4-Methoxycinnamic acid | CAS:830-09-1 | Manufacturer ChemFaces

4-Methoxycinnamic acid

ChemFaces products have been cited in many studies from excellent and top scientific journals

Product Name	4-Methoxycinnamic acid
Price:	$40 / 20mg
CAS No.:	830-09-1
Catalog No.:	CFN98191
Molecular Formula:	C₁₀H₁₀O₃
Molecular Weight:	178.18 g/mol
Purity:	>=98%
Type of Compound:	Phenylpropanoids
Physical Desc.:	White powder
Source:	The barks of Cinnamomum cassia Presl.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS SDF Manual
Similar structural:	Comparison (Web) (SDF)
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Description:

4-Methoxycinnamic acid is a photosensitive compound, it shows various pharmacologic actions such as anti-cancer, hepatoprotective and antihyperglycemic activities, it also can stimulate insulin secretion from pancreatic β-cells by increasing Ca2+ influx via the L-type Ca2+ channels, but not through the closure of ATP-sensitive K+ channels. 4-Methoxycinnamic acid can strongly inhibit the diphenolase activity of mushroom tyrosinase, with the IC 50 value of 0.42 mM, and the inhibition is reversible.

Targets:

Calcium Channel | ATPase | Potassium Channel | P450 (e.g. CYP17) | NADPH-oxidase

In vitro:

J Med Microbiol. 2011 Nov;60(Pt 11):1626-32.

Natural products modulate Shigella-host-cell interaction.[Pubmed: 21719574]

This study focused on identifying possible new options derived from natural sources for the treatment of bacterial infections. Several natural products were investigated for their potential in modulating Shigella-host-cell interactions.
METHODS AND RESULTS:
The proliferation of Shigella sonnei was effectively inhibited inside HEp-2 cells in the presence of 4-Methoxycinnamic acid and propolin D. Propolin D also significantly reduced the apoptosis of infected macrophage-like U937 cells and moderately reduced the secretion of interleukin (IL)-1β and IL-18, which probably resulted from the inhibition of invasion plasmid antigen B secretion by this compound. Further characterization showed that propolin D did not prevent escape of Shigella from phagocytic vacuoles, as evidenced by actin-based motility and by the fact that addition of chloroquine did not further reduce the number of intracellular c.f.u. The role of propolin D in modulating autophagy could not be established under the experimental conditions used.
CONCLUSIONS:
As these compounds had no direct anti-Shigella activity in vitro, it was concluded that these compounds modulated Shigella-host-cell interactions by targeting yet-to-be defined mechanisms that provide benefits to host cells.

US 8758864 B2[P]. 2014.

Photosensitive semiconductor nanocrystals, photosensitive composition comprising semiconductor nanocrystals and method for forming semiconductor nanocrystal pattern using the same[Reference: WebLink]

