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

MedKoo CAT#: 581184

CAS#: 18725-37-6

Description: Dacisteine, also known as D-cysteine. protects primary cultures of cerebellar neurons from oxidative stress induced by hydrogen peroxide and attenuates ischaemia-reperfusion injury in the kidney more than L-cysteine. A novel pathway for the production of hydrogen sulfide from D-cysteine in mammalian cells. provides a new therapeutic approach to deliver hydrogen sulphide to specific tissues.


Chemical Structure

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Dacisteine
CAS# 18725-37-6

Theoretical Analysis

MedKoo Cat#: 581184
Name: Dacisteine
CAS#: 18725-37-6
Chemical Formula: C7H11NO4S
Exact Mass: 205.0409
Molecular Weight: 205.23
Elemental Analysis: C, 40.97; H, 5.40; N, 6.83; O, 31.18; S, 15.62

Price and Availability

Size Price Availability Quantity
50.0mg USD 185.0 2 Weeks
500.0mg USD 1250.0 2 Weeks
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Synonym: Dacisteine; Dacisteina; Dacisteinum; D-cysteine; Dcysteine;

IUPAC/Chemical Name: N,S-diacetyl-L-cysteine

InChi Key: HSPYGHDTVQJUDE-LURJTMIESA-N

InChi Code: InChI=1S/C7H11NO4S/c1-4(9)8-6(7(11)12)3-13-5(2)10/h6H,3H2,1-2H3,(H,8,9)(H,11,12)/t6-/m0/s1

SMILES Code: CC(=O)SC[C@H](NC(=O)C)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

Preparing Stock Solutions

The following data is based on the product molecular weight 205.23 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

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1: Shibuya N, Koike S, Tanaka M, Ishigami-Yuasa M, Kimura Y, Ogasawara Y, Fukui K, Nagahara N, Kimura H. A novel pathway for the production of hydrogen sulfide from D-cysteine in mammalian cells. Nat Commun. 2013;4:1366. doi: 10.1038/ncomms2371. PubMed PMID: 23340406.

2: Jain SK, Micinski D, Huning L, Kahlon G, Bass PF, Levine SN. Vitamin D and L-cysteine levels correlate positively with GSH and negatively with insulin resistance levels in the blood of type 2 diabetic patients. Eur J Clin Nutr. 2014 Oct;68(10):1148-53. doi: 10.1038/ejcn.2014.114. Epub 2014 Jun 25. PubMed PMID: 24961547; PubMed Central PMCID: PMC4192028.

3: Yamane S, Nomura R, Yanagihara M, Nakamura H, Fujino H, Matsumoto K, Horie S, Murayama T. L-Cysteine/D,L-homocysteine-regulated ileum motility via system L and B°(,+) transporter: Modification by inhibitors of hydrogen sulfide synthesis and dietary treatments. Eur J Pharmacol. 2015 Oct 5;764:471-9. doi: 10.1016/j.ejphar.2015.07.042. Epub 2015 Jul 19. PubMed PMID: 26201052.

4: Huang T, Tang G, Wang H, Nie D, Tang X, Liang X, Hu K, Yi C, Yao B, Tang C. Synthesis and preliminary biological evaluation of S-11C-methyl-D-cysteine as a new amino acid PET tracer for cancer imaging. Amino Acids. 2015 Apr;47(4):719-27. doi: 10.1007/s00726-014-1899-4. Epub 2014 Dec 23. PubMed PMID: 25534431.

5: Saltman AE. D-ribose-L-cysteine supplementation enhances wound healing in a rodent model. Am J Surg. 2015 Jul;210(1):153-8. doi: 10.1016/j.amjsurg.2014.11.014. Epub 2015 Mar 27. PubMed PMID: 25935230.

6: Prieto-Lloret J, Aaronson PI. Potentiation of Hypoxic Pulmonary Vasoconstriction by Hydrogen Sulfide Precursors 3-Mercaptopyruvate and D-Cysteine Is Blocked by the Cystathionine γ Lyase Inhibitor Propargylglycine. Adv Exp Med Biol. 2015;860:81-7. doi: 10.1007/978-3-319-18440-1_10. PubMed PMID: 26303470.

7: Schafheimer N, Wang Z, Schey K, King J. Tyrosine/cysteine cluster sensitizing human γD-crystallin to ultraviolet radiation-induced photoaggregation in vitro. Biochemistry. 2014 Feb 18;53(6):979-90. doi: 10.1021/bi401397g. Epub 2014 Feb 5. PubMed PMID: 24410332; PubMed Central PMCID: PMC3954642.

8: Ishiwata S, Ogata S, Umino A, Shiraku H, Ohashi Y, Kajii Y, Nishikawa T. Increasing effects of S-methyl-L-cysteine on the extracellular D-serine concentrations in the rat medial frontal cortex. Amino Acids. 2013 May;44(5):1391-5. doi: 10.1007/s00726-013-1464-6. Epub 2013 Feb 17. PubMed PMID: 23417484.

