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2-Methoxycinnamic acid

Catalog No.GC35092

2-Methoxycinnamic acid는 tyrosinase의 비경쟁적 억제제입니다.

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2-Methoxycinnamic acid Chemical Structure

Cas No.: 6099/3/2

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Sample solution is provided at 25 µL, 10mM.

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Quality Control & SDS

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2-Methoxycinnamic acid is a noncompetitive inhibitor of tyrosinase[1].

[1]. Lee HS, et al. Tyrosinase inhibitors of Pulsatilla cernua root-derived materials. J Agric Food Chem. 2002 Mar 13;50(6):1400-3.

Chemical Properties

Cas No. 6099/3/2 SDF
Canonical SMILES O=C(O)/C=C/C1=CC=CC=C1OC
Formula C10H10O3 M.Wt 178.18
Solubility Soluble in DMSO Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.
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Research Update

Tyrosinase inhibitors of Pulsatilla cernua root-derived materials

J Agric Food Chem 2002 Mar 13;50(6):1400-3.PMID:11879010DOI:10.1021/jf011230f.

The inhibition of mushroom tyrosinase by Pulsatilla cernua root-derived materials was evaluated. The bioactive components of Pulsatilla cernua root were characterized by spectroscopic analyses as 3,4-dihydroxycinnamic acid and 4-hydroxy-3-methoxycinnamic acid, which exhibited potent antityrosinase activity. The ID50 values of 3,4-dihydroxycinnamic acid and 4-hydroxy-3-methoxycinnamic acid were 0.97 and 0.33 mM, respectively. The compounds isolated from Pulsatilla cernua roots exhibited noncompetitive inhibition against oxidation of L-DOPA by mushroom tyrosinase. This activity was compared with that of three cinnamic acid derivatives and four well-known tyrosinase inhibitors. The ID50 of 4-hydroxy-3-methoxycinnamic acid exhibited superior activity relative to anisaldehyde, anisic acid, benzoic acid, benzaldehyde, cinnamic acid, and cinnamaldehyde; but antityrosinase inhibitors and cinnamic acid derivatives, except for cinnamyl alcohol, were slightly more effective than 3,4-dihydroxycinnamic acid. In the case of benzaldehyde and cinnamaldehyde, the aldehyde group is, apparently, a key group in eliciting potent inhibitory activity, whereas anisaldehyde is more effective than anisic acid. Methoxy substitutions, such as 2-Methoxycinnamic acid, 3-methoxycinnamic acid, and 4-methoxycinnamic acid, enhanced inhibition of tyrosinase activity. As a naturally occurring tyrosinase inhibitor, 3,4-dihydroxycinnamic acid and 4-hydroxy-3-methoxycinnamic acid may be useful as new agents to inhibit the oxidation of L-3,4-dihydroxyphenylalanine (L-DOPA) by mushroom tyrosinase.

Selective growth inhibitor toward human intestinal bacteria derived from Pulsatilla cernua root

J Agric Food Chem 2001 Oct;49(10):4656-61.PMID:11600003DOI:10.1021/jf010609z.

Among 21 medicinal plants, the growth-inhibiting activity of Pulsatilla cernua root-derived materials toward human intestinal bacteria was examined by using an impregnated paper disk method. The biologically active components of P. cernua roots were characterized as 4-hydroxy-3-methoxycinnamic acid and 3,4-dihydroxycinnamic acid by spectroscopic analysis. The activity was compared with that of six commercially available cinnamic acid derivatives trans-cinnamaldehyde, trans-cinnamic acid, cinnamyl alcohol, 2-Methoxycinnamic acid, 3-methoxycinnamic acid, and 4-methoxycinnamic acid. The growth responses varied with each bacterial strain tested. Two isolated compounds revealed a potent inhibition against Clostridium perfringens, and moderate to weak activity against Escherichia coli was exhibited by 4-hydroxy-3-methoxycinnamic acid. Weak or no inhibitory activity was obtained against the bifidobacteria or Lactobacillus acidophilus. The inhibitory effect was much more pronounced in C. perfringens and E. coli as compared to B. adolescentis, B. bifidum, B. fragilis, B. longum, or L. acidophilus. Cinnamaldehyde exhibited a strong growth-inhibiting activity, but no inhibition was observed from treatments with trans-cinnamic acid, cinnamyl alcohol, 2-Methoxycinnamic acid, 3-methoxycinnamic acid, and 4-methoxycinnamic acid. These results may be an indication of at least one of the pharmacological actions of P. cernua root.

A new method for simultaneous determination of 14 phenolic acids in agricultural soils by multiwavelength HPLC-PDA analysis

RSC Adv 2022 May 18;12(23):14939-14944.PMID:35702192DOI:10.1039/d1ra09433e.

