ?is plant is ,rhus v55ata or ,rhus v]nix2 x is ! ,rhus v]nicif]a ( ,japan1 f :i* ,japanese lac is obta9$4 ,x is popul>ly kn[n 9 ! ,unit$ ,/ates z poison suma*1 poison dogwood & poison eld]4 ,x gr[s 9 swamps f ,canada to ,florida4 ,z ! poison ivy is by f> ! mo/ common ( ^! plants 9 ! ,ea/]n ,/ates1 a brief description ( x is giv5 "h3#b ,a %rub climb+ by rootlets ov] rocks1 etc41 or asc5d+ trees1 or sometimes l[ & erect2 leaflets #c1 rhombic-ovate1 mo/ly po9t$1 & r d[ny b5ea?1 v>i\sly not*$1 s9uate1 or cut-lob$2 high climb+ plants 7,r4 radicans7 hav+ usually m entire leaves4 ,x is f\nd 9 ?ickets1 l[ gr\nds1 etc4 ,gre5i% fl[]s appe> 9 ,june4 ,illu/ration3 ,fig4 #a4--,poison ivy 7,rhus radicans or ,rhus toxicod5dron74 a1 spray %[+ a]ial rootlets & leaves2 b1 fruit--bo? "o-f\r? natural size4 7,*esnut1 ,bullet9 ,no4 #bj1 ,division ( ,botany1 ,u4 ,s4 ,dep>tm5t ( ,agriculture47 ,illu/ration3 ,fig4 #b4--,poison oak 7,rhus div]siloba7 %[+ leaves1 fl[]s1 & fruit1 "o-?ird natural size4 7,*esnut1 ,bullet9 ,no4 #bj1 ,division ( ,botany1 ,u4 ,s4 ,dep>tm5t ( ,agriculture47 ,9 ! g5]al description ( ! ord] ,anac>diaciae1 ,gray#c says3 ,juice or exhalations (t5 poison\s4 ,:e!r x is contact ) "s "p ( ! plant1 or ) ! exhalation f ! plant1 t causes ! well-kn[n sk9 eruption has be5 a topic = discussion ev] s9ce its s\rce 0 kn[n4 ,on acc\nt ( its intangible nature !re has be5 m speculation ?an exp]im5tal evid5ce be>+ on ?is "q1 al?\gh a few inve/igations h be5 made ) ! object ( isolat+ ! poison4 ,x is mo/ g5]ally believ$ t ! exhalations are poison\s4 ,dr4 ,j4 ,h4 ,hunt#d /ates t ! exhalations h be5 collect$ 9 a j> & f\nd to be capable ( inflam+ & bli/]+ ! sk9 ( an arm plung$ into x4 ,illu/ration3 ,fig4 #c--,poison suma* 7,rhus v]nix71 %[+ leaves1 fruit1 & leaf-sc>s1 "o-f\r? natural size4 7,*esnut1 ,bullet9 ,no4 #bj1 ,division ( ,botany1 ,u4 ,s4 ,dep>tm5t ( ,agriculture47 ,pr(4 ,j4 ,j4 ,re91#e 9 8 treatise on ,lacqu] ,"w1 describes ! poison ( ! ,japanese lac tree1 ,rhus v]nicif]a1 z be+ volatile1 z d also ! ,japanese *emi/ ,yo%ida#f & ! ,fr5* *emi/ ,b]tr&4#g ,rec5t "w by ,pr(4 ,a4 ,b4 ,/ev5s1#h h[ev]1 seems to %[ t ?is poison is n volatile1 & is simil> to1 if n id5tical ) t obta9$ by ,pfaff#i f ,rhus toxicod5dron & ,rhus v55ata4 ,n _m cases ( int]nal poison+ by ,rhus toxicod5dron are on record 9 m$ical lit]ature4 ,two cases ( poison+ f eat+ ! fruit ( ?is plant h be5 describ$4#aj ,! subjects ( ^! cases 7 two *ildr5 :o _h eat5 ne>ly a p9t ( ! fruit4 ,! symptoms are describ$ 9 detail1 be+ 9 g5]al1 simil> to ^? ( alkaloidal poison+4 ,w>m wat] 0 giv5 to promote emesis2 aft]w>ds l>ge quantities ( c>bonate ( soda 7 giv5 9 solution "u ! belief t x 0 an antidote to ! poison4 ,o!rwise !y 7 treat$ on g5]al pr9ciples4 ,bo? *ildr5 recov]$4 ,ano!r case ( int]nal poison+ is ! foll[+3#aa ,?ree *ildr5 drank an infusion ( ! root ( poison ivy ?9k+ x 0 sassafras tea4 ,! fir/ ( ^! cases 0 diagnos$ z measles1 b on ! appe>ance ( simil> symptoms 9 ! si/]s ( ! fir/ pati5t1 ! cause ( ! tr\ble 0 f\nd4 ,all recov]$4 ,dr4 ,pfaff#ab expla9s ! few fatal cases t h foll[$ ,rhus poison+ on ! assumption t en\gh ( ! poison 0 absorb$ ?r\gh ! sk9 to cause r5al complications 9 p]sons hav+ *ronic kidney tr\ble4 ,he %[$ t ! poison1 :5 giv5 int]nally1 produces a m>k$ effect on ! kidneys1 caus+ nephritis & fatty deg5]ation ( ?is organ4 ,! irritat+ action ( poison ivy has be5 attribut$ at diff]5t times to ! exhalation1 to a volatile alkaloid1 to a volatile acid1 & to a non-volatile oil4 ,pfaff1#ac :o made ! mo/ rec5t inve/igation ( ?is poison1 obta9$ f ! plant a non-volatile oil hav+ ! same action on ! sk9 z ! plant itself4 ,he f\nd ?is oil 9 all p>ts ( ! plant & conclud$ t x 0 ! active pr9ciple1 & t "o c\ld be poison$ only by actual contact ) "s "p ( ! plant4 ,he assum$ m9ute quantities ( poll5 du/ to be 9 ! air to acc\nt = ! cases ( action at a di/ance s frequ5tly quot$4 ,pfaff says3 ,9 my op9ion1 x is m ?an d\btful if ev] a case ( ivy poison+ has occurr$ )\t direct contact ) ! plant or ) "s article t has be5 9 contact ) ! plant4 ,! long lat5t p]iod ( ! eruption 9 "s cases may obvi\sly r5d] mi/akes extremely easy z to ! occasion :5 contact ) ! plant really occurr$4 ,grant+1 h[ev]1 t ! active pr9ciple is practically non-volatile :5 isolat$ f ! plant1 we _c say positively t x is n volatile 9 ! juices ( ! plant1 or "u ! influ5ce ( vital =ces4 ,x is q conceivable t ! wat] transpir$ by ! leaves ( ! plant may c>ry ) x a quantity ( ! poison suffici5t to produce ! d]matitis on a p]son v susceptible to its action4 ,x is also conceivable t a volatile poison manufactur$ by a liv+ plant c\ld become non-volatile by *anges 9 x consequ5t ^u ! dea? ( ! plant4 ,up to ! pres5t "t1 only ?ree important *emical inve/igations ( ! active pr9ciple ( ,rhus toxicod5dron h appe>$ 9 m$ical & *emical lit]ature1 ^! be+ ! rese>*es ( ,dr4 ,j4 ,khittel1 ,j4 ,m4 ,mais*1 a ph>maci/1 & ,dr4 ,franz ,pfaff1 ( ! ,h>v>d ,univ]sity ,m$ical ,s*ool1 to ^: "w ref]5ce has be5 frequ5tly made4 ,! *emical "w ( ^! inve/igators & _! conclusions are giv5 "h 9 "s detail = ! sake ( complet5ess4 ,,footnotes3 #a ,*esnut4 ,bull4 ,no4 #bj1 ,u4 ,s4 ,dept4 ( ,agr41 ,div4 ( ,botany4 #b ,man4 ( ,bot41 p4 #aai4 #c ,man4 ( ,bot41 p4 #aai4 #d ,brook4 ,m$4 ,j\r41 ,june1 #ahig4 #e ,re91 ,! ,ind4 ( ,jap41 p4 #cch1 et seq4 #f ,h4 ,yo%ida on ,uru%i ,lacqu]1 ,j\r4 ,*em4 ,soc41 #ahhc1 p4 #dgb4 #g ,ann4 de ,*em4 et de ,phys41 ,s]ies ,,vii1 ,vol4 #ab1 p4 #abe1 #ahig4 #h ,am]4 ,j\r4 ,ph>m4 #gh1 p4 #ec1 ,feb41 #aijf4 #i ,an acc\nt ( ,pfaff's "w w be f\nd 9 ano!r "p ( ?is pap]4 #aj ,am]4 ,j\r4 ,m$4 ,sci4 #ea 7#ahff71 p4 #efj4 #aa ,m$4 & ,surg4 ,rep4 #ag1 ,nov41 #ahfg4 #ab ,j\r4 ,exp4 ,m$4 #b 7#ahig71 p4 #aha4 #ac ,ibid4 ,,khittel',s ,,inve/igation4 ,! fir/ attempt to f9d ! poison\s con/itu5t ( ?is plant 0 made by ,khittel 9 #aheg4 ,8 "w 0 publi%$ 9 ,witt/e9's ,vi]teljahrress*rift fu] praktis*e ,ph>macie1 ,,vii1 #cdh-cei4ad ,khittel obta9$ #cg-a_/b ounces ( fre% leaves ( poison ivy f ! botanical g>d5 9 ,muni*1 dri$ !m1 & got a residue ( #i-a_/b ounces :i* he analyz$4 ,n detect+ any?+ to :i* ! poison\s qualities ( ! plant c\ld be attribut$1 he made ano!r s]ies ( exp]im5ts :i*1 z he ?\ght1 %[$ t a volatile alkaloid is ! poison\s con/itu5t4 ,x 0 obta9$ by ! foll[+ process3 #c ounces ( ! p[d]$ leaves 7 infus$ ) hot di/ill$ wat]1 aft] ?ree days /ra9$1 express$1 ! liquid evaporat$ to #c ounces1 & ) ! addition ( potassa1 c>efully di/ill$ to "o-half4 ,! cle>1 colorless di/illate _h an alkal9e reaction1 & an odor resembl+ h5bane or hemlock4 ,x 0 saturat$ ) sulphuric acid1 evaporat$1 & treat$ ) a mixture ( equal quantities ( alcohol & e!r :i* left sulphate ( ammonia beh9d1 ! solution 0 evaporat$ spontane\sly1 di/ill$ ) potassa1 ! alkal9e di/illate neutraliz$ ) hydro*loric acid1 & a precipitate c\ld n[ be obta9$ ) *loride ( plat9um4 ,want ( mat]ial prev5t$ fur!r exp]im5ts4 ,! editor ( ! ,am]ican ,j\rnal ( ,ph>macy ins]ts ! foll[+ note3 ,x w\ld h be5 m satisfactory if ! au?or _h giv5 "s physiological evid5ce ( ! poison\s nature ( ! alkaloid sub/ance obta9$4 ,x is q int]e/+ to he> t ! hi!rto intangible v5om ( ?is plant has at la/ be5 detect$4 ,,footnotes3 #ad ,a free translation ( ?is pap] is giv5 9 ,am]4 ,j\r4 ,ph>m4 = #aheh1 p4 #edb4 ,,"w ,,( ,,mais*4#ae ,! next inve/igation ( ?is plant 0 made by ,mais* 9 #ahfd4 ,he criticizes ,khittel's exp]im5ts z foll[s3 ,x is well kn[n t ! exhalations ( ,rhus toxicod5dron ex]t a poison\s influ5ce on ! human body2 ! poison\s pr9ciple mu/1 !re=e1 be volatile &1 at ! same "t1 be naturally 9 su* a loose /ate ( comb9ation z to be cont9ually elim9at$ & sep>at$ ) ! usual products ( vegetable exhalations4 ,x is natural to suppose t dur+ ! process ( dry+1 ! greate/ portion ( ! poison\s pr9ciple %\ld be lo/4 ,! loss mu/ be /ill great] if ! dri$ leaves are p[d]$1 a hot infusion prep>$ f !m1 & ?is infusion evaporat$ d[n to ! orig9al weight ( ! dri$ leaves4 ,x is obvi\s t ,dr4 ,khittel c\ld n h select$ a bett] me?od = obta9+ ! lea/ possible quantity ( ! poison\s pr9ciple1 if1 inde$1 x c\ld be obta9$ by ?is process at all4 ,mais* !n work$ up #h-c_/d ounces ( ! leaves ( ! plant 9 a way to get ! alkaloid1 mak+ "s improvem5ts on ,khittel's me?od1 b fail$ to f9d x4 ,believ+ t ! poison 0 a volatile acid1 he enclos$ "s fre% leaves ( ! plant 9 a t9 box ) sev]al te/ pap]s4 ,! blue litmus pap] became r$ %[+ ! pres5ce ( an acid4 ,he conclud$ f ?is exp]im5t t ! exhalations ( ! leaves conta9$ a volatile organic acid :i* he ?\ght 0 ! poison\s sub/ance4 ,to det]m9e ?is po9t1 he prep>$ ! acid 9 l>g] quantity by mac]at+ ! leaves ) wat]1 express+ & di/ill+ ! express$ juice4 ,he 0 poison$ 9 do+ ?is "w al?\gh he _h n be5 affect$ by h&l+ ! liv+ plant & _h consid]$ himself immune4 ,he obta9$ an acid :i* inve/igation %[$ to be some:at l =mic acid1 m l acetic acid1 b hav+ "s reactions diff]5t f bo?4 ,tak+ all ! reactions toge!r1 x is unque/ionably a new organic acid = :i* ,i propose ! "n ( ,toxicod5dric ,acid1 writes ,mais*4 ,he fur!r says3 ,t x is ! pr9ciple to :i* poison oak owes its effects on ! human sy/em 0 prov$ to my entire satisfaction by ! copi\s eruption & =mation ( num]\s vesicles on ! back ( my h&1 on ! f+]s1 wri/s1 & b>e arms :ile ,i 0 di/ill+ & op]at+ ) x4 ,sev]al p]sons com+ into ! room :ile ,i 0 engag$ ) x 7 m or less poison$ by ! vap\rs diffus$ 9 ! room2 & ,i ev5 transf]r$ ! poison\s effects to "s p]sons1 m]ely by %ak+ h&s ) !m4 ,! dilut$ acid1 z obta9$ by me1 & /rong] solutions ( its salts1 7 appli$ to sev]al p]sons1 & eruptions 7 produc$ 9 sev]al in/ances1 probably by ! =m]1 ?\gh n always1 :i* 0 mo/ likely ow+ to ! dilute /ate ( ! acid4 ,:5ev] ?is 0 boil$1 ,i always felt ! same it*+ s5sation 9 ! face1 & on ! b>e arms1 :i* ,i exp]i5ce on cont9ual exposure ( my h&s to ! juice ( ! plant4 ,toxicod5dric acid 0 ?\ght to be ! active pr9ciple f ! "t ( ,mais*'s "w until ! inve/igation by ,pfaff 9 #ahie4 ,,footnotes3 #ae ,proc4 ,am]4 ,ph>m4 ,assn4 #ahfe1 p4 #aff1 & ,am]4 ,j\r4 ,ph>m4 #ahff1 p4 #d4 ,,pfaff',s ,,"w4 ,by f> ! mo/ valuable "w on ,rhus toxicod5dron is t ( ,pfaff4 ,f a cl9ical /udy ( ,rhus poison+1 ,pfaff came to ! conclusion t ! poison mu/ be a non-volatile sk9 irritant4 ,! m volatile ! irritant1 ! quick] is its action on ! sk94 ,=mic acid acts v quickly2 acetic acid1 less volatile ?an =mic1 acts m sl[ly1 b /ill mu* m quickly ?an poison ivy1 ! lat5t p]iod ( :i* is usually f two to five days4 ,pfaff ?\ght t ! volatile acid obta9$ by ,mais* might h conta9$ "s ( ! poison\s pr9ciple z an impurity1 b t x w\ld n produce ! d]matitis if prep>$ 9 a pure /ate4 ,he !re=e prep>$ a quantity ( ! acid by di/ill+ ! f9ely divid$ fre% plant ) /eam4 ,! yield 0 increas$ by acidulat+ ! mixture ) sulphuric acid be=e ! di/illation4 ,! acid di/illate s obta9$ 0 fre$ f a non-poison\s oily sub/ance by %ak+ ! solution ) e!r4 ,b>ium & sodium salts 7 made by neutraliz+ ! acid1 & 7 purifi$ by cry/allization4 ,analysis %[$ !m to be salts ( acetic acid1 & !y gave ! *>act]i/ic te/s = ?is acid4 ,! toxicod5dric acid ( ,mais* 0 ?us %[n to be acetic acid1 & 0 !re=e n ! poison\s pr9ciple ( ! plant4 ,pfaff obta9$ ! active pr9ciple by ! foll[+ process3 ,! plant 0 extract$ ) alcohol1 ! alcohol 0 di/ill$ (f1 & ! residue 0 tak5 up 9 e!r4 ,! e!r solution 0 wa%$ ) wat] & dilute sodium c>bonate solution1 & ! e!r 0 evaporat$4 ,an oily1 black1 poison\s sub/ance p>tly soluble 9 alcohol 0 obta9$4 ,to get ! active pr9ciple 9 a pure /ate1 ?is residue 0 extract$ ) alcohol & filt]$ & ! filtrate 0 precipitat$ fractionally by lead acetate4 ,! f9al precipitates consi/$ ( ! lead comp\nd ( ! poison 9 a pure /ate4 ,on decompos+ ! lead comp\nds ) ammonium sulphide1 %ak+ out ) e!r1 & lett+ ! e!r evaporate spontane\sly1 a non-volatile oil 0 obta9$ :i* gave ! *>act]i/ic sk9 eruptions4 ,! pure lead comp\nds made 9 diff]5t prep>ations 7 analyz$ & assign$ ! =mula ,c#ba;,h#cj,o#d,pb4 ,! oil itself 0 n analyz$4 ,pfaff propos$ ! "n ,toxicod5drol = ! oil4 ,he f\nd t x 0 n volatile1 0 decompos$ by heat1 0 soluble 9 alcohol1 e!r1 *lor(orm1 b5z5e1 etc41 b insoluble 9 wat]4 ,its effects ^u ! human sk9 7 /udi$ 9 _m exp]im5ts ^u himself & o!rs4 ,x 0 %[n t an exce$+ly m9ute quantity ( ! poison w produce ! d]matitis1 ev5 #a_/ajjj milligram appli$ 9 olive oil be+ active4 ,! oil 0 giv5 int]nally to rabbits1 its effects be+ mo/ m>k$ on ! kidneys4 ,! oil obta9$ by ,pfaff f ,rhus v55ata seem$ to be id5tical ) t f ,rhus toxicod5dron4 ,,exp]im5tal4 ,! writ]'s inve/igation 0 und]tak5 ) ! object ( attempt+ to ?r[ m light on ! *emical nature ( ! poison\s sub/ance f\nd 9 ,rhus toxicod5dron4 ,soon aft] comm5c+ "w1 h[ev]1 x became app>5t t ! poison c\ld be m intellig5tly /udi$ if ! sub/ances associat$ ) x 9 ! plant 7 fir/ id5tifi$2 ! scope ( ! "w 0 !re=e ext5d$ to an inve/igation ( ! o!r con/itu5ts ( ! plant1 & x 0 hop$ t a k ( ! prop]ties ( ^! con/itu5ts w\ld sugge/ a m economical way ( gett+ ! poison ?an ! me?od ( fractional precipitation4 ,! crude mat]ial = ?is "w 0 prep>$ by ,messrs4 ,p>ke1 ,davis ,co41 ( ,detroit1 ,mi*41 accord+ to special in/ructions submitt$ to !m3 #fg-a_/b p\nds ( fre% leaves & fl[]s ( poison ivy 7 collect$ ne> ,detroit & c>efully inspect$ by a compet5t botani/4 ,?is mat]ial 0 ?or\ghly mac]at$ & put into t5-lit] bottles ) e!r4 ,! mass 0 ?or\ghly %ak51 wat] be+ add$ to make x m mobile4 ,! e!r 0 !n sep>at$ (f & ! extraction 0 repeat$ ?ree times 9 ! same way to insure complete removal ( ! toxicod5drol4 ,! e!r extracts 7 comb9$1 ?or\ghly dri$ ) anhydr\s sodium sulphate1 & ! e!r 0 di/ill$ (f1 ! temp]ature be+ kept bel[ #dj deg4 ,c4 dur+ ! entire di/illation4 ,! residue aft] ! removal ( ! e!r 0 a ?ick1 black1 t>-l mass1 weigh+ #c p\nds #aa ounces4 ,9 extract+ ! plant1 ab\t tw5ty-f\r gallons ( e!r 7 us$4 ,x is a significant fact 9 reg>d to ! volatility ( ! poison t dur+ ! process ( prep>+ ?is mat]ial none ( ! employees engag$ 9 ! "w 7 9 any way affect$1 s9ce prop] precautions 7 tak5 & ! ut5sils 7 h&l$ ) rubb] gloves4 ,! crude e!r extract1 :i* w be designat$ z ! orig9al mat]ial1 0 %ipp$ to ,baltimore 9 ,augu/ & 0 kept 9 a cool place until ,novemb] :5 ! inve/igation 0 begun4 ,:5 ! bottle 0 op5$1 !re seem$ to be an escape ( a vapor1 & a nauseat+ odor sugge/+ cru%$ gre5 leaves p]vad$ ! atmosph]e4 ,"s days lat]1 irregul> r$ pat*es appe>$ on ! face ?\gh a mask ( cotton clo? 0 worn dur+ ! "w1 & ! h&s 7 protect$ by rubb] gloves4 ,assum+ f ,pfaff's "w t ?is orig9al mat]ial conta9$ ! non-volatile oil toxicod5drol1 ! fir/ exp]im5t 0 to try to di/il x out "u dim9i%$ pressure4 ,= ?is purpose1 an ,ans*uetze di/ill+ bulb conta9+ t5 grams ( ! t> 0 connect$ ) a vacuum pump4 ,aft] a pressure ( #b mm4 _h be5 e/abli%$ ! bulb 0 gradually heat$ 9 a ba? ( ,wood's metal4 ,no?+ di/ill$ ov]4 ,! mat]ial began to c>bonize at a temp]ature ( #adj deg4 to #aej deg4 ,x 0 !n ?