MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 581244 | Name: Thiamine disulfide
Featured

Description:

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

Thiamine is a essential nutrient required for carbohydrate metabolism; also involved in nerve function. Biosynthesized by microorganisms and plants. Dietary sources include whole grains, meat products, vegetables, milk, legumes and fruit. Also present in rice husks and yeast. Converted in vivo to Thiamine diphosphate, a coenzyme in the decarboxylation of α-keto acids. Chronic deficiency may lead to neurological impairment, bariberi, Wernicke-Korsakoff syndrome.

Chemical Structure

Thiamine disulfide
Thiamine disulfide
CAS#67-16-3

Theoretical Analysis

MedKoo Cat#: 581244

Name: Thiamine disulfide

CAS#: 67-16-3

Chemical Formula: C24H34N8O4S2

Exact Mass: 562.2144

Molecular Weight: 562.71

Elemental Analysis: C, 51.23; H, 6.09; N, 19.91; O, 11.37; S, 11.39

Price and Availability

Size Price Availability Quantity
25g USD 300.00
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
992-46-1 (phosphate) 67-16-3
Synonym
Thiamine disulfide; Algoneurina; Daiomin; TDS;
IUPAC/Chemical Name
Formamide, N,N'-(dithiobis(2-(2-hydroxyethyl)-1-methyl-2,1-ethenediyl))bis(N-((4-amino-2-methyl-5-pyrimidinyl)methyl)-
InChi Key
GFEGEDUIIYDMOX-YHARCJFQSA-N
InChi Code
InChI=1S/C24H34N8O4S2/c1-15(31(13-35)11-19-9-27-17(3)29-23(19)25)21(5-7-33)37-38-22(6-8-34)16(2)32(14-36)12-20-10-28-18(4)30-24(20)26/h9-10,13-14,33-34H,5-8,11-12H2,1-4H3,(H2,25,27,29)(H2,26,28,30)/b21-15+,22-16+
SMILES Code
C/C(N(CC1=CN=C(C)N=C1N)C=O)=C(SS/C(CCO)=C(N(CC2=CN=C(C)N=C2N)C=O)\C)/CCO
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 562.71 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: Xiao D, Meng FH, Dai W, Yong Z, Liu JQ, Zhou XB, Li S. Design, Synthesis and Biological Evaluation of Brain-Targeted Thiamine Disulfide Prodrugs of Ampakine Compound LCX001. Molecules. 2016 Apr 14;21(4):488. doi: 10.3390/molecules21040488. PubMed PMID: 27089316. 2: Volvert ML, Seyen S, Piette M, Evrard B, Gangolf M, Plumier JC, Bettendorff L. Benfotiamine, a synthetic S-acyl thiamine derivative, has different mechanisms of action and a different pharmacological profile than lipid-soluble thiamine disulfide derivatives. BMC Pharmacol. 2008 Jun 12;8:10. doi: 10.1186/1471-2210-8-10. PubMed PMID: 18549472; PubMed Central PMCID: PMC2435522. 3: Parkhomenko IuM, Stepuro II, Donchenko GV, Stepuro VI. [Oxidized derivatives of thiamine: formation, properties, biological role]. Ukr Biokhim Zh (1999). 2012 Nov-Dec;84(6):5-24. Review. Russian. PubMed PMID: 23387265. 4: Stepuro II, Oparin AY, Stsiapura VI, Maskevich SA, Titov VY. Oxidation of thiamine on reaction with nitrogen dioxide generated by ferric myoglobin and hemoglobin in the presence of nitrite and hydrogen peroxide. Biochemistry (Mosc). 2012 Jan;77(1):41-55. doi: 10.1134/S0006297912010051. PubMed PMID: 22339632. 5: Shoji S, Furuishi K, Misumi S, Miyazaki T, Kino M, Yamataka K. Thiamine disulfide as a potent inhibitor of human immunodeficiency virus (type-1) production. Biochem Biophys Res Commun. 1994 Nov 30;205(1):967-75. PubMed PMID: 7999140. 