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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:54:06 UTC

Update Date

2023-02-21 17:23:53 UTC

HMDB ID

HMDB0034107

Secondary Accession Numbers

HMDB34107

Metabolite Identification

Common Name

Chavicol

Description

Chavicol, 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	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

Chemical Formula

C₉H₁₀O

Average Molecular Weight

134.1751

Monoisotopic Molecular Weight

134.073164942

IUPAC Name

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

Traditional Name

chavicol

CAS Registry Number

501-92-8

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 Key

RGIBXDHONMXTLI-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.

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

Cellular substructure

Extracellular (HMDB: HMDB0034107)
Cytoplasm (HMDB: HMDB0034107)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034107)

Source

Exogenous

Exogenous (HMDB: HMDB0034107)

Food

Food (HMDB: HMDB0034107)

Herb and spice

Spice

Herb

Sweet basil (FooDB: FOOD00119)
Sweet marjoram (FooDB: FOOD00122)

Fruit

Tropical fruit

Pineapple (FooDB: FOOD00012)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Endogenous

Plant

Plant (HMDB: HMDB0034107)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034107)

Industrial application

Agriculture

Pesticide

Fungicide (HMDB: HMDB0034107)
Nematicide (HMDB: HMDB0034107)

Pesticide (HMDB: HMDB0034107)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	16 °C	Not Available
Boiling Point	234.00 to 236.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1110 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.910	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	129.36	31661259
DarkChem	[M-H]-	126.973	31661259
DeepCCS	[M+H]+	129.186	30932474
DeepCCS	[M-H]-	125.658	30932474
DeepCCS	[M-2H]-	162.854	30932474
DeepCCS	[M+Na]+	138.393	30932474
AllCCS	[M+H]+	126.6	32859911
AllCCS	[M+H-H2O]+	121.8	32859911
AllCCS	[M+NH4]+	131.0	32859911
AllCCS	[M+Na]+	132.3	32859911
AllCCS	[M-H]-	126.0	32859911
AllCCS	[M+Na-2H]-	127.5	32859911
AllCCS	[M+HCOO]-	129.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.97 minutes	32390414
Predicted by Siyang on May 30, 2022	13.8201 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.51 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	33.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1780.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	466.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	188.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	320.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	342.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	578.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	577.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	121.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1222.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	470.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1219.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	407.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	415.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	490.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	282.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	69.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Chavicol	OC1=CC=C(CC=C)C=C1	2225.1	Standard polar	33892256
Chavicol	OC1=CC=C(CC=C)C=C1	1222.9	Standard non polar	33892256
Chavicol	OC1=CC=C(CC=C)C=C1	1246.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Chavicol,1TMS,isomer #1	C=CCC1=CC=C(O[Si](C)(C)C)C=C1	1317.4	Semi standard non polar	33892256
Chavicol,1TBDMS,isomer #1	C=CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	1569.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Chavicol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a7i-5900000000-11cee9744d22eb93e167	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chavicol GC-MS (1 TMS) - 70eV, Positive	splash10-05c6-5910000000-7900910b5dbf1db02b3a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Chavicol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chavicol 10V, Positive-QTOF	splash10-000i-0900000000-a1d20c3e3cabaf3d7046	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chavicol 20V, Positive-QTOF	splash10-000i-2900000000-e73bf4d314fb93006997	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chavicol 40V, Positive-QTOF	splash10-014l-9400000000-40119cbfc7560de6be63	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chavicol 10V, Negative-QTOF	splash10-001i-0900000000-617b61173e6f36fe521e	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chavicol 20V, Negative-QTOF	splash10-001i-0900000000-8e1744ff0d8d0e413886	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chavicol 40V, Negative-QTOF	splash10-0fsl-6900000000-c8e8472546321e19a5b5	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chavicol 10V, Positive-QTOF	splash10-0a4i-2900000000-01e30c58a3acf046cc60	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chavicol 20V, Positive-QTOF	splash10-0a6u-9600000000-b0af3d932f868d71af42	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chavicol 40V, Positive-QTOF	splash10-004l-9000000000-0c47676acacbc005f602	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chavicol 10V, Negative-QTOF	splash10-001i-0900000000-b646282963ddd573b4f4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chavicol 20V, Negative-QTOF	splash10-001i-1900000000-a985243dae14c1d86bf8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chavicol 40V, Negative-QTOF	splash10-01t9-9000000000-9768124ac2659e800cc1	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chavicol

METLIN ID

Not Available

PubChem Compound

68148

PDB ID

Not Available

ChEBI ID

50158

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1015241

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Chavicol (HMDB0034107)

MOL for HMDB0034107 (Chavicol)

3D MOL for HMDB0034107 (Chavicol)

3D SDF for HMDB0034107 (Chavicol)

3D-SDF for HMDB0034107 (Chavicol)

PDB for HMDB0034107 (Chavicol)

3D PDB for HMDB0034107 (Chavicol)

SMILES for HMDB0034107 (Chavicol)

INCHI for HMDB0034107 (Chavicol)

Structure for HMDB0034107 (Chavicol)

3D Structure for HMDB0034107 (Chavicol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra