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Cinnamic acid (FDB012052)

Record Information
Version1.0
Creation date2010-04-08 22:09:58 UTC
Update date2019-11-26 03:06:04 UTC
Primary IDFDB012052
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCinnamic 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 plants to humans. trans-Cinnamic acid is a sweet, balsam, and cinnamon tasting compound. trans-Cinnamic acid is found, on average, in the highest concentration within a few different foods, such as chinese cinnamons (Cinnamomum aromaticum), olives (Olea europaea), and lingonberries (Vaccinium vitis-idaea) and in a lower concentration in corianders (Coriandrum sativum), american cranberries (Vaccinium macrocarpon), and red raspberries (Rubus idaeus). trans-Cinnamic acid has also been detected, but not quantified in, several different foods, such as black tea, broccolis (Brassica oleracea var. italica), red bell peppers (Capsicum annuum), sweet bays (Laurus nobilis), and teas (Camellia sinensis). This could make trans-cinnamic acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on trans-Cinnamic acid.
CAS Number621-82-9
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted 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
Chemical FormulaC9H8O2
IUPAC name(2E)-3-phenylprop-2-enoic acid
InChI IdentifierInChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6-
InChI KeyWBYWAXJHAXSJNI-SREVYHEPSA-N
Isomeric SMILESOC(=O)\C=C/C1=CC=CC=C1
Average Molecular Weight148.1586
Monoisotopic Molecular Weight148.0524295
Classification
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

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 72.96%; H 5.44%; O 21.60%DFC
Melting Point132-135 oC
Boiling PointNot Available
Experimental Water Solubility0.57 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP2.13HANSCH,C ET AL. (1995)
Experimental pKa4.44
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0f6t-6900000000-77686ecc684f3b46bea62014-09-20View Spectrum
GC-MStrans-Cinnamic acid, 1 TMS, GC-MS Spectrumsplash10-0ue9-0910000000-4a7bcdfadd383bf577dcSpectrum
GC-MStrans-Cinnamic acid, 1 TMS, GC-MS Spectrumsplash10-0fb9-6920000000-727a2eb761e6e52fb47dSpectrum
GC-MStrans-Cinnamic acid, 1 TMS, GC-MS Spectrumsplash10-117i-2920000000-f0d9ccc40786362ae4adSpectrum
GC-MStrans-Cinnamic acid, non-derivatized, GC-MS Spectrumsplash10-0ue9-0910000000-4a7bcdfadd383bf577dcSpectrum
GC-MStrans-Cinnamic acid, non-derivatized, GC-MS Spectrumsplash10-0fb9-6920000000-727a2eb761e6e52fb47dSpectrum
GC-MStrans-Cinnamic acid, non-derivatized, GC-MS Spectrumsplash10-117i-2920000000-f0d9ccc40786362ae4adSpectrum
Predicted GC-MStrans-Cinnamic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ue9-2900000000-b105b3fcb63636d0d16fSpectrum
Predicted GC-MStrans-Cinnamic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fl0-7930000000-f3ac0a061fb66ec84b5dSpectrum
Predicted GC-MStrans-Cinnamic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MStrans-Cinnamic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0900000000-3107a2a1bec368528f822012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0ufr-6900000000-b0299d34fa9bb16b82582012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0udi-0900000000-4a879de8ea4f3acb0ae22012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-88ad8c9c837a057bb2a52012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0udi-0900000000-18280fe18e43043d9e212012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0fb9-9600000000-04d36ba7639bc85e20232012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9000000000-a8417274c4493c5b58712012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9100000000-d3712417826a696679812012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-0900000000-37c486fa03918355413c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0f6t-0900000000-218a5babf0ab7c31c4982012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-88ad8c9c837a057bb2a52017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0udi-0900000000-e3a4fcaa911f14d3790d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0fb9-9600000000-04d36ba7639bc85e20232017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-a8417274c4493c5b58712017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9100000000-d3712417826a696679812017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0f6t-0900000000-218a5babf0ab7c31c4982017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0900000000-f095c04fe81b2890cb1a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0900000000-1bb9599f57d5b1c1688b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0002-0900000000-37c486fa03918355413c2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000t-0900000000-f5b771d960092fa83d2c2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uea-0900000000-58b4769b89ab3883fb052016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-6900000000-9f4710d90f0cafac6d7b2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-d015607beb51363244142016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f6t-0900000000-ff32add65ca52cbaae832016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fb9-3900000000-f2450299b70c3ec0faec2016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID10286933
ChEMBL IDNot Available
KEGG Compound IDC10438
Pubchem Compound ID5372954
Pubchem Substance IDNot Available
ChEBI ID27386
Phenol-Explorer ID549
DrugBank IDNot Available
HMDB IDHMDB00567
CRC / DFC (Dictionary of Food Compounds) IDHCV54-E:HCV54-E
EAFUS ID644
Dr. Duke IDCINNAMIC-ACID
BIGG IDNot Available
KNApSAcK IDC00029961
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1350711
SuperScent ID444539
Wikipedia IDCinnamic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
anestheticDUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti mutagenicDUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cholereticDUKE
dermatitigenicDUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
herbicide24527 A substance used to destroy plant pests.DUKE
laxative50503 An agent that produces a soft formed stool, and relaxes and loosens the bowels, typically used over a protracted period, to relieve constipation. Compare with cathartic, which is a substance that accelerates defecation. A substances can be both a laxative and a cathartic.DUKE
lipoxygenase inhibitor35856 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
tyrosinase inhibitor59997 Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals.DUKE
vermifuge25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
cinnamon
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
honey
  1. Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
balsam
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
storax
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).