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Revision as of 15:48, 16 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 447493947 of page Djenkolic_acid for the Chem/Drugbox validation project (updated: 'KEGG', 'CASNo').  Latest revision as of 13:17, 9 January 2024 edit The editing spirit (talk | contribs)Extended confirmed users1,346 editsmNo edit summaryTag: Visual edit 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Verifiedfields = changed
⚫ |ImageFile=Djenkolic acid.png
| verifiedrevid = 460959776
⚫ |ImageSize=200px
⚫ | ImageFile=Djenkolic acid.svg
⚫ |IUPACName=(2''R'')-2-Amino-3-<nowiki> sulfanylmethylsulfanyl]propanoic acid
⚫ | ImageSize=200px
⚫ |OtherNames=Djenkolate; Jengkolic acid; S,S'-Methylenebiscysteine<ref>{{cite web |title=Djenkolic acid |date=5 March 2000 |work=The On-line Medical Dictionary |url=http://cancerweb.ncl.ac.uk/cgi-bin/omd?djenkolic+acid |accessdate=15 November 2008 }}</ref>
⚫ | IUPACName=(2''R'')-2-Amino-3-<nowiki> sulfanylmethylsulfanyl]propanoic acid
⚫ |Section1= {{Chembox Identifiers
⚫ | OtherNames=Djenkolate; Jengkolic acid; S,S'-Methylenebiscysteine<ref>{{cite web |title=Djenkolic acid |date=5 March 2000 |work=The On-line Medical Dictionary |url=http://cancerweb.ncl.ac.uk/cgi-bin/omd?djenkolic+acid |access-date=15 November 2008 }}{{dl|date= March 2015}}</ref>
⚫ | ChemSpiderID = 61442
⚫ |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | ChemSpiderID = 61442
| InChI1 = 1/C7H14N2O4S2/c8-4(6(10)11)1-14-3-15-2-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5-/m0/s1 | InChI1 = 1/C7H14N2O4S2/c8-4(6(10)11)1-14-3-15-2-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5-/m0/s1
| InChIKey1 = JMQMNWIBUCGUDO-WHFBIAKZBK | InChIKey1 = JMQMNWIBUCGUDO-WHFBIAKZBK
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C7H14N2O4S2/c8-4(6(10)11)1-14-3-15-2-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5-/m0/s1 | StdInChI = 1S/C7H14N2O4S2/c8-4(6(10)11)1-14-3-15-2-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JMQMNWIBUCGUDO-WHFBIAKZSA-N | StdInChIKey = JMQMNWIBUCGUDO-WHFBIAKZSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = <!-- blanked - oldvalue: 498-59-9 -->
| EINECS=207-863-4 | CASNo=498-59-9
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem = 68134
| UNII = 3QHC9R0YFZ
⚫ | SMILES = O=C(O)(N)CSCSC(N)C(=O)O
| EINECS=207-863-4
⚫ | MeSHName=
⚫ | PubChem = 68134
| KEGG = <!-- blanked - oldvalue: C08275 -->
| ChEBI_Ref = {{ebicite|changed|EBI}}
⚫ }}
| ChEBI = 6211
⚫ |Section2= {{Chembox Properties
⚫ | SMILES = O=C(O)(N)CSCSC(N)C(=O)O
⚫ | Formula=C<sub>7</sub>H<sub>14</sub>N<sub>2</sub>O<sub>4</sub>S<sub>2</sub>
⚫ | MeSHName=
⚫ | MolarMass=254.33 g/mol
| KEGG_Ref = {{keggcite|changed|kegg}}
⚫ | Appearance=
| KEGG=C08275
⚫ | Density=
⚫ }}
⚫ | MeltingPt=
⚫ |Section2={{Chembox Properties
⚫ | BoilingPt=
⚫ | Formula=C<sub>7</sub>H<sub>14</sub>N<sub>2</sub>O<sub>4</sub>S<sub>2</sub>
⚫ | Solubility=1.02 g L<sup>−1</sup> (at 30±0.5°C)<ref name=Patterson/>
⚫ | MolarMass=254.33 g/mol
⚫ | Appearance=
⚫ | Density=
⚫ | MeltingPt=
⚫ | BoilingPt=
⚫ | Solubility=1.02 g L<sup>−1</sup> (at 30±0.5°C)<ref name=Patterson/>
}} }}
|Section3= {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
}} }}
'''Djenkolic acid''' (or sometimes '''jengkolic acid''') is a ]-containing non-protein ] naturally found in the djenkol beans of the Southeast Asian plant '']''. Its chemical structure is similar to ] but contains a methylene (single carbon) unit in between the two sulfur atoms. There is about 20 grams of djenkolic acid per kilogram of dry djenkol beans, and it has also been reported in smaller amounts in the seeds of other leguminous plants such as '']'' (2.2 g/kg) and '']'' (2.8 g/kg).<ref name=Mello>D'Mello, J. P. Felix (1991). Toxic Amino Acids. In J. P. F. D'Mello, C. M. Duffus, J. H. Duffus (Eds.) ''''. Woodhead Publishing. pp. 21–48. {{ISBN|0-85186-863-0}}. Google Book Search. Retrieved on November 15, 2008.</ref>

