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MedKoo Cat#: 596987 | Name: Djenkolic acid
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Djenkolic acid is an amino acid isolated from djenkol bean.

Chemical Structure

Djenkolic acid
Djenkolic acid
CAS#498-59-9

Theoretical Analysis

MedKoo Cat#: 596987

Name: Djenkolic acid

CAS#: 498-59-9

Chemical Formula: C7H14N2O4S2

Exact Mass: 254.0395

Molecular Weight: 254.31

Elemental Analysis: C, 33.06; H, 5.55; N, 11.02; O, 25.16; S, 25.21

Price and Availability

Size Price Availability Quantity
100mg USD 450.00 2 Weeks
250mg USD 850.00 2 Weeks
500mg USD 1,350.00 2 Weeks
1g USD 2,250.00 2 Weeks
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Related CAS #
No Data
Synonym
Djenkolic acid; Djenkolate; L-Cysteine thioacetal of formaldehyde; L-Djenkolic acid; NSC 76076; NSC-76076; NSC76076;
IUPAC/Chemical Name
(2R,2'R)-3,3'-(methylenebis(sulfanediyl))bis(2-aminopropanoic acid)
InChi Key
JMQMNWIBUCGUDO-WHFBIAKZSA-N
InChi Code
InChI=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
SMILES Code
N[C@@H](CSCSC[C@@H](C(O)=O)N)C(O)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 254.31 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Boughton BA, Reddy P, Boland MP, Roessner U, Yates P. Non-protein amino acids in Australian acacia seed: implications for food security and recommended processing methods to reduce djenkolic acid. Food Chem. 2015 Jul 15;179:109-15. doi: 10.1016/j.foodchem.2015.01.072. Epub 2015 Jan 20. PubMed PMID: 25722145. 2: Bunawan NC, Rastegar A, White KP, Wang NE. Djenkolism: case report and literature review. Int Med Case Rep J. 2014 Apr 16;7:79-84. doi: 10.2147/IMCRJ.S58379. eCollection 2014. PubMed PMID: 24790471; PubMed Central PMCID: PMC3998865. 3: Melnikov P, Nascimento VA, Silva AF, Consolo LZ. Structural modeling of djenkolic acid with sulfur replaced by selenium and tellurium. Molecules. 2014 Apr 17;19(4):4847-56. doi: 10.3390/molecules19044847. PubMed PMID: 24747644. 4: Kim J, Senadheera DB, Lévesque CM, Cvitkovitch DG. TcyR regulates L-cystine uptake via the TcyABC transporter in Streptococcus mutans. FEMS Microbiol Lett. 2012 Mar;328(2):114-21. doi: 10.1111/j.1574-6968.2011.02492.x. Epub 2012 Jan 17. PubMed PMID: 22212096; PubMed Central PMCID: PMC3288405. 5: Bulut H, Moniot S, Licht A, Scheffel F, Gathmann S, Saenger W, Schneider E. Crystal structures of two solute receptors for L-cystine and L-cysteine, respectively, of the human pathogen Neisseria gonorrhoeae. J Mol Biol. 2012 Jan 20;415(3):560-72. doi: 10.1016/j.jmb.2011.11.030. Epub 2011 Nov 23. PubMed PMID: 22138345. 6: Shukri R, Mohamed S, Mustapha NM, Hamid AA. Evaluating the toxic and beneficial effects of jering beans (Archidendron jiringa) in normal and diabetic rats. J Sci Food Agric. 2011 Nov;91(14):2697-706. doi: 10.1002/jsfa.4516. Epub 2011 Jul 11. PubMed PMID: 21744354. 7: Or K, Ward D. The effects of seed quality and pipecolic and djenkolic acids on bruchid beetle infestation in water deficit-stressed Acacia trees. J Chem Ecol. 2004 Nov;30(11):2297-307. PubMed PMID: 15672672. 8: Burguière P, Auger S, Hullo MF, Danchin A, Martin-Verstraete I. Three different systems participate in L-cystine uptake in Bacillus subtilis. J Bacteriol. 2004 Aug;186(15):4875-84. PubMed PMID: 15262924; PubMed Central PMCID: PMC451631. 9: Lane N, Weidenhamer JD, Romeo JT. Zapoteca formosa: sulfur chemistry and phytotoxicity. J Chem Ecol. 2004 Feb;30(2):425-37. PubMed PMID: 15112733. 10: Mikkelsen MD, Naur P, Halkier BA. Arabidopsis mutants in the C-S lyase of glucosinolate biosynthesis establish a critical role for indole-3-acetaldoxime in auxin homeostasis. Plant J. 2004 Mar;37(5):770-7. PubMed PMID: 14871316. 11: Nakano E, Williamson MP, Williams NH, Powers HJ. Copper-mediated LDL oxidation by homocysteine and related compounds depends largely on copper ligation. Biochim Biophys Acta. 2004 Jan 20;1688(1):33-42. PubMed PMID: 14732479. 12: Krajewski K, Long YQ, Marchand C, Pommier Y, Roller PP. Design and synthesis of dimeric HIV-1 integrase inhibitory peptides. Bioorg Med Chem Lett. 2003 Oct 6;13(19):3203-5. PubMed PMID: 12951093. 13: Parry J, Clark DP. Identification of a CysB-regulated gene involved in glutathione transport in Escherichia coli. FEMS Microbiol Lett. 2002 Mar 19;209(1):81-5. PubMed PMID: 12007658. 14: Piluk J, Hartel PG, Haines BL, Giannasi DE. Association of carbon disulfide with plants in the family Fabaceae. J Chem Ecol. 2001 Jul;27(7):1525-34. PubMed PMID: 11504042. 15: Sugihara Y, Yamagata S, Mizuno Y, Ezaki T. Characterization of O-acetyl-L-serine sulfhydrylase purified from an alkaliphilic bacterium. Biosci Biotechnol Biochem. 2000 Nov;64(11):2352-9. PubMed PMID: 11193402. 16: Ramírez EC, Whitaker JR. Biochemical characterization of cystine lyase from broccoli (Brassica oleracea var. italica). J Agric Food Chem. 1999 Jun;47(6):2218-25. PubMed PMID: 10794613. 17: Elbetieha A, Owais WM, Saadoun I, Hussein E. Effect of glutathione L-cystein and L-djenkolic acid in the synthesis and mutagenicity of azide metabolite in Bacillus subtilis ATCC 6633 strain. New Microbiol. 1999 Oct;22(4):315-22. PubMed PMID: 10555201. 18: Elfarra AA. Potential role of the flavin-containing monooxygenases in the metabolism of endogenous compounds. Chem Biol Interact. 1995 Apr 28;96(1):47-55. Review. PubMed PMID: 7720104. 19: Wlodek L, Rommelspacher H, Susilo R, Radomski J, Höfle G. Thiazolidine derivatives as source of free L-cysteine in rat tissue. Biochem Pharmacol. 1993 Dec 3;46(11):1917-28. PubMed PMID: 8267641. 20: Pepi M, Baldi F. Modulation of chromium(VI) toxicity by organic and inorganic sulfur species in yeasts from industrial wastes. Biometals. 1992 Autumn;5(3):179-85. PubMed PMID: 1421967.

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