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Merck
CN

04846

Sigma-Aldrich

Phenyl β-D-thioglucopyranoside

≥98% (HPLC)

Synonym(s):

Phenyl β-D-thioglucoside, Phenyl 1-thio-β-D-glucopyranoside

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About This Item

Empirical Formula (Hill Notation):
C12H16O5S
CAS Number:
2936-70-1
Molecular Weight:
272.32
MDL number:
MFCD00064097
UNSPSC Code:
12352202
PubChem Substance ID:
329747983

Key Documents

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Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +48.5±2.0°, c = 1 in ethanol

impurities

11.1-12.4% sulfur content

storage temp.

−20°C

SMILES string

OC[C@H]1O[C@@H](Sc2ccccc2)[C@H](O)[C@@H](O)[C@@H]1O

InChI

1S/C12H16O5S/c13-6-8-9(14)10(15)11(16)12(17-8)18-7-4-2-1-3-5-7/h1-5,8-16H,6H2/t8-,9-,10+,11-,12+/m1/s1

InChI key

OVLYAISOYPJBLU-ZIQFBCGOSA-N

Application

Inhibition studies of a broad-specificity β-D-glucosidase

Biochem/physiol Actions

Phenyl β-D-thioglucopyranoside was shown to inhibit the activity of sodium-D-glucose cotransporter (SGLT) 1 and 2 by a competitive inhibition mechanism. Phenyl β-D-thioglucopyranoside had a stronger inhibitory effect on SGLT2 than 1.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
1434242V
1434242

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Thioglycosides as inhibitors of hSGLT1 and hSGLT2: Potential therapeutic agents for the control of hyperglycemia in diabetes.
Castaneda, F
International Journal of Clinical and Experimental Medicine, 4, 131-139 (2007)
I Pócsi et al.
The Biochemical journal, 256(1), 139-146 (1988-11-15)
A broad-specificity beta-D-glucosidase from pig kidney cortex was isolated and purified to homogeneity by a rapid purification procedure. The pI (5.14 +/- 0.05), Mr (59,000 +/- 2000) and specific activities with several p-nitrophenyl glycosides (galactopyranoside, glucopyranoside, arabinopyranoside, xylopyranoside) were comparable

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