Record Information
Version1.0
Creation date2011-09-21 00:23:21 UTC
Update date2019-11-26 03:21:07 UTC
Primary IDFDB023019
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3,4,5-Trimethoxycinnamic acid
Description3,4,5-Trimethoxycinnamic acid is an organic acid found in normal human urine. (PMID: 6992730, 6511847) Trimethoxycinnamate is a natural aromatic ester from Piper longum that inhibits expression of cell adhesion molecules on endothelial cells (TNF- -induced expression of intercellular adhesion molecule-1 (ICAM-1) and E-Selectin and vascular adhesion molecules-1 (VCAM-1)), without being toxic to endothelial cells. (PMID: 16313198) [HMDB]
CAS Number90-50-6
Structure
Thumb
Synonyms
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC12H14O5
IUPAC name(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid
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
Isomeric SMILESCOC1=CC(\C=C\C(O)=O)=CC(OC)=C1OC
Average Molecular Weight238.2366
Monoisotopic Molecular Weight238.084123558
Classification
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
Ontology
Disposition

Biological location:

Source:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS3,4,5-Trimethoxycinnamic acid, 1 TMS, GC-MS Spectrumsplash10-0019-5980000000-481902850188a4b983e1Spectrum
GC-MS3,4,5-Trimethoxycinnamic acid, non-derivatized, GC-MS Spectrumsplash10-000i-0290000000-577fe3f81fdd216fe76bSpectrum
GC-MS3,4,5-Trimethoxycinnamic acid, non-derivatized, GC-MS Spectrumsplash10-0019-5980000000-481902850188a4b983e1Spectrum
Predicted GC-MS3,4,5-Trimethoxycinnamic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-1690000000-4bdc2e168c37e0d8c46eSpectrum
Predicted GC-MS3,4,5-Trimethoxycinnamic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dm-7390000000-279ac79fde7a9d1eb827Spectrum
Predicted GC-MS3,4,5-Trimethoxycinnamic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0890000000-73d378c5d062a43805372012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014r-0900000000-7d415b23b8c22936e9722012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-b27641d2926e1d3e69ed2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03dl-2900000000-a43198a76493a4d0f4882017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0f89-0910000000-f321fbc297d524d25e5e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0f89-0910000000-098ef1a616ba7aacdd8b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0190000000-a53a43c16d61d22ba5fd2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00dl-0970000000-e99d426adbbcf08b402b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01ox-0910000000-eb35950d925bbd52e2e72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0190000000-c166d05b1d38a4369d132017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0190000000-8e02e6181e389f2fce582017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0190000000-b96acc7d851ea2cbe4712017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0190000000-c690fb447647391475312017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00dj-0690000000-37f50a89d80a7d8e7b7c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00dj-0790000000-a0f7d5eacf28002d6c1e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0590000000-5e15df23e1760f95e5142017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0490000000-528be5b0367f05c609562017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-03dl-2900000000-a43198a76493a4d0f4882017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-01vo-0920000000-f5f28fbcb7e0a5bb9b802017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0190000000-f80ae28c9584a754308f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-1980000000-6202f47e101d4e1eb4452017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01tc-4900000000-467e437210b7102853bc2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0190000000-43a9af4188e370a734b82017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0590000000-cc97b3e7c9a32a9bebd22017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dm-1900000000-e915c52fc0eac0cfe2b92017-09-01View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID642910
ChEMBL IDCHEMBL501235
KEGG Compound IDNot Available
Pubchem Compound ID735755
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02511
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference