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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:55 UTC
Update Date2021-10-13 04:39:33 UTC
HMDB IDHMDB0002511
Secondary Accession Numbers
  • HMDB02511
Metabolite Identification
Common Name3,4,5-Trimethoxycinnamic acid
Description3, 4, 5-trimethoxycinnamic acid is a methoxycinnamic acid with three methoxy substituents at the 3-, 4- and 5-positions. It has a role as an allergen. It is a conjugate acid of a 3,4,5-trimethoxycinnamate. 3, 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 ).
Structure
Data?1582752251
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 Weight238.2366
Monoisotopic Molecular Weight238.084123558
IUPAC Name(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid
Traditional Name3,4,5-trimethoxycinnamic acid
CAS Registry Number90-50-6
SMILES
COC1=CC(\C=C\C(O)=O)=CC(OC)=C1OC
InChI Identifier
InChI=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
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point126 - 128 °CNot Available
Boiling Point396.39 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility3040 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.001 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+159.80731661259
DarkChem[M-H]-158.6431661259
DeepCCS[M+H]+155.45730932474
DeepCCS[M-H]-153.09930932474
DeepCCS[M-2H]-186.05830932474
DeepCCS[M+Na]+161.5530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,4,5-Trimethoxycinnamic acidCOC1=CC(\C=C\C(O)=O)=CC(OC)=C1OC3667.2Standard polar33892256
3,4,5-Trimethoxycinnamic acidCOC1=CC(\C=C\C(O)=O)=CC(OC)=C1OC1994.7Standard non polar33892256
3,4,5-Trimethoxycinnamic acidCOC1=CC(\C=C\C(O)=O)=CC(OC)=C1OC2108.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,4,5-Trimethoxycinnamic acid,1TMS,isomer #1COC1=CC(/C=C/C(=O)O[Si](C)(C)C)=CC(OC)=C1OC2139.4Semi standard non polar33892256
3,4,5-Trimethoxycinnamic acid,1TBDMS,isomer #1COC1=CC(/C=C/C(=O)O[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC2399.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3,4,5-Trimethoxycinnamic acid GC-MS (1 TMS)splash10-0019-5980000000-481902850188a4b983e12014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4,5-Trimethoxycinnamic acid EI-B (Non-derivatized)splash10-000i-0290000000-577fe3f81fdd216fe76b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3,4,5-Trimethoxycinnamic acid GC-MS (Non-derivatized)splash10-0019-5980000000-481902850188a4b983e12017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4,5-Trimethoxycinnamic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-1690000000-4bdc2e168c37e0d8c46e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4,5-Trimethoxycinnamic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00dm-7390000000-279ac79fde7a9d1eb8272017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,4,5-Trimethoxycinnamic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-000i-0890000000-73d378c5d062a43805372012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-014r-0900000000-7d415b23b8c22936e9722012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-0006-9000000000-b27641d2926e1d3e69ed2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid LC-ESI-qTof , Positive-QTOFsplash10-03dl-2900000000-a43198a76493a4d0f4882017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid Linear Ion Trap , negative-QTOFsplash10-0f89-0910000000-f321fbc297d524d25e5e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid Linear Ion Trap , negative-QTOFsplash10-0f89-0910000000-098ef1a616ba7aacdd8b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid LC-ESI-QTOF , positive-QTOFsplash10-00di-0190000000-a53a43c16d61d22ba5fd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid LC-ESI-QTOF , positive-QTOFsplash10-00dl-0970000000-e99d426adbbcf08b402b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid LC-ESI-QTOF , positive-QTOFsplash10-01ox-0910000000-eb35950d925bbd52e2e72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid LC-ESI-ITFT , positive-QTOFsplash10-00di-0190000000-c166d05b1d38a4369d132017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid LC-ESI-ITFT , positive-QTOFsplash10-00di-0190000000-8e02e6181e389f2fce582017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid LC-ESI-ITFT , positive-QTOFsplash10-00di-0190000000-b96acc7d851ea2cbe4712017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid LC-ESI-ITFT , positive-QTOFsplash10-00di-0190000000-c690fb447647391475312017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid Linear Ion Trap , positive-QTOFsplash10-00dj-0690000000-37f50a89d80a7d8e7b7c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid Linear Ion Trap , positive-QTOFsplash10-00dj-0790000000-a0f7d5eacf28002d6c1e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid Linear Ion Trap , positive-QTOFsplash10-001i-0590000000-5e15df23e1760f95e5142017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid Linear Ion Trap , positive-QTOFsplash10-001i-0490000000-528be5b0367f05c609562017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid , positive-QTOFsplash10-03dl-2900000000-a43198a76493a4d0f4882017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid , positive-QTOFsplash10-01vo-0920000000-f5f28fbcb7e0a5bb9b802017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid 10V, Positive-QTOFsplash10-00di-0190000000-f80ae28c9584a754308f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid 20V, Positive-QTOFsplash10-00dl-1980000000-6202f47e101d4e1eb4452017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid 40V, Positive-QTOFsplash10-01tc-4900000000-467e437210b7102853bc2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid 10V, Negative-QTOFsplash10-000i-0190000000-43a9af4188e370a734b82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid 20V, Negative-QTOFsplash10-00kr-0590000000-cc97b3e7c9a32a9bebd22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,4,5-Trimethoxycinnamic acid 40V, Negative-QTOFsplash10-03dm-1900000000-e915c52fc0eac0cfe2b92017-09-01Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2021-10-10Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.046 +/- 0.009 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023019
KNApSAcK IDNot Available
Chemspider ID642910
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6705
PubChem Compound735755
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1182681
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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. [PubMed:15721987 ]
  2. 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. [PubMed:6511847 ]
  3. Kissling E: [The detection of Azotobacter and its significance in criminal technical soil examinations]. Arch Kriminol. 1980;165(1-2):27-34. [PubMed:6992730 ]
  4. 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. [PubMed:16313198 ]