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 ;
CompTox Dashboard (EPA)	DTXSID501317544 ;
	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). verify (what is ?) Infobox 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.^[2] 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.^[3] One β-D-glucose unit elongation of the bitter disaccharide reduces its bitterness by a fifth, as determined by human volunteers using the trimer, gentiotriose.^[4] Gentiobiose is also produced via enzymatic hydrolysis of glucans, including pustulan^[5] and β-1,3-1,6-glucan.^[6]

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.
^ Berlin, Henry (1926). "The Occurrence of Gentiobiose in the Products of the Commercial Hydrolysis of Corn Starch2". Journal of the American Chemical Society. 48 (10): 2627–2630. doi:10.1021/ja01421a017.
^ Fujimoto, Yoshinori; Hattori, Takeshi; Uno, Shuji; Murata, Takeomi; Usui, Taichi (2009). "Enzymatic synthesis of gentiooligosaccharides by transglycosylation with β-glycosidases from Penicillium multicolor". Carbohydrate Research. 344 (8): 972–978. doi:10.1016/j.carres.2009.03.006. hdl:10297/3621. PMID 19362709.
^ Hattori, Takeshi; Kato, Yasuna; Uno, Shuji; Usui, Taichi (2013). "Mode of action of a β-(1→6)-glucanase from Penicillium multicolor". Carbohydrate Research. 366: 6–16. doi:10.1016/j.carres.2012.11.002. PMID 23246473.
^ Hirabayashi, Katsuki; Tashiro, Yoshiya; Kondo, Nobuhiro; Hayashi; Sachio (2017). "Production of Gentiobiose from Hydrothermally Treated Aureobasidium pullulans β-1,3-1,6-Glucan". Journal of Applied Glycoscience. 64 (2): 33–37. doi:10.5458/jag.jag.JAG-2017_002. PMC 8056935. PMID 34354494.

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[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.

[3] Berlin, Henry (1926). "The Occurrence of Gentiobiose in the Products of the Commercial Hydrolysis of Corn Starch2". Journal of the American Chemical Society. 48 (10): 2627–2630. doi:10.1021/ja01421a017.

[4] Fujimoto, Yoshinori; Hattori, Takeshi; Uno, Shuji; Murata, Takeomi; Usui, Taichi (2009). "Enzymatic synthesis of gentiooligosaccharides by transglycosylation with β-glycosidases from Penicillium multicolor". Carbohydrate Research. 344 (8): 972–978. doi:10.1016/j.carres.2009.03.006. hdl:10297/3621. PMID 19362709.

[5] Hattori, Takeshi; Kato, Yasuna; Uno, Shuji; Usui, Taichi (2013). "Mode of action of a β-(1→6)-glucanase from Penicillium multicolor". Carbohydrate Research. 366: 6–16. doi:10.1016/j.carres.2012.11.002. PMID 23246473.

[6] Hirabayashi, Katsuki; Tashiro, Yoshiya; Kondo, Nobuhiro; Hayashi; Sachio (2017). "Production of Gentiobiose from Hydrothermally Treated Aureobasidium pullulans β-1,3-1,6-Glucan". Journal of Applied Glycoscience. 64 (2): 33–37. doi:10.5458/jag.jag.JAG-2017_002. PMC 8056935. PMID 34354494.

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