U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C12H22O11
Molecular Weight 342.2965
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GENTIOBIOSE

SMILES

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

InChI

InChIKey=AYRXSINWFIIFAE-UDKQPYHCSA-N
InChI=1S/C12H22O11/c13-1-4(15)7(17)8(18)5(16)3-22-12-11(21)10(20)9(19)6(2-14)23-12/h1,4-12,14-21H,2-3H2/t4-,5+,6+,7+,8+,9+,10-,11+,12+/m0/s1

HIDE SMILES / InChI

Molecular Formula C12H22O11
Molecular Weight 342.2965
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Gentiobiose is a rare disaccharide composed of two units of D-glucose joined with a beta (1->6) linkage. It occurs in living systems which use it both structurally and as energy source. Gentiobiose was first isolated from gentian roots and was shown to be involved in signaling pathways of the plant. Gentiobiose is incorporated into the chemical structure of crocin the chemical compound that gives saffron its color and that have shown potential anti-bacterial and anti-parasitic effects. Gentiobiose serves as a growth substrate and is a constituent of cell wall and deoxyribonucleic acid in microorganisms. Gentiobiose was found to be a specific substrate of β-glucosidase BglH from Aspergillus fungi which preferentially hydrolyzed gentiobiose rather than other oligosaccharides. Gentiobiose was used to study binding of V3-7Sh sIgM to zymosan while investigating a class of common pathogens as functional ligands for a subset of somatically mutated human B cell lymphomas. It was also used in binding assays to determine if coelomic cytolytic factor 1 (CCF-1) binds to β-1,3-glucans to stimulate the pro-PO-activating system.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Methyl beta-allolactoside [methyl beta-D-galactopyranosyl-(1-->6)-beta-D-glucopyranoside] monohydrate.
2009-12
Adjuvant potential of archaeal synthetic glycolipid mimetics critically depends on the glyco head group structure.
2008-07
Molecular cloning and transcriptional expression analysis of an intracellular beta-glucosidase, a family 3 glycosyl hydrolase, from the edible straw mushroom, Volvariella volvacea.
2007-02
Lactobacillus concavus sp. nov., isolated from the walls of a distilled spirit fermenting cellar in China.
2005-09
Synthesis and hemolytic activity of some hederagenin diglycosides.
2004-08
Lactobacillus pantheris sp. nov., isolated from faeces of a jaguar.
2002-09
Weissella kimchii sp. nov., a novel lactic acid bacterium from kimchi.
2002-03
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
Binding of V3-7Sh sIgM to zymosan was studied using the flow cytometry analysis. Single colonies of bacteria and yeasts were isolated from agar plates and suspended in DMEM medium. 5 × 10^6 bacteria, 1.5 × 10^6 yeast, or ∼1 × 10^6 zymosan particles were stained with 2 µg/ml of sIgM and, subsequently, with anti-IgM F(ab′)2-PE. For inhibition experiments, ∼1 × 10^6 zymosan particles were stained in the presence of ≤10 µg/ml pustulan, mannan, or laminarin and ≤5 mM of gentiobiose. Competition by micromolar concentrations of gentiobiose inhibited binding to zymosan
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:56:38 GMT 2025
Edited
by admin
on Mon Mar 31 21:56:38 GMT 2025
Record UNII
HF30HB040V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
6-(.BETA.-D-GLUCOSIDO)-D-GLUCOSE
Preferred Name English
GENTIOBIOSE
MI  
Common Name English
6-O-.BETA.-D-GLUCOPYRANOSYL-D-GLUCOSE
Common Name English
AMYGDALOSE
Common Name English
D-GLUCOSE, 6-O-.BETA.-D-GLUCOPYRANOSYL-
Common Name English
D-GENTIOBIOSE
Common Name English
GENTIOBIOSE [MI]
Common Name English
Code System Code Type Description
CAS
554-91-6
Created by admin on Mon Mar 31 21:56:38 GMT 2025 , Edited by admin on Mon Mar 31 21:56:38 GMT 2025
PRIMARY
CHEBI
28066
Created by admin on Mon Mar 31 21:56:38 GMT 2025 , Edited by admin on Mon Mar 31 21:56:38 GMT 2025
PRIMARY
EPA CompTox
DTXSID801017741
Created by admin on Mon Mar 31 21:56:38 GMT 2025 , Edited by admin on Mon Mar 31 21:56:38 GMT 2025
PRIMARY
MERCK INDEX
m5701
Created by admin on Mon Mar 31 21:56:38 GMT 2025 , Edited by admin on Mon Mar 31 21:56:38 GMT 2025
PRIMARY Merck Index
PUBCHEM
20056559
Created by admin on Mon Mar 31 21:56:38 GMT 2025 , Edited by admin on Mon Mar 31 21:56:38 GMT 2025
PRIMARY
FDA UNII
HF30HB040V
Created by admin on Mon Mar 31 21:56:38 GMT 2025 , Edited by admin on Mon Mar 31 21:56:38 GMT 2025
PRIMARY
ECHA (EC/EINECS)
209-074-0
Created by admin on Mon Mar 31 21:56:38 GMT 2025 , Edited by admin on Mon Mar 31 21:56:38 GMT 2025
PRIMARY
WIKIPEDIA
Gentiobiose
Created by admin on Mon Mar 31 21:56:38 GMT 2025 , Edited by admin on Mon Mar 31 21:56:38 GMT 2025
PRIMARY