Nomenclature
CAS number: 6915-15-7
Hydroxybutanedioic acid; hydroxysuccinic acid.
C
4H
6O
5; mol wt 134.09.
C 35.83%, H 4.51%, O 59.66%.
Description and references
The naturally occurring isomer is the l-form which has been found in apples and many other fruits and plants.
Prepn of d- and dl-forms, and resolution of racemic
mixture: McKenzie et al., J. Chem.
Soc. 123, 2875 (1923). Solubilities: Descamps, Bull. Soc. Chim. Belg. 49, 91
(1940). Microbial production of l-form: Kitahara; Abe et al., US 2972566; US 3063910 (1961, 1962, both to Kyowa). Configuration: J. A. Mills, W. Klyne in Progress in Stereochemistry vol. 1, W. Klyne,
Ed. (Academic Press, New York, 1954) pp 182-183; E. L. Eliel, Stereochemistry of Carbon Compounds (McGraw-Hill,
New York, 1962) pp 97-98; Cymerman-Craig, Roy, Tetrahedron 21, 1847 (1965). Review of uses:
Manuf. Chem. Aerosol News 35, 56 (December, 1964). Review: S. E. Berger, “Hydroxy
Dicarboxylic Acids” in Kirk-Othmer Encyclopedia
of Chemical Technology vol 13 (Wiley-Interscience,
New York, 3rd ed., 1981) pp 103-110.
Derivative
dl-Form.
Nomenclature
CAS number: 617-48-1
Properties
Crystals, mp 131-132°. Soly in g/100 g solvent at 20°: methanol
82.70, diethyl ether 0.84, ethanol 45.53, acetone 17.75, dioxane 22.70,
water 55.8. Practically insol in benzene.Derivative
d-(+)-Form.
Nomenclature
CAS number: 636-61-3
Properties
Crystals, mp 101°.Derivative
l-(-)-Form.
Nomenclature
CAS number: 97-67-6
Apple acid.
Properties
Crystals from acetone, or acetone + CHCl3, mp 100°. Dec ≈140°.
[α]D -2.3° (c = 8.5). Soly in g/100 g solvent at 20°: methanol 197.22,
diethyl ether 2.70, ethanol 86.60, acetone 60.66, dioxane 74.35, water
36.35. Practically insol in benzene.Use
Intermediate in chemical synthesis. Chelating and
buffering agent. Flavoring agent, flavor enhancer and acidulant in
foods.