4318. Fustin

Nomenclature

CAS number: 20725-03-5
(2R,3R)-rel-2-(3,4-Dihydroxyphenyl)-2,3-dihydro-3,7-dihydroxy-4H-1-benzopyran-4-one; 3,3′,4′,7-tetrahydroxyflavanone; dihydrofisetin.
C15H12O6; mol wt 288.25.
C 62.50%, H 4.20%, O 33.30%.

Description and references

From wood of Rhus cotinus L. (Venice sumac) and R. succedanea L., Anacardiaceae: Schmid, Ber. 19, 1734 (1886); from Gleditsia triacanthos L., Leguminosae: Chadenson et al., Compt. Rend. 249, 1362 (1955). Structure: Oyamada, Ann. 538, 44 (1939). Stereochemistry: Weinges, Ann. 627, 229 (1959); Roux, Paulus, Biochem. J. 77, 315 (1960); Gaffield, Tetrahedron 26, 4093 (1970).

Chemical structure

Derivative

(±)-Form.

Properties

Crystals, mp 226-228°. [α]D21 2.4°.

Derivative

(±)-Form tetraacetate.
C23H20O10; mol wt 456.40.
C 60.53%, H 4.42%, O 35.06%.

Properties

Crystals from methanol, mp 147-148°.

Derivative

()-Form.

Properties

Crystals, mp 216-218°. [α]D25 26° (c = 2 in 1:1 acetone, water).

Derivative

()-Form tetraacetate.

Properties

Crystals, mp 117-118°. [α]D23 25.2° (c = 0.8 in tetrachloroethane).

Derivative

(+)-Form.

Properties

Needles from water, mp 228-229°. [α]D23 +28.3° (c = 0.9 in 1:1 acetone, water).

Derivative

(+)-Form tetraacetate.

Properties

Crystals from ethanol, mp 116-119°. [α]D25 +24.4° (c = 1.3 in tetrachloroethane).