WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 461715
CAS#: 200399-47-9
Description: Salacinol is a naturally occurring alpha-glucosidase inhibitor isolated from an Ayurvedic traditional medicine Salacia reticulata.
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
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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
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.
| 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.
