o-Methoxycinnamaldehyde

Names

[ Name ]:
o-Methoxycinnamaldehyde

[Synonym ]:
MFCD00007001
3-(2-Methoxyphenyl)acrylaldehyde
2-Methoxycinnamaldehyde
(2E)-3-(2-Methoxyphenyl)acrylaldehyde
2-Propenal, 3- (2-methoxyphenyl)-
β-(o-Methoxyphenyl)acrolein
o-Methoxycinnamaldehyde
o-Methoxycinnamicaldehyde crystals
(2E)-3-(2-Methoxyphenyl)Prop-2-Enal
2-Propenal, 3-(2-methoxyphenyl)-, (2E)-
EINECS 216-131-3

Biological Activity

[Description]:

2-Methoxycinnamaldehyde (o-Methoxycinnamaldehyde) is a natural compound of Cinnamomum cassia, with antitumor activity[1][2][3]. 2-Methoxycinnamaldehyde inhibits proliferation and induces apoptosis by mitochondrial membrane potential (ΔΨm) loss, activation of both caspase-3 and caspase-9[2]. 2-Methoxycinnamaldehyde effectively inhibits platelet-derived growth factor (PDGF)-induced HASMC migration[3].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

[References]

[1]. Wong HY, et al. Cinnamomum verum Component 2-Methoxycinnamaldehyde: A Novel Anticancer Agent with Both Anti-Topoisomerase I and II Activities in Human Lung Adenocarcinoma A549 Cells In Vitro and In Vivo. Phytother Res. 2016 Feb;30(2):331-40.

[2]. Liu YH, et al. Cinnamomum verum ingredient 2-methoxycinnamaldehyde: a new antiproliferative drug targeting topoisomerase I and II in human lung squamous cell carcinoma NCI-H520 cells. Eur J Cancer Prev. 2017 Jul;26(4):314-323.

[3]. Jin YH, et al. 2-Methoxycinnamaldehyde inhibits the TNF-α-induced proliferation and migration of human aortic smooth muscle cells. Int J Mol Med. 2017 Jan;39(1):191-198.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
334.8±0.0 °C at 760 mmHg

[ Melting Point ]:
44-48ºC

[ Molecular Formula ]:
C₁₀H₁₀O₂

[ Molecular Weight ]:
162.185

[ Flash Point ]:
134.4±13.9 °C

[ Exact Mass ]:
162.068085

[ PSA ]:
26.30000

[ LogP ]:
2.13

[ Vapour Pressure ]:
0.0±0.7 mmHg at 25°C

[ Index of Refraction ]:
1.559

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GD6590000

CHEMICAL NAME :: Cinnamaldehyde, o-methoxy-

CAS REGISTRY NUMBER :: 1504-74-1

BEILSTEIN REFERENCE NO. :: 2436856

LAST UPDATED :: 199712

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C10-H10-O2

MOLECULAR WEIGHT :: 162.20

WISWESSER LINE NOTATION :: VH1U1R BO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: Standard Draize test

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

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

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >2 gm/kg

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

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

MUTATION DATA

TYPE OF TEST :: Mutation in microorganisms

TEST SYSTEM :: Bacteria - Salmonella typhimurium

DOSE/DURATION :: 333 ug/plate

REFERENCE :: ENMUDM Environmental Mutagenesis. (New York, NY) V.1-9, 1979-87. For publisher information, see EMMUEG. Volume(issue)/page/year: 8(Suppl 7),1,1986

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H315-H319-H335

[ Precautionary Statements ]:
P261-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
26-37/39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
GD6590000

[ HS Code ]:
2912499000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2912499000

[ Summary ]:
2912499000. other aldehyde-ethers, aldehyde-phenols and aldehydes with other oxygen function. VAT:17.0%. Tax rebate rate:9.0%. . MFN tariff:5.5%. General tariff:30.0%

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