4. The organic-inorganic hybrid electroluminescent device according to claim 1, wherein the compound containing a photosensitive functional group is selected from a group consisting of methacrylic acid, crotonic acid, vinylacetic acid, tiglic acid, 3,3-dimethylacrylic acid, trans-2-pentenoic acid, 4-pentenoic acid, trans-2-methyl-2-pentenoic acid, 2,2-dimethyl-4-pentenoic acid, trans-2-hexenoic acid, trans-3-hexenoic acid, 2-ethyl-2-hexenoic acid, 6-heptenoic acid, 2-octenoic acid, citronellic acid, undecylenic acid, myristoleic acid, palmitoleic acid, oleic acid, elaidic acid, cis-11-elcosenoic acid, euric acid, nervonic acid, trans-2,4-pentadienoic acid, 2,4-hexadienoic acid, 2,6-heptadienoic acid, geranic acid, linoleic acid, 11,14-eicosadienoic acid, cis-8,11,14-eicosatrienoic acid, arachidonic acid, cis-5,8,11,14,17-eicosapentaenoic acid, cis-4,7,10,13,16,19-docosahexaenoic acid, fumaric acid, maleic acid, itaconic acid, ciraconic acid, mesaconic acid, trans-glutaconic acid, trans-beta-hydromuconic acid, trans-traumatic acid, trans-muconic acid, cis-aconitic acid, trans-aconitic acid, cis-3-chloroacrylic acid, trans-3-chloroacrylic acid, 2-bromoacrylic acid, 2-(trifluoromethyl)acryl-ic acid, trans-styrylacetic acid, trans-cinnamic acid, alpha.-methylcinnamic acid, 2-methylcinnamic acid, 2-fluorocinnamic acid, 2-(trifluoromethyl)cinnamic acid, 2-chlorocinnamic acid, 2-methoxycinnamic acid, 2-hydroxycinnamic acid, 2-nitrocinnamic acid, 2-carboxycinnamic acid, trans-3-fluorocinnamic acid, 3-(trifluoromethyl)cinnamic acid, 3-chlorocinnamic acid, 3-bromocinnamic acid, 3-methoxycinnamic acid, 3-hydroxycinnamic acid, 3-nitrocinnamic acid, 4-methylcinnamic acid, 4-fluorocinnamic acid, trans-4-(trifluoromethyl)-cinnamic acid, 4-chlorocinnamic acid, 4-bromocinnamic acid, 4-Methoxycinnamic acid, 4-hydroxycinnamic acid, 4-nitrocinnamic acid, 3,3-dimethoxycinnamic acid, 4-vinylbenzoic acid, allyl methyl sulfide, allyl disulfide, diallyl amine, oleylamine, 3-amino-1-propanol vinyl ether, 4-chlorocinnamonitrile, 4-methoxycinnamonitrile, 3,4-dimethoxycinnamonitrile, 4-dimethylaminocinnamonitrile, acrylonitrile, allyl cyanide, crotononitrile, methacrylonitrile, cis-2-pentenenitrile, trans-3-pentenenitrile, 3,7-dimethyl-2,6-octadienenitrile, and 1,4-dicyano-2-butene.

In vivo:

Mol Cell Biochem. 2014 Sep;394(1-2):187-98.

Protective effect of p-methoxycinnamic acid, an active phenolic acid against 1,2-dimethylhydrazine-induced colon carcinogenesis: modulating biotransforming bacterial enzymes and xenobiotic metabolizing enzymes.[Pubmed: 24908112 ]

Objective of the study is to evaluate the modifying potential of p-methoxycinnamic acid (4-Methoxycinnamic acid,p-MCA), an active rice bran phenolic acid on biotransforming bacterial enzymes and xenobiotic metabolizing enzymes in 1,2-dimethylhydrazine-induced rat colon carcinogenesis.
METHODS AND RESULTS:
48 male albino wistar rats were divided into six groups. Group1 (control) received modified pellet diet and 0.1 % carboxymethylcellulose; group2 received modified pellet diet along with p-MCA (80 mg/kg b.wt. p.o.) everyday for 16 weeks; groups 3-6 received 1,2-dimethylhydrazine (DMH) (20 mg/kg b.wt.) subcutaneous injection once a week for the first 4 weeks, while groups 4-6 received p-MCA at three different doses of 20, 40 and 80 mg/kg b.wt. p.o. everyday for 16 weeks. A significant increase in carcinogen-activating enzymes (cytochrome P450, cytochrome b5, cytochrome P4502E1, NADH-cytochrome-b5-reductase and NADPH-cytochrome-P450 reductase) with concomitant decrease in phaseII enzymes, DT-Diaphorase, glutathione S-transferase, UDP-glucuronyl-transferase and gamma glutamyltransferase were observed in group3 compared to control. DMH treatment significantly increased the activities of feacal and colonic bacterial enzymes (β-glucosidase, β-galactosidase, β-glucuronidase, nitroreductase, sulphatase and mucinase). p-MCA supplementation (40 mg/kg b.wt) to carcinogen exposed rats inhibited these enzymes, which were near those of control rats.
CONCLUSIONS:
The formation of dysplastic aberrant crypt foci in the colon and the histopathological observations of the liver also supports our biochemical findings. p-MCA (40 mg/kg b.wt.) offers remarkable modulating efficacy of biotransforming bacterial and xenobiotic metabolizing enzymes in colon carcinogenesis.

Kinase Assay:

Food Chem.,2005, 92(4):707-12.

