Methyl 4-hydroxy-3-methoxycinnamate

Names

[ Name ]:
Methyl 4-hydroxy-3-methoxycinnamate

[Synonym ]:
Ferulic acid methyl ester
Methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)acrylate
ferulic acid amide
Ferulasaeure-amid
2-Propenoic acid, 3- (4-hydroxy-3-methoxyphenyl)-, methyl ester
Ferulamid
Methyl ferulate
methyl (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
4-Hydroxy-3-methoxy-zimtsaeure-amid
Methyl 4-hydroxy-3-methoxycinnamate
4-Oxy-3-methoxy-zimtsaeure-amid
Ferulamide
4-hydroxy-3-methoxy-cinnamic acid amide
4-Hydroxy-3-Methoxycinnamide
methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
MFCD00017208
methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, methyl ester, (2E)-
2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, methyl ester (9CI)
CINNAMIC ACID,4-HYDROXY-3-METHOXY-,METHYL ESTER
CINNAMAMIDE,4-HYDROXY-3-METHOXY
methyl 3-(4-hydroxy-3-methoxyphenyl)acrylate
Ferulic amide
feruloylamide
3-(4-Hydroxy-3-methoxyphenyl)-2-propenamide

Biological Activity

[Description]:

Ferulic acid methyl ester (Methyl ferulate) is a derivative of ferulic acid, isolated from Stemona tuberosa, with anti-inflammatory and antioxidant properties[1][2]. Ferulic acid methyl ester is a cell membrane and brain permeable compound, shows free radical scavenging ability, used in the research of neurodegenerative disorders[1]. Ferulic acid methyl ester inhibits COX-2 expression, blocks p-p38 and p-JNK in primary bone marrow derived-macrophages[2].

[Related Catalog]:

Signaling Pathways >> MAPK/ERK Pathway >> p38 MAPK

Research Areas >> Inflammation/Immunology

Research Areas >> Neurological Disease

[Target]

p38

[In Vitro]

Ferulic acid methyl ester (Methyl ferulate; 5, 10, 25 µg/mL) suppresses TNFα, IL6, IFNγ but not IL10, inhibits NO generation at 10 and 25 µg/mL, in primary bone marrow derived-macrophages (BMDMs)[2]. Ferulic acid methyl ester (25 µg/mL) inhibits COX-2 expression, blocks p-p38 and p-JNK[2].

[References]

[1]. Sultana R. Ferulic acid ethyl ester as a potential therapy in neurodegenerative disorders. Biochim Biophys Acta. 2012 May;1822(5):748-52.

[2]. Phuong NT, et al. Anti-inflammatory activity of methyl ferulate isolated from Stemona tuberosa Lour. Asian Pac J Trop Med. 2014 Sep;7S1:S327-31.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
338.1±27.0 °C at 760 mmHg

[ Melting Point ]:
62-65°C

[ Molecular Formula ]:
C₁₁H₁₂O₄

[ Molecular Weight ]:
208.21

[ Flash Point ]:
130.4±17.2 °C

[ Exact Mass ]:
208.073563

[ PSA ]:
55.76000

[ LogP ]:
1.40

[ Vapour Pressure ]:
0.0±0.8 mmHg at 25°C

[ Index of Refraction ]:
1.575

[ Storage condition ]:
2-8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GD9470000

CHEMICAL NAME :: Cinnamic acid, 4-hydroxy-3-methoxy-, methyl ester

CAS REGISTRY NUMBER :: 2309-07-1

BEILSTEIN REFERENCE NO. :: 2731141

LAST UPDATED :: 199612

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C11-H12-O4

MOLECULAR WEIGHT :: 208.23

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1189 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IJEBA6 Indian Journal of Experimental Biology. (Publications & Information Directorate, CSIR, Hillside Rd., New Delhi 110 012, India) V.1- 1963- Volume(issue)/page/year: 25,187,1987

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36/37/39

[ RTECS ]:
GD9470000

[ HS Code ]:
2918990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2918990090

[ Summary ]:
2918990090. other carboxylic acids with additional oxygen function and their anhydrides, halides, peroxides and peroxyacids; their halogenated, sulphonated, nitrated or nitrosated derivatives. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%