Record Information
Version1.0
Creation date2015-05-07 19:22:20 UTC
Update date2019-11-26 03:21:47 UTC
Primary IDFDB030494
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-coumaryl alcohol
Description4-coumaryl alcohol, also known as 4-hydroxycinnamyl alcohol or 4-coumaric acid, (E)-isomer, is a member of the class of compounds known as cinnamyl alcohols. Cinnamyl alcohols are aromatic alcohols containing a 3-phenylprop-2-en-1-ol moiety. 4-coumaryl alcohol is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 4-coumaryl alcohol can be synthesized from (E)-cinnamyl alcohol. 4-coumaryl alcohol is also a parent compound for other transformation products, including but not limited to, trans-coumaryl acetate, p-hydroxyphenyl lignin, and 4-hydroxy cinnamyl alcohol diacetate. 4-coumaryl alcohol can be found in a number of food items such as lemon balm, ginseng, red raspberry, and feijoa, which makes 4-coumaryl alcohol a potential biomarker for the consumption of these food products. 4-coumaryl alcohol can be found primarily in human testes tissue. Paracoumaryl alcohol, also called p-coumaryl alcohol, 4-coumaryl alcohol, 4-hydroxycinnamyl alcohol, or 4-(3-hydroxy-1-propenyl)phenol, is a phytochemical, one of the monolignols. It is synthesized via the phenylpropanoid biochemical pathway. When polymerized, p-coumaryl alcohol forms lignin or lignans .
CAS Number3690-05-9
Structure
Thumb
Synonyms
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC9H10O2
IUPAC name4-[(1E)-3-hydroxyprop-1-en-1-yl]phenol
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
Isomeric SMILESOC\C=C\C1=CC=C(O)C=C1
Average Molecular Weight150.1745
Monoisotopic Molecular Weight150.068079564
Classification
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS4-coumaryl alcohol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0l1i-2900000000-35b232588497df392bccSpectrum
Predicted GC-MS4-coumaryl alcohol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00fu-9360000000-71f6e35237794477c995Spectrum
Predicted GC-MS4-coumaryl alcohol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f89-0900000000-d0aa38e43ffe69c65dce2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1900000000-f35b26b4169e49f896512017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9600000000-feffeb0ec4d7bfd7e4212017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-aa3fec540eb5ff87fecf2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0900000000-926f68e15b016ddc1bf92017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05nf-6900000000-53b966254d033e1958102017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a59-0900000000-ef3175d0cc2e2c422a132021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ae9-4900000000-512eaa23bb6e2ec1bf3b2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-9200000000-835e5fb65c2a8f70004b2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014j-0900000000-8d131986ef2454e289192021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0159-0900000000-c01ea2304d08f2059c072021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3900000000-6bda1a3cbe19b1fee9f72021-09-25View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference