Showing Compound Card for 4-Hydroxy-3-methoxystyrene (CDB005794)

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Record Information
Version1.0
Created at2020-04-27 16:57:14 UTC
Updated at2021-01-04 18:49:21 UTC
CannabisDB IDCDB005794
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name4-Hydroxy-3-methoxystyrene
Description2-Methoxy-4-vinylphenol, also known as 4-vinylguaiacol or 4-hydroxy-3-methoxystyrene, 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-vinylphenol exists as a clear, colorless liquid. It is weakly soluble in water and has a woody, cedar, clove-like, roasted peanut aroma and a smoky, bacon-like taste. As a food additive it is used in artificial smoke flavors. It is also used in coffee, chocolate, spice, vanilla, tea, whiskey, tum, tobacco, roasted peanut and strawberry flavors. In the cosmetic industry 2-Methoxy-4-vinylphenol is used as a perfuming agent. 2-Methoxy-4-vinylphenol occurs naturally and is found, in a number of different plants, beverages and plant foods including carrots, cauliflowers, broccoli. coffee, beer, cider, apples, asparagus, corn, oats, orange juice, roasted peanuts, raspberries, sesame seeds, rum, strawberries, tea, tomatoes, vanilla, wine and whiskey. 2-methoxy-4-vinylphenol gives beers such as Weissbier and Wit their distinctive "clove" flavor. 2-Methoxy-4-vinylphenol is also found in buckwheat and makes a major contribution to its natural aroma ( Ref:DOI ). 2-Methoxy-4-vinylphenol also acts as a pheromone for some insects such as Rhynchophorus ferrugineus (Red palm weevil). 2-Methoxy-4-vinylphenol is a constituent of cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-(4-Hydroxy-3-methoxyphenyl)etheneChEBI
2m4VPChEBI
4-Ethenyl-2-methoxyphenolChEBI
4-Hydroxy-3-methoxyphenyletheneChEBI
4-Hydroxy-3-methoxystyreneChEBI
4-Hydroxy-3-methoxyvinylbenzeneChEBI
4-Vinyl-2-methoxyphenolChEBI
4-VinylguaiacolChEBI
O-Methoxy-p-vinylphenolChEBI
p-VinylguaiacolChEBI
Para-vinylguaiacolChEBI
2-Methoxy-4-vinyl-phenolHMDB
2-Methoxy-4-vinylphenol (4-vinylguaiacol)HMDB
2-Methoxy-4-vinylphenol (vinylguaiacol)HMDB
2-Methoxy-vinylphenolHMDB
2-Metoxy-4-vinyl-phenolHMDB
4-Ethenyl-2-methoxy-phenolHMDB
4-EthenylguaiacolHMDB
4-Vinyl-2-methoxyphenol ( P-vinylguaiacol)HMDB
4-Vinyl-2-methoxyphenol (4-vinylguaiacol)HMDB
4-Vinyl-O-guaiacolHMDB
4-VinylguaiacoleHMDB
Guaiacol, 4-vinylHMDB
P-Vinyl guaicolHMDB
Phenol, 2-methoxy-4-ethenylHMDB
Phenol, 4-vinyl, 2-methoxyHMDB
VinylguaiacolHMDB
Vinylguaiacol (4-vinyl-2-methoxyphenol)HMDB
VinylguajacolHMDB
Chemical FormulaC9H10O2
Average Molecular Weight150.17
Monoisotopic Molecular Weight150.0681
IUPAC Name4-ethenyl-2-methoxyphenol
Traditional Name2-methoxy-4-vinyl-phenol
CAS Registry Number7786-61-0
SMILES
COC1=C(O)C=CC(C=C)=C1
InChI Identifier
InChI=1S/C9H10O2/c1-3-7-4-5-8(10)9(6-7)11-2/h3-6,10H,1H2,2H3
InChI KeyYOMSJEATGXXYPX-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
  • Phenoxy compound
  • Methoxybenzene
  • Styrene
  • 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 Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

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
logP1.84ALOGPS
logP2.25ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)10.03ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.19 m³·mol⁻¹ChemAxon
Polarizability15.99 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0ug0-9700000000-32bccf98e351d83089242015-03-01View Spectrum
GC-MS4-Hydroxy-3-methoxystyrene, non-derivatized, GC-MS Spectrumsplash10-0udr-6900000000-c95e8007869a915d6fe6Spectrum
GC-MS4-Hydroxy-3-methoxystyrene, non-derivatized, GC-MS Spectrumsplash10-0udr-6900000000-c95e8007869a915d6fe6Spectrum
Predicted GC-MS4-Hydroxy-3-methoxystyrene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0uki-2900000000-6a52b2fb0cd2b1888cbaSpectrum
Predicted GC-MS4-Hydroxy-3-methoxystyrene, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fr-8970000000-109c9889992939114454Spectrum
Predicted GC-MS4-Hydroxy-3-methoxystyrene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , positivesplash10-000i-9800000000-56d5ac2538cf6e5560702020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-000i-9000000000-e8dab5adaa22e054ee212020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0a4i-0900000000-0ecf25f0ebb081e295702020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, negativesplash10-001i-0900000000-90c9c5c165a18a64dbb32020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-001i-0900000000-90c9c5c165a18a64dbb32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-000i-9100000000-4fc1449d3b5ebcebcddc2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-07c85f81abcab35c8c852021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0c00-9200000000-e9c17a72d9b795c9cadc2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-142267324f6352c647e42021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-9de02cce24e40d1314af2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1900000000-04be6d79c3fa5851d78d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-9300000000-bab367ece5e140a115832016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-cd337f7259f32e912e8a2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-5cef2e884a5445e8509b2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00o0-7900000000-27870d0d63eeb1b6290d2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-1900000000-3df4f1c76f8984133ce72021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gdl-7900000000-5c60e1bd99afb019139f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fb9-9000000000-51462e1d8e8381a727122021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-e0b12c10ffeec106d7592021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1900000000-dae1e2e32bbe62db4e5a2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-6900000000-c0a65988d269dc5278a82021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
UDP-glucuronosyltransferase 1-1UGT1A12q37P22309 details
Sulfotransferase 1A3SULT1A3P0DMM9 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0013744
DrugBank IDDB03514
Phenol Explorer Compound ID632
FoodDB IDFDB000857
KNApSAcK IDC00029546
Chemspider ID325
KEGG Compound IDC17883
BioCyc IDCPD-1072
BiGG IDNot Available
Wikipedia Link2-Methoxy-4-vinylphenol
METLIN IDNot Available
PubChem Compound332
PDB IDNot Available
ChEBI ID42438
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Enzyme Details
2. Sulfotransferase 1A3
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96