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Details

Stereochemistry ACHIRAL
Molecular Formula C9H10O
Molecular Weight 134.1751
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CHAVICOL

SMILES

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

InChI

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

HIDE SMILES / InChI

Molecular Formula C9H10O
Molecular Weight 134.1751
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

PubMed

PubMed

TitleDatePubMed
Structure-function analyses of a caffeic acid O-methyltransferase from perennial ryegrass reveal the molecular basis for substrate preference.
2010-12
Fast pyrolysis of palm kernel shells: influence of operation parameters on the bio-oil yield and the yield of phenol and phenolic compounds.
2010-12
Differential detection of genetic Loci underlying stem and root lignin content in Populus.
2010-11-22
Distribution of lignin-carbohydrate complex in plant kingdom and its functionality as alternative medicine.
2010-10
Identifying new lignin bioengineering targets: 1. Monolignol-substitute impacts on lignin formation and cell wall fermentability.
2010-06-17
Free radical scavenging activity and anthocyanin profile of Cabernet Sauvignon wines from the Balkan region.
2010-06-10
Sequencing around 5-hydroxyconiferyl alcohol-derived units in caffeic acid O-methyltransferase-deficient poplar lignins.
2010-06
Functional analysis of a cinnamyl alcohol dehydrogenase involved in lignin biosynthesis in wheat.
2010-06
Advances in modifying lignin for enhanced biofuel production.
2010-06
Subunit composition of hinokiresinol synthase controls enantiomeric selectivity in hinokiresinol formation.
2010-03-07
Study of the metabolism of estragole in humans consuming fennel tea.
2009-12
Use of physiologically based biokinetic (PBBK) modeling to study estragole bioactivation and detoxification in humans as compared with male rats.
2009-08
Chemical diversity and defence metabolism: how plants cope with pathogens and ozone pollution.
2009-07-30
SAM levels, gene expression of SAM synthetase, methionine synthase and ACC oxidase, and ethylene emission from N. suaveolens flowers.
2009-07
Effect of naturally occurring hydroxychavicol acetate on the cytokine production in T helper cells.
2009-04
pH Dependence of the photoactive yellow protein photocycle recovery reaction reveals a new late photocycle intermediate with a deprotonated chromophore.
2009-02-20
Biosynthesis of t-anethole in anise: characterization of t-anol/isoeugenol synthase and an O-methyltransferase specific for a C7-C8 propenyl side chain.
2009-01
Use of biosensors as alternatives to current regulatory methods for marine biotoxins.
2009
Synthesis and Activity Evaluation of 2-(1-naphtho[2,1-b]furan-2-yl-carbonyl)-3,5-disubstituted-2,3-dihydro-1H-pyrazoles.
2008-11
A physiologically based biokinetic (PBBK) model for estragole bioactivation and detoxification in rat.
2008-09-01
Looking for syringyl peroxidases.
2007-11
Structure and reaction mechanism of basil eugenol synthase.
2007-10-03
A pinoresinol-lariciresinol reductase homologue from the creosote bush (Larrea tridentata) catalyzes the efficient in vitro conversion of p-coumaryl/coniferyl alcohol esters into the allylphenols chavicol/eugenol, but not the propenylphenols p-anol/isoeugenol.
2007-09-01
Vibrational assignment of the 4-hydroxycinnamyl chromophore in photoactive yellow protein.
2007-03-15
Mechanistic and structural studies of apoform, binary, and ternary complexes of the Arabidopsis alkenal double bond reductase At5g16970.
2006-12-29
beta-Glucosidase catalyzing specific hydrolysis of an iridoid beta-glucoside from Plumeria obtusa.
2006-08
Chavicol formation in sweet basil (Ocimum basilicum): cleavage of an esterified C9 hydroxyl group with NAD(P)H-dependent reduction.
2006-07-21
Chemical composition of abaca (Musa textilis) leaf fibers used for manufacturing of high quality paper pulps.
2006-06-28
Chemical synthesis of beta-O-4 type artificial lignin.
2006-04-07
Structural characterization of a serendipitously discovered bioactive macromolecule, lignin sulfate.
2005-09-13
Molecular requirements of lignin-carbohydrate complexes for expression of unique biological activities.
2005-09
Expeditious synthesis of bioactive allylphenol constituents of the genus Piper through a metal-free photoallylation procedure.
2005-08-07
Characterization of basic p-coumaryl and coniferyl alcohol oxidizing peroxidases from a lignin-forming Picea abies suspension culture.
2005-05
Ultrafast dynamics of isolated model photoactive yellow protein chromophores: "Chemical perturbation theory" in the laboratory.
