Cannabis Compound Database: Showing Compound Card for lsoeugenol (CDB000628)

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Record Information

Version

1.0

Created at

2020-03-19 00:47:29 UTC

Updated at

2020-12-07 19:07:35 UTC

CannabisDB ID

CDB000628

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

lsoeugenol

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. Isoeugenol is also a component of wood smoke and liquid smoke. It is one of several phenolic compounds responsible for the mold-inhibiting effect of smoke on meats and cheeses. Isoeugenol (specifically the acetate ester) has also been used in the production of vanillin. Isoeugenol is one of several non-cannabinoid phenols found in cannabis plants (PMID: 6991645 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	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

Chemical Formula

C₁₀H₁₂O₂

Average Molecular Weight

164.2

Monoisotopic Molecular Weight

164.0837

IUPAC Name

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

Traditional Name

isoeugenol

CAS Registry Number

5932-68-3

SMILES

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

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

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

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

Indirect biological role:

Allergen

Industrial application:

Personal care products:

Perfuming agent

Food and nutrition:

Flavoring agent

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	-10 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	3.04	GRIFFIN,S ET AL. (1999)

Predicted Properties

Property	Value	Source
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

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	iso-eugenol, non-derivatized, GC-MS Spectrum	splash10-03di-5900000000-d5e9036e83fd9c1033b0	Spectrum
GC-MS	iso-eugenol, non-derivatized, GC-MS Spectrum	splash10-03di-4900000000-f0dd30e91dc041336262	Spectrum
GC-MS	iso-eugenol, non-derivatized, GC-MS Spectrum	splash10-03di-1900000000-1530d67ee6f2740c4978	Spectrum
GC-MS	iso-eugenol, non-derivatized, GC-MS Spectrum	splash10-03di-5900000000-d5e9036e83fd9c1033b0	Spectrum
GC-MS	iso-eugenol, non-derivatized, GC-MS Spectrum	splash10-03di-4900000000-f0dd30e91dc041336262	Spectrum
GC-MS	iso-eugenol, non-derivatized, GC-MS Spectrum	splash10-03di-1900000000-1530d67ee6f2740c4978	Spectrum
Predicted GC-MS	iso-eugenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03ds-1900000000-54cb7bf6efac012f1f93	Spectrum
Predicted GC-MS	iso-eugenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-7790000000-39afffdef59235ab22a4	Spectrum
Predicted GC-MS	iso-eugenol, 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

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0005802

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Isoeugenol

METLIN ID

Not Available

PubChem Compound

853433

PDB ID

Not Available

ChEBI ID

50545

References

General References

Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
White IR, Johansen JD, Arnau EG, Lepoittevin JP, Rastogi S, Bruze M, Andersen KE, Frosch PJ, Goossens A, Menne T: Isoeugenol is an important contact allergen: can it be safely replaced with isoeugenyl acetate? Contact Dermatitis. 1999 Nov;41(5):272-5. doi: 10.1111/j.1600-0536.1999.tb06160.x. [PubMed:10554062 ]

Showing Compound Card for lsoeugenol (CDB000628)

Structure for CDB000628 (lsoeugenol)