chavicol profile

Chavicol, also known as estragole, is a phenylpropene derivative with a pleasant, sweet, licorice-like aroma. It is a naturally occurring compound found in various plants, including basil, tarragon, and star anise. Chavicol is synthesized through the condensation of cinnamaldehyde with sodium hydroxide. It has been shown to exhibit a range of biological activities, including antioxidant, anti-inflammatory, and antimicrobial properties. Its antifungal and antibacterial activities against various pathogens make it a potential candidate for the development of new antimicrobial agents. Chavicol's ability to inhibit the growth of certain cancer cell lines has also been investigated. Additionally, it is studied for its potential role in plant defense mechanisms. The compound is also used as a flavoring agent in the food industry.'

4-allylphenol: an inhibitor of aryl-alcohol oxidase; has free radical scavenging activity [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

chavicol : A phenylpropanoid that is phenol substituted by a prop-2-enyl group at position 4. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

ID Source	ID
PubMed CID	68148
CHEMBL ID	108862
CHEBI ID	50158
SCHEMBL ID	30870

Synonym
4-(prop-2-enyl)-phenol
4-(2-propenyl)phenol
p-chavicol
CHEBI:50158 ,
phenol, p-allyl-
p-allylphenol
nsc-290195
chavicol
nsc290195
501-92-8
4-allylphenol
p-hydroxyallylbenzene
.gamma.-(p-hydroxyphenyl)-.alpha.-propylene
phenol, 4-(2-propenyl)-
gamma-(p-hydroxyphenyl)-alpha-propylene
ccris 3208
einecs 207-929-2
nsc 290195
inchi=1/c9h10o/c1-2-3-8-4-6-9(10)7-5-8/h2,4-7,10h,1,3h2
rgibxdhonmxtli-uhfffaoysa-
4-allyl-phenol
CHEMBL108862
4-prop-2-enylphenol
C16930
AKOS006278514
unii-q5er4k6969
q5er4k6969 ,
chavicol [mi]
fema no. 4075
4-allylphenol [fhfi]
SCHEMBL30870
4-(prop-2-en-1-yl)phenol
DTXSID60198210
mfcd01940501
3-(4-hydroxyphenyl)-1-propene
alpha -propylene
4-(2-propenyl)-phenol
laquo gammaraquo -(p-hydroxyphenyl)-alpha -propylene
3-(p-hydroxyphenyl)-1-propene
phenol, p-allyl- (8ci)
p-allyl-phenol
p-hydroxyallylpropene
phenol, 4-(2-propenyl)- (9ci)
SY045829
Q2504388
AC1877
EN300-698378
CS-12298
A917800
CS-0217169
C3743

Class	Description
phenylpropanoid	Any organic aromatic compound with a structure based on a phenylpropane skeleton. The class includes naturally occurring phenylpropanoid esters, flavonoids, anthocyanins, coumarins and many small phenolic molecules as well as their semi-synthetic and synthetic analogues. Phenylpropanoids are also precursors of lignin.
phenols	Organic aromatic compounds having one or more hydroxy groups attached to a benzene or other arene ring.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathway	Proteins	Compounds
volatile cinnamoic ester biosynthesis	0	16
furcatin degradation	1	7
volatile cinnamoic ester biosynthesis	2	16
furcatin degradation	1	8

