8869. Succinic Acid
Nomenclature
CAS number: 110-15-6
Butanedioic acid; amber acid; ethylenesuccinic acid; Bernsteinsure (German); Asuccin. C4H6O4; mol wt 118.09.
C 40.68%, H 5.12%, O 54.19%.
Description and references
Observed by Agricola in 1546, in the distillate from amber. Occurs in fossils, fungi, lichens, etc. Prepn from acetic acid: Coffman et al., J. Am. Chem. Soc. 80, 2864 (1958). Manuf: Crosby, Braunwarth, US 2862028 (1958 to Pure Oil); Chafetz, Patterson, US 2978473 (1961 to Texaco). Toxicity study: H. F. Smyth et al., Arch. Ind. Hyg. Occup. Med. 4, 119 (1951).
Properties
Odorless, monoclinic prisms; very acid taste; d 1.56. mp 185-187°. bp 235° with partial conversion into the anhydride. pKa1 4.03±0.03; pKa2 5.28±0.03. Log P (octanol/water): 0.59. One gram dissolves in 13 ml cold water, 1 ml boiling water, 18.5 ml alcohol, 6.3 ml methanol, 36 ml acetone, 20 ml glycerol, 113 ml ether. Practically insol in benzene, carbon disulfide, carbon tetrachloride, petr ether. pH of 0.1 molar aq soln 2.7.Derivative
Potassium salt trihydrate.Nomenclature
CAS number: 6100-18-1
Potassium succinate. C4H4K2O4.3H2O; mol wt 248.31.
C 19.35%, H 4.06%, K 31.49%, O 45.10%.
Properties
Hygroscopic crystalline powder. d 1.564. Freely sol in water; the aq soln is practically neutral. Keep tightly closed.Derivative
Diethyl ester.Nomenclature
CAS number: 123-25-1
Ethyl succinate. C8H14O4; mol wt 174.19.
C 55.16%, H 8.10%, O 36.74%.
Description and references
Prepn: A. Zurqiyah, C. E. Castro, Org. Synth. coll. vol. V, 993 (1973).
Properties
Colorless, clear liq; faint, pleasant odor. d420 1.040. mp 21°. bp760 217-218°; bp44 129°. nD20 1.4201. Insol in water. Miscible with alcohol, ether. LD50 orally in rats: 8.53 g/kg (Smyth).Derivative
Dimethyl ester.Nomenclature
CAS number: 106-65-0
Methyl succinate. C6H10O4; mol wt 146.14.
C 49.31%, H 6.90%, O 43.79%.