Meconin
Title: Meconin
CAS Registry Number: 569-31-3
CAS Name: 6,7-Dimethoxy-1(3H)-isobenzofuranone
Additional Names: 6,7-dimethoxyphthalide; opianyl; meconinic acid lactone
Molecular Formula: C10H10O4
Molecular Weight: 194.18
Percent Composition: C 61.85%, H 5.19%, O 32.96%
Literature References: Isolated from opium by Dublanc in 1832. Occurs also in the root of Hydrastis canadensis L., Ranunculaceae: Freund, Ber. 22, 456, 459 (1889). Is formed in oxidation of noscapine with HNO3. Synthesis from o-veratric acid: Edwards et al., J. Chem. Soc. 1925, 195; Wilson et al., J. Org. Chem. 16, 792 (1951). From opianic acid: Brown, Newbold, J. Chem. Soc. 1952, 4878.
Properties: White, optically inactive needles; sharp bitter taste. mp 102-103°. uv max: 213, 308 nm (e 25000, 3800). Sol in 700 parts cold, 22 parts boiling water; sol in alcohol, benzene, chloroform, ether, glacial acetic acid; slowly sol in alkalies with formation of alkali salt of meconinic acid, (CH2OH)(CH3O)2C6H2COOH. The acid itself is unstable, rapidly changing to lactone.
Melting point: mp 102-103°
Absorption maximum: uv max: 213, 308 nm (e 25000, 3800)

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