Showing Compound (E)-Isoeugenol (FDB012403)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:09 UTC

Update date

2019-11-26 03:06:43 UTC

Primary ID

FDB012403

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(E)-Isoeugenol

Description

(e)-isoeugenol, also known as 2-methoxy-4-propenylphenol or propenylgualacol, is a member of the class of compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety (e)-isoeugenol is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). (e)-isoeugenol is a sweet, carnation, and clove tasting compound and can be found in a number of food items such as corn salad, coconut, flaxseed, and winter squash, which makes (e)-isoeugenol a potential biomarker for the consumption of these food products (e)-isoeugenol can be found primarily in saliva (e)-isoeugenol exists in all eukaryotes, ranging from yeast to humans (e)-isoeugenol is a non-carcinogenic (not listed by IARC) potentially toxic compound.

CAS Number

5932-68-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(e)-2-Methoxy-4-(prop-1-enyl)phenol	ChEBI
2-Methoxy-4-[(1E)-1-propenyl]phenol	ChEBI
2-Methoxy-4-propenylphenol	ChEBI
3-Methoxy-4-hydroxy-1-propen-1-ylbenzene	ChEBI
3-Methoxy-4-hydroxypropenylbenzene	ChEBI
4-Hydroxy-3-methoxy-1-propenylbenzene	ChEBI
Iso-eugenol 2	ChEBI
Isoeugenol (I)	ChEBI
Isoeugenol e	ChEBI
Isoeugenol trans-form	ChEBI
Propenylgualacol	ChEBI
trans-2-Methoxy-4-(1-propenyl)phenol	ChEBI
trans-2-Methoxy-4-propenylphenol	ChEBI
trans-4-Propenylgualacol	ChEBI
trans-p-Propenylquaiacol	ChEBI
2-Methoxy-4-(prop-1-en-1-yl)phenol	Kegg
(e)-2-Methoxy-4- (1-propenyl)-phenol	HMDB
(e)-2-Methoxy-4-(1-propenyl)-phenol	HMDB
(e)-2-Methoxy-4-propenyl-phenol	HMDB
(E)-Isoeugenol	HMDB
1-(3-Methoxy-4-hydroxyphenyl)-1-propane	HMDB
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	HMDB
2-Methoxy-4-[(1E)-prop-1-en-1-yl]phenol	HMDB
4-Hydroxy-3-methoxy-1-propen-1-ylbenzene	HMDB
4-Hydroxy-3-methoxypropenylbenzene	HMDB
trans-Isoeugenol	HMDB
Isoeugenol, (e)-isomer	MeSH, HMDB
Isoeugenol	MeSH
(E)-2-Methoxy-4-(1-propenyl)phenol	HMDB
(E)-2-Methoxy-4-(prop-1-en-1-yl)phenol	HMDB
1-(3-Methoxy-4-hydroxyphenyl)-1-propene	HMDB
2-Methoxy-4(E)-1-propenylphenol	HMDB
2-Methoxy-4-(1-propen-1-yl)phenol	HMDB
2-Methoxy-4-(1E)-1-propen-1-ylphenol	HMDB
2-Methoxy-4-[(E)-1-propenyl]phenol	HMDB
3-Methoxy-4-hydroxy-1-propenylbenzene	HMDB
4-(1-Propenyl) Guaiacol	HMDB
4-Hydroxy-3-methoxy-beta-methylstyrene	HMDB
4-Hydroxy-3-methoxy-β-methylstyrene	HMDB
4-Propenylguaiacol	HMDB
iso-Eugenol	HMDB
trans-4-Propenylguaiacol	HMDB
trans-p-Propenylguaiacol	HMDB
(E)-2-Methoxy-4-(prop-1-enyl)phenol	biospider
(e)-isoeugenol	biospider
2-methoxy-4-[(1E)-prop-1-en-1-yl]phenol	biospider
E-4-propenyl-2-methoxyphenol	biospider
E-Isoeugenol	biospider
Phenol, 2-methoxy-4-(1-propenyl)-, (E)-	biospider
Phenol, 2-methoxy-4-(1-propenyl)-, (E)- (9CI)	biospider
Phenol, 2-methoxy-4-propenyl-, (E)-	biospider
trans-2-methoxy-4-(1-propenyl)phenol	biospider
Trans-isoeugenol	biospider
Trans-p-propenylquaiacol	biospider