\ght t p]haps ! oil c\ld be conv]t$ into an e/] :i* might be m volatile & c\ld be di/ill$ out4 #bj grams ( ! orig9al mat]ial 7 dissolv$ 9 #ajj cc4 ( absolute alcohol conta9+ #c gra9s ( hydro*loric acid gas1 & ! mixture 0 heat$ #aj h\rs on a wat]-ba? "u a return cond5s]4 ,aft] ! heat+1 ! mixture _h a delightful e!real odor4 ,! flask 0 cork$ & left /&+ sev]al weeks :ile o!r "w 0 9 progress4 ,! e/] solution 0 !n put 9 a vacuum desiccator ov] sulphuric acid & ! alcohol evaporat$4 ,a black1 t>ry1 solid mass 0 left hav+ ! e/] odor4 ,x 0 extract$ ) w>m wat] & filt]$ f insoluble t>4 ,! filtrate _h a gre5 color & ! e!real odor4 ,x 0 %ak5 out ) e!r2 ! e!r lay] _h a blood-r$ color :ile ! wat] lay] 0 deep gre54 ,! extraction ) e!r 0 cont9u$ until ! wat] lay] 0 no long] gre54 ,! comb9$ e!r extracts 7 evaporat$ 9 a desiccator )\t heat4 ,a black t>-l solid 0 left v mu* l ! orig9al mat]ial1 b x _h ! e/] odor4 ,x 0 p>tly soluble 9 wat] & readily soluble 9 alcohol4 ,! alcoholic solution 0 te/$ on ! sk9 & f\nd to be n poison\s4 ,! e/]1 or mixture ( e/]s1 0 n inve/igat$ fur!r 9 ?is connection1 b 0 lat] %[n to give ! reactions = gallic acid & me?yl furfurol4 ,^! reactions w be ref]r$ to 9 connection ) o!r exp]im5ts4 ,aft] a few o!r prelim9>y exp]im5ts1 x became evid5t t ! orig9al mat]ial 0 a complex mixture ( sub/ances & t x w\ld h to be fractionat$ by "s means & ! fractions /udi$ sep>ately4 ,a portion ( ! orig9al sub/ance 0 treat$ ) #ej p] c5t4 alcohol & 0 f\nd to be p>tly soluble 9 ?is m$ium4 ,! solution 0 filt]$ f insoluble t>4 ,a portion ( ! yell[ filtrate gave a r$di% yell[ precipitate ) lead acetate4 ,! alcoholic solution 0 di/ill$ 9 an ,ans*uetze flask "u dim9i%$ pressure2 a yell[ liquid cond5s$ 9 ! arm ( ! flask :ile mo/ ( ! alcohol 0 collect$ 9 a bottle connect$ ) ! arm4 ,! yell[ liquid 0 acid to litmus4 ,wat] 0 add$1 ! solution 0 %ak5 out ) e!r & ! e!r 0 evaporat$4 ,:5 ! small residue 0 completely dry1 x 0 a yell[ solid soluble 9 dilute alcohol & acid to litmus4 ,! sub/ance 0 n volatile en\gh to ju/ify ! use ( ?is me?od = gett+ x4 ,*lorophyll c\ld n be remov$ f ! orig9al sub/ance because ! solv5ts = *lorophyll su* z alcohol1 e!r1 fats1 petroleum1 & c>bon bisulphide dissolve l>ge quantities ( ! mixture4 ,a precipitate obta9$ by add+ lead acetate to a filt]$ solution ( ! orig9al sub/ance 9 #ej p] c5t4 alcohol 0 susp5d$ 9 wat]1 decompos$ by hydrog5 sulphide1 %ak5 out ) e!r & ! e!r evaporat$4 ,! residue appe>$ at fir/ to be a yell[ oil1 b on complete evaporation ( ! e!r 9 a desiccator1 a yell[ solid 0 obta9$--app>5tly ! same z t obta9$ by vacuum di/illation4 ,a solution ( ! orig9al mat]ial 9 #ej p] c5t4 alcohol 0 filt]$ ?r\gh bone-black & ! filtrate 0 colorless4 ,exam9ation %[$ t ev]y?+ _h be5 remov$ by ! bone-black & ! filtrate 0 app>5tly pure alcohol & wat]4 ,9 precipitat+ an alcoholic solution ( ! crude mat]ial ) a solution ( lead acetate1 x 0 notic$ t at lea/ two k9ds ( precipitates 7 =m$4 ,! "p t w5t d[n fir/ 0 d>k] 9 color ?an t ?r[n d[n lat]4 ,pfaff us$ ! la/ fractions 9 obta9+ 8 oil & /at$ t ^! precipitates consi/$ ( ! lead comp\nd ( ! oil 9 a pure /ate4 ,x 0 f\nd by exp]im5t t ! d>k] "p 0 soluble 9 e!r :ile ! light] "p 0 n4 ,?is indicat$ t ! d>k] "p consi/$ ( t>ry matt] :i* 0 br\ght d[n me*anically or sep>at$ out :5 ! alcoholic solution 0 dilut$ by ! lead acetate solution1 or 0 p]haps a lead comp\nd soluble 9 e!r4 ,to te/ ?is po9t an exp]im5t 0 made z foll[s3 ,"s ( ! crude mat]ial 0 ?or\ghly extract$ ) #ej p] c5t4 alcohol4 ,! t> insoluble 9 #ej p] c5t4 alcohol 0 !n treat$ ) #ie p] c5t4 alcohol2 mo/ ( x dissolv$2 ! solution 0 filt]$ & lead acetate 9 #ej p] c5t4 alcohol 0 add$4 ,a gre5i% color$ precipitate 0 =m$ :i* 0 filt]$ (f & f\nd to be completely soluble 9 e!r & soluble to a consid]able ext5t 9 /rong alcohol4 ,^! exp]im5ts sugge/$ t ! light color$ lead comp\nd :i* 0 ?\ght to conta9 ! poison c\ld be purifi$ by extraction ) e!r 9 a ,soxhlet app>atus m conv5i5tly ?an by ! t$i\s process ( fractional precipitation4 ,fur!r prelim9>y exp]im5ts %[$ t #ej p] c5t4 alcohol extract$ f ! orig9al mat]ial all ( ! sub/ance or sub/ances :i* gave ! light color$ precipitate & dissolv$ only a small am\nt ( ! t>4 ,two hundr$ & eighty-eight grams ( ! crude mat]ial 7 !n extract$ sev]al times ) #ej p] c5t4 alcohol & filt]$2 ! insoluble t> 0 wa%$ & sav$ = exam9ation4 ,to ! filtrate 0 add$ an excess ( a solution ( lead acetate 9 #ej p] c5t4 alcohol4 ,! l>ge precipitate1 :i* w be designat$ z precipitate ,a1 0 filt]$ & dra9$ by suction 9 a ,bue*n] funnel4 ,! alcoholic filtrate ,a 0 sav$4 ,precipitate ,a 0 extract$ ) e!r 9 ,soxhlet extractors until ! e!r came ov] practically colorless1 ! op]ation be+ int]rupt$ f "t to "t to /ir up ! precipitate 9 ! ?imble4 ,! gre5 color$ e!r solution 0 sav$ = future exam9ation4 ,! lead precipitate1 aft] extraction ) e!r & dry+1 weigh$ ab\t #aaf grams4 ,a portion ( ?is lead comp\nd 0 decompos$ by hydrog5 sulphide 9 a mixture ( wat] & e!r :i* 0 well %ak5 dur+ ! op]ation4 ,! e!r 0 sep>at$1 filt]$1 & evaporat$ "u dim9i%$ pressure )\t heat1 & !re rema9$ a yell[ oily look+ residue hav+ a pleasant odor4 ,:5 ! e!r & wat] 7 completely remov$ 9 a vacuum desiccator1 a h>d1 brittle1 yell[ res9 weigh+ ab\t #af grams 0 obta9$4 ,x 0 soluble 9 alcohol1 _h a /rong acid reaction & 0 free f nitrog5#af & sulphur4 ,! nitrog5 te/s 7 made by ! ,lassaign & soda lime me?ods1#ag & ! sulphur te/ 0 made ) sodium nitroprusside aft] fus+ ! residue ) sodium4 ,! ma9 portion ( ! lead comp\nd 0 decompos$ "u alcohol by hydrog5 sulphide1 filt]$1 & ! alcoholic filtrate evaporat$ 9 vacuo4 ,! same yell[ acid res9 0 obta9$4 ,exp]im5ts cont9u+ ?r\gh sev]al weeks 7 made 9 apply+ solutions ( ?is res9 to rats1 rabbits & gu9ea pigs4 ,f9d+ x to be )\t effect ^u ^! animals x 0 tri$ on ! writ] & f\nd to be n poison\s4#ah ,9 ! meantime ! res9 0 be+ /udi$ 9 ! laboratory4 ,,gallic ,,acid4 ,an alcoholic solution ( ! res9 0 j neutraliz$ ) potassium hydroxide4 ,dur+ ! titration1 ! solution rapidly became d>k br[n4 ,aft] neutralization x 0 %ak5 ) e!r2 ! wat] solution rema9$ br[n :ile ! e!r lay] 0 ne>ly colorless & conta9$ practically no dissolv$ sub/ance4 ,a portion ( ! wat] solution ( ! potassium salt on be+ acidifi$ ) sulphuric acid & /&+ ov] night1 deposit$ a slight precipitate4 ,! solution ( ! potassium salt gave a heavy precipitate ) lead acetate some:at simil> to ! orig9al lead precipitate ,a1 & also slight precipitates ) salts ( z9c1 m]cury1 copp]1 & silv] 7) r$uction74 ,x gave a blui%-black color ) impure f]r\s sulphate & a d>k color ) f]ric *loride4 ,x r$uc$ ammoniacal silv] nitrate & ,fehl+ solution4 ,^! exp]im5ts indicat$ ! pres5ce ( a tann9 comp\nd4 ,an alcoholic solution ( ! res9 gave ! same color reactions ) iron salts z did ! potassium salt4 ,to det]m9e :i* "o ( ! tann9 comp\nds 0 pres5t 0 a matt] ( "s difficulty s9ce ! di- & tri-hydroxyb5zoic acids h 9 g5]al ! same color reactions4 ,! pres5ce ( o!r plant sub/ances 9 ! solution also int]f]es ) ! color te/s1 & f9ally1 a sub/ance :i* gives a blue color ) iron salts & "o giv+ a gre5 color may be f\nd toge!r 9 ! same plant4#ai ,fur!r te/s ) a solution ( ! res9 9 dilute alcohol1 & ) a wat] solution ( ! acid precipitat$ by add+ sulphuric acid to a solution ( ! res9 9 potassium hydroxide1 l$ to ! conclusion t ! acid is gallic acid4 ,^! te/s 7 ! foll[+3 7#a7 ,boil+ ) an excess ( potassium hydroxide gave a black sub/ance 7tauromelanic acid74 7#b7 ,! acid 0 n precipitat$ by gelat94 7#c7 ,on addition ( potassium cyanide a transitory r$ color appe>$ :i* reappe>$ on %ak+ ) air4 ,gallic acid is di/+ui%$ f tannic acid by te/s 7#b7 & 7#c74 ,at lat] /ages 9 ! "w ! potassium1 b>ium1 & sodium salts ( gallic acid 7 obta9$1 & f9ally ! pure acid 0 made by decompos+ ! sodium salt ) sulphuric acid & cry/alliz+ f wat]4 ,a portion ( ! acid s obta9$ 0 fur!r purifi$ by dissolv+ 9 absolute alcohol & p\r+ into absolute e!r4#bj ,! melt+ po9t behavior ( ! acid corresponds ) t ( gallic acid2 x melt$ ) decomposition at ab\t #bcj deg4 ,= fur!r id5tification1 "s ( ! acid 0 conv]t$ into an e/] by ! foll[+ process3 x 0 dissolv$ 9 #hj p] c5t4 alcohol1 hydro*loric acid gas 0 pass$ 91 & ! solution 0 heat$ an h\r on ! wat] ba?4 ,x 0 !n evaporat$ to a small bulk1 neutraliz$ ) b>ium c>bonate & extract$ ) e!r4 ,! e!r1 on evaporation1 left ! e/] :i* 0 cry/alliz$ f wat] & dri$ 9 a desiccator ov] sulphuric acid4 ,! anhydr\s e/] agre$ 9 melt+ po9t 7#aef deg4 to #aei deg47 & o!r prop]ties ) ! e/] ( gallic acid describ$ by ,grimaux4#ba ,= ! sake ( comp>ison1 an e/] 0 made f gallic acid obta9$ f ano!r s\rce & ! two agre$ 9 prop]ties4 ,a mixture ( ! two e/]s melt$ )9 ! limits giv5 = ! e/] ( gallic acid4 ,:ile ! te/s lead+ to ! id5tification ( gallic acid 7 be+ made1 ano!r s]ies ( exp]im5ts 0 9 progress4 ,elev5 & "o-half grams ( ! res9 obta9$ f lead precipitate ,a by decomposition ) hydrog5 sulphide 7 treat$ ) #j4a n4 potassium hydroxide add$ f a burette until ! acid 0 exactly neutraliz$4 ,all w5t into solution4 ,on %ak+ ) e!r1 "s ( ! potassium salt sep>at$ out & 0 sav$ = exam9ation4 ,! solution became br[n on exposure to air & got d>k] z ! "w proce$$4 ,! acid 9 solution z a potassium salt 0 precipitat$ out 9 f\r fractions by add+ = ea* fraction "o-f\r? ! am\nt ( #j4a n4 sulphuric acid requir$ to neutralize ! potassium hydroxide us$4 ,! precipitates 7 filt]$ (f & exam9$4 ,! fir/ 0 small 9 am\nt1 gummy & h>d to filt]4 ,! solution 0 %ak5 ) e!r aft] ea* precipitate _h be5 filt]$ (f4 ,! succe$+ precipitates 7 9 bett] condition1 b 7 n pure4 ,all appe>$ to be impure gallic acid :i* _h become br[n by absorption ( oxyg54 ,!y 7 sav$1 h[ev]1 to be te/$ = poison4 ,aft] ! la/ fraction _h sep>at$1 ! filtrate 0 %ak5 sev]al times ) e!r & sav$ = fur!r exam9ation1 :i* w be describ$ "u ,rhamnose4 ,?is filtrate is designat$ z ,b4 ,at ?is /age ( ! "w a portion ( ! res9 obta9$ f lead precipitate ,a 0 te/$ & f\nd to be n poison\s z already m5tion$4 ,by ?is te/1 all ! sub/ances conta9$ 9 ! lead precipitate ,a aft] its extraction ) e!r 9 ! ,soxhlet app>atus1 7 elim9at$ f ! possible poison\s sub/ances4 ,! poison mu/ !re=e h be5 extract$ by ! e!r4 ,a fre% portion ( ! orig9al poison\s mat]ial 0 treat$ ) #ej p] c5t4 alcohol & filt]$ f insoluble t>4 ,! filtrate 0 precipitat$ 9 six fractions by lead acetate4 ,! la/ fractions 7 light] 9 color & app>5tly mu* pur] ?an ! fir/4 ,! six? lead precipitate 0 decompos$ by hydrog5 sulphide1 ! light-yell[ wat] solution 0 te/$ & f\nd to be n poison\s4 ,x gave ! *>act]i/ic reactions = gallic acid4 ,! poison1 if precipitat$ at all by lead acetate1 mu/ h gone d[n 9 "o ( ! prec$+ fractions4 ,lat] exp]im5ts %[$ t x is br\ght d[n p>tly me*anically & p>tly z a lead comp\nd 9 ! fir/ precipitates4 ,,fiset94 ,hav+ id5tifi$ gallic acid1 & n f9d+ any o!r ph5ol d]ivative 9 ! lead precipitate1 "s ( ! orig9al mat]ial 0 extract$ ) hot wat] to remove gallic acid & filt]$ f t> :ile hot4 ,! filtrate _h a deep yell[ color4 ,on cool+ ov] night1 an olive gre5 precipitate sep>at$ out :i* 0 dri$ & f\nd to be a light p[d]4 ,x 0 practically insoluble 9 cold wat]1 soluble ) great difficulty 9 boil+ wat] f :i* x sep>at$ 9 yell[ flakes1 slightly soluble 9 e!r & 9 acetic acid1 b readily soluble 9 alcohol4 ,! solutions 7 n acid to litmus1 gave a d>k color ) f]ric *loride1 an orange-r$ precipitate ) lead acetate :i* 0 easily soluble 9 acetic acid1 & an orange-yell[ precipitate ) /ann\s *loride4 ,^! prop]ties & reactions indicat$ t ! sub/ance 0 ! dye-/uff fiset9 & t x occurs 9 ! free /ate 9 ?is plant ?\gh x is usually f\nd z a glucoside ( fiset9 comb9$ ) tannic acid4 ,a comp\nd ( ?is k9d 0 f\nd 9 ,rhus cot9us & nam$ fu/9-tannide by ,s*mid#bb4 ,he %[$ t ! fu/9-tannide c\ld be decompos$ by acetic acid into tannic acid & a glucoside1 fu/9 ,c#df;,h#db,o#ba4 ,fu/91 on heat+ ) dilute sulphuric acid1 gave fiset9 & a sug> suppos$ to be rhamnose4 ,fiset9 0 also f\nd z a glucoside comp\nd 9 ,rhus rhodan!ma by ,p]k94#bc ,! yell[ sub/ance :i* sep>at$ f ! boil+ wat] solution 0 fur!r purifi$ by dissolv+ 9 a small quantity ( hot alcohol & add+ hot wat]4 ,on cool+1 ! yell[ sub/ance sep>at$ out 9 a floccul5t condition4 ,exam9$ "u ! microscope1 ! flakes appe>$ to be made up ( masses ( f9e cry/als4 ,an alcoholic solution ( ! sub/ance gave a black color ) ammonia :i* became r$ on addition ( m ammonia4 ,conc5trat$ acids int5sifi$ ! yell[ color ( ! alcoholic solution4 ,fehl+ solution & ammoniacal silv] nitrate 7 r$uc$ by x4 ,potassium hydroxide add$ to an alcoholic solution gave at fir/ a deep r$ color accompani$ by a gre5 fluoresc5ce :i* disappe>$1 leav+ a yell[ liquid4 ,) an excess ( cau/ic pota%1 ! r$ color return$ & 0 p]man5t4 ,^! reactions are *>act]i/ic = fiset94#bd ,fur!rmore1 fiset9 %\ld give protocate*uic acid & phlorogluc9ol by fusion ) cau/ic pota% "u prop] conditions4#be ,! exp]im5t 0 c>ri$ out z foll[s3 #b grams ( fiset9 7 g5tly heat$ 9 a nickel crucible ) #f grams ( cau/ic pota% dissolv$ 9 #f cc4 wat]4 ,an inflammable gas1 app>5tly hydrog51 0 evolv$ dur+ ! fusion4 ,! pa/y mass 0 dissolv$ 9 wat]1 acidifi$ ) sulphuric acid1 & filt]$4 ,! filtrate 0 %ak5 out ) e!r conta9+ "o-f\r? its volume ( alcohol4 ,! e!r 0 evaporat$ & ! residue 0 extract$ ) w>m wat] & filt]$4 ,lead acetate 0 add$ to ! filtrate to precipitate protocate*uic acid1 :ile phlorogluc9ol rema9$ 9 ! filtrate f ?is precipitate4 ,! lead precipitate 0 susp5d$ 9 wat]1 decompos$ by hydrog5 sulphide1 filt]$1 & evaporat$ to obta9 protocate*uic acid4 ,t ! sub/ance obta9$ 0 protocate*uic acid 0 %[n by ! foll[+ *>act]i/ic te/s3 7#a7 ,x gave a gre5i% br[n color ) f]ric *loride2 on addition ( "o drop ( a dilute solution ( sodium c>bonate1 ! color became d>k blue2 on add+ m sodium c>bonate ! color became r$4 7#b7 ,a violet color 0 obta9$ :5 a solution ( ! acid 0 treat$ ) a drop ( sodium c>bonate solution & !n ) a drop ( f]r\s sulphate4 7#c7 ,x r$uc$ ammoniacal silv] nitrate4 7#d7 ,x did n r$uce ,fehl+ solution4 ,! filtrate suppos$ to conta9 phlorogluc9ol 0 treat$ ) hydrog5 sulphide to remove lead1 filt]$1 & %ak5 ) e!r4 ,! residue left on evaporat+ ! e!r 0 tak5 up 9 wat]4 ,?is solution gave ! foll[+ reactions *>act]i/ic = phlorogluc9ol3 7#a7 ,x r$uc$ bo? silv] nitrate & ,fehl+ solution4 7#b7 ,x color$ p9e wood moi/5$ ) hydro*loric acid r$4 7#c7 ,x gave a r$ color ) vanill9 & hydro*loric acid1 & 7#d7 ,a deep] r$ color ) oil ( cloves & hydro*loric acid1 becom+ purple on /&+4 7#e7 ,x gave a violet color ) f]ric *loride4 ,! sub/ance is !n1 )\t d\bt1 fiset94 ,! =mula#bf ( fiset9 is suppos$ to be ,c#ae;,h#aj,o#f4 ,,rhamnose4 ,x 0 /at$ above t ,s*mid obta9$ a sug> solution by ! decomposition ( a fiset9-glucoside f ,rhus cot9us1 & ,p]k9 obta9$ ! same f a glucoside 9 ,rhus rhodan!ma4 ,^! inve/igators ?\ght t ! sug> 0 isodulcite or rhamnose1 b !y did n isolate x on acc\nt ( ! small quantities ( mat]ial at _! disposal4 ,moreov]1 ! sug> is v h>d to cry/allize 9 ! pres5ce ( o!r soluble sub/ances & is n f\nd 9 l>ge quantity 9 plants4 ,maqu5ne#bg c\ld obta9 only #ae to #bj gm4 ( rhamnose by work+ up #a kilogram ( ! b]ries ( ,rhamnus infectorius4 ,assum+ t ! free fiset9 f\nd 9 poison ivy leaves _h its orig9 9 ! decomposition ( a fiset9-glucoside by natural processes1 x 0 reasonable to suppose t ! sug> w\ld also be f\nd 9 ! free /ate1 al?\gh1 accord+ to ,roscoe & ,s*orlemm]3#bh ,isodulcite does n occur 9 ! free /ate 9 nature1 b is f\nd z a peculi> e!real salt belong+ to ! class ( glucosides4 ,on boil+ ) dilute sulphuric acid1 ?is splits up into isodulcite & o!r bodies4444 ,! m rec5t works on ! sug>s & on plant *emi/ry#bi m5tion ! occurr5ce ( rhamnose only 9 ! glucoside =m1 ) "o possible exception4 ,! exception ref]r$ to is ! occurr5ce ( a free sug>1 suppos$ to be rhamnose1 9 a c]ta9 palm-w9e4#cj ,czapek says3#ca ,! well-kn[n me?yl p5toses d n occur 9 ! free /ate 9 plant organisms s f> z we "k4 ,s9ce rhamnose =ms a lead comp\nd1 ! sug>1 if pres5t1 %\ld be f\nd 9 ! fir/ lead precipitate1 ,a1 & also 9 filtrate ,a 9 case x is n completely precipitat$ 9 ! pres5ce ( acetic acid & alcohol4 ,! filtrate ,a 7ab\t two lit]s7 0 exam9$ fir/4 ,x _h a light yell[ color1 conta9$ an excess ( lead acetate1 & 0 acid f ! acetic acid lib]at$ 9 ! precipitation ( ! lead comp\nd ,a4#cb ,?is filtrate 0 evaporat$ to dryness "u dim9i%$ pressure to remove alcohol1 wat]1 & acetic acid4 ,! cle> di/illate _h a peculi> odor sugge/+ bo? tea & amyl =mate4 ,x 0 sav$ = exam9ation & 0 f\nd to be n poison\s4 ,! residue 9 ! di% aft] evaporation 0 a t\gh r$di% br[n1 gummy mass :i* c\ld be drawn out into f9e ?reads4 ,x _h a pleasant sweet odor4 ,x 0 extract$ sev]al times ) hot wat]1 ea* portion be+ filt]$4 ,a br[ni% yell[ p[d] rema9$ undissolv$ & 0 sav$4 ,! comb9$ filtrates deposit$ m ( ! yell[ solid on /&+4 ,?is p[d] w be ref]r$ to lat] z ,p4 ,! filt]$ liquid 0 fre$ f lead by hydrog5 sulphide4 ,! solution !n _h a lemon yell[ color1 a sweet odor & 0 acid f acetic acid4 ,on conc5trat+ ! solution by evaporation & mak+ a small portion ( x alkal9e ) sodium hydroxide1 ! yell[ color came out v int5se#cc4 ,! alkal9e solution r$uc$ ,fehl+ solution & ammoniacal silv] nitrate1 indicat+ ! pres5ce ( a sug>4 ,ano!r portion ( ! solution gave a slight precipitate ) ph5yl hydraz9e 9 ! cold4 ,! rema9d] ( ! solution 0 evaporat$ to dryness1 extract$ ) wat]1 filt]$1 & aga9 evaporat$4 ,a d>k /icky syrup 0 left :i* 0 only p>tly soluble 9 wat]4 ,?is 0 treat$ ) wat]1 filt]$1 & ! filtrate 0 evaporat$1 ! wat] be+ replac$ f "t to "t to remove acetic acid4 ,f9ally ! liquid gave ! foll[+ te/s = rhamnose1 besides ^? already m5tion$3 7#a7 ,) alpha-naph?ol#cd & sulphuric acid1 a purple violet color4 7#b7 ,) ?ymol#ce & sulphuric acid1 a r$ color4 7#c7 ,) resorc9ol#cf & sulphuric acid1 r$ color4 7#d7 ,) orc9ol#cg & hydro*loric acid1 r$ color4 7#e7 ,) ammonium picrate & sodium picrate1 yell[i% r$ color4 7#f7 ,) phlorogluc9ol & hydro*loric acid1 r$ color4 7#g7 ,x decoloriz$ an alkal9e solution ( potassium f]ricyanide4 7#h7 ,x gave a :ite precipitate ) lead acetate4 ,! filtrate ,b 7p4 #bj7 f :i* gallic acid 0 precipitat$ by sulphuric acid 9 f\r fractions 0 sav$ to exam9e = sug>4 ,to remove gallic acid completely1 & o!r vegetable matt]1 x 0 %ak5 out sev]al times ) e!r1 & 0 kept at a l[ temp]ature ) salt & ice = a long "t4 ,x 0 left /&+ = sev]al weeks1 dur+ :i* "t m br[n matt] sep>at$ out & 0 filt]$ (f4 ,! filtrate 0 evaporat$ to a small bulk1 cool$1 & filt]$ f cry/als ( potassium sulphate4 ,! filtrate 0 evaporat$ to dryness1 ! residue tak5 up 9 wat] & filt]$ ?r\gh bone-black4 ,addition ( alcohol caus$ complete precipitation ( potassium sulphate4 ,! solution !n gave ! above m5tion$ *>act]i/ic te/s = rhamnose4 ,all attempts to get ! osazone ( ! sug> by ! me?od ( ,fis*]#ch fail$1 probably on acc\nt ( ! small quantity ( ! sug> pres5t4 ,! plant1 x w be rememb]$1 0 orig9ally extract$ ) e!r 9 :i* rhamnose is practically insoluble4 ,! above describ$ te/s1 h[ev]1 c leave no d\bt z to ! id5tity ( ! sug>4 ,additional evid5ce t ! sug> is rhamnose 0 obta9$ by a me?od describ$ by ,maqu5ne#ci z foll[s3 ,! production ( me?yl furfurol 9 ! dehydration ( isodulcite furni%es a v simple means ( *>act]iz+ ?is sug> 9 mixtures :i* conta9 x2 x is suffici5t1 = example1 to di/il #ej gm4 ( qu]citron wood ) z mu* sulphuric acid & ab\t #aej gm4 ( wat]1 !n to rectify ! liquid obta9$ 9 ord] to get sev]al drops ( ! crude furfurol1 :i* on addition ( alcohol & conc5trat$ sulphuric acid gives imm$iately ! gre5 coloration *>act]i/ic ( me?yl furfurol4 ,?is proc$ure is applicable to extracts z well z to entire plants1 & has ! advantage t x does n require ! sep>ation ( isodulcite1 ! cry/allization ( :i* is (t5 v sl[ & at times impossible :5 x is mix$ ) o!r v soluble sub/ances4 ,! exp]im5t 0 tri$ ) ! crude e!r extract ( ! plant accord+ to ! directions ( ,maqu5ne1 & ! gre5 color ) alcohol & sulphuric acid 0 obta9$ f ! ?ick] oily portion ( ! di/illate4 ,?is te/ c be made ) hydro*loric acid#dj z well z ) sulphuric4 ,!re=e ! color te/ 0 tri$ ) ! e/] mixture prep>$ 9 "o ( ! e>ly exp]im5ts by boil+ ! orig9al plant mat]ial ) hydro*loric acid & alcohol4 ,me?yl furfurol 0 f\nd "h also1 ?is me?od inde$ giv+ bett] results ?an t ( ,maqu5ne4 ,! pres5ce ( free rhamnose has ?us be5 %[n 9 ! orig9al mat]ial1 9 ! fir/ precipitate by lead acetate1 & 9 ! filtrate f ?is precipitate4 ,exp]im5ts to be describ$ "u ,! ,poison %[$ t ! e!r extract f ! ,soxhlet app>atus conta9$ a sub/ance :i* yield$ rhamnose :5 hydrolyz$ by dilute sulphuric acid4 ,! pres5ce ( free gallic acid1 fiset91 & rhamnose 9 ! plant c be readily expla9$ by a s]ies ( assumptions = :i* !re is a consid]able am\nt ( exp]im5tal evid5ce4 ,!re is reason to believe t tann9-l bodies are =m$ at ! exp5se ( *lorophyll1#da t complex tann9 bodies c be brok5 d[n by acetic acid 7also f\nd 9 ,rhus toxicod5dron7 into a tannic acid & a glucoside 7= example1 ! fu/9-tannide m5tion$ above yields tannic acid & fiset9-glucoside72 & f9ally t ! glucoside c be hydrolyz$ by acids or enzymes giv+1 9 ! suma* plants1 fiset9 & rhamnose4 ,nitrog5\s f]m5ts :i* c effect ! hydrolysis ( glucosides & give rise to sug>s are frequ5tly f\nd 9 plants1 = example1 emuls9 9 almonds1 myros9 9 mu/>d1 & ery?rozym 9 madd]4 ,acree & ,h9k9s#db f\nd t dia/ase1 pancreat91 & a numb] ( o!r enzymes cause hydrolysis ( triacetyl glucose ) ! =mation ( glucose & acetic acid4 ,/ev5s#dc obta9$ a nitrog5\s oxidiz+ enzyme f ,rhus v]nicif]a4 ,! close relation%ip betwe5 ! poison\s species ( ,rhus w\ld lead u to suppose t ! same soluble f]m5t exi/s 9 poison ivy1 ?\gh x 0 n detect$ 9 ! orig9al mat]ial us$ 9 ^! exp]im5ts1 probably because ! plant 0 extract$ ) e!r 9 :i* ! enzyme is insoluble4 ,! exi/5ce ( su* a soluble f]m5t w\ld expla9 ! pres5ce ( free sug> & free fiset94 ,,evid5ce ,,( ,,! ,,pres5ce ,,( ,a ,,fatty ,,acid ,,9 ,,filtrate ,a4 ,! br[n sub/ance ,p1 obta9$ f filtrate ,a by evaporation & extract+ ! residue ) hot wat]1 0 susp5d$ 9 w>m wat] & dilute sulphuric 0 add$4 ,a :ite precipitate 0 =m$ & a /rong fatty acid odor 0 develop$4 ,aft] ! mixture _h be5 heat$ = "s h\rs on ! wat] ba? a small portion 0 made alkal9e & x r$uc$ ,fehl+ solution4 ,! ma9 solution 0 filt]$ & ! precipitate suppos$ to be a fatty acid 0 sav$4 ,! filtrate 0 neutraliz$ ) b>ium c>bonate1 filt]$1 evaporat$1 fre$ f c>amel1 & ! solution !n gave ! te/s m5tion$ above = rhamnose4 ,a portion ( ! precipitate suppos$ to be a fatty acid 0 ignit$ 9 a porcela9 spoon4 ,x fus$1 c>boniz$1 & burn$4 ,! rema9d] 0 heat$ ) alcoholic pota% & reprecipitat$ ) hydro*loric acid4 ,! precipitate 0 wa%$ & heat$ ) alcohol4 ,"p ( x dissolv$4 ,! insoluble "p 0 f\nd to be a lead comp\nd4 ,on boil+ x ) hydro*loric acid & cool+1 lead *loride cry/alliz$ out4 ,?is 0 confirm$ by dissolv+ ! lead *loride 9 hot wat] & precipitat+ z lead sulphide4 ,^! exp]im5ts 7 n c>ri$ f>!r on acc\nt ( ! small quantity ( mat]ial1 b !y %[ t ! gummy sub/ance obta9$ f filtrate ,a conta9$ rhamnose 7ei!r z a lead comp\nd ( free sug> or z a lead comp\nd ( a rhamnoside71 & also1 mo/ probably1 ! lead comp\nd ( an organic acid4#dd ,,! ,,fragrant ,,di/illate4 ,sev]al times 9 ! c\rse ( ?is "w1 extracts ( ! orig9al plant mat]ial 9 alcohol & 9 wat] 7 di/ill$ "u dim9i%$ pressure = ! purpose ( conc5trat+ ! solutions4 ,! di/illate1 9 e case1 _h an e!real odor sugge/+ amyl =mate 9 v dilute solution1 b 0 m fragrant4 ,! di/illate f a wat] extract 0 exam9$4 ,x 0 a cle> liquid1 a little d>k] ?an pure wat]1 0 n poison\s1 0 neutral to litmus pap]1 gave no color ) f]ric *loride1 r$uc$ ammoniacal silv] nitrate1 b n ,fehl+ solution1 & gave a fa9t r$ color ) dilute ammonium hydroxide & ) sodium c>bonate4 ,a small quantity ( a f9ely divid$ black precipitate sep>at$ out f ! wat] di/illate on /&+4 ,! sub/ance ) ! fragrant odor 0 extract$ by %ak+ ! di/illate ) e!r & lett+ ! e!r evaporate spontane\sly4 ,a v small quantity ( a yell[ solid 0 deposit$ on ! sides ( ! di%4 ,?is sub/ance _h a /rong & p]si/5t odor1 s sweet z to be almo/ nauseat+4 ,n en\gh 0 obta9$ = exam9ation or analysis4 ,?is fragrant residue 0 difficultly soluble 9 wat] & ! solution r$uc$ silv] nitrate 9 ammonia4 ,a /eam di/illate ( ! orig9al plant mat]ial _h ! same fragrant odor z ! di/illate f a wat] extract4 ,,! ,,poison4 #bhh grams ( ! orig9al poison\s mat]ial 7 extract$ ) #ej p] c5t4 alcohol1 & ?is alcoholic solution 0 precipitat$ ) lead acetate 9 ! mann] already describ$ 7p4 #ag74 ,! lead precipitate s obta9$ 0 extract$ ) e!r 9 ,soxhlet extractors & aft] ! extraction 0 f\nd by te/ to be free f poison4 ,!re=e ! poison1 if precipitat$ by ! lead acetate1 mu/ h be5 extract$ by ! e!r4 ,?is e!r solution _h a d>k gre5 color1 & 0 acid f acetic acid br\ght d[n 9 ! lead precipitate4 ,! e!r 0 evaporat$ 9 a vacuum desiccator )\t heat & !re rema9$ a small quantity ( an acid mixture ( wat] & a s(t t>2 ! wat]y "p 0 color$ gre51 %[+ t ! t> 0 soluble to "s ext5t 9 dilute acetic acid4 ,! mixture _h ! peculi> odor ( ! orig9al mat]ial4 ,a small drop ( ! gre5 wat]y "p 0 appli$ to ! wri/1 all[$ to rema9 a few m9utes & 0 !n remov$ by absorb5t pap]1 b ! spot 0 n wa%$4 ,it*+ & r$d5+ ( ! sk9 comm5c$ )9 tw5ty-f\r h\rs4 ,at ! end ( =ty-eight h\rs1 !re 0 a well develop$ case ( poison+4 ,h[ ?is 0 cur$ w be describ$ 9 ano!r place4 ,a small portion ( ! poison\s mixture 0 dissolv$ 9 alcohol1 & ?is solution 0 divid$ into ?ree p>ts4 ,! fir/ "p 0 treat$ ) f]ric *loride1 b x gave no color reaction4 ,ano!r portion ( ! alcoholic solution 0 dilut$ ) wat]4 ,x became turbid4 ,! ?ird portion gave a dirty-gre5 precipitate ) lead acetate1 :i* seem$ to come d[n m readily :5 ! solution 0 dilut$ ) wat]4 ,! ma9 portion ( ! poison\s mixture 0 !n dissolv$ 9 #ie p] c5t4 alcohol & lead acetate 9 #ej p] c5t4 alcohol 0 add$4 ,! precipitate 0 filt]$1 wa%$1 & decompos$ by hydrog5 sulphide 9 a mixture ( wat] & e!r4 ,! e!r solution 0 filt]$ & evaporat$4 ,! residue 0 a t> :i*1 on /&+ 9 a desiccator = "s "t1 became dry en\gh to break into /icky lumps4 ,an alcoholic solution ( ?is sub/ance gave a d>k color ) f]ric *loride & a light color$ precipitate ) lead acetate4 ,to get m ( ! poison\s t> = /udy1 #bcc grams ( orig9al mat]ial 7 extract$ ) #ie p] c5t4 alcohol4 ,/rong alcohol 0 us$ 9 ord] to dissolve z mu* ( ! t> z possible4 ,! solution _h a d>k gre5i% color1 b 0 some:at yell[ 9 ?9 lay]s4 ,! undissolv$ t> 0 filt]$ (f & extract$ twice aga9 9 ! same way4 ,! t> left aft] ! ?ird extraction 0 only slightly soluble 9 alcohol1 & its solution 0 n poison\s4 ,! ?ree filtrates f ^! ?ree extractions 7 precipitat$ sep>ately by lead acetate 9 #ej p] c5t4 alcohol4 ,! fir/ precipitate 0 l>ge/1 d>ke/ 9 color1 & c>ri$ d[n m t>ry matt]4 ,! second 0 light gre51 & ! ?ird 0 q small1 black1 & 0 n a lead comp\nd at all1 b "s ( ! t> :i* sep>at$ out on dilut+ ! /rong alcohol ) ! weak] grade conta9+ lead acetate4 ,x 0 soluble 9 e!r & less soluble 9 alcohol4 ,! alcoholic solution ( ?is ?ird lot gave no precipitate ) hydrog5 sulphide4 ,! fir/ & second lead precipitates 7 filt]$ by suction & wa%$ ) wat]4 ,!y 7 kept a day or two 9 a desiccator ov] sulphuric acid1 b did n become completely dry4 ,! weight ( ^! two moi/ precipitates toge!r 0 #agb grams4 ,!y 7 comb9$ & extract$ ) e!r 9 ,soxhlet extractors :i* 7 kept 9 op]ation dur+ "w h\rs = ?ree days4 ,9 ! meantime ! alcoholic filtrates f ^! lead precipitates 7 comb9$ & conc5trat$ on ! wat] ba? by di/ill+ (f two lit]s ( alcohol4 ,! alcohol obta9$ _h ! peculi> odor ( ! orig9al mat]ial1 b 0 n poison\s4 ,aft] a long extraction ( ! lead precipitate 9 ! ,soxhlet extractors1 ! gre5 e!r solutions 7 comb9$ & wa%$ by %ak+ !m ) wat] to remove lead acetate & acetic acid 9 case any %\ld h be5 held 9 ! lead precipitate4 ,! e!r 0 di/ill$ (f at a l[ temp]ature & !re rema9$ a s(t t>1 a portion ( :i* 0 n completely soluble 9 #ie p] c5t4 alcohol4 ,! alcoholic solution _h a gre5i% yell[ color & 0 poison\s4 ,! t> 0 also p>tly soluble 9 acetic acid1 & ?is solution 0 f\nd to conta9 lead4 ,?9k+ t ! lead acetate _h n be5 completely wa%$ out1 ! ma9 "p ( ! t> 0 dissolv$ 9 e!r & %ak5 ) wat]4 ,! wa% wat] cont9u$ to give a te/ = lead z long z ! wa%+ 0 cont9u$4 ,?is indicat$ probably ! hydrolysis ( an un/able lead comp\nd4 ,hydrog5 sulphide 0 pass$ into ! e!r solution mix$ ) wat] to remove ! lead4 ,lead sulphide 0 filt]$ (f1 & ! e!r 0 evaporat$4 ,a small portion ( ! t> residue 9 alcoholic solution gave a color reaction ) f]ric *loride4 ,z ?is may h be5 due to traces ( lead gallate dissolv$ 9 ! extraction ) e!r & aft]w>ds decompos$ by hydrog5 sulphide1 ! ma9 portion ( ! t> 0 r$issolv$ 9 e!r & %ak5 ) wat] until x no long] react$ ) f]ric *loride4 ,! e!r 0 !n evaporat$ & a s(t1 black1 poison\s t> or gum ( uni=m consi/5cy 0 left :i* 0 %[n by te/s to be free f gallic acid & lead4 ,^! exp]im5ts %[$ t "s ( ! poison 0 precipitat$ z a lead comp\nd soluble 9 e!r & "s 0 br\ght d[n me*anically 9 ! free /ate4 ,to see if ! extraction ) e!r 9 ! ,soxhlet app>atus 0 complete1 ! residue 9 ! ?imbles 0 decompos$ by hydrog5 sulphide & %ak5 ) e!r4 ,! d>k color$ e!r solution 0 fre$ f gallic acid by %ak+ ) wat] & dilute sodium c>bonate solution1 & 0 evaporat$4 ,a small quantity ( t> 0 obta9$ :i* 0 add$ to ! ma9 portion4 ,a solution ( ! poison\s t> 9 #ie p] c5t4 alcohol did n r$uce ,fehl+ solution & did n give a precipitate ) lead acetate except ! sep>ation ( a small quantity ( t>1 :i* 0 n a lead comp\nd4 ,! lead comp\nd ( ! poison 0 app>5tly soluble 9 #ie p] c5t4 alcohol z well z 9 e!r1 = x w\ld n precipitate 9 ?is m$ium1 al?\gh x 0 f\nd 9 ! orig9al precipitate by lead acetate4 ,! alcoholic solution ( ! t> became turbid on dilut+ ) wat]4 ,9 ord] to see if ! poison is volatile ) vapor ( acetic acid1 s9ce ?is acid is f\nd 9 ! plant & x is ?\ght by "s t ! poison is volatile1 a portion ( ! t> 0 di/ill$ "u dim9i%$ pressure ) acetic acid4 ,x 0 soluble to "s ext5t 9 ! acid4 ,! temp]ature did n g high] ?an #ee deg4 dur+ ! di/illation4 ,a tube conta9+ cotton wet ) sweet oil 0 plac$ betwe5 ! receiv] & ! wat] suction s t ! uncond5s$ vapors w\ld h to pass ?r\gh ! cotton4 ,?is cotton 0 rubb$ on ! sk9 & 0 n poison\s4 ,! yell[ di/illate collect$ 9 ! receiv] 0 also te/$ & 0 n poison\s4 ,,hydrolysis ,,( ,,! ,,poison4 ,ab\t #e grams ( ! poison\s t> free f gallic acid & sug> 0 dissolv$ 9 alcohol1 & dilute 7#b p] c5t47 sulphuric acid 0 add$4 ,"s ( ! t> sep>at$ out on dilut+ ! alcohol ) ! acid4 ,! mixture 0 heat$ on a wat] ba? dur+ "w h\rs = f\r days4 ,a purple & gre5 fluoresc5t solution 0 =m$1 ?\gh mu* t> 0 left app>5tly un*ang$4 ,! alcohol 0 evaporat$ (f & ! solution 0 filt]$ f t>4 ,! fluoresc5t filtrate 0 %ak5 ) e!r1 by :i* ! gre5 sub/ance 0 remov$1 leav+ ! solution purple4 ,! e!r left1 on evaporation1 a small quantity ( a gre5 sub/ance hav+ a pleasant e/] odor4 ,x 0 n fur!r exam9$4 ,a portion ( ! purple solution 0 exactly neutraliz$ ) sodium c>bonate4 ,?is solution gave a blue-black color ) f]ric *loride :i* became r$ on addition ( ano!r drop ( sodium c>bonate1 indicat+ gallic acid4 ,x also r$uc$ ,fehl+ solution4 ,ano!r portion ( ! purple solution 0 made alkal9e ) sodium c>bonate4 ,a r$di%-br[n floccul5t precipitate 0 =m$ & 0 filt]$ (f4 ,! filtrate did n give any color ) f]ric *loride1 b x r$uc$ ,fehl+ solution4 ,x also gave ! te/ = rhamnose ) alpha-naph?ol4 ,! ma9 portion ( ! purple solution 0 made alkal9e ) sodium c>bonate2 ! precipitate 0 filt]$ (f & dissolv$ 9 acetic acid4 ,?is solution 0 yell[ & gave a reaction ) f]ric *loride simil> to t ( gallic acid4 ,! filtrate f ! precipitate by sodium c>bonate 0 conc5trat$ by evaporation until sodium sulphate began to cry/allize out4 ,alcohol 0 add$ to precipitate ! sodium sulphate completely1 ! mixture 0 heat$ & filt]$4 ,! alcoholic filtrate 0 conc5trat$ to a syrup :i* r$uc$ ,fehl+ solution & gave ! *>act]i/ic te/s = rhamnose already describ$4 ,by ?is hydrolysis1 ! t> 0 split up into rhamnose & "s =m ( gallic acid :i* c\ld be precipitat$ by sodium c>bonate4 ,?is comp\nd1 ^: acetic acid solution 0 yell[1 probably conta9$ fiset9 also4 ,! reason = ?is la/ /atem5t w appe> f ! foll[+ exp]im5t3 ,,decomposition ,,( ,,! ,,poison ,,) ,,acetic ,,acid4 ,a portion ( ! poison\s t> 0 heat$ 9 an op5 di% ) /rong acetic acid4 ,! t> seem$ to be decompos$ to "s ext5t1 giv+ a yell[ sub/ance4 ,acetic acid 0 add$ f "t to "t z x evaporat$4 ,aft] sev]al evaporations1 wat] 0 add$1 ! mixture 0 heat$ to boil+ & filt]$4 ,?is filtrate ,no4 #a w be m5tion$ lat]4 ,! residue 9 ! di% consi/$ ( undecompos$ t> & an olive-gre5 flaky sub/ance4 ,?is sub/ance 0 heat$ ) a fre% portion ( glacial acetic acid4 ,wat] 0 add$1 & ! mixture 0 boil$ & filt]$4 ,! filtrate _h a deep yell[ color sugge/+ fiset94 ,x 0 %ak5 out ) e?yl acetate :i* became color$ yell[4 ,a portion ( ! e?yl acetate solution gave an orange r$ precipitate ) lead acetate %[+ ! pres5ce ( fiset94 ,! e?yl acetate 0 remov$ f ! rema9d] ( ! solution by evaporation & ! yell[ residue 0 tak5 up 9 alcohol4 ,?is alcoholic solution gave ! *>act]i/ic reactions = fiset9 ) /ann\s *loride1 ) potassium hydroxide1 ) f]ric *loride & ) ,fehl+ solution4 ,filtrate ,no4 #a obta9$ by heat+ ! poison\s t> ) acetic acid & hot wat] z describ$ above 0 inve/igat$ z foll[s3 ,a portion ( x gave a r$di% color$ precipitate ) sodium c>bonate z 9 ! case :5 ! t> 0 hydrolyz$ ) sulphuric acid4 ,! rema9d] 0 ne>ly neutraliz$ ) sodium c>bonate & lead acetate 0 add$ 9 excess to remove gallic acid4 ,! excess ( lead 0 remov$ by sulphuric acid1 & ! sulphuric acid 0 remov$ by b>ium c>bonate4 ,! solution on evaporation r$uc$ ,fehl+ solution to "s ext5t1 b a :ite precipitate 0 also =m$4 ,9 ?is exp]im5t1 gallic acid & fiset9 & probably sug> 7 =m$ by decomposition ( ! poison\s gum ) acetic acid1 ! acid f\nd 9 ! plant by ,pfaff4 ,! pres5ce ( free gallic acid1 fiset9 & rhamnose 9 ! plant c !re=e be expla9$ by ! natural hydrolysis ( a complex gum or t> or a con/itu5t !re(4 ,! poison\s prop]ty is lo/ 9 ! g5]al re>rangem5t :i* takes place dur+ hydrolysis4 ,! poison\s t> 0 n hydrolyz$ by boil+ ) a dilute solution ( sodium c>bonate4 ,x 0 f\nd1 z has be5 /at$ else:]e1 t ! lead comp\nd ( ! poison c\ld n be precipitat$ 9 #ie p] c5t4 alcohol4 ,fur!r exp]im5ts1 h[ev]1 %[$ t on extract+ ! poison\s gum ) #ej p] c5t4 alcohol1 a portion ( x dissolv$1 & ?is solution gave a precipitate ) lead acetate :i* 0 a true lead comp\nd4 ,! rema9d] ( ! purifi$ t> 7ab\t #aj gm47 0 treat$ ) #ej p] c5t4 alcohol & filt]$4 ,v little dissolv$ 9 alcohol ( ?is /r5g?1 b on addition ( lead acetate 9 #ej p] c5t4 alcohol to ! solution1 a light color$ precipitate 0 =m$1 :i* became d>k on /&+4 ,x 0 filt]$ (f1 wa%$ free f lead acetate1 decompos$ by hydrog5 sulphide1 & %ak5 out ) e!r4 ,! e!r left1 on evaporation1 a yell[ res9\s sub/ance hav+ a fa9t odor l g>lic4 ,by dry+ 9 a desiccator1 a small quantity ( a solid yell[ res9 0 obta9$ :i* 0 completely soluble 9 alcohol4 ,a v small drop ( ?is solution appli$ to ! sk9 on ! end ( a glass rod :i* _h be5 drawn out to a po9t caus$ an eruption 9 ab\t ?irty-six h\rs4 ,foll[+ ! nom5clature us$ by ,mais* & ,pfaff1 ?is sub/ance w be designat$ z ,toxicod5dr91 ! end+ 9 indicat+ its glucoside nature4 ,! filtrate f ! lead precipitate j describ$ 0 fre$ f ! excess ( lead acetate by hydrog5 sulphide1 0 te/$ = poison1 & 0 f\nd to be poison\s1 %[+ t ! precipitation by lead acetate 0 n complete ev5 9 #ej p] c5t4 alcohol4 ,on spontane\s evaporation ( ! solution1 a yell[1 sweet smell+ res9 0 left4 ,a portion ( ! alcoholic solution ( ! toxicod5dr9 gave a d>k coloration ) f]ric *loride1 did n r$uce ,fehl+ solution & 0 slightly acid to litmus4 ,to see :e!r ! toxicod5dr9 c\ld be hydrolyz$1 ! rema9d] 0 dissolv$ 9 alcohol & dilute sulphuric acid 0 add$4 ,a f9e1 :ite precipitate 0 =m$ at once :i* rose to ! surface on /&+ z a light floccul5t sub/ance4 ,! mixture 0 heat$ = sev]al days on a wat] ba?1 filt]$ f unhydrolyz$ res9 & ! filtrate 0 neutraliz$ & conc5trat$ 9 ! way already describ$4 ,! solution obta9$ r$uc$ ,fehl+ solution4 ,n en\gh 0 obta9$ = fur!r sug> te/s1 b all ! hydrolysis exp]im5ts po9t to ! conclusion t ! poison\s sub/ance is a rhamnoside1 & is ! s\rce ( ! sug> 9 ! plant4 ,! reaction ) f]ric *loride obs]v$ :5ev] a lead comp\nd ( ! poison is decompos$ by hydrog5 sulphide may be expla9$ by ! =mation ( traces ( gallic acid or fiset9 ?r\gh ! action ( ! weak acids pres5t4 ,! supply ( purifi$ poison\s t> hav+ be5 exhau/$ 9 ! prec$+ exp]im5ts1 fur!r /udy ( ! active pr9ciple is po/pon$ until m c be prep>$4 ,x is highly desirable to inve/igate ! :ite precipitate =m$ by addition ( sulphuric acid to an alcoholic solution ( ! toxicod5dr94 ,,oxidation ,,( ,,! ,,purifi$ ,,t> ,,) ,,nitric ,,acid4 ,:5 ! purifi$ poison\s mat]ial 7p4 #cb7 0 extract$ ) #ej p] c5t4 alcohol1 only a small quantity 0 dissolv$ z 0 /at$ above4 ,! insoluble residue 0 treat$ ) fum+ nitric acid4 ,viol5t reaction took place at once ) copi\s evolution ( r$ fumes & heat4 ,:5 ! reaction 0 ov]1 a /icky r$ gummy mass 0 left :i* 0 slightly soluble 9 cold wat] & readily soluble 9 w>m alcohol4 ,! wat] extract 0 yell[1 & ! alcoholic solution 0 r$4 ,t ! wat] extract conta9$ picric acid 0 %[n by ! foll[+ exp]im5ts3 7#a7 ,a portion 0 g5tly w>m$ ) a few drops ( a /rong solution ( potassium cyanide & two drops ( sodium hydroxide4 ,! r$ color ( potassium isopurpurate 0 =m$4 7#b7 ,a portion ( ! wat] solution 0 heat$ ) glucose & a few drops ( sodium hydroxide4 ,! deep r$ color ( picram9ic acid 0 produc$4 7#c7 ,a few drops ( an ammoniacal solution ( copp] sulphate 0 add$ to ! wat] extract4 ,a yell[-gre5 precipitate 0 =m$4 7#d7 ,! wat] extract dy$ silk1 b did n dye cotton clo?4 ,,di/illation ,,( ,,! ,,t> ,,) ,,soda ,,lime4 ,ab\t #be gm4 ( ! t> left aft] extract+ ! orig9al mat]ial ) hot wat] 0 dissolv$ 9 e!r & p\r$ into a glass retort conta9+ soda lime4 ,! e!r 0 di/ill$ out1 leav+ ! t> intimately mix$ ) ! soda lime4 ,! retort 0 !n gradually heat$4 ,vapors & liquid 7 giv5 (f1 bo? ( :i* turn$ r$ litmus blue & _h a /rong odor l tobacco smoke4 ,no odor ( ammonia 0 detect$4#de ,at ! high temp]ature ( ! triple burn]1 a semi-solid1 r$1 greasy sub/ance collect$ 9 & clos$ ! cond5s] tube4 ,?is sub/ance _h ! same p[]ful odor z ! liquid portion ( ! di/illate4 ,! cle>1 wat]y portion ( ! di/illate 0 sep>at$ f ! ?ick] p>ts1 & 0 f\nd to conta9 pyrrol & pyrid9e d]ivatives by ! foll[+ *>act]i/ic te/s3 7#a7 ,wood moi/5$ ) hydro*loric acid 0 turn$ r$ by x4 7#b7 ,colorless fumes 7 =m$ :5 br\ght ne> hydro*loric acid2 mix$ ) hydro*loric acid1 a r$ insoluble sub/ance 0 =m$4 7#c7 ,x precipitat$ ! hydroxides ( iron1 gave a light blue precipitate ) copp] sulphate1 & a :ite precipitate ) m]curic *loride4 ,! greasy1 semi-solid mass 0 extract$ ) #aj p] c5t4 hydro*loric acid & filt]$4 ,on addition ( a solution ( m]curic *loride to ! r$ filtrate1 a br[n floccul5t precipitate 0 =m$4 ,x 0 filt]$ (f & di/ill$ ) cau/ic soda1 b ! di/illate did n conta9 pyrid9e4 ,,potassium ,,p]manganate ,,z ,a ,,rem$y ,,= ,,rhus ,,poison+4#df ,9 ! e>ly /ages ( ?is "w "s exp]im5ts 7 made to see if potassium p]manganate c\ld be us$ to purify ! lead precipitate by oxidiz+ ! t> br\ght d[n 9 precipitation4 ,x 0 f\nd t ! p]manganate attack$ ! lead precipitate z well z ! o!r organic matt] 9 ! vessel4 ,?is fact & ! well-kn[n value ( p]manganate 9 treat+ sk9 diseases1 its use z an antidote = "s k9ds ( alkaloid poison+1#dg z an antidote giv5 to cattle poison$ by plants1#dh & z an antidote = snake bites1#di sugge/$ its use z a rem$y = ,rhus poison+4 ,mais*#ej m5tion$ t he _h us$ x ) success1 b x nev] came into g5]al use1 probably on acc\nt ( its /a9+ ! sk9 & clo?