Isolation of 2,4,5-trimethoxyallylbenzene from Caesulia axillaries oil

Abstract

The phenolic ether obtained from the essential oil of Caesulia axillaries has been shown to be 2,4,5-trimethoxyallylbenzene (I), on the basis of chemical and spectroscopic evidence. It has tentatively been named as γ-asarone.

A Mild and Convenient Procedure for the Conversion of Toxic β-Asarone into Rare Phenylpropanoids: 2,4,5-Trimethoxycinnamaldehyde and γ-Asarone

“…In nature asarones exist in three isomeric forms, namely, α-, β-, and γ-asarone ( trans -2,4,5-trimethoxy-1-propenylbenzene, cis -2,4,5-trimethoxy-1-propenylbenzene, and 1-allyl-2,4,5-trimethoxybenzene, respectively). γ-Asarone ( 1 ) is a rare phenylpropanoid first isolated from Caesulia axillaries and later detected as a biologically active constituent of various essential oil bearing plants …”

Constituents of Acorus calamus: Structure of Acoramone. Carbon-13 NMR Spectra of Cis- and Trans-Asarone

“…In a previous communication (1) we reported the isolation of 2,4,5-trimethoxybenzaldehyde, 2,5-dimethoxybenzoquinone, galangin and sitosterol along with the new cyclobutanolignan acoradin from the rhizomes of A corns calamus Linn. Further investigation has resulted in the isolation of isoeugenol methyl ether (1), 7-asarone [1,2,4-trimethoxy-5(2-propenyl)benzene] (2), m-asarone [/3-asarone or cú-l,2,4-trimethoxy-5(l-propenyl)benzene] (3), Aans-asarone [«-asarone or trans-1,2,4-trimethoxy-5 (1 -propenyl) benzene] (4) and acoramone [1,2,4-trimethoxy-5 (2-propanonyl)benzene or l(2,4,5-trimethoxyphenyl)-propan-2-one] ( 5) along with asarylaldehyde [2,4,5-trimethoxybenzaldehyde] ( 6) from the oil of the same…”

“…y-As.ARONE (sekishone) (2)(3)(4) (2).-The constituent was a liquid (5 mg), Ci2Hi603 (M* 208.1124, ca. 208.1099).…”

“…Table 1. Carbon-13 chemical shifts" of cfj-asarone (3), transasarone (4) and their dihydroderivative (7). "The chemical shifts are in (ppm).…”

Fluorometric analysis

“…The phosphorescence spectra of several carbonyl compounds have been noted (4), and the 2-hydroxy-5methoxybenzohydrazides and 5-methoxy-3-nitrosalicylhydrazides have been proposed as fluorescent derivatives of carbonyl compounds (172). Acrolein can be determined by fluorometry after reaction with resorcinol in the presence of any of a number of amines (5), which suggests the possibility of sensitive methods also for allylamine, benzylamine, spermine, etc.…”