Showing Compound Card for trans-Anethol (CDB000333)

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Record Information
Version1.0
Created at2020-03-19 00:31:27 UTC
Updated at2020-12-07 19:07:22 UTC
CannabisDB IDCDB000333
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Nametrans-Anethol
DescriptionTrans-Anethole, also known as E-Anethole, Anise camphor or simply Anethole belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof. It is also classified as a phenylpropene. There are two known Anethole isomers including Trans- and Cis-anethole. The more abundant isomer, and the one preferred for use, is the trans or E isomer. Trans-Anethole is a neutral, hydrophobic molecule that is not water soluble. Anethole has a sweet, anise, licorice aroma. Anethole is distinctly sweet, measuring 13 times sweeter than sugar. It is perceived as being pleasant to the taste even at higher concentrations. It is used in alcoholic drinks ouzo, rakı, anisette and absinthe, among others. It is also used in seasoning and confectionery applications, oral hygiene products, and in small quantities in natural berry flavors. It is a widely used food additive and fragrance agent. Anethole is found in a number of different foods and spices such as anises, star anises, fennels sweet basils, dills, and sweet marjorams. Anethole has also been detected, but not quantified in, common oregano, cumins, white mustards, pepper (spice), and caraway. Trans-Anethole is also one of many non-cannabinoid phenols that are found in cannabis plants (PMID: 6991645 ). Anethole has potent antimicrobial, nematicidal and antifungal activities (PMID:11807977 , 17078111 , 18944489 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(e)-1-(4-Methoxyphenyl)propeneChEBI
(e)-1-Methoxy-4-(1-propenyl)benzeneChEBI
(e)-AnetholeChEBI
(e)-p-PropenylanisoleChEBI
trans-4-(1-Propenyl)anisoleChEBI
trans-p-Methoxy-beta-methylstyreneChEBI
t-AnetholeKegg
trans-AnetholeKegg
trans-p-Methoxy-b-methylstyreneGenerator
trans-p-Methoxy-β-methylstyreneGenerator
Anethole, (Z)-isomerMeSH
1-Methoxy-4-(1-propenyl)benzeneMeSH
Anethole, (e)-isomerMeSH
p-PropenylanisoleMeSH
1-(4-Methoxyphenyl)propeneMeSH
1-Methoxy-4-(1E)-1-propen-1-ylbenzenePhytoBank
(E)-1-p-MethoxyphenylpropenePhytoBank
(E)-AnetholPhytoBank
1-Methoxy-4-[(1E)-1-propenyl]benzenePhytoBank
trans-1-(4-Methoxyphenyl)-1-propenePhytoBank
trans-1-(p-Methoxyphenyl)-1-propenePhytoBank
trans-1-(p-Methoxyphenyl)propenePhytoBank
trans-1-p-AnisylpropenePhytoBank
trans-AnetholPhytoBank
trans-p-AnetholePhytoBank
1-Methoxy-4-(1-propen-1-yl)benzenePhytoBank
1-Methoxy-4-propenylbenzenePhytoBank
1-Propene, 1-(4-methoxyphenyl)-PhytoBank
4-(1-Propenyl)anisolePhytoBank
4-(Propen-1-yl)anisolePhytoBank
4-Methoxy-1-propenylbenzenePhytoBank
4-MethoxypropenylbenzenePhytoBank
4-PropenylanisolePhytoBank
AnetholPhytoBank
AnetholePhytoBank
Anise camphorPhytoBank
IsoestragolePhytoBank
p-1-PropenylanisolePhytoBank
p-AnetholePhytoBank
p-Methoxy-beta-methylstyrenePhytoBank
p-Methoxy-β-methylstyrenePhytoBank
p-Propenylphenyl methyl etherPhytoBank
Chemical FormulaC10H12O
Average Molecular Weight148.21
Monoisotopic Molecular Weight148.0888
IUPAC Name1-methoxy-4-[(1E)-prop-1-en-1-yl]benzene
Traditional Nameanethole
CAS Registry Number12002-40-3
SMILES
COC1=CC=C(\C=C\C)C=C1
InChI Identifier
InChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3-8H,1-2H3/b4-3+
InChI KeyRUVINXPYWBROJD-ONEGZZNKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as anisoles. These are organic compounds containing a methoxybenzene or a derivative thereof.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassAnisoles
Direct ParentAnisoles
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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.4ALOGPS
logP2.94ChemAxon
logS-2.9ALOGPS
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area9.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity47.88 m³·mol⁻¹ChemAxon
Polarizability17.46 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MStrans-Anethol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-007k-1900000000-6b0b95ae56bd0b27ee12Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0002-0900000000-bfec50cc06010c66f2f62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0002-0900000000-90d955c9cfaf352cdf922020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-006t-0900000000-d77f74b9e25056082f472020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-00dj-0900000000-f7e82599c9afb925f6fe2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-00di-0900000000-8635dd0b15dd10a4bc832020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-00di-0900000000-cec0a9a52424ef59c68c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-00di-0900000000-4b056688218e5df1d9d92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-00di-0900000000-5fb552b62bd5b51a2c142020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-00di-2900000000-2025d1a8c37d1430def42020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-00dl-5900000000-833a39db24ba102e3d842020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-0096-9600000000-2be4c6fe22307d19d4902020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 11V, positivesplash10-002f-9200000000-f04f3112b1d4617f5fce2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 13V, positivesplash10-00ou-9100000000-aceb3fe1562024ff36b92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-00di-0900000000-c70a1009bba6e4f3a2c82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-0006-9000000000-de4ad288da2744eda9892020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, positivesplash10-004i-9000000000-791c4364189bf936d4c32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-00di-1900000000-91e07b08a0a8b9313cbd2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-00di-3900000000-82171be86f6a553d59fa2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-00dl-7900000000-e648f7744375626c9f7d2020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-436711faeb648ff2a2d52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-2900000000-7d9dfbe23492f9be6a292016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fr6-9600000000-582716ef7e52a802bbc12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-e66c5cd440af8e6d0c882016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-709cb24546c67c386dde2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-3900000000-ecda3d7970e587876f662016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00002713
Chemspider IDNot Available
KEGG Compound IDC10428
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAnethole
METLIN IDNot Available
PubChem Compound637563
PDB IDNot Available
ChEBI ID35616
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. De M, De AK, Sen P, Banerjee AB: Antimicrobial properties of star anise (Illicium verum Hook f). Phytother Res. 2002 Feb;16(1):94-5. doi: 10.1002/ptr.989. [PubMed:11807977 ]
  3. Fujita K, Fujita T, Kubo I: Anethole, a potential antimicrobial synergist, converts a fungistatic dodecanol to a fungicidal agent. Phytother Res. 2007 Jan;21(1):47-51. doi: 10.1002/ptr.2016. [PubMed:17078111 ]
  4. Oka Y, Nacar S, Putievsky E, Ravid U, Yaniv Z, Spiegel Y: Nematicidal activity of essential oils and their components against the root-knot nematode. Phytopathology. 2000 Jul;90(7):710-5. doi: 10.1094/PHYTO.2000.90.7.710. [PubMed:18944489 ]