2005-03-10
Xylem parenchyma cells deliver the H2O2 necessary for lignification in differentiating xylem vessels.
2005-03
Mass spectrometry in the study of anthocyanins and their derivatives: differentiation of Vitis vinifera and hybrid grapes by liquid chromatography/electrospray ionization mass spectrometry and tandem mass spectrometry.
2005-01
A heartwood norlignan, (E)-hinokiresinol, is formed from 4-coumaryl 4-coumarate by a Cryptomeria japonica enzyme preparation.
2004-12-21
Furcatin hydrolase from Viburnum furcatum Blume is a novel disaccharide-specific acuminosidase in glycosyl hydrolase family 1.
2004-05-28
Resonance Raman spectroscopy reveals the origin of an intermediate wavelength form in photoactive yellow protein.
2004-03-02
Analysis of grape and wine anthocyanins by HPLC-MS.
2003-09-10
Initial steps of signal generation in photoactive yellow protein revealed with femtosecond mid-infrared spectroscopy.
2003-09-02
Adsorption of anthocyanins by yeast cell walls during the fermentation of red wines.
2003-07-02
Differential production of meta hydroxylated phenylpropanoids in sweet basil peltate glandular trichomes and leaves is controlled by the activities of specific acyltransferases and hydroxylases.
2002-11
Transcriptional control of monolignol biosynthesis in Pinus taeda: factors affecting monolignol ratios and carbon allocation in phenylpropanoid metabolism.
2002-05-24
First in vitro norlignan formation with Asparagus officinalis enzyme preparation.
2002-05-21
Resonance Raman spectroscopy and quantum chemical calculations reveal structural changes in the active site of photoactive yellow protein.
2002-04-30
Characterization of phenylpropene O-methyltransferases from sweet basil: facile change of substrate specificity and convergent evolution within a plant O-methyltransferase family.
2002-02
Quantitative analysis of detailed lignin monomer composition by pyrolysis-gas chromatography combined with preliminary acetylation of the samples.
2001-11-15
Differential activity and structure of highly similar peroxidases. Spectroscopic, crystallographic, and enzymatic analyses of lignifying Arabidopsis thaliana peroxidase A2 and horseradish peroxidase A2.
2001-09-18
A sensitive fluorescence monitor for the detection of activated Ras: total chemical synthesis of site-specifically labeled Ras binding domain of c-Raf1 immobilized on a surface.
2001-03
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:57:15 GMT 2025
Edited
by admin
on Mon Mar 31 19:57:15 GMT 2025
Record UNII
Q5ER4K6969
Record Status Validated (UNII)
Record Version
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Name Type Language
4-ALLYLPHENOL
FHFI  
Preferred Name English
CHAVICOL
MI  
Systematic Name English
CHAVICOL [MI]
Common Name English
NSC-290195
Code English
PHENOL, P-ALLYL-
Common Name English
4-ALLYLPHENOL [FHFI]
Common Name English
FEMA NO. 4075
Code English
PHENOL, 4-(2-PROPENYL)-
Systematic Name English
P-HYDROXYALLYLBENZENE
Common Name English
P-ALLYLPHENOL
Common Name English
Classification Tree Code System Code
JECFA EVALUATION 4-ALLYLPHENOL
Created by admin on Mon Mar 31 19:57:15 GMT 2025 , Edited by admin on Mon Mar 31 19:57:15 GMT 2025
Code System Code Type Description
ECHA (EC/EINECS)
207-929-2
Created by admin on Mon Mar 31 19:57:15 GMT 2025 , Edited by admin on Mon Mar 31 19:57:15 GMT 2025
PRIMARY
MESH
C007633
Created by admin on Mon Mar 31 19:57:15 GMT 2025 , Edited by admin on Mon Mar 31 19:57:15 GMT 2025
PRIMARY
EPA CompTox
DTXSID60198210
Created by admin on Mon Mar 31 19:57:15 GMT 2025 , Edited by admin on Mon Mar 31 19:57:15 GMT 2025
PRIMARY
CHEBI
50158
Created by admin on Mon Mar 31 19:57:15 GMT 2025 , Edited by admin on Mon Mar 31 19:57:15 GMT 2025
PRIMARY
NSC
290195
Created by admin on Mon Mar 31 19:57:15 GMT 2025 , Edited by admin on Mon Mar 31 19:57:15 GMT 2025
PRIMARY
WIKIPEDIA
CHAVICOL
Created by admin on Mon Mar 31 19:57:15 GMT 2025 , Edited by admin on Mon Mar 31 19:57:15 GMT 2025
PRIMARY
FDA UNII
Q5ER4K6969
Created by admin on Mon Mar 31 19:57:15 GMT 2025 , Edited by admin on Mon Mar 31 19:57:15 GMT 2025
PRIMARY
CAS
501-92-8
Created by admin on Mon Mar 31 19:57:15 GMT 2025 , Edited by admin on Mon Mar 31 19:57:15 GMT 2025
PRIMARY
PUBCHEM
68148
Created by admin on Mon Mar 31 19:57:15 GMT 2025 , Edited by admin on Mon Mar 31 19:57:15 GMT 2025
PRIMARY
JECFA MONOGRAPH
1518
Created by admin on Mon Mar 31 19:57:15 GMT 2025 , Edited by admin on Mon Mar 31 19:57:15 GMT 2025
PRIMARY
MERCK INDEX
m3319
Created by admin on Mon Mar 31 19:57:15 GMT 2025 , Edited by admin on Mon Mar 31 19:57:15 GMT 2025
PRIMARY Merck Index