CHAVICOL

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 Search

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

Approval Year

PubMed

Title	Date	PubMed
An investigation of the storage and biosynthesis of phenylpropenes in sweet basil.	2001 Feb	11161012
Quantitative analysis of detailed lignin monomer composition by pyrolysis-gas chromatography combined with preliminary acetylation of the samples.	2001 Nov 15	11816569
Resonance Raman spectroscopy and quantum chemical calculations reveal structural changes in the active site of photoactive yellow protein.	2002 Apr 30	11969428
First in vitro norlignan formation with Asparagus officinalis enzyme preparation.	2002 May 21	12122678
Transcriptional control of monolignol biosynthesis in Pinus taeda: factors affecting monolignol ratios and carbon allocation in phenylpropanoid metabolism.	2002 May 24	11891223
Adsorption of anthocyanins by yeast cell walls during the fermentation of red wines.	2003 Jul 2	12822951
Analysis of grape and wine anthocyanins by HPLC-MS.	2003 Sep 10	12952411
Initial steps of signal generation in photoactive yellow protein revealed with femtosecond mid-infrared spectroscopy.	2003 Sep 2	12939133
A heartwood norlignan, (E)-hinokiresinol, is formed from 4-coumaryl 4-coumarate by a Cryptomeria japonica enzyme preparation.	2004 Dec 21	15599432
Resonance Raman spectroscopy reveals the origin of an intermediate wavelength form in photoactive yellow protein.	2004 Mar 2	14979724
Furcatin hydrolase from Viburnum furcatum Blume is a novel disaccharide-specific acuminosidase in glycosyl hydrolase family 1.	2004 May 28	14976214
Expeditious synthesis of bioactive allylphenol constituents of the genus Piper through a metal-free photoallylation procedure.	2005 Aug 7	16032365
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 Jan	15619268
Xylem parenchyma cells deliver the H2O2 necessary for lignification in differentiating xylem vessels.	2005 Mar	15747145
Ultrafast dynamics of isolated model photoactive yellow protein chromophores: "Chemical perturbation theory" in the laboratory.	2005 Mar 10	16851482
Characterization of basic p-coumaryl and coniferyl alcohol oxidizing peroxidases from a lignin-forming Picea abies suspension culture.	2005 May	16027971
Molecular requirements of lignin-carbohydrate complexes for expression of unique biological activities.	2005 Sep	15978643
Structural characterization of a serendipitously discovered bioactive macromolecule, lignin sulfate.	2005 Sep-Oct	16153124
Chemical synthesis of beta-O-4 type artificial lignin.	2006 Apr 7	16557323
beta-Glucosidase catalyzing specific hydrolysis of an iridoid beta-glucoside from Plumeria obtusa.	2006 Aug	16894479
Mechanistic and structural studies of apoform, binary, and ternary complexes of the Arabidopsis alkenal double bond reductase At5g16970.	2006 Dec 29	17028190
Chavicol formation in sweet basil (Ocimum basilicum): cleavage of an esterified C9 hydroxyl group with NAD(P)H-dependent reduction.	2006 Jul 21	16826298
Chemical composition of abaca (Musa textilis) leaf fibers used for manufacturing of high quality paper pulps.	2006 Jun 28	16787004
Vibrational assignment of the 4-hydroxycinnamyl chromophore in photoactive yellow protein.	2007 Mar 15	17311445
Looking for syringyl peroxidases.	2007 Nov	17928259
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 Sep 1	17624297
Synthesis and Activity Evaluation of 2-(1-naphtho[2,1-b]furan-2-yl-carbonyl)-3,5-disubstituted-2,3-dihydro-1H-pyrazoles.	2008 Nov	21369430
Use of biosensors as alternatives to current regulatory methods for marine biotoxins.	2009	22291571
Use of physiologically based biokinetic (PBBK) modeling to study estragole bioactivation and detoxification in humans as compared with male rats.	2009 Aug	19447879
Study of the metabolism of estragole in humans consuming fennel tea.	2009 Dec	19908891
pH Dependence of the photoactive yellow protein photocycle recovery reaction reveals a new late photocycle intermediate with a deprotonated chromophore.	2009 Feb 20	19091750
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 Jan	18987218
SAM levels, gene expression of SAM synthetase, methionine synthase and ACC oxidase, and ethylene emission from N. suaveolens flowers.	2009 Jul	19396585
Chemical diversity and defence metabolism: how plants cope with pathogens and ozone pollution.	2009 Jul 30	20111684
Structure-function analyses of a caffeic acid O-methyltransferase from perennial ryegrass reveal the molecular basis for substrate preference.	2010 Dec	21177481
Fast pyrolysis of palm kernel shells: influence of operation parameters on the bio-oil yield and the yield of phenol and phenolic compounds.	2010 Dec	20667720
Sequencing around 5-hydroxyconiferyl alcohol-derived units in caffeic acid O-methyltransferase-deficient poplar lignins.	2010 Jun	20427467
Functional analysis of a cinnamyl alcohol dehydrogenase involved in lignin biosynthesis in wheat.	2010 Jun	20400532
Advances in modifying lignin for enhanced biofuel production.	2010 Jun	20359939
Free radical scavenging activity and anthocyanin profile of Cabernet Sauvignon wines from the Balkan region.	2010 Jun 10	20657436
Identifying new lignin bioengineering targets: 1. Monolignol-substitute impacts on lignin formation and cell wall fermentability.	2010 Jun 17	20565789
Subunit composition of hinokiresinol synthase controls enantiomeric selectivity in hinokiresinol formation.	2010 Mar 7	20165801
Differential detection of genetic Loci underlying stem and root lignin content in Populus.	2010 Nov 22	21151641
Distribution of lignin-carbohydrate complex in plant kingdom and its functionality as alternative medicine.	2010 Oct	20547183

Patents

Name

Type

Language

CHAVICOL

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

4-ALLYLPHENOL

Systematic Name

English

P-HYDROXYALLYLBENZENE

Common Name

English

P-ALLYLPHENOL

Common Name

English

Classification Tree Code System Code

JECFA EVALUATION

4-ALLYLPHENOL