Np mrd loader

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Record Information
Version1.0
Created at2006-05-22 14:17:55 UTC
Updated at2021-08-19 20:22:34 UTC
NP-MRD IDNP0000110
Secondary Accession NumbersNone
Natural Product 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
Thumb
Synonyms
ValueSource
3,4,5-TrimethoxycinnamateGenerator
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-enoateHMDB
3-(3,4,5-Trimethoxyphenyl)-2-propenoic acidHMDB
3,4,5-Trimethoxycinnamic acidMeSH
Chemical FormulaC12H14O5
Average Mass238.2366 Da
Monoisotopic Mass238.08412 Da
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)V.dorna832021-08-10View Spectrum
Species
Species of Origin
  • Animalia
  • Plantae
  • 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 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
    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
    External Links
    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
    Good Scents IDrw1182681
    References
    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 ]
    5. 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 ]