Showing metabocard for 3,4,5-Trimethoxycinnamic acid (BMDB0002511)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:00:40 UTC
Update Date2020-04-22 15:11:06 UTC
MCDB ID BMDB0002511
Secondary Accession Numbers
  • BMDB02511
Metabolite Identification
Common Name3,4,5-Trimethoxycinnamic acid
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.
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 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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point126 - 128 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0019-5980000000-481902850188a4b983e12014-06-16View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-000i-0290000000-577fe3f81fdd216fe76b2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0019-5980000000-481902850188a4b983e12017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-1690000000-4bdc2e168c37e0d8c46e2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dm-7390000000-279ac79fde7a9d1eb8272017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0890000000-73d378c5d062a43805372012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014r-0900000000-7d415b23b8c22936e9722012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-b27641d2926e1d3e69ed2012-07-25View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-03dl-2900000000-a43198a76493a4d0f4882017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0f89-0910000000-f321fbc297d524d25e5e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0f89-0910000000-098ef1a616ba7aacdd8b2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00di-0190000000-a53a43c16d61d22ba5fd2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-00dl-0970000000-e99d426adbbcf08b402b2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01ox-0910000000-eb35950d925bbd52e2e72017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0190000000-c166d05b1d38a4369d132017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0190000000-8e02e6181e389f2fce582017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0190000000-b96acc7d851ea2cbe4712017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00di-0190000000-c690fb447647391475312017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00dj-0690000000-37f50a89d80a7d8e7b7c2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-00dj-0790000000-a0f7d5eacf28002d6c1e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0590000000-5e15df23e1760f95e5142017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0490000000-528be5b0367f05c609562017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03dl-2900000000-a43198a76493a4d0f4882017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-01vo-0920000000-f5f28fbcb7e0a5bb9b802017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0190000000-f80ae28c9584a754308f2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-1980000000-6202f47e101d4e1eb4452017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01tc-4900000000-467e437210b7102853bc2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0190000000-43a9af4188e370a734b82017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0590000000-cc97b3e7c9a32a9bebd22017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dm-1900000000-e915c52fc0eac0cfe2b92017-09-01View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not Available2012-12-05View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not Available2021-10-10View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0002511
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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. [PubMed:23438684 ]