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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:32:07 UTC
Update Date2023-02-21 17:19:03 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 a sweet, balsam, and cinnamic tasting compound. trans-Cinnamyl alcohol is found, on average, in the highest concentration within highbush blueberries (Vaccinium corymbosum). trans-Cinnamyl alcohol has also been detected, but not quantified in, several different foods, such as dandelions (Taraxacum officinale), annual wild rice (Zizania aquatica), lemons (Citrus limon), celery stalks (Apium graveolens var. dulce), and white cabbages (Brassica oleracea L. var. capitata L. f. alba DC.). This could make trans-cinnamyl alcohol a potential biomarker for the consumption of these foods. trans-Cinnamyl alcohol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on trans-Cinnamyl alcohol.
Structure
Thumb
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
Physiological effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point33 °CNot Available
Boiling Point247.00 to 250.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility6188 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.700The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
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
FooDB IDFDB000888
KNApSAcK IDC00032375
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
MarkerDB IDNot Available
Good Scents IDrw1040881
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