==Toxicity==
The toxicity of djenkolic acid in humans arises from its poor ] under acidic conditions after consumption of the djenkol bean.<ref name=Mello/> The amino acid precipitates into crystals which cause mechanical irritation of the ] and ], resulting in symptoms such as abdominal discomfort, loin pains, severe ], nausea, vomiting, ], gross ], and ], occurring 2 to 6 hours after the beans were ingested.<ref name=Schrier>Barsoum, R. S., & Sitprija, V. (2007). Tropical Nephrology. In R. W. Schrier (Ed.) ''''. Lippincott Williams & Wilkins. p. 2037. {{ISBN|0-7817-9307-6}}. Google Book Search. Retrieved on November 15, 2008.</ref> Urine analysis of patients reveals erythrocytes, epithelial cells, protein, and the needle-like crystals of djenkolic acid. ] can also happen, with djenkolic acid as the nucleus. In young children, it has also been reported to produce painful swelling of the genitalia.<ref>J. B. Harborne, H. Baxter, G. P. Moss (Eds.) (1999) ''''. CRC Press. p. 81. {{ISBN|0-7817-9307-6}}. Google Book Search. Retrieved on November 16, 2008.</ref>

Treatment for this toxicity requires hydration to increase urine flow and alkalinization of urine by ]. Furthermore, this poisoning can be prevented when consuming djenkol beans by boiling them beforehand, since djenkolic acid is removed from the beans.<ref name=Schrier/>

== Discovery and synthesis ==
Djenkolic acid was first isolated by Van Veen and Hyman in 1933<ref>{{cite journal
| author = van Veen AG, Hyman AJ
| title = On the toxic component of the djenkol bean
| journal = Geneesk. Tijdschr. Nederl. Indie
| volume = 73
| pages = 991
| date = 1933}}</ref> from the urine of the natives of ] who had eaten the djenkol bean and were suffering from poisoning. They then isolated the djenkolic acid crystals by treating the djenkol beans with ] at 30°C for a prolonged period.<ref name=Patterson>{{cite journal
| author = du Vigneaud V, Patterson WI
| title = The synthesis of djenkolic acid
| journal = J. Biol. Chem.
| volume = 114
| pages = 533–538
| date = 1936
| url=http://www.jbc.org/cgi/reprint/114/2/533.pdf | issue=2| doi = 10.1016/S0021-9258(18)74825-4
| doi-access = free
}}</ref>

Du Vigneaud and Patterson managed to synthesize djenkolic acid by condensation of ] with 2 moles of L-cysteine in liquid ].<ref name=Patterson/> Later on, Armstrong and du Vigneaud prepared djenkolic acid by the direct combination of 1 mole of ] with 2 moles of L-cysteine in a strongly acidic solution.<ref>{{cite journal
| author = Armstrong MD, du Vigneaud V
| title = A new synthesis of djenkolic acid
| journal = J. Biol. Chem.
| volume = 168
| pages = 373–377
| date = 1947
| url=http://www.jbc.org/cgi/reprint/168/1/373.pdf | pmid = 20291097
| issue = 1 | doi = 10.1016/S0021-9258(17)35126-8
| doi-access = free
}}</ref>

== References ==

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