4-coumaryl alcohol (CHEM042020)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:47:31 UTC
Update Date2016-11-09 01:22:35 UTC
Accession NumberCHEM042020
Identification
Common Name4-coumaryl alcohol
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(E)-4-Coumaryl alcoholChEBI, HMDB
4-Hydroxycinnamyl alcoholChEBI
p-Coumaryl alcoholChEBI
3-(4-Hydroxyphenyl)-1-propaneHMDB
3-OHPPHMDB
4-CoumarinolHMDB
4-Hydroxy-2H-1-benzopyran-2-oneHMDB
4-Hydroxy-2H-chromen-2-oneHMDB
4-HydroxycoumarinHMDB
4-HydroxycoumarineHMDB
BenzotetronateHMDB
Benzotetronic acidHMDB
Hydroxy coumarinHMDB
trans-3-(4'-Hydroxyphenyl)-2-propenoic acidMeSH, HMDB
trans-HPPAMeSH, HMDB
p-Hydroxycinnamic acidMeSH, HMDB
Para-coumaric acidMeSH, HMDB
4-Coumaric acid, (E)-isomerMeSH, HMDB
4-Hydroxycinnamic acidMeSH, HMDB
p-Coumaric acidMeSH, HMDB
4-Coumaric acidMeSH, HMDB
(E)-4-Coumaroyl alcoholChEBI
(E)-p-Coumaryl alcoholHMDB
3-(p-Hydroxyphenyl)-2-propen-1-olHMDB
4-(3-Hydroxy-1-propen-1-yl)phenolHMDB
4-Coumaryl alcoholHMDB
4-Hydroxycinnamic alcoholHMDB
4-[(1E)-3-Hydroxy-1-propenyl]phenolHMDB
Paracoumaryl alcoholHMDB
p-Coumaric alcoholHMDB
p-Cumaric alcoholHMDB
p-Hydroxycinnamic alcoholHMDB
p-Hydroxycinnamyl alcoholHMDB
trans-p-Coumaryl alcoholHMDB
Chemical FormulaC9H10O2
Average Molecular Mass150.175 g/mol
Monoisotopic Mass150.068 g/mol
CAS Registry NumberNot Available
IUPAC Name4-[(1E)-3-hydroxyprop-1-en-1-yl]phenol
Traditional Nameparacoumaryl alcohol
SMILESOC\C=C\C1=CC=C(O)C=C1
InChI IdentifierInChI=1S/C9H10O2/c10-7-1-2-8-3-5-9(11)6-4-8/h1-6,10-11H,7H2/b2-1+
InChI KeyPTNLHDGQWUGONS-OWOJBTEDSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cinnamyl alcohols. These are aromatic alcohols containing a 3-phenylprop-2-en-1-ol moiety.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamyl alcohols
Sub ClassNot Available
Direct ParentCinnamyl alcohols
Alternative Parents
Substituents
  • Cinnamyl alcohol
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.97 g/LALOGPS
logP1.55ALOGPS
logP1.51ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)9.51ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity45.17 m³·mol⁻¹ChemAxon
Polarizability16.35 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0l1i-2900000000-35b232588497df392bccSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00fu-9360000000-71f6e35237794477c995Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0900000000-d0aa38e43ffe69c65dceSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1900000000-f35b26b4169e49f89651Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9600000000-feffeb0ec4d7bfd7e421Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-aa3fec540eb5ff87fecfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-926f68e15b016ddc1bf9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05nf-6900000000-53b966254d033e195810Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a59-0900000000-ef3175d0cc2e2c422a13Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ae9-4900000000-512eaa23bb6e2ec1bf3bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9200000000-835e5fb65c2a8f70004bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014j-0900000000-8d131986ef2454e28919Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0159-0900000000-c01ea2304d08f2059c07Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3900000000-6bda1a3cbe19b1fee9f7Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0003654
FooDB IDFDB030494
Phenol Explorer IDNot Available
KNApSAcK IDC00000613
BiGG ID2299830
BioCyc IDCOUMARYL-ALCOHOL
METLIN ID6971
PDB IDNot Available
Wikipedia LinkParacoumaryl_alcohol
Chemspider ID4444166
ChEBI ID64555
PubChem Compound ID5280535
Kegg Compound IDC02646
YMDB IDNot Available
ECMDB IDM2MDB004598
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Takahashi, Yukio; Kato, Keiichi; Kubota, Koichi. One-pot preparation of high-purity 4-hydroxycoumarin. Jpn. Kokai Tokkyo Koho (2005), 7 pp.
2. Takahashi, Yukio; Kato, Keiichi; Kubota, Koichi. One-pot preparation of high-purity 4-hydroxycoumarin. Jpn. Kokai Tokkyo Koho (2005), 7 pp.
3. Janssen LH, Van Wilgenburg MT, Wilting J: Human serum albumin as an allosteric two-state protein. Evidence from effects of calcium and warfarin on proton binding behaviour. Biochim Biophys Acta. 1981 Jul 28;669(2):244-50.
4. Maurer HH, Arlt JW: Detection of 4-hydroxycoumarin anticoagulants and their metabolites in urine as part of a systematic toxicological analysis procedure for acidic drugs and poisons by gas chromatography-mass spectrometry after extractive methylation. J Chromatogr B Biomed Sci Appl. 1998 Sep 4;714(2):181-95.
5. LE Lain R, Barrell KJ, Saeed GS, Nicholls PJ, Simons C, Kirby A, Smith HJ: Some coumarins and triphenylethene derivatives as inhibitors of human testes microsomal 17beta-hydroxysteroid dehydrogenase (17beta-HSD type 3): further studies with tamoxifen on the rat testes microsomal enzyme. J Enzyme Inhib Med Chem. 2002 Apr;17(2):93-100.
6. Vorum H, Fisker K, Brodersen R: High-affinity binding of two molecules of warfarin and phenprocoumon to human serum albumin. Biochim Biophys Acta. 1994 Apr 13;1205(2):178-82.