There are phenolic acids with allelopathy in the rhizosphere soil of plants. At present, the identification and quantification of phenolic acids in different matrix mixtures is usually analysed by high performance liquid chromatography, but the detection of phenolic acids in soil has rarely been studied. As well as, previous studies have evaluated a limited number of target compounds. In this work, we proposed and verified a method for quantitative determination of 14 phenolic acids, including gallic acid, vanillic acid, p-hydroxybenzoic acid, protocatechuic acid, caffeic acid, syringic acid, p-coumaric acid, ferulic acid, chlorogenic acid, benzoic acid, salicylic acid, 2-Methoxycinnamic acid, 3-methoxycinnamic acid, and cinnamic acid, which are widely present in rhizosphere soil of plants and have allelopathy. This method used multiwavelength HPLC-PDA analysis for simultaneous determination of these compounds. The detection wavelengths selected 254 nm, 280 nm, 300 nm, and 320 nm. Chromatographic separation of all compounds was achieved using a column of Shim-pack VP-ODS (250 mm × 4.6 mm, 5 μm), kept at 30 °C. Mobile phase A was acetonitrile, B was a 0.5% acetic acid aqueous solution, and the flow rate was 1.0 mL min-1. Under the condition of gradient elution, the mobile phase A was acetonitrile, B was a 0.5% acetic acid aqueous solution, and the flow rate was kept constant at 1.0 mL min-1. The 14 target phenolic acids were completely separated within 45 min. All the calibration curves showed good linearity, and the correlation coefficient was 0.9994-0.9999. With the detection limit varying from 0.003 mg L-1 to 0.239 mg L-1. The recovery rates and the RSD of 14 phenolic acids were 80.54∼107.0% and 1.43-4.35%, respectively. This method has the characteristics of high sensitivity, high accuracy, and high recovery rate. This method is a novel technical means for the simultaneous analysis of compound phenolic acids in soil.

Cinnamic acid derivative rare-earth dinuclear complexes and one-dimensional architectures: synthesis, characterization and magnetic properties

Dalton Trans 2017 Mar 21;46(12):3943-3952.PMID:28265631DOI:10.1039/c7dt00326a.

Discrete and extended architectures based on the association of lanthanide ions with two derivatives of cinnamic acid (2-Methoxycinnamic acid and 3-methoxycinnamic acid) have been synthesized and characterized by IR spectroscopy, elemental analyses, X-ray diffraction and magnetic measurements. The use of the 2-methoxycinnamic ligand enables the synthesis of a series of dinuclear complexes (Ce3+ (1), Nd3+ (2), Gd3+ (3), Dy3+ (4)), while the presence of 3-methoxycinnamic acid induces the formation of one-dimensional coordination polymers (Ce3+ (5), Nd3+ (6), Dy3+ (7)). Investigations of the magnetic properties of the complexes reveal that they all exhibit field-induced slow relaxation of the magnetisation, mainly induced by Raman and direct relaxation processes.

Comparative Analysis of Phytochemical Profiles and Antioxidant Activities between Sweet and Sour Wampee ( Clausena lansium) Fruits

Foods 2022 Apr 25;11(9):1230.PMID:35563953DOI:10.3390/foods11091230.

As a local medicine and food, wampee fruit, with abundant bioactive compounds, is loved by local residents in Southern China. Titratable acid (TA), total sugar (TS), and total phenolic and flavonoid contents were detected, and phytochemical profiles and cellular antioxidant activities were analyzed by the HPLC and CAA (cellular antioxidant activity) assay in five sweet wampee varieties and five sour wampee varieties. Results showed that the average TS/TA ratio of sweet wampee varieties was 29 times higher than sour wampee varieties, while TA content was 19 times lower than sour wampee varieties. There were much lower levels of total phenolics, flavonoids, and antioxidant activities in sweet wampee varieties than those in sour wampee varieties. Eight phytochemicals were detected in sour wampee varieties, including syringin, rutin, benzoic acid, 2-Methoxycinnamic acid, kaempferol, hesperetin, nobiletin, and tangeretin, while just four of them were detected in sweet wampee varieties. Syringin was the only one that was detected in all the sour wampee varieties and was not detected in all sweet wampee varieties. Correlation analysis showed significant positive correlations between TA with phenolics, flavonoids, and total and cellular (PBS wash) antioxidant activities, while there were significant negative correlations between TS/TA with phenolic and cellular (no PBS wash) antioxidant activities. This suggested that the content of titratable acid in wampee fruit might have some relationship with the contents of phenolics and flavonoids. Sour wampee varieties should be paid much attention by breeders for their high phytochemical contents and antioxidant activities for cultivating germplasms with high health care efficacy.


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Average Rating: 5 ★★★★★ (Based on Reviews and 21 reference(s) in Google Scholar.)

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