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MedKoo Cat#: 461715 | Name: Salacinol

Description:

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

Salacinol is a naturally occurring alpha-glucosidase inhibitor isolated from an Ayurvedic traditional medicine Salacia reticulata.

Chemical Structure

Salacinol
Salacinol
CAS#200399-47-9

Theoretical Analysis

MedKoo Cat#: 461715

Name: Salacinol

CAS#: 200399-47-9

Chemical Formula: C9H18O9S2

Exact Mass: 334.0392

Molecular Weight: 334.35

Elemental Analysis: C, 32.33; H, 5.43; O, 43.07; S, 19.18

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Salacinol;
IUPAC/Chemical Name
(2S,3S)-4-((1S,2R,3S,4S)-3,4-dihydroxy-2-(hydroxymethyl)tetrahydro-1H-thiophen-1-ium-1-yl)-1,3-dihydroxybutan-2-yl sulfate
InChi Key
SOWRVDSZMRPKRG-YRPOCYRVSA-N
InChi Code
InChI=1S/C9H18O9S2/c10-1-7(18-20(15,16)17)5(12)3-19-4-6(13)9(14)8(19)2-11/h5-14H,1-4H2/t5-,6-,7+,8-,9+,19-/m1/s1
SMILES Code
OC[C@H](OS(=O)([O-])=O)[C@H](O)C[S@+]1[C@H](CO)[C@@H](O)[C@H](O)C1
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

