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Record Information
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:36 UTC
Secondary Accession Numbers
  • HMDB00930
Metabolite Identification
Common Nametrans-Cinnamic acid
DescriptionCinnamic acid (CAS: 621-82-9) has the formula C6H5CHCHCOOH and is an odourless white crystalline acid, which is slightly soluble in water. It has a melting point of 133-degree centigrade and a boiling point of 300-degree centigrade. Cinnamic acid has been shown to be a microbial metabolite; it can be found in Alcaligenes, Brevibacterium, Cellulomonas, and Pseudomonas (PMID: 16349793 ).
(2E)-3-Phenyl-2-propenoic acidChEBI
(2E)-3-Phenylacrylic acidChEBI
(e)-3-Phenyl-2-propenoic acidChEBI
(e)-Cinnamic acidChEBI
Benzeneacrylic acidChEBI
trans-3-Phenylacrylic acidChEBI
(2E)-2-Phenyl-2-propenoic acidHMDB
(e)-3-Phenylacrylic acidHMDB
(e)-3-Phenylprop-2-enoic acidHMDB
trans-3-Phenyl-2-propenoic acidHMDB
Cinnamic acid, 14C-labeled CPDHMDB
Cinnamic acid, 2-(14)C-labeled CPDHMDB
Cinnamic acid, 3-(14)C-labeled CPDHMDB
Cinnamic acid, (Z)-isomerHMDB
Cinnamic acid, 2-(13)C-labeled CPDHMDB
Cinnamic acid, 3H-labeled CPD (e)-isomerHMDB
Cinnamic acid, 3H-labeled CPD (Z)-isomerHMDB
Cinnamic acid, ion(1-)-(e)-isomerHMDB
Cinnamic acid, sodium saltHMDB
Cinnamic acid, sodium salt(e)-isomerHMDB
Cinnamic acid, sodium salt(Z)-isomerHMDB
Cinnamic acid, (trans)-(e)-isomerHMDB
Cinnamic acid, 14C-labeled CPD (e)-isomerHMDB
Cinnamic acid, ion(1-)HMDB
Cinnamic acid, nickel (+2) saltHMDB
Cinnamic acid, potassium saltHMDB
Cinnamic acid, zinc salt(e)-isomerHMDB
Cinnamic acid, 13C-labeled CPDHMDB
Cinnamic acidHMDB
(2E)-3-Phenylprop-2-enoic acidHMDB
(2E)-Cinnamic acidHMDB
3-Phenyl-(E)-2-propenoic acidHMDB
3-Phenyl-2-propenoic acidHMDB
3-Phenylacrylic acidHMDB
Phenylacrylic acidHMDB
beta-Phenylacrylic acidHMDB
trans-Cinnamic acidHMDB
β-Phenylacrylic acidHMDB
Chemical FormulaC9H8O2
Average Molecular Weight148.1586
Monoisotopic Molecular Weight148.0524295
IUPAC Name(2E)-3-phenylprop-2-enoic acid
Traditional Namecinnamic acid
CAS Registry Number140-10-3
InChI Identifier
Chemical Taxonomy
Description belongs to the class of organic compounds known as cinnamic acids. These are organic aromatic compounds containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassCinnamic acids
Direct ParentCinnamic acids
Alternative Parents
  • Cinnamic acid
  • Styrene
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors

Route of exposure:


Biological location:


Industrial application:

