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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:07 UTC
HMDB IDHMDB0000930
Secondary Accession Numbers
  • HMDB00930
Metabolite Identification
Common Nametrans-Cinnamic acid
Descriptiontrans-Cinnamic acid, also known as (e)-cinnamic acid or phenylacrylic acid, 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. trans-Cinnamic acid exists in all living species, ranging from bacteria to humans. trans-Cinnamic acid is a sweet, balsam, and cinnamon tasting compound. Outside of the human body, trans-Cinnamic acid is found, on average, in the highest concentration within a few different foods, such as chinese cinnamons, olives, and lingonberries and in a lower concentration in redcurrants, red raspberries, and corianders. trans-Cinnamic acid has also been detected, but not quantified in several different foods, such as common oregano, pepper (spice), fennels, pomegranates, and european cranberries. This could make trans-cinnamic acid a potential biomarker for the consumption of these foods. Cinnamic acid has been shown to be a microbial metabolite; it can be found in Alcaligenes, Brevibacterium, Cellulomonas, and Pseudomonas (PMID:16349793 ). trans-Cinnamic acid is a potentially toxic compound.
Structure
Data?1582752165
Synonyms
ValueSource
(2E)-3-Phenyl-2-propenoic acidChEBI
(2E)-3-Phenylacrylic acidChEBI
(e)-3-Phenyl-2-propenoic acidChEBI
(e)-CinnamateChEBI
(e)-Cinnamic acidChEBI
Benzeneacrylic acidChEBI
PHENYLETHYLENECARBOXYLIC ACIDChEBI
trans-3-Phenylacrylic acidChEBI
trans-beta-CarboxystyreneChEBI
trans-CinnamateChEBI
trans-ZimtsaeureChEBI
(2E)-3-Phenyl-2-propenoateGenerator
(2E)-3-PhenylacrylateGenerator
(e)-3-Phenyl-2-propenoateGenerator
BenzeneacrylateGenerator
PHENYLETHYLENECARBOXYLateGenerator
trans-3-PhenylacrylateGenerator
trans-b-CarboxystyreneGenerator
trans-Β-carboxystyreneGenerator
(2E)-2-Phenyl-2-propenoateHMDB
(2E)-2-Phenyl-2-propenoic acidHMDB
(e)-3-PhenylacrylateHMDB
(e)-3-Phenylacrylic acidHMDB
(e)-3-Phenylprop-2-enoateHMDB
(e)-3-Phenylprop-2-enoic acidHMDB
trans-3-Phenyl-2-propenoateHMDB
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
Β-phenylacrylic acidHMDB
trans-Cinnamic 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
SMILES
OC(=O)\C=C\C1=CC=CC=C1
InChI Identifier
InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+
InChI KeyWBYWAXJHAXSJNI-VOTSOKGWSA-N
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
Substituents
  • 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
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point133 °CNot Available
Boiling Point298.00 to 300.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.55 mg/mLNot Available
LogP2.13HANSCH,C ET AL. (1995)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available135.5http://allccs.zhulab.cn/database/detail?ID=AllCCS00000542
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.62 g/LALOGPS
logP2.38ALOGPS
logP2.14ChemAxon
logS-2.4ALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+133.74131661259
DarkChem[M-H]-129.42831661259
AllCCS[M+H]+130.48132859911
AllCCS[M-H]-128.56532859911
DeepCCS[M+H]+129.40730932474
DeepCCS[M-H]-126.60630932474
DeepCCS[M-2H]-162.72430932474
DeepCCS[M+Na]+137.96830932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
trans-Cinnamic acidOC(=O)\C=C\C1=CC=CC=C12773.6Standard polar33892256
trans-Cinnamic acidOC(=O)\C=C\C1=CC=CC=C11370.5Standard non polar33892256
trans-Cinnamic acidOC(=O)\C=C\C1=CC=CC=C11442.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
trans-Cinnamic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/C1=CC=CC=C11551.3Semi standard non polar33892256
trans-Cinnamic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/C1=CC=CC=C11791.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - trans-Cinnamic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-0ue9-0910000000-4a7bcdfadd383bf577dc2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - trans-Cinnamic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)splash10-0fb9-6920000000-727a2eb761e6e52fb47d2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - trans-Cinnamic acid GC-MS (1 TMS)splash10-117i-2920000000-f0d9ccc40786362ae4ad2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - trans-Cinnamic acid GC-EI-TOF (Non-derivatized)splash10-0ue9-0910000000-4a7bcdfadd383bf577dc2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - trans-Cinnamic acid GC-EI-TOF (Non-derivatized)splash10-0fb9-6920000000-727a2eb761e6e52fb47d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - trans-Cinnamic