Title: Reticuline
CAS Registry Number: 485-19-8
CAS Name: 1,2,3,4-Tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-7-isoquinolinol
Additional Names: 1,2,3,4-tetrahydro-6-methoxy-2-methyl-1-vanillyl-7-isoquinolinol; 2-methyl-7-hydroxy-6-methoxy-1-(3-hydroxy-4-methoxybenzyl)-1,2,3,4-tetrahydroisoquinoline; coclanoline
Molecular Formula: C19H23NO4
Molecular Weight: 329.39
Percent Composition: C 69.28%, H 7.04%, N 4.25%, O 19.43%
Literature References: Precursor of many aporphine and morphine-type alkaloids. Isoln of d-form from Anona reticulata Linn., Anonaceae: Gopinath et al., Ber. 92, 776 (1959); dl-form from opium: Brochmann-Hanssen, Furuya, J. Pharm. Sci. 53, 575 (1964); Planta Med. 12, 328 (1964). Structure: Brochmann-Hanssen, Nielson, Tetrahedron Lett. 1965, 1271. Configuration: Battersby, Evans, ibid. 1275. Synthesis of amorphous dl-form: Gopinath et al., Ber. 92, 1657 (1959); P. Kerekes et al., Acta Chim. Acad. Sci. Hung. 98, 491 (1978). Synthesis of crystalline dl-form: Baxter et al., J. Chem. Soc. C 1965, 3645; Chan, Maitland, ibid. 1966, 753; K. C. Rice, A. Brossi, J. Org. Chem. 45, 592 (1980); G. Dornyei et al., Tetrahedron Lett. 1982, 2913. Asymmetric synthesis of (S)-reticuline: Konda et al., Chem. Pharm. Bull. 23, 1063 (1975). Biosynthesis: D. S. Dewan et al., J. Chem. Soc. Perkin Trans. 1 1977, 1662; A. Barrett et al., ibid. 1979, 652.
Derivative Type: dl-Form
Properties: Pink crystals, mp 146°. uv max: 284 nm (log e 3.85). Sol in aqueous buffer of pH <7.5 or >11. Practically insol in water at pH 8-10.
Melting point: mp 146°
Absorption maximum: uv max: 284 nm (log e 3.85)
Derivative Type: (S)-Form perchlorate
Molecular Formula: C19H23NO4.HClO4
Molecular Weight: 429.85
Percent Composition: C 53.09%, H 5.63%, N 3.26%, O 29.78%, Cl 8.25%
Properties: Colorless prisms from ethanol, mp 203-204°. [a]D18 +88.3° (c = 0.21 in alc).
Melting point: mp 203-204°
Optical Rotation: [a]D18 +88.3° (c = 0.21 in alc)
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