Physical Properties
Experimental Properties
Melting Point133 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.55 mg/mLNot Available
LogP2.13HANSCH,C ET AL. (1995)
Predicted Properties
Water Solubility0.62 g/LALOGPS
pKa (Strongest Acidic)4.51ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity43.06 m³·mol⁻¹ChemAxon
Polarizability15.43 ųChemAxon
Number of Rings1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-0ue9-0910000000-4a7bcdfadd383bf577dcJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-0fb9-6920000000-727a2eb761e6e52fb47dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-117i-2920000000-f0d9ccc40786362ae4adJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ue9-0910000000-4a7bcdfadd383bf577dcJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fb9-6920000000-727a2eb761e6e52fb47dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-117i-2920000000-f0d9ccc40786362ae4adJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ue9-2900000000-b105b3fcb63636d0d16fJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fl0-7930000000-f3ac0a061fb66ec84b5dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0900000000-3107a2a1bec368528f82JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0ufr-6900000000-b0299d34fa9bb16b8258JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0udi-0900000000-4a879de8ea4f3acb0ae2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-88ad8c9c837a057bb2a5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udi-0900000000-18280fe18e43043d9e21JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0fb9-9600000000-04d36ba7639bc85e2023JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9000000000-a8417274c4493c5b5871JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9100000000-d3712417826a69667981JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-0900000000-37c486fa03918355413cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0f6t-0900000000-218a5babf0ab7c31c498JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-88ad8c9c837a057bb2a5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-e3a4fcaa911f14d3790dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0fb9-9600000000-04d36ba7639bc85e2023JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-a8417274c4493c5b5871JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9100000000-d3712417826a69667981JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0f6t-0900000000-218a5babf0ab7c31c498JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0900000000-f095c04fe81b2890cb1aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0900000000-1bb9599f57d5b1c1688bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0900000000-37c486fa03918355413cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0900000000-f5b771d960092fa83d2cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uea-0900000000-58b4769b89ab3883fb05JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-6900000000-9f4710d90f0cafac6d7bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-d015607beb5136324414JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6t-0900000000-ff32add65ca52cbaae83JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-3900000000-f2450299b70c3ec0faecJSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-0f6t-6900000000-77686ecc684f3b46bea6JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Normal Concentrations
SalivaDetected and Quantified0.869 +/- 1.14 uMAdult (>18 years old)Male
    • Sugimoto et al. (...
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID549
FoodDB IDFDB008784
KNApSAcK IDC00029961
Chemspider ID392447
KEGG Compound IDC10438
BioCyc IDCPD-674
BiGG IDNot Available
Wikipedia LinkCinnamic_acid
PubChem Compound444539
PDB IDNot Available
ChEBI ID35697
Food Biomarker OntologyNot Available
VMH IDNot Available
Synthesis ReferenceZhu, Min; Shentu, Chao; Zhou, Zhong Shi. Microwave-assisted base-free synthesis of trans-cinnamic acids using hypervalent iodonium salts. Chinese Chemical Letters (2007), 18(3), 272-274.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Blanquet S, Meunier JP, Minekus M, Marol-Bonnin S, Alric M: Recombinant Saccharomyces cerevisiae expressing P450 in artificial digestive systems: a model for biodetoxication in the human digestive environment. Appl Environ Microbiol. 2003 May;69(5):2884-92. [PubMed:12732562 ]
  2. Boulat O, Gradwohl M, Matos V, Guignard JP, Bachmann C: Organic acids in the second morning urine in a healthy Swiss paediatric population. Clin Chem Lab Med. 2003 Dec;41(12):1642-58. [PubMed:14708889 ]
  3. Sarkissian CN, Shao Z, Blain F, Peevers R, Su H, Heft R, Chang TM, Scriver CR: A different approach to treatment of phenylketonuria: phenylalanine degradation with recombinant phenylalanine ammonia lyase. Proc Natl Acad Sci U S A. 1999 Mar 2;96(5):2339-44. [PubMed:10051643 ]
  4. Wahl HG, Hong Q, Stube D, Maier ME, Haring HU, Liebich HM: Simultaneous analysis of the di(2-ethylhexyl)phthalate metabolites 2-ethylhexanoic acid, 2-ethyl-3-hydroxyhexanoic acid and 2-ethyl-3-oxohexanoic acid in urine by gas chromatography-mass spectrometry. J Chromatogr B Biomed Sci Appl. 2001 Jul 15;758(2):213-9. [PubMed:11486831 ]
  5. Larue C, Munnich A, Charpentier C, Saudubray JM, Frezal J, Remy MH, Rivat C: An extracorporeal hollow-fiber reactor for phenylketonuria using immobilized phenylalanine ammonia lyase. Dev Pharmacol Ther. 1986;9(2):73-81. [PubMed:3956347 ]
  6. Olivera ER, Carnicero D, Jodra R, Minambres B, Garcia B, Abraham GA, Gallardo A, Roman JS, Garcia JL, Naharro G, Luengo JM: Genetically engineered Pseudomonas: a factory of new bioplastics with broad applications. Environ Microbiol. 2001 Oct;3(10):612-8. [PubMed:11722541 ]
  7. Lee HS, Beon MS, Kim MK: Selective growth inhibitor toward human intestinal bacteria derived from Pulsatilla cernua root. J Agric Food Chem. 2001 Oct;49(10):4656-61. [PubMed:11600003 ]
  8. Douros JD, Frankenfeld JW: Effects of Culture Conditions on Production of trans-Cinnamic Acid from Alkylbenzenes by Soil Microorganisms. Appl Microbiol. 1968 Feb;16(2):320-5. [PubMed:16349793 ]


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:
Uniprot ID:
Molecular weight:
trans-Cinnamic acid → 3,4,5-trihydroxy-6-{[(2E)-3-phenylprop-2-enoyl]oxy}oxane-2-carboxylic aciddetails