acid GC-MS (Non-derivatized)splash10-117i-2920000000-f0d9ccc40786362ae4ad2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-Cinnamic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ue9-2900000000-b105b3fcb63636d0d16f2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-Cinnamic acid GC-MS (1 TMS) - 70eV, Positivesplash10-0fl0-7930000000-f3ac0a061fb66ec84b5d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-Cinnamic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-Cinnamic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0f6t-6900000000-77686ecc684f3b46bea62014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-001i-0900000000-3107a2a1bec368528f822012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0ufr-6900000000-b0299d34fa9bb16b82582012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0udi-0900000000-4a879de8ea4f3acb0ae22012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOFsplash10-0002-0900000000-88ad8c9c837a057bb2a52012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOFsplash10-0udi-0900000000-18280fe18e43043d9e212012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOFsplash10-0fb9-9600000000-04d36ba7639bc85e20232012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOFsplash10-004i-9000000000-a8417274c4493c5b58712012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOFsplash10-004i-9100000000-d3712417826a696679812012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-0002-0900000000-37c486fa03918355413c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-0f6t-0900000000-218a5babf0ab7c31c4982012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid LC-ESI-QQ , negative-QTOFsplash10-0002-0900000000-88ad8c9c837a057bb2a52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid LC-ESI-QQ , negative-QTOFsplash10-0udi-0900000000-e3a4fcaa911f14d3790d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid LC-ESI-QQ , negative-QTOFsplash10-0fb9-9600000000-04d36ba7639bc85e20232017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid LC-ESI-QQ , negative-QTOFsplash10-004i-9000000000-a8417274c4493c5b58712017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid LC-ESI-QQ , negative-QTOFsplash10-004i-9100000000-d3712417826a696679812017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid LC-ESI-QTOF , negative-QTOFsplash10-0f6t-0900000000-218a5babf0ab7c31c4982017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid Linear Ion Trap , negative-QTOFsplash10-0udi-0900000000-f095c04fe81b2890cb1a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid Linear Ion Trap , negative-QTOFsplash10-0udi-0900000000-1bb9599f57d5b1c1688b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-Cinnamic acid LC-ESI-QTOF , positive-QTOFsplash10-0002-0900000000-37c486fa03918355413c2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Cinnamic acid 10V, Positive-QTOFsplash10-000t-0900000000-f5b771d960092fa83d2c2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Cinnamic acid 20V, Positive-QTOFsplash10-0uea-0900000000-58b4769b89ab3883fb052016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Cinnamic acid 40V, Positive-QTOFsplash10-0udi-6900000000-9f4710d90f0cafac6d7b2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Cinnamic acid 10V, Negative-QTOFsplash10-0002-0900000000-d015607beb51363244142016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Cinnamic acid 20V, Negative-QTOFsplash10-0f6t-0900000000-ff32add65ca52cbaae832016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-Cinnamic acid 40V, Negative-QTOFsplash10-0fb9-3900000000-f2450299b70c3ec0faec2016-09-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Quadrupole Ion Trap, ESI-, Adduct: [M-H]-)2022-02-11FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
SalivaDetected and Quantified0.869 +/- 1.14 uMAdult (>18 years old)Male
Normal
    • Sugimoto et al. (...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID549
FooDB IDFDB012052
KNApSAcK IDC00000170
Chemspider ID392447
KEGG Compound IDC10438
BioCyc IDCPD-674
BiGG IDNot Available
Wikipedia LinkCinnamic_acid
METLIN ID5880
PubChem Compound444539
PDB IDNot Available
ChEBI ID35697
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1350711
References
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. 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 ]
  2. 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 ]
  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 ]

Enzymes

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