PHENYL-BETA-D-GLUCOPYRANOSIDE

PHENYL-BETA-D-GLUCOPYRANOSIDE Basic information
Product Name:PHENYL-BETA-D-GLUCOPYRANOSIDE
Synonyms:beta-d-glucopyranosid;beta-d-glucopyranoside,phenyl;phenolglucoside;(2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-phenoxy-tetrahydro-2H-pyran-3,4,5-triol;b-D-Glucopyranoside, phenyl;-6-phenoxytetrahydro-2H-pyran-3,4,5-triol;Phenyl β-D-Glucoside Hydrate;(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-phenoxyoxane-3,4,5-triol
CAS:1464-44-4
MF:C12H16O6
MW:256.25
EINECS:215-978-6
Product Categories:Biochemistry;Glucose;Glycosides;Sugars;Glucosidase, beta-Specialty Synthesis;Carbohydrate Synthesis;Enzyme Substrates;Monosaccharides;Substrates by Enzyme
Mol File:1464-44-4.mol
PHENYL-BETA-D-GLUCOPYRANOSIDE Structure
PHENYL-BETA-D-GLUCOPYRANOSIDE Chemical Properties
Melting point 176-178 °C(lit.)
Boiling point 359.49°C (rough estimate)
density 1.2993 (rough estimate)
refractive index -70.5 ° (C=2, H2O)
storage temp. Sealed in dry,Room Temperature
solubility Methanol (Slightly), Water (Slightly, Sonicated)
pka12.70±0.70(Predicted)
form Powder
color White to Off-white
optical activity[α]25/D 70°, c = 1 in H2O
Water Solubility Soluble in water
BRN 87517
Stability:Stable. Incompatible with strong oxidizing agents.
CAS DataBase Reference1464-44-4(CAS DataBase Reference)
EPA Substance Registry System.beta.-D-Glucopyranoside, phenyl (1464-44-4)
Safety Information
Hazard Codes F,C
Safety Statements 16-26-36/37/39-45-24/25
WGK Germany 3
RTECS LZ5985510
3-10-21
TSCA Yes
HS Code 29400090
ToxicityLD50 ipr-mus: 980 mg/kg NYKZAU49,84,53
MSDS Information
ProviderLanguage
SigmaAldrich English
PHENYL-BETA-D-GLUCOPYRANOSIDE Usage And Synthesis
Chemical Propertieswhite powder
UsesPhenyl β-D-glucopyranoside can be used:
  • As a starting material for the synthesis of various derivatives of β-D-glucopyranosides with potential application as anti-HIV agents.
  • As a model for glycosides in the gas phase for their spectroscopic investigation.
  • As an internal standard in GC and GC-MS quantitative analyses.

DefinitionChEBI: Phenyl beta-D-glucopyranoside is a glycoside.
Safety ProfileModerately toxic by intraperitoneal route. When heated to decomposition it emits acrid smoke and irritating vapors.
Purification MethodsPhenyl--D-glucopyranoside recrystallises from H2O with 2H2O and can be dried in vacuo at 100o/P2O5. The dry preparation has [] 25D -70.7o (c 2, H2O). [Robertson & Waters J Chem Soc 2729 1930, IR: Bunton et al. J Chem Soc 4419 1955, Takahashi Yakugaku Zasshi (J Pharm Soc Jpn) 74 7436 1954, Whixtler & House Anal Chem 25 1463 1953, UV: Lewis J Am Chem Soc 57 898 1935.] It is a substrate for D-glucosidase [deBryne Eur J Biochem 102 257 1979]. [Beilstein 17 III/V 2946.]
PHENYL-BETA-D-GLUCOPYRANOSIDE Preparation Products And Raw materials
Raw materialsPHENYL-2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSIDE
Preparation ProductsPhenyl β-D-Glucuronide Methyl Ester
ELEUTHEROSIDE B Phlorizin NARIRUTIN D-(-)-Salicin 4'-Deoxyphlorizin APIIN BETA-2-ALIZARIN PRIMEVEROSIDE 3-hydroxy-5-[2-(3-hydroxy-4-methoxyphenyl)vinyl]phenyl-beta-D-glucopyranoside Hesperidin methylchalcone 3',5'-Dimethoxytricetin 7-O-β-D-glucopypranoside L-PICEIN Diosmin Arbutin FRAXIN RHOIFOLIN HELICIN 4-NITROPHENYL-BETA-D-GLUCOPYRANOSIDE Genistin

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