+4 ,9 c>ry+ out ?is "w abundant opportunities = te/+ its value z a rem$y = ! d]matitis caus$ by poison ivy 7 af=d$ by _m cases ( accid5tal & int5tional poison+4 ,! be/ example ( ! latt] 0 obta9$ ) ! e!r solution f ! extraction ( ! lead precipitate 9 ! ,soxhlet app>atus 7page #bh74 ,aft] remov+ ! e!r1 a small drop ( ! residue 0 appli$ to ! wri/ z describ$4 ,an it*+ r$ spot ab\t ! size ( a dime 0 notic$ 9 ?irty-six h\rs1 & x /eadily increas$ 9 size4 ,ne>ly two days aft] ! application ( ! poison1 a dilute solution ( potassium p]manganate conta9+ a little cau/ic pota% 0 rubb$ into ! spot until ! pimples 7 de/roy$4 ,a little black spot 0 left :]ev] !re _h be5 a pimple1 %[+ t ! p]manganate _h be5 r$uc$ to oxide 9 ! sk94 ,! place 0 wa%$ & no?+ m 0 ?\ght ( x until ! morn+ foll[+1 :5 x 0 notic$ t ! wri/ _h comm5c$ to swell dur+ ! night1 & ! *>act]i/ic wat]y secretion 0 runn+ f ! poison$ spot4 ,m p]manganate solution 0 appli$ )\t pota% & ! wri/ 0 b&ag$1 ?9k+ t ?is w\ld prev5t ! spread+ ( ! eruption1 b x really facilitat$ spread+ by becom+ saturat$ ) ! poison\s fluid & keep+ x 9 contact ) a l>g] surface ( sk94 ,9 ! meantime ! swell+ & inflammation _h ext5d$ ne>ly to ! elb[4 ,! arm n[ _h ! appe>ance ( hav+ be5 bitt5 by a snake4 ,to r$uce ! swell+ x 0 imm]s$ 9 hot wat]4 ,?is seem$ to br+ out ! eruption v quickly & ! bli/]s 7 treat$ ) p]manganate z fa/ z !y appe>$4 ,! swell+ 0 r$uc$1 b return$ dur+ ! night4 ,on ! ev5+ foll[+1 ! =e>m 0 imm]s$ 9 a b[l ( hot p]manganate solution conta9+ a little cau/ic pota%4 ,! solution 0 kept z hot z c\ld be borne = ab\t half an h\r4 ,aft] ?is ba?1 ! poison 0 completely oxidiz$1 = ! swell+ 0 r$uc$ & did n return1 nor 0 !re any fre% eruption4 ,:at appe>$ to be a sev]e case ( poison+ 0 ?us cur$ v quickly4 ,! use ( hot wat] n only r$uces ! swell+1 b also helps to de/roy ! poison4 ,! action ( p]manganate is also m rapid at high temp]atures4 ,! oxidiz+ p[] ( p]manganate1 z is well kn[n1 is great] 9 acid solution ?an 9 alkal9e1 five atoms ( oxyg5 be+ available 9 ! =m] & ?ree 9 ! latt]1 accord+ to ^! equations3 #b ,k,mn,o#d #c ,h#b,,s#d ,k#b,,s#d #b ,mn,s,o#d #c ,h#b,o #e ,o4 #b ,k,mn,o#d ,h#b,o #b ,mn,o#b #b ,,koh #c ,o4 ,p]manganate 0 us$ z a rem$y 9 "s cases mix$ ) dilute sulphuric acid1 & 9 o!rs1 ) z9c sulphate2 also ) lime wat]4 ,x 0 f\nd to be satisfactory :e!r us$ alone or ) any ( ! sub/ances m5tion$1 provid$ x 0 well rubb$ into ! sk94 ,! conc5tration ( ! solution us$ 0 v>i$ accord+ to ! location & condition ( ! eruption4 ,:]e ! sk9 0 ?9 or already brok51 dilute solutions 7"o p] c5t47 7 us$4 ,9 "o case1 ! eruption appe>$ 9 ! palm ( ! h& :]e ! sk9 0 s ?ick t x 0 necess>y to op5 x be=e ! rem$ies c\ld rea* ! poison4 ,! difficulty ( gett+ ! rem$y 9 contact ) ! poison 9 ! sk9 is ! reason :y ! eruption is h>d to cure4 ,! rem$y mo/ commonly us$ = ?is eruption is an alcoholic solution ( lead acetate4 ,?is rem$y is unsatisfactory = ! reason t its action consi/s 9 deposit+ an un/able lead comp\nd ( ! poison 9 ! sk9 :]e ! conditions ( moi/ure & temp]ature are favorable = its decomposition1 lib]at+ ! poison ) all its irritant prop]ties4 ,moreov]1 alcoholic prep>ations %\ld n be us$ because ! alcohol dissolves ! poison &1 on evaporation1 leaves x spread ov] a l>g] surface l a v>ni%4 ,potassium p]manganate1 h[ev]1 oxidizes ! poison completely4 ,! only objection to ! use ( p]manganate ( :i* ! writ] is aw>e is t x /a9s ! sk94 ,! /a9 c be remov$ by vigor\s scrubb+ ) soap1 or x w we> (f gradually 9 a few days4 ,x c be remov$ at once by c]ta9 acids1 b ^! %\ld n be us$ by p]sons n famili> ) _! action4 ,) ! k ( ! facts m5tion$1 _m solutions 7 te/$ = poison by apply+ !m to ! sk91 & :5 an eruption appe>$1 x 0 cur$ quickly & p]man5tly by rubb+ 9 a p]manganate solution1 usually mix$ ) dilute sulphuric acid4 ,,footnotes3 #af ,nitrog5 0 f\nd v readily by ! soda lime te/ 9 ! t> left aft] extract+ ! orig9al mat]ial ) #ej p] c5t4 alcohol1 b 0 n f\nd by ! ,lassaign te/4 #ag ,/ev5s4 ,am]4 ,j\r4 ,ph>m4 #gg1 #bee1 ,june1 #aije4 #ah ,:5ev] x is /at$ 9 ?is pap] t a solution 0 poison\s or n poison\s1 ! te/ 0 made by ! writ] ^u himself4 #ai ,liebig's ,annal51 ,,cxi1 p4 #bae4 #bj ,ueb] ,mateg]b/(f1 p4 #bj4 #ba ,bull4 ,soc4 ,*im4 7,,ii71 ,vol4 #b1 #ie 7#ahfd74 #bb ,b]i*te #ai1 #agce 7#ahhf74 #bc ,j\r4 ,*em4 ,soc4 #ga1 #aaid 7#ahig74 #bd ,b]i*te #ai1 #agdj4 #be ,ibid4 #agdg2 ,annal51 #aab1 #ig4 #bf ,bio*em4 ,pflan4 ,,ii1 #eba4 #bg ,ann4 de ,*im4 et de ,phys41 #f? ,s]ies1 ,,xxii1 #gf 7#ahia74 #bh ,treatise on ,*em41 ,vol4 ,,iii1 ,pt4 ,,iii1 #dib4 #bi ,les ,sucres2 ,*em4 d] ,zuck42 ,bio*em4 d] ,pflan4 #cj ,*em4 ,zeit4 #bc1 ,rep4 #agg4 #ca ,loc4 cit4 #a1 #bji4 #cb ,on /&+ sev]al weeks1 a small quantity ( t> sep>at$ out on ! walls ( ! vessel1 also a br[n precipitate :i* 0 filt]$ (f1 susp5d$ 9 wat]1 & hydrog5 sulphide 0 be+ pass$ 9 :5 an accid5t occurr$ & x 0 lo/4 #cc ,by w>m+ ) alkalies or b>ium hydroxide1 rhamnose is color$ yell[4 ,*em4 d] ,zuck4 ,i1 #agg4 #cd ,ibid4 #ahh4 #ce ,ibid4 #cf ,rayman1 ,sur ,l',isodulcite1 ,bull4 ,soc4 ,*im4 #dg1 #ffh 7#ahhg74 #cg ,acides ,gummiques4 #ch ,b]i*te ,,xx1 pp4 #ajhi1 #ajia1 #aahh1 #beff4 #ci ,ann4 de ,*im4 et de ,phys4 7#f7 ,,xxii1 #ic 7#ahia74 #dj ,bio*em4 d] ,pflan4 ,i1 #baj4 #da ,comptes r5dus ,,cxv1 #hib4 #db ,am]4 ,*em4 ,j\r4 #bh1 #cgj4 #dc ,am]4 ,j\r4 ,ph>m4 #gg1 #bee 7,june1 #aije72 #gh1 #ec 7,feb41 #aijf74 #dd ,a wax obta9$ f ,rhus succ$anea 0 %[n by ,/ahm] to conta9 palmitic acid & glyc]ol 9 ! =m ( glyc]ol palmitate4 ,annal5 #dc1 #cdc1 7#ahdb74 #de ,see ,am]4 ,j\r4 ,ph>m4 #gg1 #bef4 #df ,?is section is add$ 9 ! hope t x may be ( use to o!rs :o are subject to ?is =m ( poison+4 #dg ,moor1 ,n4 ,y4 ,m$4 ,rec4 #de 7#ahid71 #bjj4 #dh ,bull4 ,no4 #bf1 ,u4 ,s4 ,dept4 ,agr41 ,div4 ( ,bot4 #dg4 #di ,lac]da1 ,comptes r5dus #ic 7#ahha7 #dff-dfi4 #ej ,am]4 ,j\r4 ,m$4 ,sci4 #eb 7#ahff71 #bhe4 ,,summ>y4 ,leaves & fl[]s ( ! poison ivy plant 7 extract$ ) e!r & ! e!r 0 remov$ by evaporation4 ,9 ! residue1 ! foll[+ sub/ances 7 f\nd & /udi$3 gallic acid1 fiset91 ! sug> rhamnose1 & a poison\s t>1 gum1 or wax4 ,! lead comp\nd ( ! poison 0 soluble 9 e!r2 ?is fact gave a means ( sep>at+ ! poison\s sub/ance f ! non-poison\s matt] 9 "o op]ation4 ,! poison 0 n volatile ) vapor ( acetic acid1 or ) vapor ( alcohol4 ,! poison\s t> or wax 0 decompos$ by acids & yield$ gallic acid1 fiset91 & rhamnose1 %[+ ! probable s\rce ( ^! comp\nds 9 ! plant1 & indicat+ t ! poison is a complex sub/ance ( a glucoside nature4 ,x 0 f\nd t a portion ( ! poison\s sub/ance c\ld be precipitat$ by lead acetate f a solution ( ! purifi$ t> 9 #ej p] c5t4 alcohol4 ,all cases ( poison+ develop$ on ! writ] 7 easily cur$ ) potassium p]manganate4 ,! foll[+ me?od is sugge/$ = obta9+ ! poison\s sub/ance f ! plant3 ,extract ! plant ) alcohol1 filt]1 & precipitate at once ) lead acetate4 ,wa% ! precipitate1 dry1 & extract ) e!r 9 ,soxhlet extractors 7loosely fill$74 ,comb9e ! e!r extracts1 mix ) wat]1 & pass 9 hydrog5 sulphide4 ,sep>ate ! wat] & ! e!r solution1 & filt] ! latt]4 ,wa% ! e!r solution ?or\ghly by %ak+ ) wat]1 & !n evaporate at a l[ temp]ature4 ,,biography4 ,william ,&]son ,syme1 ! au?or ( ?is diss]tation1 0 born 9 ,raleigh1 ,n4 ,c41 on ,july #aa1 #ahgi4 ,he 0 prep>$ = college at ! ,raleigh ,male ,academy1 ent]$ ! ,nor? ,c>ol9a ,college ( ,agriculture & ,me*anic ,arts 9 #ahif1 & 0 graduat$ 9 #ahii ) ! degree ,b4 ,s4 ,he 0 an ,in/ructor 9 ,*emi/ry at ! same ,college f ,janu>y #a/1 #aijj1 until ,june1 #aijc1 :5 he receiv$ ! degree ,m4 ,s4 = graduate "w4 ,9 ,octob] foll[+1 he ent]$ ,johns ,hopk9s ,univ]sity z a graduate /ud5t 9 ,*emi/ry1 & 0 aw>d$ "o ( ! ,nor? ,c>ol9a ,s*ol>%ips4 ,8 m9or subjects are ,physical ,*emi/ry & ,biology4