Showing Compound Chavicol (FDB012373)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:08 UTC

Update date

2019-11-26 03:06:39 UTC

Primary ID

FDB012373

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Chavicol

Description

Chavicol, also known as p-allylphenol or alpha -propylene, belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. Chavicol is an extremely weak basic (essentially neutral) compound (based on its pKa). Chavicol is a medicinal and phenolic tasting compound. Chavicol is found, on average, in the highest concentration within a few different foods, such as cloves, sweet marjorams, and sweet basils and in a lower concentration in pineapples. Chavicol has also been detected, but not quantified in, several different foods, such as allspices, chinese cinnamons, fats and oils, and gingers. This could make chavicol a potential biomarker for the consumption of these foods.

CAS Number

501-92-8

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
4-(2-Propenyl)phenol	ChEBI
4-(Prop-2-enyl)-phenol	ChEBI
4-Allylphenol	ChEBI
gamma-(p-Hydroxyphenyl)-alpha-propylene	ChEBI
p-Allylphenol	ChEBI
p-Chavicol	ChEBI
p-Hydroxyallylbenzene	ChEBI
g-(p-Hydroxyphenyl)-a-propylene	Generator
Γ-(p-hydroxyphenyl)-α-propylene	Generator
3-(p-Hydroxyphenyl)-1-propene	HMDB
4-(2-Propenyl)-phenol	HMDB
alpha -Propylene	HMDB
Laquo gammaraquo -(p-hydroxyphenyl)-alpha -propylene	HMDB
p-Allyl-phenol	HMDB
p-Hydroxyallylpropene	HMDB
Phenol, 4-(2-propenyl)- (9ci)	HMDB
Phenol, p-allyl- (8ci)	HMDB
α-propylene	biospider
«gamma»-(p-hydroxyphenyl)-α-propylene	biospider
Chavicol	db_source
g-(P-Hydroxyphenyl)-a-propylene	Generator
Gamma-(p-hydroxyphenyl)-alpha-propylene	biospider
Laquo gammaraquo -(P-hydroxyphenyl)-alpha -propylene	HMDB
P-Allyl-phenol	HMDB
P-chavicol	biospider
Phenol, 4-(2-propenyl)-	biospider
Phenol, 4-(2-propenyl)- (9CI)	biospider
Phenol, p-allyl-	biospider
Phenol, p-allyl- (8CI)	biospider
γ-(P-hydroxyphenyl)-α-propylene	Generator

Predicted Properties

Property	Value	Source
Water Solubility	2.46 g/L	ALOGPS
logP	2.46	ALOGPS
logP	2.77	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	42.33 m³·mol⁻¹	ChemAxon
Polarizability	14.95 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	Yes	ChemAxon

Chemical Formula

C9H10O

IUPAC name

4-(prop-2-en-1-yl)phenol

InChI Identifier

InChI=1S/C9H10O/c1-2-3-8-4-6-9(10)7-5-8/h2,4-7,10H,1,3H2

InChI Key

RGIBXDHONMXTLI-UHFFFAOYSA-N

Isomeric SMILES

OC1=CC=C(CC=C)C=C1

Average Molecular Weight

134.1751

Monoisotopic Molecular Weight

134.073164942

Classification

Description

belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-2-unsubstituted benzenoids

Direct Parent

1-hydroxy-2-unsubstituted benzenoids

Alternative Parents

Substituents

1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:50158 )
phenylpropanoid (CHEBI:50158 )
Monolignols (C16930 )
a phenol (CPD-6483 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Nutrient

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 80.56%; H 7.51%; O 11.92%	DFC
Melting Point	Mp 16°	DFC
Boiling Point	Bp17 120°	DFC
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	pKa1 10.23 (25°)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a7i-5900000000-11cee9744d22eb93e167	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05c6-5910000000-7900910b5dbf1db02b3a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0900000000-a1d20c3e3cabaf3d7046	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-2900000000-e73bf4d314fb93006997	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014l-9400000000-40119cbfc7560de6be63	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-617b61173e6f36fe521e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0900000000-8e1744ff0d8d0e413886	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fsl-6900000000-c8e8472546321e19a5b5	JSpectraViewer

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

50158

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB34107

CRC / DFC (Dictionary of Food Compounds) ID

HGQ74-N:HGQ74-N

EAFUS ID

118

Dr. Duke ID

4-ALLYL-PHENOL|CHAVICOL

BIGG ID

Not Available

KNApSAcK ID

C00000621

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

501-92-8

GoodScent ID

rw1015241

SuperScent ID

Not Available

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
fungicide	24127	A substance used to destroy fungal pests.	DUKE
nematicide	25491	A substance used to destroy pests of the phylum Nematoda (roundworms).	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

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
medicine	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
phenol	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
phenolic	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
medicinal	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

Not Available

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).

Showing Compound Chavicol (FDB012373)

Structure for FDB012373 (Chavicol)