579. Ampelopsin

Nomenclature

CAS number: 27200-12-0
(2R,3R)-2,3-Dihydro-3,5,7-trihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-1-benzopyran-4-one; 3,3′,4′,5,5′,7-hexahydroxyflavanone; ampeloptin; dihydromyricetin.
C15H12O8; mol wt 320.25.
C 56.26%, H 3.78%, O 39.97%.

Description and references

From leaves of Ampelopsis meliaefolia Kudo, Vitaceae: Kotake, Kubota, Ann. 544, 253 (1940); from bark of Pinus contoria Dougl., Pinaceae: Hergert, J. Org. Chem. 21, 534 (1956); US 2870165 (1959 to Rayonier); from Erythrophleum africanum (Welw.) Harms, Caesalpiniaceae: Hansel, Klaffenbach, Arch. Pharm. 294, 158 (1961). Synthesis from myricetin, q.v.: Kotake, Kubota, J. Inst. Polytech. Osaka City Univ. 1, no. 2, 47 (1950), C.A. 46, 2052e (1952).

Chemical structure

Derivative

Hemipentahydrate.

Properties

Needles from water, mp 245-246°.

Derivative

Hexaacetate.
C27H24O14; mol wt 572.47.
C 56.65%, H 4.23%, O 39.13%.

Properties

Needles from alc, mp 174-175°.

Derivative

Hexabenzoate.
C57H42O14; mol wt 950.93.
C 71.99%, H 4.45%, O 23.56%.

Properties

Needles from alc, mp 174°.