AFCDB: Isoeugenol (FDB002728)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:30 UTC

Update date

2020-09-17 15:35:23 UTC

Primary ID

FDB002728

Secondary Accession Numbers

Not Available

Chemical Information

FooDB 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
Not Available	Not Available

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

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Environmental:

Tobacco smoke

Biological:

Animal

Plant:

Biological location:

Subcellular:

Biofluid and excreta:

Saliva

Role

Industrial application:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 73.15%; H 7.37%; O 19.49%	DFC
Melting Point	-10 oC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	3.04	GRIFFIN,S ET AL. (1999)
Experimental pKa	9.88
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
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0ik9-7900000000-d378eaa3d6e1b33ea92e	2014-09-20	View 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	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 11V, positive	splash10-0a4i-0900000000-66bdcdfc1f3c9d7059ef	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 11V, positive	splash10-0a4i-2900000000-1eef4e3fa8cc372a7bd0	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, positive	splash10-000i-0900000000-568dabede3d6d65eef27	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-000i-0900000000-704d8c207b799f62a165	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-0079-1900000000-dc5eb5b27b41f37fff51	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-00du-6900000000-724fc19b181ae95ed7f0	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, positive	splash10-0006-9400000000-e33fcab9c4877cbfaaa8	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, positive	splash10-00kf-9100000000-7581434dd013744b10fe	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 11V, positive	splash10-014l-9000000000-a332174b204c08062e14	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 14V, positive	splash10-014i-9000000000-eca4e980b9dcfbfa0d88	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-51b1ddd89b75760804fb	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-59e54fb66a534d3ff6dc	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-92bea35f22ee86583e9f	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0900000000-976746f8642ed9cede8f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-2900000000-aeeef853384070786115	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f6x-9400000000-28c3454817ba3f918700	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-ba4c51d900ead0baa741	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0900000000-b71be30e0aefb9374dd3	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0535-4900000000-dc2d63615991af22ecd9	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0159-0900000000-6f75a3780b4d03c3f78f	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00m3-2900000000-f418214add56c19743ea	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00or-9000000000-95268ee51bd407edd9b8	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-8db47caa9667c101bd0f	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03ds-0900000000-c240e3167c4ef90295d0	2021-09-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

18224

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB05802

CRC / DFC (Dictionary of Food Compounds) ID

CNH06-V:CNH06-V

EAFUS ID

1886

Dr. Duke ID

ISOEUGENOL

BIGG ID

Not Available

KNApSAcK ID

C00000620

HET ID

EUG

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

97-54-1

GoodScent ID

rw1006911

SuperScent ID

Not Available

Wikipedia ID

Isoeugenol

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
allergenic	50904	A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.	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 TNF	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
bacteristat	33282	A substance that kills or slows the growth of bacteria.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
candidistat			DUKE
cytotoxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE
fungistat			DUKE
motor depressant			DUKE
motor stimulant			DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
sedative	35717	A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.	DUKE
trichomonistat			DUKE

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
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.
clove	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.
carnation	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.

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Isoeugenol (FDB002728)

Structure for FDB002728 (Isoeugenol)