Methyl 4-hydroxy-3-methoxy-cinnamate

HCID 16830CAS 2309-07-1

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Grundinformationen

Standard-SMILES: COC(=O)C=Cc1ccc(O)c(OC)c1
InChIKey: AUJXJFHANFIVKH-UHFFFAOYSA-N
Summenformel: C11H12O4
Durchschnittliche Molmasse: 208,21 g/mol
Monoisotopische Masse: 208,07355886

Überblick

methyl (EZ)-ferulate has been reported in Iris milesii, Hibiscus taiwanensis, and other organisms with data available.

Namen und Bezeichner

Bevorzugter Name: Methyl 4-hydroxy-3-methoxy-cinnamate
IUPAC: methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
Englischer Name: Ferulic acid methyl ester
Summenformel: C11H12O4
Molmasse: 208.21

Namen und Synonyme

methyl 4-hydroxy-3-methoxy-cinnamateRefChem:1089473methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoateSCHEMBL510492orb1303446AUJXJFHANFIVKH-UHFFFAOYSA-Nmethyl 3-methoxy-4-hydroxycinnamates5451METHYL-4-HYDROXY-3-METHOXYCINNAMATEmethyl 3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoate4-HYDROXY-3-METHOXYCINNAMIC ACID METHYL ESTERMETHYL FERULATE

Weitere Namen anzeigen

METHYL 4-HYDROXY-3-METHOXYCINNAMATEtrans-methylferulateMethyl 3-(4-hydroxy-3-methoxyphenyl)acrylate2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, methyl ester4-hydroxy-3-methoxycinnamateMaritin Frans-methylferulate4-HYDROXY-3-METHOXYCINNAFerulic acid methyl este

Datenbank-Bezeichner

CAS: 2309-07-1
PubChem CID: 16830
DTXSID: DTXSID801347441

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 1,8
Polarare Oberfläche (TPSA): 55,8 Å²
H-Brücken-Donoren: 1
H-Brücken-Akzeptoren: 4
Frei drehbare Bindungen: 4
Schwere Atome: 15
Formalladung: 0
Komplexität: 237

Physikochemische Eigenschaften

Schmelzpunkt: 62 · 62-65°C
Siedepunkt: 163 °C · 163 °C(Press: 1 Torr)
Dichte: 1.204 · 1.204±0.06 g/cm3(Predicted)
storage temp.: 2 · 2-8°C
Löslichkeit: Acetone (Slightly), Chloroform (Slightly), Ethyl Acetate (Sparingly)
Aggregatzustand: Solid
pka: 8.88 · 8.88±0.18(Predicted)
Farbe: White to Off-White
Wasserlöslichkeit: Slightly soluble in water.
InChI: InChI=1S/C11H12O4/c1-14-10-7-8(3-5-9(10)12)4-6-11(13)15-2/h3-7,12H,1-2H3
InChIKey: AUJXJFHANFIVKH-UHFFFAOYSA-N
SMILES: C(OC)(=O)C=CC1=CC=C(O)C(OC)=C1
LogP: 2.209 · 2.209 (est)
CAS Datenbank: 2309 · 2309-07-1(CAS DataBase Reference)
NIST chemische Informationen: 2 · 2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, methyl ester(2309-07-1)

Sicherheit und Regulatorisches

Sicherheitsdaten

hs_code: 2918999090
RTECS-Nr.: GD9470000
risk_code: 36/37/38
safety_code: 26-36/37/39

Chemie und Industrie

Anwendungen · 1 Eintrag

VerwendenFerulic acid is a hydroxycinnamic acid that is abundant in plants and originally derived from giant fennel (F. communis). This naturally-occurring phenolic has antioxidant activities that provide protection against inflammation and cancer. Ferulic acid methyl ester is a lipophilic derivative of ferulic acid, demonstrating increased ability to cross cell membranes. Ferulic acid methyl ester has less antioxidant capacity than ferulic acid in neuronal PC12 cells (IC50 = 74.7 μM for ferulic acid ethyl ester vs. 44.6 μM for ferulic acid, 2,2-diphenyl-1-picrylhydrazyl radical scavenging). Ferulic acid methyl ester, at 10-25 μg/ml, inhibits the release of pro-inflammatory cytokines, blocks the expression of COX-2, and reduces nitric oxide generation from LPS-stimulated macrophages.