PRODUCT IDENTIFICATION
H.S. CODE
TOXICITY
Oral Rat: LD50: 1230 mg/kg
1-Methoxy-4-(2-propen-1-yl)benzene; p-Allylanisole;
1-Allyl-4-methoxybenzene; 1-Methoxy-4-(2-propenyl)benzene; 3-(p-Methoxyphenyl)propene; 4-Allyl-1-methoxybenzene; 4-Allylanisole; 4-Allylmethoxybenzene; 4-Methoxyallylbenzene; Esdragol; Esdragole; Esdragon; Estragole; Isoanethole; Methyl chavicol; Tarragon; p-Allylmethoxybenzene; p-Methoxyallylbenzene; Other RN: 1407-27-8, 77525-18-9
CLASSIFICATION
Flavor and Fragrance agent
EXTRA NOTES
PHYSICAL AND CHEMICAL PROPERTIES
215 - 216 C
0.96
5.11
REFRACTIVE INDEX
NFPA RATINGS
AUTOIGNITION
81 C
Stable under ordinary conditions
EXTERNAL LINKS & GENERAL DESCRIPTION
http://abstracts.aspb.org
Eugenol
and related volatile phenylpropenes, such as isoeugenol, and methylchavicol,
are important components of many economically important spices and
are highly valued as flavoring/fragrance additives and for their
biological properties. For example, these spices have been used
for centuries as food preservation agents. These compounds are widely
distributed in the plant kingdom, and are produced by plants as
defense compounds against animals and microorganisms and as floral
attractants of pollinators. Previous research suggested that the
phenylpropenes are synthesized in plants via the phenylpropanoid
pathway, although the identity of the enzymes and the nature of
the reaction mechanisms involved in their formation remained obscure.
We have identified in glandular trichomes of sweet basil (Ocimum
basilicum L.), which are known to synthesize and accumulate large
amounts of such phenylpropenes, an enzyme, which we have called
eugenol synthase (EGS), that uses esters of coniferyl alcohol to
form eugenol and of p-coumaryl alcohol to form chavicol. Petunia
(Petunia hybrida L. Mitchell) flowers, which emit large amounts
of isoeugenol, possess a homologous protein (isoeugenol synthase,
IGS) that also uses coniferyl alcohol esters as substrate, but instead
of forming eugenol, IGS forms isoeugenol. We have obtained the corresponding
cDNAs and characterized the recombinant proteins. In addition, we
have identified in these plants the acyltransferases responsible
for formation of the substrates for EGS and IGS. The relationships
of these enzymes (EGS, IGS and acyltransferases) to other members
of their respective protein families, their substrate preferences,
and a discussion of the catalytic mechanisms of EGS and IGS will
be presented.
http://en.scientificcommons.org/
Phenylpropenes
such as chavicol, t-anol, eugenol, and isoeugenol are produced by
plants as defense compounds against animals and microorganisms and
as floral attractants of pollinators. Moreover, humans have used
phenylpropenes since antiquity for food preservation and flavoring
and as medicinal agents. Previous research suggested that the phenylpropenes
are synthesized in plants from substituted phenylpropenols, although
the identity of the enzymes and the nature of the reaction mechanism
involved in this transformation have remained obscure. We show here
that glandular trichomes of sweet basil (Ocimum basilicum), which
synthesize and accumulate phenylpropenes, possess an enzyme that
can use coniferyl acetate and NADPH to form eugenol. Petunia (Petunia
hybrida cv. Mitchell) flowers, which emit large amounts of isoeugenol,
possess an enzyme homologous to the basil eugenol-forming enzyme
that also uses coniferyl acetate and NADPH as substrates but catalyzes
the formation of isoeugenol. The basil and petunia phenylpropene-forming
enzymes belong to a structural family of NADPH-dependent reductases
that also includes pinoresinol–lariciresinol reductase, isoflavone
reductase, and phenylcoumaran benzylic ether reductase.
Phenylpropenes: AAnethole, Apiol, Asarone, Carpacin, Chavibetol, Chavicol, Dillapiole, Elemicin, Estragole, Eugenol, Isoeugenol, Isosafrole, Myristicin, Phenylpropene, Safrole
APPEARANCE
ASSAY
97.0% min
REFRACTIVE INDEX