6299. Muconic Acid
Nomenclature
CAS number: 505-70-4
2,4-Hexadienedioic acid; 1,3-butadiene-1,4-dicarboxylic acid. C6H6O4; mol wt 142.11.
C 50.71%, H 4.26%, O 45.03%.
Description and references
Prepd by oxidation of phenol and peracetic acid: Boeseken, Engelberts, C.A. 26, 2970 (1932); by treatment of ethyl 1,4-dibromoadipate with alcoholic potassium hydroxide: Guha, Sankaran, Org. Synth. 26, 57 (1946); by isomerization of 3-hydroxy-4-carbomethoxybut-1-ene-1-carboxylic acid lactone: Elvidge et al., J. Chem. Soc. 1950, 2235; by carbonylation of acetylene: Tsuji et al., J. Am. Chem. Soc. 86, 2095 (1964). Configuration and separation of isomers: Boeseken, Kerkhoven, Rec. Trav. Chim. 51, 964 (1932); Elvidge et al., J. Chem. Soc. 1953, 708.
Derivative
(E,E)-Form.Nomenclature
CAS number: 3588-17-8
Properties
Prisms from water, mp 301°. uv max (0.1N NaOH): 251, 259, 264 nm (ε 25600, 29100, 25600). One gram dissolves in about 5 liters water at 15°. Quite sol in hot alcohol and glacial acetic acid.Derivative
(E,E)-Form dimethyl ester.Nomenclature
CAS number: 1119-43-3
C8H10O4; mol wt 170.16.
C 56.47%, H 5.92%, O 37.61%.
Properties
Crystals from alcohol, mp 159°. Insol in ether.Derivative
(E,E)-Form diethyl ester.Nomenclature
CAS number: 6032-74-2
C10H14O4; mol wt 198.22.
C 60.59%, H 7.12%, O 32.29%.
Properties
Needles from alcohol, mp 64°; d4100 0.9829. nHe99 1.4675.Derivative
(Z,Z)-Form.Nomenclature
CAS number: 1119-72-8
Properties
Prisms from ethanol, mp 194-195°. uv max (0.1N NaOH): 251, 258, 264 nm (ε 15600, 17000, 15300). Freely sol in boiling water; sparingly sol in ether.Derivative
(Z,Z)-Form dimethyl ester.Nomenclature
CAS number: 692-91-1
C8H10O4; mol wt 170.16.
C 56.47%, H 5.92%, O 37.61%.
Properties
Needles from petr ether, mp 75°. Soluble in ether.Derivative
(Z,Z)-Form diethyl ester.Nomenclature
CAS number: 6032-77-5
C10H14O4; mol wt 198.22.
C 60.59%, H 7.12%, O 32.29%.
Properties
Minute crystals from alcohol at -25°; mp 13°. Changes to the trans-trans-form on storage at room temp.Derivative
(2E,4Z)-Form.Nomenclature
CAS number: 1119-73-9
Properties
Needles from hot water, mp 190-191°. uv max (0.1N NaOH): 251, 259, 265 nm (ε 23400, 25600, 23400).Derivative
(2E,4Z)-Form dimethyl ester.Nomenclature
CAS number: 692-92-2
C8H10O4; mol wt 170.16.
C 56.47%, H 5.92%, O 37.61%.