Gentiobiose
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Gentiobiose is a
disaccharide A disaccharide (also called a double sugar or ''biose'') is the sugar formed when two monosaccharides are joined by glycosidic linkage. Like monosaccharides, disaccharides are simple sugars soluble in water. Three common examples are sucrose, la ...
composed of two units of
D-glucose Glucose is a simple sugar with the molecular formula . Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, usin ...
joined with a β(1->6) linkage. It is a white crystalline solid that is soluble in water or hot
methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is ...
. Gentiobiose is incorporated into the chemical structure of
crocin Crocin is a carotenoid chemical compound that is found in the flowers of crocus and gardenia. Crocin is the chemical primarily responsible for the color of saffron. Chemically, crocin is the diester formed from the disaccharide gentiobiose and ...
, the chemical compound that gives
saffron Saffron () is a spice derived from the flower of ''Crocus sativus'', commonly known as the "saffron crocus". The vivid crimson stigma (botany), stigma and stigma (botany)#style, styles, called threads, are collected and dried for use mainly ...
its color. It is a product of the
caramelization Caramelization is a process of browning of sugar used extensively in cooking for the resulting sweet nutty flavor and brown color. The brown colors are produced by three groups of polymers: caramelans (C24H36O18), caramelens (C36H50O25), and ca ...
of
glucose Glucose is a simple sugar with the molecular formula . Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, u ...
. 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 Glucose is a simple sugar with the molecular formula . Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, usin ...
molecules. One β-D-glucose unit elongation of the bitter
disaccharide A disaccharide (also called a double sugar or ''biose'') is the sugar formed when two monosaccharides are joined by glycosidic linkage. Like monosaccharides, disaccharides are simple sugars soluble in water. Three common examples are sucrose, la ...
reduces its bitterness by a fifth, as determined by human volunteers using the trimer, gentiotriose. Gentiobiose is also produced via enzymatic hydrolysis of glucans, including pustulan and β-1,3-1,6-glucan.


References

Disaccharides {{organic-compound-stub