Showing Compound Card for trans-Cinnamic acid (CDB006175)

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Record Information
Version1.0
Created at2020-03-18 23:22:34 UTC
Updated at2020-12-07 19:06:59 UTC
CannabisDB IDCDB006175
Secondary Accession NumbersNot Available
Cannabis Compound 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. Cinnamic acid can exist in both the cis and trans form, with the trans-form being most common. Trans-cinnamic acid is a weakly acidic compound (based on its pKa). It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Trans-cinnamic acid occurs naturally in a number of plants. It is a sweet, balsam, or cinnamon tasting compound. Trans-cinnamic acid is characterized by a honey-like odor. Trans-cinnamic acid is found in a number of foods with the highest concentration found in chinese cinnamons (cinnamon bark), 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 common oregano, pepper (spice), fennels, pomegranates, and european cranberries. Trans-cinnamic acid has also been shown to be a microbial metabolite as it is produced by microbes belonging to the Alcaligenes, Brevibacterium, Cellulomonas, and Pseudomonas families (PMID: 16349793 ). In plants, cinnamic acid is a central intermediate in the biosynthesis of myriad natural products include lignols (precursors to lignin and lignocellulose), flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids. Its biosynthesis involves the action of the enzyme phenylalanine ammonia-lyase (PAL) on phenylalanine (PMID:20035037 ). Cinnamic acid is used in flavorings, the production of synthetic indigo, and certain pharmaceuticals. A major use of trans-cinnamic acid is as a precursor to produce methyl cinnamate, ethyl cinnamate, and benzyl cinnamate for the perfume industry.
Structure
Thumb
MOLSDFPDBSMILESInChI
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 Weight148.16
Monoisotopic Molecular Weight148.0524
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

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point133 °CNot Available
Boiling Point300 °CWikipedia
Water Solubility0.55 mg/mLNot Available
logP2.13HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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
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
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
UDP-glucuronosyltransferase 1-1UGT1A12q37P22309 details
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000930
DrugBank IDNot Available
Phenol Explorer Compound ID549
FoodDB 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
References
General References
  1. 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 ]
  2. Vogt T: Phenylpropanoid biosynthesis. Mol Plant. 2010 Jan;3(1):2-20. doi: 10.1093/mp/ssp106. Epub 2009 Dec 24. [PubMed:20035037 ]

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
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