松三糖, D-Melezitose hydrate

Melezitose is a non-reducing trisaccharide that is produced by many plant sap-consuming insects, such as aphids (e.g. Cinara pilicornis).  Melezitose is a component of honeydew which acts as an attractant for ants and also as food for bees. Partial hydrolysis of melizitose releases glucose and turanose, an isomer of sucrose.

Title: Melezitose

CAS Registry Number: 597-12-6

CAS Name: O-a-D-Glucopyranosyl-(1®3)-b-D-fructofuranosyl-a-D-glucopyranoside

Molecular Formula: C18H32O16

Molecular Weight: 504.44

Percent Composition: C 42.86%, H 6.39%, O 50.75%

Literature References: Trisaccharide built from 2 mols glucose and 1 mol fructose. Acid hydrolysis yields at first glucose and turanose. Occurs in a manna that forms upon the Douglas fir, jack pine (Pinus virginiana Mill., Pinaceae) and other trees. During periods of drought, bees collect it from the manna in sufficient quantity to change the character of the honey, making it unsuitable for maintaining the bees, but providing a source of melezitose: Hudson, Sherwood, J. Am. Chem. Soc. 42, 116 (1920). Procedure: Bates, Natl. Bur. Std. Circ. C440, p 472 (1942). Structure: Hehre, Carlson, Arch. Biochem. Biophys. 36, 158 (1952); Hehre, Adv. Carbohydr. Chem. 8, 277 (1953). Review: E. B. Rathbone, Dev. Food Carbohydr. 2, 145-185 (1980).

Derivative Type: Dihydrate

Properties: Crystals from water. The water of crystn is given up at 110°. When anhydr, mp 153-154°. [a]D20 +88° (c = 4). Sol in water, very sparingly sol in alc. Not fermented by baker's yeast; does not reduce Fehling's soln.

Melting point: mp 153-154°

Optical Rotation: [a]D20 +88° (c = 4)