Showing Compound Aceteugenol (FDB012393)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:09 UTC

Update date

2020-09-17 15:35:09 UTC

Primary ID

FDB012393

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Aceteugenol

Description

Eugenyl acetate, also known as acetyleugenol, is an allyl chain-substituted guaiacol, a member of the allylbenzene class of chemical compounds. Eugenyl acetate is constituted by a benzene ring, substituted by a methoxy group acetoxy group in position 1, a methoxy group in position 2 and a propenoil moiety in position 4. It is the acetylated derivative of eugenol. Eugenyl acetate is a sweet, carnation, and clove tasting compound. It is found in the highest concentration in a few different foods, such as cloves, ceylon cinnamons, and sweet bay. It has also been detected, but not quantified, in nutmegs, herbs and spices, cumins, star anises, and lemon balms.

CAS Number

93-28-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1,3,4-Eugenol acetate	HMDB
1-Acetoxy-2-methoxy-4-allylbenzene	HMDB
2-Methoxy-4-(2-propen-1-yl)phenyl acetate	HMDB
2-Methoxy-4-(2-propenyl)phenyl acetate	HMDB
4-Allyl-2-methoxyphenol acetate	HMDB
4-Allyl-2-methoxyphenyl acetate	HMDB
aceto Eugenol	HMDB
Acetyl eugenol	HMDB
Acetyleugenol	HMDB, MeSH
Eugenol acetate	HMDB
Eugenyl acetate	HMDB, MeSH
FEMA 2469	HMDB
Phenol, 2-methoxy-4-(2-propen-1-yl)-, 1-acetate	HMDB
Phenol, 2-methoxy-4-(2-propenyl)-, acetate	HMDB
Phenol, 4-allyl-2-methoxy-, acetate	HMDB
(2-Methoxy-4-prop-2-enylphenyl) acetate	HMDB
2-Methoxy-4-(2-propenyl)phenol acetate	HMDB
Aceteugenol	HMDB
O-Acetyleugenol	HMDB
Aceto eugenol	biospider
Eugenyl acetic acid	Generator

Predicted Properties

Property	Value	Source
Water Solubility	0.15 g/L	ALOGPS
logP	3	ALOGPS
logP	2.52	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	57.94 m³·mol⁻¹	ChemAxon
Polarizability	22.28 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C12H14O3

IUPAC name

2-methoxy-4-(prop-2-en-1-yl)phenyl acetate

InChI Identifier

InChI=1S/C12H14O3/c1-4-5-10-6-7-11(15-9(2)13)12(8-10)14-3/h4,6-8H,1,5H2,2-3H3

InChI Key

SCCDQYPEOIRVGX-UHFFFAOYSA-N

Isomeric SMILES

COC1=C(OC(C)=O)C=CC(CC=C)=C1

Average Molecular Weight

206.2378

Monoisotopic Molecular Weight

206.094294314

Classification

Description

Belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol esters

Sub Class

Not Available

Direct Parent

Phenol esters

Alternative Parents

Substituents

Phenol ester
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Carboxylic acid ester
Carboxylic acid derivative
Ether
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:34522 )
benzoate ester (CHEBI:34522 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Subcellular:

Source:

Food

Biological:

Plant

Role

Industrial application:

Food and nutrition:

Flavoring agent

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 69.89%; H 6.84%; O 23.27%	DFC
Melting Point	Mp 30-31°	DFC
Boiling Point	Bp13 163-164°	DFC
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Aceteugenol, non-derivatized, GC-MS Spectrum	splash10-03dl-5900000000-07dccf5db214bbe5da36	Spectrum
GC-MS	Aceteugenol, non-derivatized, GC-MS Spectrum	splash10-03di-1900000000-9c3ff0de59c85e8294b0	Spectrum
GC-MS	Aceteugenol, non-derivatized, GC-MS Spectrum	splash10-03di-4900000000-67c6396f6b356ed19199	Spectrum
GC-MS	Aceteugenol, non-derivatized, GC-MS Spectrum	splash10-03dl-5900000000-07dccf5db214bbe5da36	Spectrum
GC-MS	Aceteugenol, non-derivatized, GC-MS Spectrum	splash10-03di-1900000000-9c3ff0de59c85e8294b0	Spectrum
GC-MS	Aceteugenol, non-derivatized, GC-MS Spectrum	splash10-03di-4900000000-67c6396f6b356ed19199	Spectrum
Predicted GC-MS	Aceteugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03dl-4900000000-a304eb063db0dbfb4754	Spectrum
Predicted GC-MS	Aceteugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-0a4i-0190000000-aac08a05e91542bc8ee6	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-0a4i-0490000000-7b507551acbb774fdb39	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-0a4r-0970000000-103298343d2eeedb4b71	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-052r-0930000000-790979ed2c402e55985f	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-052r-0920000000-fca2cfe497d7997a05d9	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-052r-0910000000-85b083c7cb397c23ae7d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-052r-0900000000-cd22b7ee4e8289af04cd	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, positive	splash10-059i-0900000000-bffea5112bca02611ffb	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 8V, positive	splash10-05br-0900000000-b4fc4d81a5f5db11ba7d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, positive	splash10-05dr-0900000000-9c4086a215cced0aaebc	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 12V, positive	splash10-00bi-0900000000-d5a5b0376c1d44d53269	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 15V, positive	splash10-004i-1900000000-fa5b9e1fa96c52be882a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 18V, positive	splash10-004i-3900000000-cf5ef9e2fee8299440e9	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 21V, positive	splash10-004l-5900000000-e7818cc62a6d1f999ef8	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 27V, positive	splash10-0fvi-9700000000-096c27413dd813f427c8	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 14V, positive	splash10-000i-0900000000-34fbb1b55cebae7182b3	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 14V, positive	splash10-004i-0900000000-73ec60ea1131e1a25937	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 14V, positive	splash10-000i-0900000000-af68f4a566c5bf7574cb	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 14V, positive	splash10-0a4i-4900000000-cd4aeb3ab174f068fb15	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 14V, positive	splash10-00di-0900000000-3742e23de9fd8aace948	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 14V, positive	splash10-0a4j-0900000000-9720dfd149796e13f607	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-000i-0900000000-a327ab73af988d78e268	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-000i-0900000000-5a75ad949f6ef3df602a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, positive	splash10-000i-0900000000-b0b4702efee1e3322428	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, positive	splash10-0079-0900000000-7ecf1428cf5a2ae600b5	2020-07-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

647

DrugBank ID

Not Available

HMDB ID

HMDB34122

CRC / DFC (Dictionary of Food Compounds) ID

HDW90-Y:HGS52-P

EAFUS ID

1327

Dr. Duke ID

EUGENYL-ACETATE|ACETOEUGENOL|ACETYL-EUGENOL|EUGENOL-ACETATE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1005011

SuperScent ID

7136

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
acaricide	22153	A substance used to destroy pests of the subclass Acari (mites and ticks).	DUKE
anti aggregant			DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE
anti prostaglandin	49020	A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.	DUKE
anti radicular			DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
cholagogue			DUKE
perfumery	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
prostaglandin synthesis inhibitor	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
trypsin enhancer			DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
clove	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fresh	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
floral	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
carnation	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
malt	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spice	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.