Showing Compound Card for 1-Methoxy-4(1-propenyl)-benzene (CDB000732)

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Record Information
Version1.0
Created at2020-03-19 00:53:42 UTC
Updated at2020-11-18 16:35:28 UTC
CannabisDB IDCDB000732
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name1-Methoxy-4(1-propenyl)-benzene
DescriptionAnethole 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 ). Anethol is one of small numbers of methyl ethers of phenols including cis-anethol, tram- anetliol and methyleugenol found in cannabis plants (PMID:6991645 ). There are two known anethol isomers including Cis- and Trans-anethol.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Methoxy-4-[(1Z)-prop-1-en-1-yl]benzeneChEBI
(e)-1-(4-Methoxyphenyl)propeneHMDB
(e)-1-Methoxy-4-(1-propenyl)benzeneHMDB
(e)-1-P-MethoxyphenylpropeneHMDB
(e)-AnetholHMDB
(e)-AnetholeHMDB
(e)-P-PropenylanisoleHMDB
1-(4-Methoxyphenyl)-1(3)-propeneHMDB
1-(Methyloxy)-4-[(1E)-prop-1-en-1-yl]benzeneHMDB
1-(P-Methoxyphenyl)-propeneHMDB
1-Methoxy-4-((1E)-1-propenyl)benzeneHMDB
1-Methoxy-4-(1-propenyl)-(e)-benzeneHMDB
1-Methoxy-4-(1-propenyl)benzene, 9ciHMDB
1-Methoxy-4-(1E)-1-propen-1-yl-benzeneHMDB
1-Methoxy-4-(1E)-1-propenyl-benzeneHMDB
1-Methoxy-4-(propen-1-yl)-benzeneHMDB
1-Methoxy-4-(propenyl)-benzeneHMDB
1-Methoxy-4-propenylbenzeneHMDB
1-Methoxy-4-[(1E)-prop-1-en-1-yl]benzeneHMDB
4-Methoxy-1-propenylbenzeneHMDB
4-MethoxypropenylbenzeneHMDB
4-PropenylanisoleHMDB
Anethole, usanHMDB
Anise camphorHMDB
Anisole, P-propenyl-, (e)- (8ci)HMDB
AnistearopteneHMDB
e-AnetholeHMDB
FEMA 2086HMDB
IsoestragoleHMDB
Methoxy-4-propenylbenzeneHMDB
P-AnetholeHMDB
P-Propenyl-trans-anisoleHMDB
P-Propenylanisole, 8ciHMDB
P-Propenylphenyl methyl etherHMDB
trans-1-(4-Methoxyphenyl)-1-propeneHMDB
trans-1-(P-Methoxyphenyl)-1-propeneHMDB
trans-1-(P-Methoxyphenyl)propeneHMDB
trans-1-Methoxy-4-(1-propenyl)benzeneHMDB
trans-1-P-AnisylpropeneHMDB
trans-4-(1-Propenyl)anisoleHMDB
trans-AnetholeHMDB
trans-Anise camphorHMDB
trans-P-AnetholeHMDB
trans-P-Methoxy-beta-methylstyreneHMDB
trans-P-PropenylanisoleHMDB
Chemical FormulaC10H12O
Average Molecular Weight148.2
Monoisotopic Molecular Weight148.0888
IUPAC Name1-methoxy-4-[(1Z)-prop-1-en-1-yl]benzene
Traditional Nameanethole (trans)
CAS Registry Number25679-28-1
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-ARJAWSKDSA-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
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point22.5 °CNot 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
Polarizability17.21 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-MScis-anethol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000t-2900000000-0665985a70ac9c27eb53Spectrum
Predicted GC-MScis-anethol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
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
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-c2f74e33d816bec66aa02021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-5aa2093882ee9ccdc8862021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-3900000000-03b30da0f9adb9d580ff2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-d856cd34f2f6f83def662021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dj-2900000000-b32a050861e7a927efa52021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9100000000-e059cbeab65dc16bd3b42021-09-23View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0030837
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002793
KNApSAcK IDC00002713
Chemspider ID1266027
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAnethole
METLIN IDNot Available
PubChem Compound1549040
PDB IDNot Available
ChEBI ID78412
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]