Record Information
Version1.0
Creation date2010-04-08 22:10:08 UTC
Update date2019-11-26 03:06:39 UTC
Primary IDFDB012373
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameChavicol
DescriptionChavicol, also known as 4-allylphenol, 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 a medicinal and phenolic tasting compound. Chavicol is found, on average, in the highest concentration within a few different foods, such as cloves (Syzygium aromaticum), sweet marjorams (Origanum majorana), and sweet basils (Ocimum basilicum) and in a lower concentration in pineapples (Ananas comosus). Chavicol has also been detected, but not quantified in, several different foods, such as allspices (Pimenta dioica), chinese cinnamons (Cinnamomum aromaticum), fats and oils, and gingers (Zingiber officinale). This could make chavicol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Chavicol.
CAS Number501-92-8
Structure
Thumb
Synonyms
SynonymSource
4-(2-Propenyl)phenolChEBI
4-(Prop-2-enyl)-phenolChEBI
4-AllylphenolChEBI
gamma-(p-Hydroxyphenyl)-alpha-propyleneChEBI
p-AllylphenolChEBI
p-ChavicolChEBI
p-HydroxyallylbenzeneChEBI
g-(p-Hydroxyphenyl)-a-propyleneGenerator
Γ-(p-hydroxyphenyl)-α-propyleneGenerator
3-(P-Hydroxyphenyl)-1-propeneHMDB
4-(2-Propenyl)-phenolHMDB
alpha -PropyleneHMDB
laquo gammaraquo -(P-Hydroxyphenyl)-alpha -propyleneHMDB
P-Allyl-phenolHMDB
P-HydroxyallylpropeneHMDB
Phenol, 4-(2-propenyl)- (9ci)HMDB
Phenol, P-allyl- (8ci)HMDB
α-propylenebiospider
«gamma»-(p-hydroxyphenyl)-α-propylenebiospider
3-(p-Hydroxyphenyl)-1-propenedb_source
Chavicoldb_source
g-(P-Hydroxyphenyl)-a-propyleneGenerator
Gamma-(p-hydroxyphenyl)-alpha-propylenebiospider
Laquo gammaraquo -(P-hydroxyphenyl)-alpha -propyleneHMDB
P-chavicolbiospider
p-Hydroxyallylpropenebiospider
Phenol, 4-(2-propenyl)-biospider
Phenol, 4-(2-propenyl)- (9CI)biospider
Phenol, p-allyl-biospider
Phenol, p-allyl- (8CI)biospider
γ-(P-hydroxyphenyl)-α-propyleneGenerator
Predicted Properties
PropertyValueSource
Water Solubility2.46 g/LALOGPS
logP2.46ALOGPS
logP2.77ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)9.5ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.33 m³·mol⁻¹ChemAxon
Polarizability14.95 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H10O
IUPAC name4-(prop-2-en-1-yl)phenol
InChI IdentifierInChI=1S/C9H10O/c1-2-3-8-4-6-9(10)7-5-8/h2,4-7,10H,1,3H2
InChI KeyRGIBXDHONMXTLI-UHFFFAOYSA-N
Isomeric SMILESOC1=CC=C(CC=C)C=C1
Average Molecular Weight134.1751
Monoisotopic Molecular Weight134.073164942
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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub Class1-hydroxy-2-unsubstituted benzenoids
Direct Parent1-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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 80.56%; H 7.51%; O 11.92%DFC
Melting PointMp 16°DFC
Boiling PointBp17 120°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKapKa1 10.23 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSChavicol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a7i-5900000000-11cee9744d22eb93e167Spectrum
Predicted GC-MSChavicol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05c6-5910000000-7900910b5dbf1db02b3aSpectrum
Predicted GC-MSChavicol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0900000000-a1d20c3e3cabaf3d7046Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-2900000000-e73bf4d314fb93006997Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9400000000-40119cbfc7560de6be63Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-617b61173e6f36fe521eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-8e1744ff0d8d0e413886Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fsl-6900000000-c8e8472546321e19a5b5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-2900000000-01e30c58a3acf046cc60Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6u-9600000000-b0af3d932f868d71af42Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004l-9000000000-0c47676acacbc005f602Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-b646282963ddd573b4f4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1900000000-a985243dae14c1d86bf8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-9000000000-9768124ac2659e800cc1Spectrum
NMRNot Available
ChemSpider ID21105856
ChEMBL IDCHEMBL108862
KEGG Compound IDC16930
Pubchem Compound ID68148
Pubchem Substance IDNot Available
ChEBI ID50158
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34107
CRC / DFC (Dictionary of Food Compounds) IDHGQ74-N:HGQ74-N
EAFUS ID118
Dr. Duke ID4-ALLYL-PHENOL|CHAVICOL
BIGG IDNot Available
KNApSAcK IDC00000621
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID501-92-8
GoodScent IDrw1015241
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
fungicide24127 A substance used to destroy fungal pests.DUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
medicine
  1. 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
  1. 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
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
medicinal
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).