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
2D NMR[1H, 13C]-HSQC 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
Species NameSourceReference
Anas platyrhynchos
Anatidae
Anser anser
Bison bison
Bos taurus
Bos taurus X Bison bison
Bubalus bubalis
Capra aegagrus hircus
Cervidae
Cervus canadensis
Columba
Columbidae
Dromaius novaehollandiae
Equus caballus
Gallus gallus
Lagopus muta
Leporidae
Lepus timidus
Melanitta fusca
Meleagris gallopavo
Numida meleagris
Odocoileus
Oryctolagus
Ovis aries
Phasianidae
Phasianus colchicus
Struthio camelus
Sus scrofa
Sus scrofa domestica
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
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 ]