Preparing Stock Solutions

The following data is based on the product molecular weight 334.35 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: Morikawa T, Akaki J, Ninomiya K, Kinouchi E, Tanabe G, Pongpiriyadacha Y, Yoshikawa M, Muraoka O. Salacinol and related analogs: new leads for type 2 diabetes therapeutic candidates from the Thai traditional natural medicine Salacia chinensis. Nutrients. 2015 Feb 27;7(3):1480-93. doi: 10.3390/nu7031480. PubMed PMID: 25734563; PubMed Central PMCID: PMC4377863. 2: Tanabe G, Xie W, Balakishan G, Amer MF, Tsutsui N, Takemura H, Nakamura S, Akaki J, Ninomiya K, Morikawa T, Nakanishi I, Muraoka O. Hydrophobic substituents increase the potency of salacinol, a potent α-glucosidase inhibitor from Ayurvedic traditional medicine 'Salacia'. Bioorg Med Chem. 2016 Aug 15;24(16):3705-15. doi: 10.1016/j.bmc.2016.06.013. Epub 2016 Jun 7. PubMed PMID: 27325449. 3: Mohan S, Pinto BM. Zwitterionic glycosidase inhibitors: salacinol and related analogues. Carbohydr Res. 2007 Sep 3;342(12-13):1551-80. Epub 2007 May 18. Review. PubMed PMID: 17559821. 4: Tanabe G, Nakamura S, Tsutsui N, Balakishan G, Xie W, Tsuchiya S, Akaki J, Morikawa T, Ninomiya K, Nakanishi I, Yoshikawa M, Muraoka O. In silico design, synthesis and evaluation of 3'-O-benzylated analogs of salacinol, a potent α-glucosidase inhibitor isolated from an Ayurvedic traditional medicine "Salacia". Chem Commun (Camb). 2012 Sep 7;48(69):8646-8. doi: 10.1039/c2cc34144a. Epub 2012 Jul 20. PubMed PMID: 22820468. 5: Nakamura S, Takahira K, Tanabe G, Morikawa T, Sakano M, Ninomiya K, Yoshikawa M, Muraoka O, Nakanishi I. Docking and SAR studies of salacinol derivatives as alpha-glucosidase inhibitors. Bioorg Med Chem Lett. 2010 Aug 1;20(15):4420-3. doi: 10.1016/j.bmcl.2010.06.059. Epub 2010 Jun 12. PubMed PMID: 20598536. 6: Rossi EJ, Sim L, Kuntz DA, Hahn D, Johnston BD, Ghavami A, Szczepina MG, Kumar NS, Sterchi EE, Nichols BL, Pinto BM, Rose DR. Inhibition of recombinant human maltase glucoamylase by salacinol and derivatives. FEBS J. 2006 Jun;273(12):2673-83. PubMed PMID: 16817895. 7: Tanabe G, Otani T, Cong W, Minematsu T, Ninomiya K, Yoshikawa M, Muraoka O. Biological evaluation of 3'-O-alkylated analogs of salacinol, the role of hydrophobic alkyl group at 3' position in the side chain on the α-glucosidase inhibitory activity. Bioorg Med Chem Lett. 2011 May 15;21(10):3159-62. doi: 10.1016/j.bmcl.2011.02.109. Epub 2011 Mar 29. PubMed PMID: 21454075. 8: Nasi R, Sim L, Rose DR, Pinto BM. New chain-extended analogues of salacinol and blintol and their glycosidase inhibitory activities. Mapping the active-site requirements of human maltase glucoamylase. J Org Chem. 2007 Jan 5;72(1):180-6. PubMed PMID: 17194097. 9: Yoshikawa M, Morikawa T, Matsuda H, Tanabe G, Muraoka O. Absolute stereostructure of potent alpha-glucosidase inhibitor, Salacinol, with unique thiosugar sulfonium sulfate inner salt structure from Salacia reticulata. Bioorg Med Chem. 2002 May;10(5):1547-54. PubMed PMID: 11886816. 10: Shao Y, Osamu M, Kazuya Y, Yoshiharu M, Eriko Y, Toshie M, Genzoh T, Hisashi M, Masayuki Y, You QD. Synthesis of a salacinol analogue and its alpha-glucosidase inhibitory activity. Yao Xue Xue Bao. 2006 Jul;41(7):647-53. PubMed PMID: 17007358. 11: Chen W, Pinto BM. Synthesis of aza- and thia-spiroheterocycles and attempted synthesis of spiro sulfonium compounds related to salacinol. Carbohydr Res. 2007 Nov 5;342(15):2163-72. Epub 2007 Jul 13. PubMed PMID: 17669386. 12: Muraoka O, Morikawa T, Miyake S, Akaki J, Ninomiya K, Yoshikawa M. Quantitative determination of potent alpha-glucosidase inhibitors, salacinol and kotalanol, in Salacia species using liquid chromatography-mass spectrometry. J Pharm Biomed Anal. 2010 Sep 5;52(5):770-3. doi: 10.1016/j.jpba.2010.02.025. Epub 2010 Feb 25. PubMed PMID: 20303690. 13: Ghavami A, Johnston BD, Jensen MT, Svensson B, Pinto BM. Synthesis of nitrogen analogues of salacinol and their evaluation as glycosidase inhibitors. J Am Chem Soc. 2001 Jul 4;123(26):6268-71. PubMed PMID: 11427050. 14: Muraoka O, Ying S, Yoshikai K, Matsuura Y, Yamada E, Minematsu T, Tanabe G, Matsuda H, Yoshikawa M. Synthesis of a nitrogen analogue of salacinol and its alpha-glucosidase inhibitory activity. Chem Pharm Bull (Tokyo). 2001 Nov;49(11):1503-5. PubMed PMID: 11724251. 15: Ghavami A, Johnston BD, Pinto BM. A new class of glycosidase inhibitor: synthesis of salacinol and its stereoisomers. J Org Chem. 2001 Apr 6;66(7):2312-7. PubMed PMID: 11281771. 16: Chen W, Sim L, Rose DR, Pinto BM. Synthesis of analogues of salacinol containing a carboxylate inner salt and their inhibitory activities against human maltase glucoamylase. Carbohydr Res. 2007 Sep 3;342(12-13):1661-7. Epub 2007 Jun 9. PubMed PMID: 17597595. 17: Nasi R, Pinto BM. Synthesis of new analogues of salacinol containing a pendant hydroxymethyl group as potential glycosidase inhibitors. Carbohydr Res. 2006 Oct 16;341(14):2305-11. Epub 2006 Jul 18. PubMed PMID: 16854397. 18: Tanabe G, Yoshikai K, Hatanaka T, Yamamoto M, Shao Y, Minematsu T, Muraoka O, Wang T, Matsuda H, Yoshikawa M. Biological evaluation of de-O-sulfonated analogs of salacinol, the role of sulfate anion in the side chain on the alpha-glucosidase inhibitory activity. Bioorg Med Chem. 2007 Jun 1;15(11):3926-37. Epub 2006 Oct 13. PubMed PMID: 17416527. 19: Kumar NS, Pinto BM. Synthesis of D-lyxitol and D-ribitol analogues of the naturally occurring glycosidase inhibitor salacinol. Carbohydr Res. 2005 Dec 12;340(17):2612-9. Epub 2005 Sep 29. PubMed PMID: 16198322. 20: Johnston BD, Ghavami A, Jensen MT, Svensson B, Pinto BM. Synthesis of selenium analogues of the naturally occurring glycosidase inhibitor salacinol and their evaluation as glycosidase inhibitors. J Am Chem Soc. 2002 Jul 17;124(28):8245-50. PubMed PMID: 12105902.