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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:32:07 UTC
Update Date2020-02-26 21:44:13 UTC
HMDB IDHMDB0029698
Secondary Accession Numbers
  • HMDB29698
Metabolite Identification
Common Nametrans-Cinnamyl alcohol
Descriptiontrans-Cinnamyl alcohol, also known as 3-phenyl-2-propen-1-ol or styrylcarbinol, belongs to the class of organic compounds known as cinnamyl alcohols. These are aromatic alcohols containing a 3-phenylprop-2-en-1-ol moiety. trans-Cinnamyl alcohol is an extremely weak basic (essentially neutral) compound (based on its pKa). The E (trans) stereoisomer of cinnamyl alcohol. trans-Cinnamyl alcohol is a sweet, balsam, and cinnamic tasting compound. Outside of the human body, trans-Cinnamyl alcohol is found, on average, in the highest concentration within highbush blueberries. trans-Cinnamyl alcohol has also been detected, but not quantified in, several different foods, such as safflowers, pot marjorams, chicory roots, shallots, and java plums. This could make trans-cinnamyl alcohol a potential biomarker for the consumption of these foods.
Structure
Data?1582753453
Synonyms
ValueSource
(e)-3-Phenyl-2-propen-1-olChEBI
3-Phenyl-2-propen-1-olChEBI
StyrylcarbinolChEBI
(2E)-3-Phenyl-2-propen-1-olHMDB
(2E)-3-Phenylprop-2-en-1-olHMDB
(e)-Cinnamyl alcoholHMDB
e-Cinnamic alcoholHMDB
e-Cinnamyl alcoholHMDB
3-Phenyl-2-propene-1-olMeSH
Cinnamyl alcohol, titanium (4+) saltMeSH
Cinnamic alcoholMeSH
3-Phenylprop-2-en-1-olMeSH
Cinnamyl alcoholMeSH
Cinnamyl alcohol, (e)-isomerMeSH
Chemical FormulaC9H10O
Average Molecular Weight134.1751
Monoisotopic Molecular Weight134.073164942
IUPAC Name(2E)-3-phenylprop-2-en-1-ol
Traditional Namecinnamyl alcohol
CAS Registry Number4407-36-7
SMILES
OC\C=C\C1=CC=CC=C1
InChI Identifier
InChI=1S/C9H10O/c10-8-4-7-9-5-2-1-3-6-9/h1-7,10H,8H2/b7-4+
InChI KeyOOCCDEMITAIZTP-QPJJXVBHSA-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
  • 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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point33 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.34 g/LALOGPS
logP1.93ALOGPS
logP1.82ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)15.62ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.19 m³·mol⁻¹ChemAxon
Polarizability15.41 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05qc-9700000000-718fd9691cbd38d42c60Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001l-6900000000-44b04269b7d35e886fb9Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-002f-9400000000-da49ee491f3478b8fa96Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0036-9400000000-540e90374e70aac0f48bSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-0931100000-d1566613e817621550baSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-1910000000-f620d5e707e1170fdbb6Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05qc-9700000000-718fd9691cbd38d42c60Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-001l-6900000000-44b04269b7d35e886fb9Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-002f-9400000000-da49ee491f3478b8fa96Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0036-9400000000-540e90374e70aac0f48bSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-014i-0931100000-d1566613e817621550baSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-1910000000-f620d5e707e1170fdbb6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uyl-4900000000-f5041423af8993736d98Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-010c-9500000000-c3c6821e801767306100Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-1900000000-09cdb433d6c848c26e89Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-2900000000-c2a8b6fbde5be8d99b16Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbc-9500000000-e0d0b2dcc1928d2290e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-4b79ccedfe3d5be75d78Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1900000000-71c55132d7ccd6582b5fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fr6-9600000000-ce4480c7ad782675bdaaSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000888
KNApSAcK IDC00032375 C00042390
Chemspider ID21105870
KEGG Compound IDC02394
BioCyc IDCINNAMYL-ALC
BiGG IDNot Available
Wikipedia LinkCinnamyl_alcohol
METLIN IDNot Available
PubChem Compound5315892
PDB IDNot Available
ChEBI ID33227
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
trans-Cinnamyl alcohol → {[(2E)-3-phenylprop-2-en-1-yl]oxy}sulfonic aciddetails
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
Reactions
trans-Cinnamyl alcohol → 3,4,5-trihydroxy-6-{[(2E)-3-phenylprop-2-en-1-yl]oxy}oxane-2-carboxylic aciddetails