12-07664. Piscidic Acid [Archived]
Nomenclature
CAS number: 35388-57-9
2,3-Dihydroxy-2-[(4-hydroxyphenyl)methyl]butanedioic acid; (p-hydroxybenzyl)tartaric acid. C11H12O7; mol wt 256.21.
C 51.57%, H 4.72%, O 43.71%.
Description and references
Isoln from root bark of Piscidia piscipula (L.) Sarg. (P. erythrina L.), Leguminosae (Jamaica dogwood): Freer, Clover, Am. Chem. J. 25, 390 (1901); from Narcissus poeticus L., Amaryllidaceae: Smeby et al., J. Am. Chem. Soc. 76, 6127 (1954). Structure: Bridge et al., J. Chem. Soc. 1948, 257. Synthesis of p-O-methyl deriv: Buckle et al., ibid. 1954, 3981.
Properties
Elongated prisms. mp 186-187°. [α]D20 +41.02° (c = 2.65). Sol in water, ethyl acetate; practically insol in CHCl3.Derivative
p-O-Methyl derivative.Nomenclature
(p-Methoxybenzyl)tartaric acid.C12H14O7; mol wt 270.24.
C 53.33%, H 5.22%, O 41.44%.
Properties
Crystals, mp 169-170°. [α]D23 +44.01 ±5.0° (c = 1.262).Status
This monograph has been retired and is no longer subject to revision or update.