Djenkolic acid
featured

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

Hodoodo CAT#: H592447

CAS#: 498-59-9

Description: Djenkolic acid is an amino acid isolated from djenkol bean.


Chemical Structure

img
Djenkolic acid
CAS# 498-59-9

Theoretical Analysis

Hodoodo Cat#: H592447
Name: Djenkolic acid
CAS#: 498-59-9
Chemical Formula: C7H14N2O4S2
Exact Mass: 254.04
Molecular Weight: 254.319
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 350 2 weeks
Bulk inquiry

Synonym: Djenkolic acid; NSC 76076; NSC-76076; NSC76076

IUPAC/Chemical Name: 3,3'-(Methylenedithio)dialanine

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: >3 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: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 254.32 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

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.