Assay ID	Title	Year	Journal	Article
AID247905	Cytotoxicity of compound against human liver tumor cell line (Hep-G2) was determined	2005	Bioorganic & medicinal chemistry letters, Jan-03, Volume: 15, Issue:1	Cytotoxic neolignans: an SAR study.
AID1110759	Nematocidal activity against Caenorhabditis elegans assessed as mortality	2002	Annual review of phytopathology, , Volume: 40	Phytochemical based strategies for nematode control.
AID166551	Percentage inhibition against release of beta-hexosaminidase from RBL-2H3 cells at 100 uM from control	2003	Bioorganic & medicinal chemistry letters, Oct-06, Volume: 13, Issue:19	Antiallergic principles from Alpinia galanga: structural requirements of phenylpropanoids for inhibition of degranulation and release of TNF-alpha and IL-4 in RBL-2H3 cells.
AID252044	Percent inhibition of nitric oxide (NO) production in lipopolysaccharide activated mouse peritoneal macrophages at 100 uM of compound	2005	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 15, Issue:7	Structure-activity relationships of 1'S-1'-acetoxychavicol acetate for inhibitory effect on NO production in lipopolysaccharide-activated mouse peritoneal macrophages.
AID248765	Inhibitory concentration of compound on nitric oxide (NO) production in lipopolysaccharide activated mouse peritoneal macrophages	2005	Bioorganic & medicinal chemistry letters, Apr-01, Volume: 15, Issue:7	Structure-activity relationships of 1'S-1'-acetoxychavicol acetate for inhibitory effect on NO production in lipopolysaccharide-activated mouse peritoneal macrophages.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	5 (50.00)	29.6817
2010's	3 (30.00)	24.3611
2020's	2 (20.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (9.09%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	10 (90.91%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
acetone methyl ketone : A ketone of formula RC(=O)CH3 (R =/= H).	2.02	1	ketone body; methyl ketone; propanones; volatile organic compound	EC 3.5.1.4 (amidase) inhibitor; human metabolite; polar aprotic solvent
catechol [no description available]	3.11	1	catechols	allelochemical; genotoxin; plant metabolite
bis(2-guanidinoethyl)disulfide bis(2-guanidinoethyl)disulfide: bifunctional cation; RN given refers to parent cpd; structure	2.02	1
methyleugenol methyleugenol: structure	7.97	4	phenylpropanoid
acetyleugenol acetyleugenol: from cloves; inhibits arachidonate-, adrenaline-, & collagen-induced platelet aggregation	2.01	1	benzoate ester; phenols
estragole estragole : A phenylpropanoid that is chavicol in which the hydroxy group is replaced by a methoxy group.	2.13	1	alkenylbenzene; monomethoxybenzene; phenylpropanoid	carcinogenic agent; flavouring agent; genotoxin; insect attractant; plant metabolite
2,2'-biphenol biphenyl-2,2'-diol : A member of the class of hydroxybiphenyls carrying hydroxy groups at positions 2 and 2'.	2.02	1	hydroxybiphenyls
rhamnose [no description available]	2.21	1	L-rhamnose
tomatine alpha-tomatine: in tomato fruits and vegetative plant tissues; structure in first source	3.11	1	alkaloid antibiotic; glycoalkaloid; glycoside; steroid alkaloid; tetrasaccharide derivative	antifungal agent; immunological adjuvant; phytotoxin
1'-hydroxyestragole 1'-hydroxyestragole: structure	2.02	1
4-vinylphenol 4-vinylphenol: RN given refers to cpd with locants as specified. 4-hydroxystyrene : A member of the class of phenols that is styrene carrying a hydroxy substituent at position 4.	3.11	1	phenols	human urinary metabolite; human xenobiotic metabolite
glucose, (beta-d)-isomer beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.	2.21	1	D-glucopyranose	epitope; mouse metabolite
allicin [no description available]	3.11	1	botanical anti-fungal agent; sulfoxide	antibacterial agent
2-hydroxychavicol 2-hydroxychavicol: antimutagen from betel leaf; structure given in first source	3.81	3
magnolol [no description available]	2.02	1	biphenyls
honokiol [no description available]	2.02	1	biphenyls
1'-acetoxychavicol acetate 1'-acetoxychavicol acetate: antifungal component of Alpinia galanga; structure given in first source. 1'-acetoxychavicol acetate : An acetate ester that is chavicol acetate substituted by an acetoxy group at position 1'.	7.42	2	acetate ester; phenylpropanoid	antineoplastic agent; NF-kappaB inhibitor; plant metabolite
xylose xylopyranose: structure in first source	2.21	1	D-xylose
rhodioloside [no description available]	2.21	1	glycoside
dihydroguaiaretic acid dihydroguaiaretic acid: lignan extracted form Larrea divaricata; inhibitory to beef heart mitochondrial succinoxidase & NADH-oxidase; RN given refers to cpd without isomeric designation	3.11	1
dehydrodieugenol dehydrodieugenol: structure in first source	2.02	1	biphenyls
3-n-butyl-4,5-dihydrophthalide 3-N-butyl-4,5-dihydrophthalide: from seeds of Apium graveolens Linn.; RN given refers to (-)-isomer; structure given in first source	3.11	1
arabinose [no description available]	2.21	1	L-arabinose	Escherichia coli metabolite; mouse metabolite
e-z cinnamic acid cinnamic acid : A monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia.. trans-cinnamic acid : The E (trans) isomer of cinnamic acid	2.42	2	cinnamic acid	plant metabolite
