cinnamic acid - CAS 621-82-9
Catalog number: 621-82-9
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Molecular Formula:
Chemical Family:
Cinnamic acid is classified as an unsaturated carboxylic acid. It occurs naturally in a number of plants. It exists as both a cis and a trans isomer, although the latter is more common.
3-Phenylpropenoic acid; Phenylacrylic acid; Beta-Phenylacrylic acid; FEMA 2288; 2-Propenoic acid, 3-phenyl-, (2E)-; AKOS B004228
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1.Differential metabolism of L-phenylalanine in the formation of aromatic volatiles in melon (Cucumis melo L.) fruit.
Gonda I;Davidovich-Rikanati R;Bar E;Lev S;Jhirad P;Meshulam Y;Wissotsky G;Portnoy V;Burger J;Schaffer AA;Tadmor Y;Giovannoni JJ;Fei Z;Fait A;Katzir N;Lewinsohn E Phytochemistry. 2018 Apr;148:122-131. doi: 10.1016/j.phytochem.2017.12.018. Epub 2018 Feb 20.
Studies on the active pathways and the genes involved in the biosynthesis of L-phenylalanine-derived volatiles in fleshy fruits are sparse. Melon fruit rinds converted stable-isotope labeled L-phe into more than 20 volatiles. Phenylpropanes, phenylpropenes and benzenoids are apparently produced via the well-known phenylpropanoid pathway involving phenylalanine ammonia lyase (PAL) and being (E)-cinnamic acid a key intermediate. Phenethyl derivatives seemed to be derived from L-phe via a separate biosynthetic route not involving (E)-cinnamic acid and PAL. To explore for a biosynthetic route to (E)-cinnamaldehyde in melon rinds, soluble protein cell-free extracts were assayed with (E)-cinnamic acid, CoA, ATP, NADPH and MgSO;4;, producing (E)-cinnamaldehyde in vitro. In this context, we characterized CmCNL, a gene encoding for (E)-cinnamic acid:coenzyme A ligase, inferred to be involved in the biosynthesis of (E)-cinnamaldehyde. Additionally we describe CmBAMT, a SABATH gene family member encoding a benzoic acid:S-adenosyl-L-methionine carboxyl methyltransferase having a role in the accumulation of methyl benzoate.
2.In silico development, validation and comparison of predictive QSAR models for lipid peroxidation inhibitory activity of cinnamic acid and caffeic acid derivatives using multiple chemometric and cheminformatics tools.
Mitra I;Saha A;Roy K J Mol Model. 2012 Aug;18(8):3951-67. doi: 10.1007/s00894-012-1392-5. Epub 2012 Mar 21.
The design and development of antioxidant molecules have lately gained a great deal of focus which is attributed to their immense biomedicinal importance in combating the free radical associated health hazards. In a situation to replenish the endogenous antioxidant loss, synthetic molecules with potent antioxidant activity is demanded. The present work thus aims at in silico modeling of antioxidant molecules that may facilitate in searching and designing of new chemical entities with enhanced activity profile. A series of cinnamic acid and caffeic acid derivatives having the ability to inhibit lipid peroxidation have been modeled in the present work. Three different types of models were developed using different chemometric and cheminformatics tools to identify the essential structural attributes: (a) descriptor based QSAR models, (b) 3D pharmacophore models and (c) HQSAR (hologram QSAR) models. For the conventional QSAR modeling, descriptors belonging to different categories [quantum chemical descriptors (Mulliken charges of the common atoms of the molecules), thermodynamic descriptors, electronic descriptors, structural descriptors and spatial descriptors] were calculated for the development of statistically significant as well as well interpretable quantitative structure-activity relationship (QSAR) models.
3.Effects of piperine, cinnamic acid and gallic acid on rosuvastatin pharmacokinetics in rats.
Basu S;Jana S;Patel VB;Patel H Phytother Res. 2013 Oct;27(10):1548-56. doi: 10.1002/ptr.4894. Epub 2012 Dec 3.
The purpose of this study was to investigate the potential pharmacokinetic interactions with natural products (such as piperine (PIP), gallic acid (GA) and cinnamic acid (CA)) and rosuvastatin (RSV) (a specific breast cancer resistance protein, BCRP substrate) in rats. In Caco2 cells, the polarized transport of RSV was effectively inhibited by PIP, CA and GA at concentration of 50 μM. After per oral (p.o.) coadministration of PIP, CA and GA (10 mg/kg) significantly increased intravenous exposure (AUC(last)) of RSV (1 mg/kg) by 73.5%, 62.9% and 53.3% (p < 0.05), respectively than alone group (control). Compared with the control (alone) group, p.o. coadministration of PIP, CA and GA (10 mg/kg) significantly increased the oral exposure (AUC(last)) of RSV (5 mg/kg) by 2.0-fold, 1.83-fold (p < 0.05) and 2.34 -fold (p < 0.05), respectively. Moreover, the cumulative biliary excretion of RSV (5 mg/kg, p.o.) was significantly decreased by 53.3, 33.
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