Showing Compound Card for 2-Methoxy-4-propylphenol (CDB006385)

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Record Information
Version1.0
Created at2021-01-13 17:43:52 UTC
Updated at2021-01-13 17:43:54 UTC
CannabisDB IDCDB006385
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name2-Methoxy-4-propylphenol
Description2-Methoxy-4-propylphenol, also known as dihydroeugenol, 4-propyl-2-methoxyphenol or 4-propylguaiacol, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. 2-Methoxy-4-propylphenol is one of several structural isomers of propylmethoxyphenol wherein the propyl and methoxy groups are substituted at different positions of phenol. 2-Methoxy-4-propylphenol exists as a clear, colorless liquid that is water soluble. It has a spicey, sharp, sweet, allspice odor and a spicy peppery or clove like taste. 2-Methoxy-4-propylphenol is found naturally in a number of foods including beer, brandy, gruyere cheese, fish, pork, rum, sherry, tea and whiskey. It is also found in Bordeaux windes liquid smoke, karanda fruit and oregano. 2-Methoxy-4-propylphenol is widely used as a food additive and a perfuming agent in cosmetics and household products. It is used to enhance the profile of smoke flavors, clove, spicy nuances for cinnamon and pepper, vanilla, and fruit nuances. Traces (0.5-1%) can be found in many consumer products such as candles, detergent, shampoo, softeners and soap. 2-Methoxy-4-propylphenol is also used as a pheromone for the Northern corn rootworm. It has also been shown to have anti-oxidant effects and inhibits lipid peroxidation and scanvenges superoxide and hydroxyl radicals (PMID: 11045452 ). Propylmethoxyphenols are found in marijuana (cannabis) smoke. 2-Methoxy-4-propylphenol is formed during the combustion of cannabis and is therefore a constituent of cannabis smoke ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(4-Hydroxy-3-methoxyphenyl)propaneHMDB
1-(4-Hydroxy-3-methoxyphenyl)propaneHMDB
1-Propyl-3-methoxy-4-hydroxybenzeneHMDB
2-Methoxy-4-(1-propyl)phenolHMDB
2-Methoxy-4-N-propylphenolHMDB
2-Methoxy-4-propyl-phenolHMDB
2-Methoxy-4-propylphenol (P-propylguaiacol)HMDB
2-Methoxy-4-propylphenol, 9ciHMDB
4-Hydroxy-3-methoxypropylbenzeneHMDB
4-Propyl-2-methoxyphenolHMDB
4-Propyl-2-methoxyphenol (4-propylguaiacol)HMDB
4-Propyl-guaiacolHMDB
4-Propyl-O-methoxyphenolHMDB
4-PropylguaiacolHMDB
5-Propyl-O-hydroxyanisoleHMDB
CerulignolHMDB
CoerulignolHMDB
DihydroeugenolHMDB
Eugenol dihydroHMDB
GuaiacylpropaneHMDB
P-N-PropylguaiacolHMDB
P-PropylguaiacolHMDB
Phenol, 4-propyl, 2-methoxyHMDB
PropylguaiacolHMDB
Chemical FormulaC10H14O2
Average Molecular Weight166.217
Monoisotopic Molecular Weight166.099379692
IUPAC Name2-methoxy-4-propylphenol
Traditional Namephenol, 2-methoxy-4-propyl-
CAS Registry NumberNot Available
SMILES
CCCC1=CC(OC)=C(O)C=C1
InChI Identifier
InChI=1S/C10H14O2/c1-3-4-8-5-6-9(11)10(7-8)12-2/h5-7,11H,3-4H2,1-2H3
InChI KeyPXIKRTCSSLJURC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenylpropane
  • Phenoxy compound
  • Methoxybenzene
  • Phenol ether
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.87ALOGPS
logP2.91ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)10.29ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.75 m³·mol⁻¹ChemAxon
Polarizability18.78 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-000i-7900000000-972dcdcdab5502fe481a2014-09-20View Spectrum
Predicted GC-MS2-Methoxy-4-propylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f9i-2900000000-51ab1f04188439c1f663Spectrum
Predicted GC-MS2-Methoxy-4-propylphenol, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-8690000000-12ed44035d829a9f7ff4Spectrum
Predicted GC-MS2-Methoxy-4-propylphenol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-646bc22bdc72fdc8df592016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2900000000-60aaf34920a151b1ce532016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9200000000-bb7502bb9a87017830952016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-397c386607b8c61e83b42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-a72a438f24be53c7f6402016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05mn-4900000000-c92b92d205fe2182af192016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-349584a3f625d5b5807f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-93843d8e2b9d8bf8ec662021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06dl-9600000000-470288177a1f018791d92021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0900000000-516a0ffed3b219171b902021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016v-5900000000-b4131d503f35ea1463862021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-005c-9100000000-0fc7a6cb0cf0bac4a9062021-09-22View Spectrum
NMR
TypeDescriptionView
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0032135
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008859
KNApSAcK IDNot Available
Chemspider ID16763
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound17739
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Ogata M, Hoshi M, Urano S, Endo T: Antioxidant activity of eugenol and related monomeric and dimeric compounds. Chem Pharm Bull (Tokyo). 2000 Oct;48(10):1467-9. doi: 10.1248/cpb.48.1467. [PubMed:11045452 ]