methyl cinnamate methyl cinnamate: RN given refers to cpd without isomeric designation. methyl cinnamate : A methyl ester resulting from the formal condensation of methyl cinnamic acid with methanol. It is found naturally in the essential oils of Alpinia and Basil leaf oil, and widely used in the flavor and perfume industries.. methyl trans-cinnamate : The E (trans) isomer of methyl cinnamate.	2.13	1	methyl cinnamate	antibacterial agent; fungal metabolite; nematicide; plant metabolite
2-hydroxycinnamic acid trans-2-coumaric acid : The trans-isomer of 2-coumaric acid.. 2-coumaric acid : A monohydroxycinnamic acid in which the hydroxy substituent is located at C-2 of the phenyl ring.	2.42	2	2-coumaric acid; phenols	antioxidant; metabolite
3-coumaric acid 3-coumaric acid: RN given refers to cpd without isomeric designation in Chemline. trans-3-coumaric acid : A 3-coumaric acid that is phenol substituted with trans-2-propenoic acid at position C-3.. 3-coumaric acid : A monohydroxycinnamic acid in which the hydroxy substituent is located at C-3 of the phenyl ring.	2.42	2	3-coumaric acid
trans-4-coumaric acid hydroxycinnamic acid : Any member of the class of cinnamic acids carrying one or more hydroxy substituents.. trans-4-coumaric acid : The trans-isomer of 4-coumaric acid.. 4-coumaric acid : A coumaric acid in which the hydroxy substituent is located at C-4 of the phenyl ring.	2.01	1	4-coumaric acid	food component; mouse metabolite; plant metabolite
glycosides [no description available]	2.21	1
sinapinic acid sinapinic acid: a matrix for matrix-assisted laser desorption technique for protein MW determination; a constituent of propolis. trans-sinapic acid : A sinapic acid in which the double bond has trans-configuration.	2.42	2	sinapic acid	MALDI matrix material; plant metabolite
p-hydroxycinnamaldehyde p-hydroxycinnamaldehyde: an antibacterial substance from the saw fly, Acantholyda parki S.; structure in first source. 4-hydroxycinnamaldehyde : A cinnamaldehyde that is (E)-cinnamaldehyde substituted at position 4 on the phenyl ring by a hydroxy group.	2.42	2	cinnamaldehydes	apoptosis inducer; EC 1.14.13.39 (nitric oxide synthase) inhibitor; plant metabolite
caffeic acid trans-caffeic acid : The trans-isomer of caffeic acid.	2.42	2	caffeic acid	geroprotector; mouse metabolite
4-methoxycinnamic acid [no description available]	2.42	2	cinnamic acids
3-(3,4-dimethoxyphenyl)propenoic acid 3-(3,4-dimethoxyphenyl)propenoic acid: structure given in first source; RN given refers to parent cpd. 3,4-dimethoxycinnamic acid : A methoxycinnamic acid that is trans-cinnamic acid substituted by methoxy groups at positions 3' and 4' respectively.	2.42	2	methoxycinnamic acid
luteolin [no description available]	2.01	1	3'-hydroxyflavonoid; tetrahydroxyflavone	angiogenesis inhibitor; anti-inflammatory agent; antineoplastic agent; apoptosis inducer; c-Jun N-terminal kinase inhibitor; EC 2.3.1.85 (fatty acid synthase) inhibitor; immunomodulator; nephroprotective agent; plant metabolite; radical scavenger; vascular endothelial growth factor receptor antagonist
linoleic acid Linoleic Acid: A doubly unsaturated fatty acid, occurring widely in plant glycosides. It is an essential fatty acid in mammalian nutrition and is used in the biosynthesis of prostaglandins and cell membranes. (From Stedman, 26th ed). linoleic acid : An octadecadienoic acid in which the two double bonds are at positions 9 and 12 and have Z (cis) stereochemistry.	3.11	1	octadecadienoic acid; omega-6 fatty acid	algal metabolite; Daphnia galeata metabolite; plant metabolite
3-(4-hydroxyphenyl)-1-propane 3-(4-hydroxyphenyl)-1-propane: structure given in first source. trans-p-coumaryl alcohol : 4-Hydroxycinnamyl alcohol with E-configuration of the propenyl double bond. It is one of the main monolignols.. 4-hydroxycinnamyl alcohol : A primary alcohol being cinnamyl alcohol hydroxylated at C-4 of the phenyl ring.	2.42	2	4-hydroxycinnamyl alcohol; phenols; phenylpropanoid	monolignol
Pinosylvin methyl ether [no description available]	3.11	1	stilbenoid
caffeic acid phenethyl ester phenethyl caffeate : An alkyl caffeate ester in which 2-phenylethyl is the alkyl component.	2.02	1	alkyl caffeate ester	anti-inflammatory agent; antibacterial agent; antineoplastic agent; antioxidant; antiviral agent; immunomodulator; metabolite; neuroprotective agent
tranilast tranilast: antiallergic drug; potent inhibitor of homologous passive cutaneous anaphylaxis. tranilast : An amidobenzoic acid that is anthranilic acid in which one of the anilino hydrogens is replaced by a 3,4-dimethoxycinnamoyl group.	2.01	1	amidobenzoic acid; cinnamamides; dimethoxybenzene; secondary carboxamide	anti-allergic agent; anti-asthmatic drug; antineoplastic agent; aryl hydrocarbon receptor agonist; calcium channel blocker; hepatoprotective agent; nephroprotective agent
apis apiose: RN given refers to (D)-isomer; structure	2.21	1	carbohydrate

chavicol

Description

Cross-References

Synonyms (51)

Drug Classes (2)

Pathways (2)

Bioassays (5)

Research

Studies (10)

Market Indicators

Research Demand Index: 58.63

Study Types