Structure via PubChem · Public domain (PubChem)
β-gentiobiose (closed ring)
Sign in to saveAlso known as beta-D-glucosyl-(1->6)-beta-D-glucose, Glcbeta1-6Glcbeta, 6-O-beta-D-glucopyranosyl-beta-D-glucopyranose, beta-D-Glc-(1->6)-beta-D-Glc, Glcb1-6Glcb, beta-gentiobiose
Gentiobiose is a disaccharide composed of two units of D-glucose joined with a β(1→6) linkage. It is a white crystalline solid that is soluble in water or hot methanol. Gentiobiose is incorporated into the chemical structure of crocin, the chemical compound that gives saffron its color. It is a product of the caramelization of glucose. During a starch hydrolysis process for glucose syrup, gentiobiose, which has bitterness, is formed as an undesirable product through the acid-catalyzed condensation reaction of two D-glucose molecules. A further elongation of the unit elongation of the bitter di
In the Vinony graph
Within Vinony's link graph, β-gentiobiose (closed ring) is referenced by 16 other articles, and connects out to glucose, International Standard Book Number and carbohydrate.
Vinony files it under Chembox image size set, Disaccharides and Glucosides.
Its subject is documented across 21 Wikipedia language editions.
Chemical data
- Formula
- C12H22O11
- Molecular weight
- 342.3 g/mol
- IUPAC name
- (2R,3R,4S,5S,6R)-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxane-2,3,4,5-tetrol
- SMILES
- C([C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)O)O)O)O)O)O)O)O
- InChIKey
- DLRVVLDZNNYCBX-LIZSDCNHSA-N
- XLogP
- -4.7
- Polar surface area
- 190 Ų
- H-bond donors
- 8
- H-bond acceptors
- 11
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- allolactose
- Has part
- hydrogen
- Mass
- 342.116212
Show 6 more facts
- found in taxon
- Caenorhabditis elegans
- canonical SMILES
- C(C1C(C(C(C(O1)OCC2C(C(C(C(O2)O)O)O)O)O)O)O)O
- chemical formula
- C₁₂H₂₂O₁₁
- Commons category
- Gentiobiose
- isomeric SMILES
- C([C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)O)O)O)O)O)O)O)O
- has characteristic
- bitterness
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
Gentiobiose is a disaccharide composed of two units of D-glucose joined with a β(1→6) linkage. It is a white crystalline solid that is soluble in water or hot methanol. Gentiobiose is incorporated into the chemical structure of crocin, the chemical compound that gives saffron its color. It is a product of the caramelization of glucose. During a starch hydrolysis process for glucose syrup, gentiobiose, which has bitterness, is formed as an undesirable product through the acid-catalyzed condensation reaction of two D-glucose molecules. A further elongation of the unit elongation of the bitter disaccharide by a third β-D-glucose to give the trimer gentiotriose reduces its bitterness by a fifth. Gentiobiose is also produced via enzymatic hydrolysis of glucans, including pustulan and β-1,3-1,6-glucan.
==References==
Excerpted from Wikipedia’s “β-gentiobiose (closed ring)” article, available under the CC BY-SA 4.0 licence.