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Details

Stereochemistry ABSOLUTE
Molecular Formula C13H18O6
Molecular Weight 270.2784
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BENZYL .BETA.-D-GLUCOSIDE

SMILES

OC[C@H]1O[C@@H](OCC2=CC=CC=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI

InChIKey=GKHCBYYBLTXYEV-UJPOAAIJSA-N
InChI=1S/C13H18O6/c14-6-9-10(15)11(16)12(17)13(19-9)18-7-8-4-2-1-3-5-8/h1-5,9-17H,6-7H2/t9-,10-,11+,12-,13-/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18305416 | https://www.ncbi.nlm.nih.gov/pubmed/25127165

Benzyl-beta-D-glucoside (benzyl beta-D-glucopyranoside, BG) is a benzoyl glucoside, a natural substance that can be found in Pteris ensiformis. Benzyl beta-D-glucopyranoside, the constituent of the fruit of Prunus mume has been shown to relieve tension in experimental menopausal model rats (M-rats) caused by ether stress.

CNS Activity

Curator's Comment: Benzyl-beta-D-glucoside relieved tension in experimental menopausal model rats (M-rats) caused by ether stress.

Originator

Sources: Justus Liebigs Annalen der Chemie Volume 383 Pages 68-91, 1911https://www.ncbi.nlm.nih.gov/pubmed/18305416

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Engineering of glucoside acceptors for the regioselective synthesis of beta-(1-->3)-disaccharides with glycosynthases.
2008 Nov 24
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Curator's Comment: Spontaneous EBV-EA activation in our Raji cell subline was less than 0.1%. Inhibition of EBV-EA activation was assayed using Raji cells (virus nonproducer type). Indicator cells (Raji, 13106 cells/ml) were incubated at 37 °C for 48 in 1 ml of medium containing 0.5 M n-butyric acid [8 ul, 4 mmol (coinducer)] and 12-O-tetradecanoylphorbol 13-acetate (TPA) [32 pmol=20 ng in dimethylsulfoxide (DMSO), 2 ul] as an inducer, with or without various amounts of Benzyl-beta-D-glucoside.
Benzoyl-beta-D-glucoside antiinflammatory activity was evaluated in mouse RAW264.7 cells assessed as inhibition of LPS-stimulated TNFalpha production at 0.4, 2 and 10 mkM. Benzoyl-beta-D-glucoside (compound 4) at 10 mkM decrease LPS-stimulated TNFalpha on 13.02%
Name Type Language
BENZYL .BETA.-D-GLUCOSIDE
Common Name English
BENZYL .BETA.-D-GLUCOPYRANOSIDE
Common Name English
.BETA.-D-GLUCOPYRANOSIDE, PHENYLMETHYL
Common Name English
BENZYL-O-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
(-)-BENZYL .BETA.-D-GLUCOSIDE
Common Name English
BENZYL GLUCOSIDE
Common Name English
BENZYL GLUCOPYRANOSIDE
Common Name English
BENZYL ALCOHOL GLUCOSIDE
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID30962864
Created by admin on Fri Dec 15 18:59:51 GMT 2023 , Edited by admin on Fri Dec 15 18:59:51 GMT 2023
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PUBCHEM
188977
Created by admin on Fri Dec 15 18:59:51 GMT 2023 , Edited by admin on Fri Dec 15 18:59:51 GMT 2023
PRIMARY
FDA UNII
7ILL1IJM8R
Created by admin on Fri Dec 15 18:59:51 GMT 2023 , Edited by admin on Fri Dec 15 18:59:51 GMT 2023
PRIMARY
CAS
4304-12-5
Created by admin on Fri Dec 15 18:59:51 GMT 2023 , Edited by admin on Fri Dec 15 18:59:51 GMT 2023
PRIMARY