6: ITADA N. Studies on the disulfide form of thiamine. III. Reformation of disulfide after reduction of disulfide-thiamine by active thiol compounds in an alkaline medium. J Vitaminol (Kyoto). 1959 Mar 10;5(1):72-9. PubMed PMID: 13655419. 7: Panijpan B, Ratanaubolchai K. Kinetics of thiamine-polyphenol interactions and mechanism of thiamine disulphide formation. Int J Vitam Nutr Res. 1980;50(3):247-53. PubMed PMID: 7429752. 8: Fan W, Wu Y, Li XK, Yao N, Li X, Yu YG, Hai L. Design, synthesis and biological evaluation of brain-specific glucosyl thiamine disulfide prodrugs of naproxen. Eur J Med Chem. 2011 Sep;46(9):3651-61. doi: 10.1016/j.ejmech.2011.05.029. Epub 2011 May 20. PubMed PMID: 21641697. 9: Iwashima A, Wakabayashi Y, Nose Y. Inhibition of thiamine transport in Saccharomyces cerevisiae by thiamine disulfides. J Bacteriol. 1977 Sep;131(3):1013-5. PubMed PMID: 330492; PubMed Central PMCID: PMC235561. 10: BONVICINO GE, HENNESSY DJ. [Studies on some oxidation and reduction products of thiamin. III. Thiamin-disulfide in the thiochrome assay]. Int Z Vitaminforsch. 1959;30:83-9. German. PubMed PMID: 13802638. 11: Komata Y, Inaoka M, Kaneko A, Fujie T. In vitro percutaneous absorption of thiamine disulfide from a mixture of propylene glycol and fatty acid. J Pharm Sci. 1992 Aug;81(8):744-6. PubMed PMID: 1403716. 12: Harada K, Kohno K, Daira I, Saito I, Utsumi I. Retention in the body of various O-acyl-thiamine disulfides and several properties of O-butyryl-thiamine disulfide. J Vitaminol (Kyoto). 1966 Sep 10;12(3):221-30. PubMed PMID: 5956793. 13: Komata Y, Kaneko A, Fujie T. In vitro percutaneous absorption of thiamine disulfide through rat skin from a mixture of propylene glycol and fatty acid or its analog. Chem Pharm Bull (Tokyo). 1992 Aug;40(8):2173-6. PubMed PMID: 1423776. 14: Miyazaki Y, Ogihara K, Yakou S, Nagai T, Takayama K. Bioavailability of theophylline and thiamine disulfide incorporated into mucoadhesive microspheres consisting of dextran derivatives and cellulose acetate butyrate. Biol Pharm Bull. 2003 Dec;26(12):1744-7. PubMed PMID: 14646183. 15: Yasuo H, Yoneda N. Aminomethylation of thiamine disulfides and formation of cyclobis-methylenethiamine from N-aminomethylated thiamine disulfide. Chem Pharm Bull (Tokyo). 1976 Jun;24(6):1128-32. PubMed PMID: 1021278. 16: CHIBATA I, YAMADA S, ITO H, FURUTSU S, UTSUMI I. Studies on thiamine disulfide. VI. The action of thiaminase on O-benzoylthiamine disulfide derivaties. J Vitaminol (Kyoto). 1962 Dec 10;8:259-61. PubMed PMID: 14020785. 17: UTSUMI I, HARADA K, KOBAYASHI H, KOHNO K, YASUDA K, KONDO Y, HIRAO H. Studies on thiamine disulfide. II. Biological properties of O-benzoylthimine disulfide. J Vitaminol (Kyoto). 1962 Sep 10;8:213-9. PubMed PMID: 13995577. 18: UTSUMI I, HARADA K, HIRAO H, KOTERA K. Studies on thiamine disulfide. I. Physicochemical properties of O-benzoylthiamine disulfide. J Vitaminol (Kyoto). 1962 Sep 10;8:206-12. PubMed PMID: 13995575. 19: UTSUMI I, HARADA K, HIRAO Y, HIRAO H. Studies on thiamine disulfide. III. determination of O-benzoylthiamine disulfide. J Vitaminol (Kyoto). 1962 Sep 10;8:220-7. PubMed PMID: 13995576. 20: PETRELLI F, SILIPRANDI N. Effect of thiamine disulfide administration on liver cocarboxylase in thiamine deficient rats. Int Z Vitaminforsch. 1959;30:111-3. PubMed PMID: 14432295.