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
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.