Predicted Properties

Property	Value	Source
Water Solubility	1.36 g/L	ALOGPS
logP	2.79	ALOGPS
logP	2.64	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	10.01	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	49.86 m³·mol⁻¹	ChemAxon
Polarizability	18.3 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

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

Classification

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

Substituents

Methoxyphenol
Phenoxy compound
Methoxybenzene
Styrene
Phenol ether
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

isoeugenol (CHEBI:50545 )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 73.15%; H 7.37%; O 19.49%	DFC
Melting Point	Mp 33°	DFC
Boiling Point	Bp12 140-141°	DFC
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	pKa 9.88 (25°)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	[neutral] lmax 260 (e 15135) (EtOH)	DFC
Density	Not Available
Refractive Index	n20D 1.5790	DFC

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0ik9-7900000000-d378eaa3d6e1b33ea92e	Spectrum
GC-MS	Isoeugenol, non-derivatized, GC-MS Spectrum	splash10-03di-5900000000-d5e9036e83fd9c1033b0	Spectrum
GC-MS	Isoeugenol, non-derivatized, GC-MS Spectrum	splash10-03di-4900000000-f0dd30e91dc041336262	Spectrum
GC-MS	Isoeugenol, non-derivatized, GC-MS Spectrum	splash10-03di-1900000000-1530d67ee6f2740c4978	Spectrum
GC-MS	Isoeugenol, non-derivatized, GC-MS Spectrum	splash10-03di-5900000000-d5e9036e83fd9c1033b0	Spectrum
GC-MS	Isoeugenol, non-derivatized, GC-MS Spectrum	splash10-03di-4900000000-f0dd30e91dc041336262	Spectrum
GC-MS	Isoeugenol, non-derivatized, GC-MS Spectrum	splash10-03di-1900000000-1530d67ee6f2740c4978	Spectrum
Predicted GC-MS	Isoeugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03ds-1900000000-54cb7bf6efac012f1f93	Spectrum
Predicted GC-MS	Isoeugenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-7790000000-39afffdef59235ab22a4	Spectrum
Predicted GC-MS	Isoeugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - n/a 11V, positive	splash10-0019-0900000000-95d2bb40c1282fcc841b	Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 11V, positive	splash10-0a4i-0900000000-66bdcdfc1f3c9d7059ef	Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 11V, positive	splash10-0a4i-2900000000-1eef4e3fa8cc372a7bd0	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-000i-0900000000-568dabede3d6d65eef27	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-000i-0900000000-704d8c207b799f62a165	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-0079-1900000000-dc5eb5b27b41f37fff51	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-00du-6900000000-724fc19b181ae95ed7f0	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, positive	splash10-0006-9400000000-e33fcab9c4877cbfaaa8	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, positive	splash10-00kf-9100000000-7581434dd013744b10fe	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 11V, positive	splash10-014l-9000000000-a332174b204c08062e14	Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 14V, positive	splash10-014i-9000000000-eca4e980b9dcfbfa0d88	Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-51b1ddd89b75760804fb	Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-59e54fb66a534d3ff6dc	Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-92bea35f22ee86583e9f	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-976746f8642ed9cede8f	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-2900000000-aeeef853384070786115	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f6x-9400000000-28c3454817ba3f918700	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-ba4c51d900ead0baa741	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0900000000-b71be30e0aefb9374dd3	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0535-4900000000-dc2d63615991af22ecd9	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0159-0900000000-6f75a3780b4d03c3f78f	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00m3-2900000000-f418214add56c19743ea	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00or-9000000000-95268ee51bd407edd9b8	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-8db47caa9667c101bd0f	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03ds-0900000000-c240e3167c4ef90295d0	Spectrum

NMR

Type	Description		View
1D NMR	1H NMR Spectrum		Spectrum
1D NMR	13C NMR Spectrum		Spectrum

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

853433

Pubchem Substance ID

Not Available

ChEBI ID

50545

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

CNH06-V:HGS84-A

EAFUS ID

Not Available

Dr. Duke ID

TRANS-ISOEUGENOL

BIGG ID

Not Available

KNApSAcK ID

C00035095

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

GoodScent ID

SuperScent ID

Wikipedia ID

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

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
flower	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
clove	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spicy	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.
phenolic	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.