Muconic Acid
Title: Muconic Acid
CAS Registry Number: 505-70-4
CAS Name: 2,4-Hexadienedioic acid
Additional Names: 1,3-butadiene-1,4-dicarboxylic acid
Molecular Formula: C6H6O4
Molecular Weight: 142.11
Percent Composition: C 50.71%, H 4.26%, O 45.03%
Line Formula: HOOCCH=CHCH=CHCOOH
Literature 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 Type: trans,trans-Form
Properties: Prisms from water, mp 301°. uv max (0.1N NaOH): 251, 259, 264 nm (e 25600, 29100, 25600). One gram dissolves in about 5 liters water at 15°. Quite sol in hot alcohol and glacial acetic acid.
Melting point: mp 301°
Absorption maximum: uv max (0.1N NaOH): 251, 259, 264 nm (e 25600, 29100, 25600)
 
Derivative Type: Dimethyl ester
Molecular Formula: C8H10O4
Molecular Weight: 170.16
Percent Composition: C 56.47%, H 5.92%, O 37.61%
Properties: Crystals from alcohol, mp 159°. Insol in ether.
Melting point: mp 159°
 
Derivative Type: Diethyl ester
Molecular Formula: C10H14O4
Molecular Weight: 198.22
Percent Composition: C 60.59%, H 7.12%, O 32.29%
Properties: Needles from alcohol, mp 64°; d4100 0.9829. nHe99 1.4675.
Melting point: mp 64°
Index of refraction: nHe99 1.4675
Density: d4100 0.9829
 
Derivative Type: cis,cis-Form
Properties: Prisms from ethanol, mp 194-195°. uv max (0.1N NaOH): 251, 258, 264 nm (e 15600, 17000, 15300). Freely sol in boiling water; sparingly sol in ether.
Melting point: mp 194-195°
Absorption maximum: uv max (0.1N NaOH): 251, 258, 264 nm (e 15600, 17000, 15300)
 
Derivative Type: Dimethyl ester
Molecular Formula: C8H10O4
Molecular Weight: 170.16
Percent Composition: C 56.47%, H 5.92%, O 37.61%
Properties: Needles from petr ether, mp 75°. Soluble in ether.
Melting point: mp 75°
 
Derivative Type: Diethyl ester
Molecular Formula: C10H14O4
Molecular Weight: 198.22
Percent Composition: 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.
Melting point: mp 13°
 
Derivative Type: cis,trans-Form
Properties: Needles from hot water, mp 190-191°. uv max (0.1N NaOH): 251, 259, 265 nm (e 23400, 25600, 23400).
Melting point: mp 190-191°
Absorption maximum: uv max (0.1N NaOH): 251, 259, 265 nm (e 23400, 25600, 23400)
 
Derivative Type: Dimethyl ester
Molecular Formula: C8H10O4
Molecular Weight: 170.16
Percent Composition: C 56.47%, H 5.92%, O 37.61%
Properties: Needles from aqueous methanol, mp 75°.
Melting point: mp 75°

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