Methyl cinnamate

Names

[ CAS No. ]:
103-26-4

[ Name ]:
Methyl cinnamate

[Synonym ]:
METHYLCINNAMATE
METHYL CINANMATE
Cinnamic acid methylester
E-3-phenyl-acrylic acid methyl ester
(E)-cinnamic acid methyl ester
TRANS-CINNAMIC ACID METHYL ESTER
cinnamic acid methyl ester
(2E)-3-Phenyl-2-propenoic acid methyl ester
trans-3-Phenylacrylic Acid Methyl Ester
METHYL-3-PHENYLPROPENOTE
Methyl (2E)-3-phenylacrylate
Methyl cinnamate
METHYL CINNAMATE/CINNAMIC ACID METHYL ESTER
EINECS 203-093-8
Methyl (E)-cinnamate
2-Propenoic acid, 3-phenyl-, methyl ester, (2E)-
CINNAMICACIDMETHYLESTER
MFCD00008458
Methyl trans-3-Phenylacrylate
METHYL 3-PHENYLACRYLATE
methyl (2E)-3-phenylprop-2-enoate
METHYL CIMNAMATE NATURAL
METHYL CINNAMYLATE
Methyl trans-cinnamate
FEMA 2698

Biological Activity

[Description]:

Methyl cinnamate (Methyl 3-phenylpropenoate), an active component of Zanthoxylum armatum, is a widely used natural flavor compound. Methyl cinnamate (Methyl 3-phenylpropenoate) possesses antimicrobial activity and is a tyrosinase inhibitor that can prevent food browning. Methyl cinnamate (Methyl 3-phenylpropenoate) has antiadipogenic activity through mechanisms mediated, in part, by the CaMKK2-AMPK signaling pathway[1].

[Related Catalog]:

Signaling Pathways >> Epigenetics >> AMPK

Research Areas >> Infection

Signaling Pathways >> Metabolic Enzyme/Protease >> Tyrosinase

Signaling Pathways >> PI3K/Akt/mTOR >> AMPK

Research Areas >> Metabolic Disease

Signaling Pathways >> Anti-infection >> Bacterial

[In Vitro]

In 3T3-L1 cell model, Methyl cinnamate (Methyl 3-phenylpropenoate) inhibits adipocyte differentiation by attenuating expression of the adipogenic transcription factors SREBP-1, PPARγ, and C/EBPα and the transcriptional activity of PPARγ. In addition, Methyl cinnamate (Methyl 3-phenylpropenoate) activates the CaMKK2−AMPK signaling cascade involved in the regulation of adipogenesis[1].

[References]

[1]. Chen YY, et al. Methyl cinnamate inhibits adipocyte differentiation via activation of the CaMKK2-AMPK pathwayin 3T3-L1 preadipocytes. J Agric Food Chem. 2012 Feb 1;60(4):955-63.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
261.9±0.0 °C at 760 mmHg

[ Melting Point ]:
34-38 °C(lit.)

[ Molecular Formula ]:
C₁₀H₁₀O₂

[ Molecular Weight ]:
162.185

[ Flash Point ]:
141.3±9.9 °C

[ Exact Mass ]:
162.068085

[ PSA ]:
26.30000

[ LogP ]:
2.18

[ Vapour Pressure ]:
0.0±0.5 mmHg at 25°C

[ Index of Refraction ]:
1.559

[ Storage condition ]:
0-10°C

[ Water Solubility ]:
insoluble

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GE0190000

CHEMICAL NAME :: Cinnamic acid, methyl ester

CAS REGISTRY NUMBER :: 103-26-4

LAST UPDATED :: 199712

DATA ITEMS CITED :: 5

MOLECULAR FORMULA :: C10-H10-O2

MOLECULAR WEIGHT :: 162.20

WISWESSER LINE NOTATION :: 1OV1U1R

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2610 mg/kg

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

REFERENCE :: FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 13,849,1975

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

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: >5 gm/kg

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

REFERENCE :: FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 13,849,1975 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 83204 No. of Facilities: 21 (estimated) No. of Industries: 1 No. of Occupations: 19 No. of Employees: 2695 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 83204 No. of Facilities: 3528 (estimated) No. of Industries: 15 No. of Occupations: 36 No. of Employees: 57284 (estimated) No. of Female Employees: 39442 (estimated)

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xn

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
1

[ RTECS ]:
GE0190000

[ HS Code ]:
2916399090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2916399090

[ Summary ]:
2916399090 other aromatic monocarboxylic acids, their anhydrides, halides, peroxides, peroxyacids and their derivatives VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

Articles

Contribution of cinnamic acid analogues in rosmarinic acid to inhibition of snake venom induced hemorrhage.

Bioorg. Med. Chem. 19 , 2392-6, (2011)

In our previous paper, we reported that rosmarinic acid (1) of Argusia argentea could neutralize snake venom induced hemorrhagic action. Rosmarinic acid (1) consists of two phenylpropanoids: caffeic a...

BF3·OEt2-promoted diastereoselective diacetoxylation of alkenes by PhI(OAc)2.

J. Org. Chem. 76(24) , 9997-10004, (2011)

Selective syn and anti diacetoxylations of alkenes have been achieved using a PhI(OAc)(2)/BF(3)·OEt(2) system in the presence and absence of water, respectively. A broad range of substrates including ...

Stoichiometric model of alpha-cyclodextrin complex formation.

J. Pharm. Sci. 69(5) , 564-7, (1980)

The solubility, spectral, and kinetic methods were used to study complexing between alpha-cyclodextrin (ligand, L) and 3,5-dimethoxycinnamic acid, benzalacetone, and methyl cinnamate (substrates, S). ...