Inhibitory effects of cinnamic acid and its derivatives on the diphenolase activity of mushroom ( Agaricus bisporus ) tyrosinase.[Reference: WebLink]

The effects of cinnamic acid and its derivatives (2-hydroxycinnamic acid, 4-hydroxycinnamic acid and 4-Methoxycinnamic acid) on the activity of mushroom tyrosinase have been studied.
METHODS AND RESULTS:
Results showed that cinnamic acid, 4-hydroxycinnamic acid and 4-Methoxycinnamic acid strongly inhibited the diphenolase activity of mushroom tyrosinase and the inhibition was reversible. The IC 50 values were estimated to be 2.10, 0.50 and 0.42 mM, respectively. 2-Hydroxycinnamic acid had no inhibitory effect on the diphenolase activity of the enzyme. Kinetic analyses showed that the inhibition type of cinnamic acid and 4-Methoxycinnamic acid was noncompetitive with the constants ( K I) determined to be 1.994 and 0.458 mM, respectively.
CONCLUSIONS:
The inhibition type of 4-hydroxycinnamic acid was competitive, with the inhibition constant ( K I) was 0.244 mM.

Horm. Metab. Res.,2011 Oct;43(11): 766-73.

Mechanisms of p-methoxycinnamic acid-induced increase in insulin secretion.[Pubmed: 22009371 ]

p-Methoxycinnamic acid (4-Methoxycinnamic acid,p-MCA) is a cinnamic acid derivative that shows various pharmacologic actions such as hepatoprotective and antihyperglycemic activities.
METHODS AND RESULTS:
The present study was to elucidate the mechanisms by which p-MCA increases [Ca2⁺]i and insulin secretion in INS-1 cells. p-MCA (100 μM) increased [Ca2⁺]i in INS-1 cells. The p-MCA-induced insulin secretion and rise in [Ca2⁺]i were markedly inhibited in the absence of extracellular Ca2⁺ or in the presence of an L-type Ca2⁺ channel blocker nimodipine. These results suggested that p-MCA increased Ca2⁺ influx via the L-type Ca2⁺ channels. Diazoxide, an ATP-sensitive K⁺ channel opener, did not alter p-MCA-induced insulin secretion, nor [Ca2⁺]i response. In addition, p-MCA enhanced glucose-, glibenclamide-induced insulin secretion whereas it also potentiated the increase in insulin secretion induced by arginine, and Bay K 8644, an L-type Ca2⁺ channel agonist.
CONCLUSIONS:
Taken together, our results suggest that p-MCA stimulated insulin secretion from pancreatic β-cells by increasing Ca2⁺ influx via the L-type Ca2⁺ channels, but not through the closure of ATP-sensitive K⁺ channels.

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	5.6123 mL	28.0615 mL	56.123 mL	112.246 mL	140.3076 mL
5 mM	1.1225 mL	5.6123 mL	11.2246 mL	22.4492 mL	28.0615 mL
10 mM	0.5612 mL	2.8062 mL	5.6123 mL	11.2246 mL	14.0308 mL
50 mM	0.1122 mL	0.5612 mL	1.1225 mL	2.2449 mL	2.8062 mL
100 mM	0.0561 mL	0.2806 mL	0.5612 mL	1.1225 mL	1.4031 mL

CFN96152	Methyl 3-(4-methoxyphenyl)propanoate	15823-04-8	194.2	C₁₁H₁₄O₃
CFN96138	Ethyl 3-(4-methoxyphenyl)propanoate	22767-72-2	208.3	C₁₂H₁₆O₃
CFN96379	Methyl p-hydroxyphenyllactate	51095-47-7	196.2	C₁₀H₁₂O₄
CFN96363	Ethyl p-hydroxyphenyllactate	62517-34-4	210.2	C₁₁H₁₄O₄
CFN95446	4-Methoxybenzoylacetic acid	13422-77-0	194.2	C₁₀H₁₀O₄
CFN99018	2,3-dihydroxy-3-(4-hydroxyphenyl)propanoic acid	100201-57-8	198.2	C₉H₁₀O₅
CFN98185	4-Nitrocinnamic acid	619-89-6	193.16	C₉H₇NO₄
CFN98184	4-Chlorocinnamic acid	1615-02-7	182.60	C₉H₇ClO₂
CFN98190	2-Chlorocinnamic acid	3752-25-8	182.61	C₉H₇ClO₂
CFN95341	New compound 8	N/A	388.4	C₁₇H₂₄O₁₀

Source:	The barks of Cinnamomum cassia Presl.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.