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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:54:06 UTC
Update Date2021-10-13 06:38:48 UTC
HMDB IDHMDB0034107
Secondary Accession Numbers
  • HMDB34107
Metabolite Identification
Common 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. Chavicol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Chavicol.
Structure
Data?1563862512
Synonyms
ValueSource
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
Chemical FormulaC9H10O
Average Molecular Weight134.1751
Monoisotopic Molecular Weight134.073164942
IUPAC Name4-(prop-2-en-1-yl)phenol
Traditional Namechavicol
CAS Registry Number501-92-8
SMILES
OC1=CC=C(CC=C)C=C1
InChI Identifier
InChI=1S/C9H10O/c1-2-3-8-4-6-9(10)7-5-8/h2,4-7,10H,1,3H2
InChI KeyRGIBXDHONMXTLI-UHFFFAOYSA-N
Chemical Taxonomy
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

Biological location

Source

Route of exposure

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point16 °CNot Available
Boiling Point234.00 to 236.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1110 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.910The Good Scents Company Information System
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.46 g/LALOGPS
logP10(2.46) g/LALOGPS
logP10(2.77) g/LChemAxon
logS10(-1.7) g/LALOGPS
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
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+129.3631661259
DarkChem[M-H]-126.97331661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Chavicol,1TMS,#1C=CCC1=CC=C(O[Si](C)(C)C)C=C11317.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Chavicol,1TBDMS,#1C=CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C11569.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Chavicol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a7i-5900000000-11cee9744d22eb93e1672017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chavicol GC-MS (1 TMS) - 70eV, Positivesplash10-05c6-5910000000-7900910b5dbf1db02b3a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Chavicol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chavicol 10V, Positive-QTOFsplash10-000i-0900000000-a1d20c3e3cabaf3d70462015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chavicol 20V, Positive-QTOFsplash10-000i-2900000000-e73bf4d314fb930069972015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chavicol 40V, Positive-QTOFsplash10-014l-9400000000-40119cbfc7560de6be632015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chavicol 10V, Negative-QTOFsplash10-001i-0900000000-617b61173e6f36fe521e2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chavicol 20V, Negative-QTOFsplash10-001i-0900000000-8e1744ff0d8d0e4138862015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chavicol 40V, Negative-QTOFsplash10-0fsl-6900000000-c8e8472546321e19a5b52015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chavicol 10V, Positive-QTOFsplash10-0a4i-2900000000-01e30c58a3acf046cc602021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chavicol 20V, Positive-QTOFsplash10-0a6u-9600000000-b0af3d932f868d71af422021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chavicol 40V, Positive-QTOFsplash10-004l-9000000000-0c47676acacbc005f6022021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chavicol 10V, Negative-QTOFsplash10-001i-0900000000-b646282963ddd573b4f42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chavicol 20V, Negative-QTOFsplash10-001i-1900000000-a985243dae14c1d86bf82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Chavicol 40V, Negative-QTOFsplash10-01t9-9000000000-9768124ac2659e800cc12021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012373
KNApSAcK IDC00000621
Chemspider ID21105856
KEGG Compound IDC16930
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChavicol
METLIN IDNot Available
PubChem Compound68148
PDB IDNot Available
ChEBI ID50158
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1015241
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .