2-Chlorocinnamic acid | CAS:3752-25-8 | Manufacturer ChemFaces

2-Chlorocinnamic acid

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Product Name	2-Chlorocinnamic acid
Price:	$30 / 20mg
CAS No.:	3752-25-8
Catalog No.:	CFN98190
Molecular Formula:	C₉H₇ClO₂
Molecular Weight:	182.61 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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Size /Price /Stock	10 mM * 1 mL in DMSO / $7.0 / In-stock
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Description:

2-Chlorocinnamic acid is a photosensitive compound, it can inhibit tyrosinase activity. 2-Chlorocinnamic acid and 4-chlorocinnamic acid show potent urease inhibitory activities with the respective IC50 values of 0.66 and 1.10 uM.

In vitro:

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.

2-Chlorocinnamic acid Description

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.

Kinase Assay:

J Biosci Bioeng. 2014 Feb;117(2):142-6.

Inhibitory kinetics of chlorocinnamic acids on mushroom tyrosinase.[Pubmed: 23958639]

Tyrosinase (EC 1.14.18.1) is the key enzyme of most food enzymatic oxidation. Tyrosinase inhibitors are important in food industry.
METHODS AND RESULTS:
In the present paper, 2-chlorcinnamic acid and 2,4-dichlorocinnamic acid were synthesized and the inhibitory kinetics on mushroom tyrosinase were investigated. The results showed that both compounds synthesized could inhibit tyrosinase activity. For monophenolase activity, both chlorocinnamic acids could extended the lag time and decrease the steady-state activities, 2-chlorcinnamic acid extended the lag time just by 5%, and 2,4-dichlorcinnamic acid extended the lag time more than by 30.4%. For diphenolase activity, the IC50 values of 2-chlorcinnamic acid and 2,4-dichlorocinnamic acid were determined to be 0.765 mM and 0.295 mM, respectively.
CONCLUSIONS:
The inhibition kinetics showed that 2-chlorcinnamic acid and 2,4-dichlorocinnamic acid displayed a reversible and uncompetitive mechanism. The inhibition constants were determined to be 0.348 mM and 0.159 mM, respectively. The research may supply the basis for designing new tyrosinase inhibitors.

Zeitschrift Für Anorganische Und Allgemeine Chemie,2014, 640(2):423-8.

Synthesis, Characterization and Biological Evaluation of Two Silver(I) trans‐Cinnamate Complexes as Urease Inhibitors.[Reference: WebLink]

Two new silver(I) trans‐cinnamates, namely [Ag(2‐cca)(H2O)]2 (1) and [Ag(4‐cca)] n (2) (2‐ccaH = 2-Chlorocinnamic acid and 4‐ccaH = 4‐chlorocinnamic acid), were synthesized and structurally characterized.
METHODS AND RESULTS:
Single crystal X‐ray studies reveal that each silver(I) atom in 1 is two‐coordinate by a 2‐chlorocinnamate ligand and one water molecule to afford a discrete centrosymmetric dimer with the ligand‐unsupported Ag···Ag interactions (3.218(4) Å), while a pair of symmetry‐related silver(I) atoms in 2 are clamped by two μ2‐η1:η1 4‐chlorocinnamate ligands to yield a binuclear silver(I) moiety incorporating a ligand‐supported Ag···Ag interaction (2.819(5) Å).
CONCLUSIONS:
Both complexes 1 and 2 show potent urease inhibitory activities with the respective IC50 values of 0.66 and 1.10 μM.

Structure Identification:

Chemosphere. 2000 Jun;40(12):1417-25.

A novel ortho-dehalogenation reaction of 2-chlorocinnamic acid catalyzed by the pink yeast Rhodotorula rubra Y-1529.[Pubmed: 10789983]

In the present study, a resting cells suspension of Rhodotorula rubra Y-1529 was shown to have the capacity to perform an ortho-dehalogenation reaction on 2-Chlorocinnamic acid.
METHODS AND RESULTS:
The results from the biodegradation of U-[14C]benzoic acid, cinnamic acid, 3-chlorocinnamic acid and 4-chlorocinnamic acid suggest that the first step of the ortho-dehalogenation reaction occurred during the oxidation of the unsaturated C3 side chain of 2-Chlorocinnamic acid to 2-chlorobenzoic acid. None of the 2-chlorobenzoic acid was found in the biodegradation system, suggesting that this step was a highly regulated step. After the side-chain oxidation reaction, the hydroxylation of the benzene ring was determined to be at the para-position first, followed by the meta-position. The occurrence of 3:4-position ring fission reactions and the production of the final product, CO2, was proven by the biodegradation of U-[14C] benzoic acid. This oxidative dehalogenation reaction catalyzed by R. rubra was found to be regiospecific for 2-Chlorocinnamic acid; the chloride ion was probably removed after the ring fission reaction.
CONCLUSIONS:
A pathway of the ortho-dehalogenation reaction of 2-Chlorocinnamic acid catalyzed by R. rubra was proposed based on these data.

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Inhibitors Compound Library Food additives Compound Library Photosensitizer Compound Library Phenylpropanoids Compound Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	5.4762 mL	27.3808 mL	54.7615 mL	109.523 mL	136.9038 mL
5 mM	1.0952 mL	5.4762 mL	10.9523 mL	21.9046 mL	27.3808 mL
10 mM	0.5476 mL	2.7381 mL	5.4762 mL	10.9523 mL	13.6904 mL
50 mM	0.1095 mL	0.5476 mL	1.0952 mL	2.1905 mL	2.7381 mL
100 mM	0.0548 mL	0.2738 mL	0.5476 mL	1.0952 mL	1.369 mL

CFN98178	4-Acetoxycinnamic acid	15486-19-8	206.19	C₁₁H₁₀O₄
CFN98191	4-Methoxycinnamic acid	830-09-1	178.18	C₁₀H₁₀O₃
CFN93803	4-O-beta-Glucopyranosyl-cis-coumaric acid	117405-48-8	326.29	C₁₅H₁₈O₈
CFN91462	Linocinnamarin	554-87-0	340.3	C₁₆H₂₀O₈
CFN96113	Methyl 4-hydroxycinnamate	19367-38-5	178.2	C₁₀H₁₀O₃
CFN97218	p-Coumaric acid ethyl ester	7362-39-2	192.2	C₁₁H₁₂O₃
CFN98180	Ethyl 4-methoxycinnamate	24393-56-4	206.24	C₁₂H₁₄O₃
CFN95563	Octyl 3-(4-hydroxyphenyl)prop-2-enoate	N/A	276.4	C₁₇H₂₄O₃
CFN96152	Methyl 3-(4-methoxyphenyl)propanoate	15823-04-8	194.2	C₁₁H₁₄O₃
CFN96138	Ethyl 3-(4-methoxyphenyl)propanoate	22767-72-2	208.3	C₁₂H₁₆O₃