9: Sakimura K, Nakao K, Yoshikawa M, Suzuki M, Kimura H. A novel Na(+) -Independent alanine-serine-cysteine transporter 1 inhibitor inhibits both influx and efflux of D-Serine. J Neurosci Res. 2016 Oct;94(10):888-95. doi: 10.1002/jnr.23772. Epub 2016 Jun 14. PubMed PMID: 27302861.

10: Soutourina J, Blanquet S, Plateau P. Role of D-cysteine desulfhydrase in the adaptation of Escherichia coli to D-cysteine. J Biol Chem. 2001 Nov 2;276(44):40864-72. Epub 2001 Aug 29. PubMed PMID: 11527960.

11: Takeo T, Horikoshi Y, Nakao S, Sakoh K, Ishizuka Y, Tsutsumi A, Fukumoto K, Kondo T, Haruguchi Y, Takeshita Y, Nakamuta Y, Tsuchiyama S, Nakagata N. Cysteine analogs with a free thiol group promote fertilization by reducing disulfide bonds in the zona pellucida of mice. Biol Reprod. 2015 Apr;92(4):90. doi: 10.1095/biolreprod.114.125443. Epub 2015 Feb 25. PubMed PMID: 25715791.

12: Green CO, Badaloo AV, Hsu JW, Taylor-Bryan C, Reid M, Forrester T, Jahoor F. Effects of randomized supplementation of methionine or alanine on cysteine and glutathione production during the early phase of treatment of children with edematous malnutrition. Am J Clin Nutr. 2014 May;99(5):1052-8. doi: 10.3945/ajcn.113.062729. Epub 2014 Mar 5. PubMed PMID: 24598154; PubMed Central PMCID: PMC3985210.

13: Kim HJ, Shin HS. Simple derivatization of aldehydes with D-cysteine and their determination in beverages by liquid chromatography-tandem mass spectrometry. Anal Chim Acta. 2011 Sep 30;702(2):225-32. doi: 10.1016/j.aca.2011.07.006. Epub 2011 Jul 18. PubMed PMID: 21839202.

14: Tsai SJ, Chiu CP, Yang HT, Yin MC. s-Allyl cysteine, s-ethyl cysteine, and s-propyl cysteine alleviate β-amyloid, glycative, and oxidative injury in brain of mice treated by D-galactose. J Agric Food Chem. 2011 Jun 8;59(11):6319-26. doi: 10.1021/jf201160a. Epub 2011 May 12. PubMed PMID: 21548553.

15: Aydillo C, Compañón I, Avenoza A, Busto JH, Corzana F, Peregrina JM, Zurbano MM. S-Michael additions to chiral dehydroalanines as an entry to glycosylated cysteines and a sulfa-Tn antigen mimic. J Am Chem Soc. 2014 Jan 15;136(2):789-800. doi: 10.1021/ja411522f. Epub 2014 Jan 7. PubMed PMID: 24372047.

16: Carrillo AK, VanNieuwenhze MS. Synthesis of the AviMeCys-containing D-ring of mersacidin. Org Lett. 2012 Feb 17;14(4):1034-7. doi: 10.1021/ol2034806. Epub 2012 Feb 1. PubMed PMID: 22296295; PubMed Central PMCID: PMC4096711.

17: Freeman F. Mechanism of the cysteine sulfenic acid O-sulfenylation of 1,3-cyclohexanedione. Chem Commun (Camb). 2014 Apr 21;50(31):4102-4. doi: 10.1039/c4cc00925h. PubMed PMID: 24619216.

18: Lin R, Zhang H, Li S, Chen L, Zhang W, Wen TB, Zhang H, Xia H. pH-switchable inversion of the metal-centered chirality of metallabenzenes: opposite stereodynamics in reactions of ruthenabenzene with L- and D-cysteine. Chemistry. 2011 Feb 18;17(8):2420-7. doi: 10.1002/chem.201001867. Epub 2011 Jan 21. PubMed PMID: 21259347.

19: Freeman F, Adesina IT, La JL, Lee JY, Poplawski AA. Conformers of cysteine and cysteine sulfenic acid and mechanisms of the reaction of cysteine sulfenic acid with 5,5-dimethyl-1,3-cyclohexanedione (dimedone). J Phys Chem B. 2013 Dec 19;117(50):16000-12. doi: 10.1021/jp409022m. Epub 2013 Dec 6. PubMed PMID: 24274619.

20: Guo J, Gaffrey MJ, Su D, Liu T, Camp DG 2nd, Smith RD, Qian WJ. Resin-assisted enrichment of thiols as a general strategy for proteomic profiling of cysteine-based reversible modifications. Nat Protoc. 2014 Jan;9(1):64-75. doi: 10.1038/nprot.2013.161. Epub 2013 Dec 12. PubMed PMID: 24336471; PubMed Central PMCID: PMC4038159.