Title: Thevetose
CAS Registry Number: 5675-98-9
CAS Name: 6-Deoxy-3-O-methylglucose
Additional Names: 3-O-methylglucomethylose; quinovose 3-methyl ether
Molecular Formula: C7H14O5
Molecular Weight: 178.18
Percent Composition: C 47.19%, H 7.92%, O 44.90%
Literature References: Isoln of L-thevetose from Thevetia nereifolia Juss. and Tanghinia venenifera Poir., Apocynaceae: Frèrejacque, Compt. Rend. 221, 645 (1945); Frèrejacque, Hasenfratz, ibid. 222, 815 (1946); Sigg et al., Helv. Chim. Acta 38, 166 (1955); from thevetin: Helfenberger, Reichstein, ibid. 31, 1470 (1948); from Bowiea volubilis Harv., Liliaceae: Tschesche, Dölberg, Ber. 90, 2378 (1957). Synthesis: Blindenbacher, Reichstein, Helv. Chim. Acta 31, 1669 (1948). Isoln of D-thevetose from Adenium honghel D.C., Apocynaceae: Frèrejacque, Compt. Rend. 230, 127 (1950). Rare instance of two optical isomers of the same sugar being present in the vegetable kingdom.
Derivative Type: L-Form
Properties: Needles from acetone + ether, mp 128-130°. [a]D19 -66 to -36.9° (c = 1.46 in water).
Melting point: mp 128-130°
Optical Rotation: [a]D19 -66 to -36.9° (c = 1.46 in water)
Derivative Type: b-L-Triacetate
Molecular Formula: C13H20O8
Molecular Weight: 304.29
Percent Composition: C 51.31%, H 6.62%, O 42.06%
Properties: Crystals, mp 118-119°. [a]D18 -7.5° (c = 1.12 in acetone).
Melting point: mp 118-119°
Optical Rotation: [a]D18 -7.5° (c = 1.12 in acetone)
Derivative Type: L-Thevetosazone
Properties: Crystals, mp 136-139°. [a]D24 +110.8 to +40.3°.
Melting point: mp 136-139°
Optical Rotation: [a]D24 +110.8 to +40.3°
Derivative Type: D-Form
Properties: Crystals, mp 116°. [a]D20 +84 to +33°.
Melting point: mp 116°
Optical Rotation: [a]D20 +84 to +33°
Derivative Type: b-D-Triacetate
Molecular Formula: C13H20O8
Molecular Weight: 304.29
Percent Composition: C 51.31%, H 6.62%, O 42.06%
Properties: Crystals, mp 121°. [a]D20 +6° (acetone).
Melting point: mp 121°
Optical Rotation: [a]D20 +6° (acetone)
Derivative Type: a-D-Triacetate
Properties: Crystals, mp 105°. [a]D20 +122° (acetone).
Melting point: mp 105°
Optical Rotation: [a]D20 +122° (acetone)
Derivative Type: D-Thevetosazone
Properties: Crystals, mp 123-128°. [a]D16 -117.8 to -26.4°.
Melting point: mp 123-128°
Optical Rotation: [a]D16 -117.8 to -26.4°
Status: This monograph has been retired and is no longer subject to revision or update. |