References of 4H-1-Benzopyran-4-one,2-(3,4-dihydroxyphenyl)-2,3-dihydro-3,7-dihydroxy-, (2R,3R)-rel-
Title: Fustin
CAS Registry Number: 20725-03-5
CAS Name: (2
R,3
R)-
rel-2-(3,4-Dihydroxyphenyl)-2,3-dihydro-3,7-dihydroxy-4
H-1-benzopyran-4-one
Synonyms: 3,3¢,4¢,7-tetrahydroxyflavanone; dihydrofisetin
Molecular Formula: C15H12O6
Molecular Weight: 288.25
Percent Composition: C 62.50%, H 4.20%, O 33.30%
Literature 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).
Derivative Type: (±)-Form
Properties: Crystals, mp 226-228°. [a]D21 -2.4°.
Melting point: mp 226-228°
Optical Rotation: [a]D21 -2.4°
Derivative Type: (±)-Form tetraacetate
Molecular Formula: C23H20O10
Molecular Weight: 456.40
Percent Composition: C 60.53%, H 4.42%, O 35.06%
Properties: Crystals from methanol, mp 147-148°.
Melting point: mp 147-148°
Derivative Type: (-)-Form
Properties: Crystals, mp 216-218°. [a]D25 -26° (c = 2 in 1:1 acetone, water).
Melting point: mp 216-218°
Optical Rotation: [a]D25 -26° (c = 2 in 1:1 acetone, water)
Derivative Type: (-)-Form tetraacetate
Properties: Crystals, mp 117-118°. [a]D23 -25.2° (c = 0.8 in tetrachloroethane).
Melting point: mp 117-118°
Optical Rotation: [a]D23 -25.2° (c = 0.8 in tetrachloroethane)
Derivative Type: (+)-Form
Properties: Needles from water, mp 228-229°. [a]D23 +28.3° (c = 0.9 in 1:1 acetone, water).
Melting point: mp 228-229°
Optical Rotation: [a]D23 +28.3° (c = 0.9 in 1:1 acetone, water)
Derivative Type: (+)-Form tetraacetate
Properties: Crystals from ethanol, mp 116-119°. [a]D25 +24.4° (c = 1.3 in tetrachloroethane).
Melting point: mp 116-119°
Optical Rotation: [a]D25 +24.4° (c = 1.3 in tetrachloroethane)