FComEx: Isoeugenol (PC000932)

Record Information

Version

1.0

Creation date

2015-10-09 22:33:27 UTC

Update date

2017-01-19 02:36:41 UTC

FoodComEx ID

PC000932

FoodDB Record

FDB002728

Chemical Information

Name

Isoeugenol

Description

Isoeugenol is an isomer of eugenol, wherein the double bond on the alkyl chain is shifted by one carbon. It also known as propenylgualacol, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Isoeugenol is also classified as a phenylpropene, a propenyl-substituted guaiacol. Isoeugenol may occur as either the cis (Z) or trans (E) isomer. Trans (E) isoeugenol is crystalline while cis (Z) isoeugenol is a pale, yellow liquid. Isoeugenol is very slightly soluble in water and soluble in organic solvents. It has a spicy, sweet, carnation-like odour and tastes of sweet spice and clove. Isoeugenol is a widely used food flavoring agent and a perfuming agent. As a food flavoring agent, it is responsible for the flavor of nutmeg (in pumpkin pies), As a fragrance, it is extensively used as a scent agent in consumer products such as soaps, shampoos, perfumes, detergents and bath tissues (often labeled as ‚ÄúFragrance‚Äù rather than isoeugenol). However, some individuals can develop allergies to isoeugenol as it appears to be a strong contact allergen (PMID: 10554062). Isoeugenol can be prepared from eugenol by heating. In addition to its industrial production via eugenol, isoeugenol can also be extracted from certain essential oils especially from clove oil and cinnamon. It is found naturally in a wide number of foods, spices and plants including allspice, basil, blueberries, cinnamon, cloves, coffee, dill, ginber, nutmeg, thyme and turmeric.

CAS Number

97-54-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(e)-2-Methoxy-4- (1-propenyl)-phenol	HMDB
(e)-2-Methoxy-4-(1-propenyl)-phenol	HMDB
(e)-2-Methoxy-4-propenyl-phenol	HMDB
1-(3-Methoxy-4-hydroxyphenyl)-1-propane	HMDB
1-(3-Methoxy-4-hydroxyphenyl)-1-propene	biospider
1-Hydroxy-2-methoxy-4-propen-1-ylbenzene	HMDB
2-Methoxy-4-(1-propenyl)-phenol	HMDB
2-Methoxy-4-(1-propenyl)phenol	HMDB
2-Methoxy-4-(1-propenyl)phenol (acd/name 4.0)	HMDB
2-Methoxy-4-propenyl phenol	biospider
2-Methoxy-4-propenyl-phenol	HMDB
2-Methoxy-4-propenylphenol	biospider
3-Methoxy-4-hydroxy-1-propen-1-ylbenzene	HMDB
3-Methoxy-4-hydroxypropenylbenzene	biospider
4-Hydroxy-3-methoxy-1-propen-1-ylbenzene	HMDB
4-Hydroxy-3-methoxy-1-propenylbenzene	db_source
4-Hydroxy-3-methoxypropenylbenzene	biospider
4-Propenylguaiacol	biospider
5-(1-Propenyl)guaiacol	db_source
FEMA 2468	db_source
Iso-eugenol 2	ChEBI
Isoeugenol	db_source
Isoeugenol (I)	ChEBI
Isoeugenol e	ChEBI
Phenol, 2-methoxy-4-(1-propen-1-yl)-	biospider
Phenol, 2-methoxy-4-(1-propenyl)-	biospider
Phenol, 2-methoxy-4-propenyl-	biospider
Propenylgualacol	HMDB
trans-4-Propenylgualacol	HMDB

Chemical Formula

C10H12O2

IUPAC name

2-methoxy-4-[(1E)-prop-1-en-1-yl]phenol

InChI Identifier

InChI=1S/C10H12O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h3-7,11H,1-2H3/b4-3+

InChI Key

BJIOGJUNALELMI-ONEGZZNKSA-N

Isomeric SMILES

COC1=CC(\C=C\C)=CC=C1O

Average Molecular Weight

164.2011

Monoisotopic Molecular Weight

164.083729628

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents