Showing Compound Anethole (FDB002793)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:31 UTC

Update date

2020-09-17 15:36:19 UTC

Primary ID

FDB002793

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Anethole

Description

Anethole or 1-Methoxy-4(1-propenyl)-benzene, belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. Anethole is an extremely weak basic (essentially neutral) compound (based on its pKa). Anethol is a naturally occurring organic compound found in the essential oils of many plants such as anise, fennel, anise myrtle, liquorice as their large component of the odor and flavor. Anethole is a sweet, anise, and balsam tasting compound. It is used as a flavoring agent in alcoholic drinks and in small quantities in natural berry flavors. Anethole is found in a lower concentration in peppermints, wild celeries, and corianders. Anethole has also been detected, but not quantified in, several different foods, such as nutmegs, cumins, lemon balms, common thymes, and herbs and spices. This could make anethole a potential biomarker for the consumption of these foods. Anethole has potent antimicrobial, nematicidal and antifungal activities (PMID:11807977, 17078111, 18944489). There are two known anethol isomers including Cis- and Trans-anethol.

CAS Number

4180-23-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1-Methoxy-4-[(1Z)-prop-1-en-1-yl]benzene	ChEBI
(e)-1-(4-Methoxyphenyl)propene	HMDB
(e)-1-Methoxy-4-(1-propenyl)benzene	HMDB
(e)-1-P-Methoxyphenylpropene	HMDB
(e)-Anethol	HMDB
(e)-Anethole	HMDB
(e)-P-Propenylanisole	HMDB
1-(4-Methoxyphenyl)-1(3)-propene	HMDB
1-(Methyloxy)-4-[(1E)-prop-1-en-1-yl]benzene	HMDB
1-(P-Methoxyphenyl)-propene	HMDB
1-Methoxy-4-((1E)-1-propenyl)benzene	HMDB
1-Methoxy-4-(1-propenyl)-(e)-benzene	HMDB
1-Methoxy-4-(1-propenyl)benzene, 9ci	HMDB
1-Methoxy-4-(1E)-1-propen-1-yl-benzene	HMDB
1-Methoxy-4-(1E)-1-propenyl-benzene	HMDB
1-Methoxy-4-(propen-1-yl)-benzene	HMDB
1-Methoxy-4-(propenyl)-benzene	HMDB
1-Methoxy-4-propenylbenzene	HMDB
1-Methoxy-4-[(1E)-prop-1-en-1-yl]benzene	HMDB
4-Methoxy-1-propenylbenzene	HMDB
4-Methoxypropenylbenzene	HMDB
4-Propenylanisole	HMDB
Anethole, usan	HMDB
Anise camphor	HMDB
Anisole, P-propenyl-, (e)- (8ci)	HMDB
Anistearoptene	HMDB
e-Anethole	HMDB
FEMA 2086	HMDB
Isoestragole	HMDB
Methoxy-4-propenylbenzene	HMDB
P-Anethole	HMDB
P-Propenyl-trans-anisole	HMDB
P-Propenylanisole, 8ci	HMDB
P-Propenylphenyl methyl ether	HMDB
trans-1-(4-Methoxyphenyl)-1-propene	HMDB
trans-1-(P-Methoxyphenyl)-1-propene	HMDB
trans-1-(P-Methoxyphenyl)propene	HMDB
trans-1-Methoxy-4-(1-propenyl)benzene	HMDB
trans-1-P-Anisylpropene	HMDB
trans-4-(1-Propenyl)anisole	HMDB
trans-Anethole	HMDB
trans-Anise camphor	HMDB
trans-P-Anethole	HMDB
trans-P-Methoxy-beta-methylstyrene	HMDB
trans-P-Propenylanisole	HMDB
(E)-1-(4-Methoxyphenyl)propene	biospider
(E)-1-Methoxy-4-(1-propenyl)benzene	biospider
(E)-1-p-Methoxyphenylpropene	biospider
(E)-Anethol	biospider
(E)-anethole	biospider
(E)-p-propenylanisole	biospider
1-Methoxy-4-(1-propenyl)benzene, (E)-	biospider
1-Methoxy-4-(1-propenyl)benzene, 9CI	db_source
1-methoxy-4-[(1E)-prop-1-en-1-yl]benzene	biospider
Anethole, USAN	db_source
Anisole, p-propenyl-, (E)- (8CI)	biospider
Anisole, p-propenyl-, trans-	biospider
Benzene, 1-methoxy-4-(1-propenyl)-, (E)-	biospider
Benzene, 1-methoxy-4-(1E)-1-propen-1-yl-	biospider
Benzene, 1-methoxy-4-(1E)-1-propenyl-	biospider
Benzene, 1-methoxy-4-(propen-1-yl)-	biospider
Benzene, 1-methoxy-4-(propenyl)-	biospider
E-anethole	biospider
Methoxy-beta-methylstyrene, trans-p-	biospider
P-anethole	biospider
p-Propenylanisole, 8CI	db_source
P-propenylphenyl methyl ether	biospider
Propene, 1-(p-methoxyphenyl)-	biospider
trans-1-(p-Methoxyphenyl)-1-propene	biospider
trans-1-(p-Methoxyphenyl)propene	biospider
trans-1-p-Anisylpropene	biospider
Trans-anethole	biospider
Trans-anise camphor	biospider
Trans-p-anethole	biospider
Trans-p-methoxy-beta-methylstyrene	biospider
Trans-p-propenylanisole	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.18 g/L	ALOGPS
logP	3.4	ALOGPS
logP	2.94	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.88 m³·mol⁻¹	ChemAxon
Polarizability	17.21 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

Chemical Formula

C10H12O

IUPAC name

1-methoxy-4-[(1Z)-prop-1-en-1-yl]benzene

InChI Identifier

InChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3/b4-3-

InChI Key

RUVINXPYWBROJD-ARJAWSKDSA-N

Isomeric SMILES

COC1=CC=C(\C=C/C)C=C1

Average Molecular Weight

148.2017

Monoisotopic Molecular Weight

148.088815006

Classification

Description

Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Phenoxy compound
Methoxybenzene
Styrene
Anisole
Alkyl aryl ether
Monocyclic benzene moiety
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

anethole (CHEBI:78412 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Subcellular:

Biofluid and excreta:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	liquid
Physical Description	Not Available
Mass Composition	C 81.04%; H 8.16%; O 10.80%	DFC
Melting Point	Mp 22.5°	DFC
Boiling Point	Bp 235°	DFC
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	[neutral] lmax 259 (e 22300) (MeOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Anethole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000t-2900000000-0665985a70ac9c27eb53	Spectrum
Predicted GC-MS	Anethole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-436711faeb648ff2a2d5	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-2900000000-7d9dfbe23492f9be6a29	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fr6-9600000000-582716ef7e52a802bbc1	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-e66c5cd440af8e6d0c88	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-709cb24546c67c386dde	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-3900000000-ecda3d7970e587876f66	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-c2f74e33d816bec66aa0	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-5aa2093882ee9ccdc886	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-053r-3900000000-03b30da0f9adb9d580ff	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-d856cd34f2f6f83def66	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dj-2900000000-b32a050861e7a927efa5	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9100000000-e059cbeab65dc16bd3b4	Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

637563

Pubchem Substance ID

Not Available

ChEBI ID

35616

Phenol-Explorer ID

645

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

HBT07-B:CNR12-S

EAFUS ID

213

Dr. Duke ID

ANETHOL|ANETHOLE|TRANS-ANETHOLE

BIGG ID

Not Available

KNApSAcK ID

C00029334

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1001151

SuperScent ID

637563

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Knapsack: C00002713

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
allergenic	50904	A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.	DUKE
analgesic	35480	An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.	DUKE
anesthetic			DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti genotoxic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti hepatotic	62868	Any compound that is able to prevent damage to the liver.	DUKE
anti inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti NF-kappa-B	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	DUKE
anti radicular			DUKE
anti salmonella	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti TNF	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
anti yeast	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
calcium antagonist	48706	Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
candidicide			DUKE
carminative			DUKE
dermatitigenic			DUKE
digestive			DUKE
estrogenic			DUKE
expectorant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
gastrostimulant	55324	A drug used for its effects on the gastrointestinal system, e.g. controlling gastric acidity, regulating gastrointestinal motility and water flow, and improving digestion.	DUKE
hepatotoxic	50908	A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.	DUKE
immunostimulant	50847	A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.	DUKE
insecticide	24852	Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.	DUKE
irritant			DUKE
lactagogue			DUKE
leucocytogenic			DUKE
mutagenic			DUKE
nephroprotective	76595	Any protective agent that is able to prevent damage to the kidney.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
secretogogue			DUKE
secretolytic			DUKE
sweetener	50505	Substance that sweeten food, beverages, medications, etc.	DUKE
sympathomimetic	35524	A drug that mimics the effects of stimulating postganglionic adrenergic sympathetic nerves. Included in this class are drugs that directly stimulate adrenergic receptors and drugs that act indirectly by provoking the release of adrenergic transmitters.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
anise	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
balsam	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
licorice	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
mimosa	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.