Gentiobiose

Gentiobiose^[1]
Names
	IUPAC name 6-O-β-D-glucopyranosyl-D-glucose
	Other names amygdalose
Identifiers
CAS Number	554-91-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28066 ;
ChemSpider	390156 ;
PubChem CID	441422;
UNII	HF30HB040V ;
	InChI InChI=1S/C12H22O11/c13-1-3-5(14)8(17)10(19)12(23-3)21-2-4-6(15)7(16)9(18)11(20)22-4/h3-20H,1-2H2/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1 Key: DLRVVLDZNNYCBX-LIZSDCNHSA-N ; InChI=1/C12H22O11/c13-1-3-5(14)8(17)10(19)12(23-3)21-2-4-6(15)7(16)9(18)11(20)22-4/h3-20H,1-2H2/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1 Key: DLRVVLDZNNYCBX-LIZSDCNHBH;
	SMILES O(C[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O)[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)CO;
Properties
Chemical formula	C12H22O11
Molar mass	342.30 g/mol
Density	1.768 g/mL
Melting point	190 to 195 °C (374 to 383 °F; 463 to 468 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.^[2]

References

^ The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (11th ed.), Merck, 1989, p. 4288, ISBN 091191028X
^ Sugisawa, Hirqshi; Edo, Hiroshi (1966). "The Thermal Degradation of Sugars I. Thermal Polymerization of Glucose". Journal of Food Science. 31 (4): 561. doi:10.1111/j.1365-2621.1966.tb01905.x.

[1] The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (11th ed.), Merck, 1989, p. 4288, ISBN 091191028X

[2] Sugisawa, Hirqshi; Edo, Hiroshi (1966). "The Thermal Degradation of Sugars I. Thermal Polymerization of Glucose". Journal of Food Science. 31 (4): 561. doi:10.1111/j.1365-2621.1966.tb01905.x.

[1]

[2]

Names

IUPAC name 6-O-β-D-glucopyranosyl-D-glucose
Other names amygdalose
Identifiers
CAS Number	554-91-6
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28066
ChemSpider	390156
PubChem CID	441422
UNII	HF30HB040V
InChI InChI=1S/C12H22O11/c13-1-3-5(14)8(17)10(19)12(23-3)21-2-4-6(15)7(16)9(18)11(20)22-4/h3-20H,1-2H2/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1 Key: DLRVVLDZNNYCBX-LIZSDCNHSA-N InChI=1/C12H22O11/c13-1-3-5(14)8(17)10(19)12(23-3)21-2-4-6(15)7(16)9(18)11(20)22-4/h3-20H,1-2H2/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1 Key: DLRVVLDZNNYCBX-LIZSDCNHBH
SMILES O(C[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O)[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)CO
Properties
Chemical formula	C₁₂H₂₂O₁₁
Molar mass	342.30 g/mol
Density	1.768 g/mL
Melting point	190 to 195 °C (374 to 383 °F; 463 to 468 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).