12-08292. Raunescine [Archived]

Nomenclature

CAS number: 117-73-7
(3β,16β,17α,18β,20α)-17-Hydroxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid methyl ester; 3,4,5-trimethoxybenzoyl methyl raunescate.
C31H36N2O8; mol wt 564.63.
C 65.94%, H 6.43%, N 4.96%, O 22.67%.

Description and references

Isoln from Rauwolfia canescens L., R. tetraphylla and other Rauwolfia spp, Apocynaceae. Isoln and structure: Hosansky, Smith, J. Am. Pharm. Assoc. Sci. Ed. 44, 639 (1955); Huebner, Schlittler, J. Am. Chem. Soc. 79, 250 (1957); van Tamelen, Taylor, ibid. 79, 5256 (1957). Extraction: GB 833149 (1960 to Ciba).

Chemical structure

Derivative

Monohydrate.

Nomenclature

CAS number: 6105-85-7

Properties

Hexagonal prisms from 90% methanol, mp 160-170°. [α]D25 74° (chloroform). uv max (U.S.P. alc): 218, 271 nm (log ε 4.77, 4.26).

Derivative

Nitrate.

Nomenclature

CAS number: 6159-98-4
C31H36N2O8.HNO3; mol wt 627.64.
C 59.32%, H 5.94%, N 6.69%, O 28.04%.

Properties

mp 223-225°; (mp 208-210°). [α]D25 80° (5N acetic acid).

Derivative

Monoacetate monohydrate.

Nomenclature

CAS number: 6105-86-8
C33H38N2O9.H2O; mol wt 624.68.
C 63.45%, H 6.45%, N 4.48%, O 25.61%.

Properties

mp 159-162°. [α]D25 157° (chloroform).

Status

This monograph has been retired and is no longer subject to revision or update.