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
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
| Molecular Formula | C13H18O6 |
| Molecular Weight | 270.2784 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 5 / 5 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/25497988https://www.ncbi.nlm.nih.gov/pubmed/18305416 | https://www.ncbi.nlm.nih.gov/pubmed/14709918 |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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25497988https://www.ncbi.nlm.nih.gov/pubmed/18305416 | https://www.ncbi.nlm.nih.gov/pubmed/14709918 |
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.
Originator
Sources: Justus Liebigs Annalen der Chemie Volume 383 Pages 68-91, 1911https://www.ncbi.nlm.nih.gov/pubmed/18305416
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| New benzoyl glucosides and cytotoxic pterosin sesquiterpenes from Pteris ensiformis Burm. | 2008 Feb 5 |
|
| Engineering of glucoside acceptors for the regioselective synthesis of beta-(1-->3)-disaccharides with glycosynthases. | 2008 Nov 24 |
|
| Anti-inflammatory components of Chrysanthemum indicum flowers. | 2015 Jan 15 |
|
| Characterization of Secondary Metabolites from Purple Ipomoea batatas Leaves and Their Effects on Glucose Uptake. | 2016 Jun 8 |
Patents
Sample Use Guides
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%
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
7ILL1IJM8R
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| Record Status |
Validated (UNII)
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