3,4,5-Trimethoxycinnamic acid (CHEM022458)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:35:39 UTC
Update Date2016-11-09 01:17:31 UTC
Accession NumberCHEM022458
Identification
Common Name3,4,5-Trimethoxycinnamic acid
ClassSmall Molecule
Description3,4,5-Trimethoxycinnamic acid, also known as 3,4,5-trimethoxyphenylacrylate or O-methylsinapate, belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. 3,4,5-Trimethoxycinnamic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
3,4,5-TrimethoxycinnamateGenerator
3-(3,4,5-Trimethoxyphenyl)-2-propenoic acidMeSH
3,4,5-Trimethoxy cinnamateHMDB
3,4,5-Trimethoxy cinnamic acidHMDB
3,4,5-TrimethoxyphenylacrylateHMDB
3,4,5-Trimethoxyphenylacrylic acidHMDB
O-MethylsinapateHMDB
O-Methylsinapic acidHMDB
(2E)-3-(3,4,5-Trimethoxyphenyl)prop-2-enoateGenerator, HMDB
3,4,5-Trimethoxycinnamic acidMeSH
Chemical FormulaC12H14O5
Average Molecular Mass238.237 g/mol
Monoisotopic Mass238.084 g/mol
CAS Registry Number90-50-6
IUPAC Name(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid
Traditional Name3,4,5-trimethoxycinnamic acid
SMILESCOC1=CC(\C=C\C(O)=O)=CC(OC)=C1OC
InChI IdentifierInChI=1S/C12H14O5/c1-15-9-6-8(4-5-11(13)14)7-10(16-2)12(9)17-3/h4-7H,1-3H3,(H,13,14)/b5-4+
InChI KeyYTFVRYKNXDADBI-SNAWJCMRSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentCoumaric acids and derivatives
Alternative Parents
Substituents
  • Cinnamic acid
  • Coumaric acid or derivatives
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Styrene
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Ether
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.21 g/LALOGPS
logP2.24ALOGPS
logP1.66ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)3.71ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area64.99 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity62.45 m³·mol⁻¹ChemAxon
Polarizability24.17 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0019-5980000000-481902850188a4b983e1Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-0290000000-577fe3f81fdd216fe76bSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0019-5980000000-481902850188a4b983e1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-1690000000-4bdc2e168c37e0d8c46eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dm-7390000000-279ac79fde7a9d1eb827Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0890000000-73d378c5d062a4380537Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014r-0900000000-7d415b23b8c22936e972Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-b27641d2926e1d3e69edSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03dl-2900000000-a43198a76493a4d0f488Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0f89-0910000000-f321fbc297d524d25e5eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0f89-0910000000-098ef1a616ba7aacdd8bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0190000000-a53a43c16d61d22ba5fdSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00dl-0970000000-e99d426adbbcf08b402bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01ox-0910000000-eb35950d925bbd52e2e7Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0190000000-c166d05b1d38a4369d13Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0190000000-8e02e6181e389f2fce58Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0190000000-b96acc7d851ea2cbe471Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0190000000-c690fb44764739147531Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00dj-0690000000-37f50a89d80a7d8e7b7cSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00dj-0790000000-a0f7d5eacf28002d6c1eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0590000000-5e15df23e1760f95e514Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0490000000-528be5b0367f05c60956Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03dl-2900000000-a43198a76493a4d0f488Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-01vo-0920000000-f5f28fbcb7e0a5bb9b80Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0190000000-f80ae28c9584a754308fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-1980000000-6202f47e101d4e1eb445Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01tc-4900000000-467e437210b7102853bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0190000000-43a9af4188e370a734b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0590000000-cc97b3e7c9a32a9bebd2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dm-1900000000-e915c52fc0eac0cfe2b9Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0002511
FooDB IDFDB023019
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID6705
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID642910
ChEBI IDNot Available
PubChem Compound ID735755
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.
2. Jenner AM, Rafter J, Halliwell B: Human fecal water content of phenolics: the extent of colonic exposure to aromatic compounds. Free Radic Biol Med. 2005 Mar 15;38(6):763-72.
3. Kissling E: [The detection of Azotobacter and its significance in criminal technical soil examinations]. Arch Kriminol. 1980;165(1-2):27-34.
4. Todoriki H, Hayashi T, Naruse H: High-performance liquid chromatographic method for screening disorders of aromatic acid metabolism using a multi-detection system. J Chromatogr. 1984 Oct 12;310(2):273-81.
5. Kumar S, Arya P, Mukherjee C, Singh BK, Singh N, Parmar VS, Prasad AK, Ghosh B: Novel aromatic ester from Piper longum and its analogues inhibit expression of cell adhesion molecules on endothelial cells. Biochemistry. 2005 Dec 6;44(48):15944-52.