Coclaurine
Title: Coclaurine
CAS Registry Number: 486-39-5
CAS Name: (1S)-1,2,3,4-Tetrahydro-1-[(4-hydroxyphenyl)methyl]-6-methoxy-7-isoquinolinol
Additional Names: 1-(p-hydroxybenzyl)-6-methoxy-7-hydroxy-1,2,3,4-tetrahydroisoquinoline; machiline
Molecular Formula: C17H19NO3
Molecular Weight: 285.34
Percent Composition: C 71.56%, H 6.71%, N 4.91%, O 16.82%
Literature References: Isolated as the racemate from species of Machilus (Lauraceae) and Cocculus (Menispermaceae). First isoln from C. laurifolius D.C. believed to be of the d-form: Kondo, Kondo, J. Pharm. Soc. Jpn. No. 524, 876 (1925), C.A. 20, 6047 (1926); see also Johns et al., Aust. J. Chem. 20, 1729 (1967). Structure: Kondo, Kondo, J. Pharm. Soc. Jpn. 48, 1156 (1928); Tomita, Kusuda, ibid. 72, 280 (1952). Synthesis: Kratzl, Billek, Monatsh. Chem. 82, 568 (1951); Finkelstein, J. Am. Chem. Soc. 73, 550 (1951). Identity with machiline: Tomita et al., J. Pharm. Soc. Jpn. 83, 218 (1963), C.A. 59, 2874a (1963). Crystal structure and absolute configuration: Fridrichsons, Mathieson, Tetrahedron 24, 5785 (1968).
Properties: Plates, tablets from alc, mp 220-221°. Sol in hot alc, hot acetone; slightly sol in water, alc, chloroform, ether, acetone; practically insol in benzene, petr ether.
Melting point: mp 220-221°
 
Derivative Type: Hydrochloride
Molecular Formula: C17H19NO3.HCl
Molecular Weight: 321.80
Percent Composition: C 63.45%, H 6.26%, N 4.35%, O 14.92%, Cl 11.02%
Properties: Crystals, mp 263-264°.
Melting point: mp 263-264°

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