Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C9H7O2.Na |
| Molecular Weight | 170.1404 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[O-]C(=O)\C=C\C1=CC=CC=C1
InChI
InChIKey=DXIHILNWDOYYCH-UHDJGPCESA-M
InChI=1S/C9H8O2.Na/c10-9(11)7-6-8-4-2-1-3-5-8;/h1-7H,(H,10,11);/q;+1/p-1/b7-6+;
Cinnamic acid is a polyphenol found in cinnamon oil and used in commercial flavorings. Recent studies have shown the pharmacological properties of cinnamic acid and its derivatives, including hepatoprotective, anti-oxidant, and anti-diabetic activities. In preclinical studies cinnamic acid demonstrated to be a promising candidate for the treatment ob obesity and diabetes. The mechanism of action of cinnamic acid in obesity is explained by its ability to inhibit lipases and ACE (angiotensin-converting enzyme). However, there are several hypotesis regarding the effect of cinnamic acid in diabetes: cinnamic acid enhances glucose-induced insulin secretion, prevents palmitic acid-induced lipotoxicity, inhibits palmitic acid-induced alteration of lipogenic gene and protein expression (AMPK, SREBP-1c, FAS, ACC), inhibits DPP IV, exhibits an additive effect on the uptake of glucose, stimulates adiponectin secretion, etc.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: Lipid digestive enzymes |
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Target ID: P12821 Gene ID: 1636.0 Gene Symbol: ACE Target Organism: Homo sapiens (Human) |
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Target ID: P27487 Gene ID: 1803.0 Gene Symbol: DPP4 Target Organism: Homo sapiens (Human) |
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Target ID: P18031 Gene ID: 5770.0 Gene Symbol: PTPN1 Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Inhibition of rat liver mevalonate pyrophosphate decarboxylase and mevalonate phosphate kinase by phenyl and phenolic compounds. | 1979 Jul 1 |
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| An extracorporeal hollow-fiber reactor for phenylketonuria using immobilized phenylalanine ammonia lyase. | 1986 |
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| Synergistic activities of antituberculous drugs with cerulenin and trans-cinnamic acid against Mycobacterium tuberculosis. | 1998 Jun |
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| A different approach to treatment of phenylketonuria: phenylalanine degradation with recombinant phenylalanine ammonia lyase. | 1999 Mar 2 |
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| Simultaneous analysis of the di(2-ethylhexyl)phthalate metabolites 2-ethylhexanoic acid, 2-ethyl-3-hydroxyhexanoic acid and 2-ethyl-3-oxohexanoic acid in urine by gas chromatography-mass spectrometry. | 2001 Jul 15 |
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| Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens. | 2001 Mar |
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| Genetically engineered Pseudomonas: a factory of new bioplastics with broad applications. | 2001 Oct |
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| Selective growth inhibitor toward human intestinal bacteria derived from Pulsatilla cernua root. | 2001 Oct |
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| Organic acids in the second morning urine in a healthy Swiss paediatric population. | 2003 Dec |
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| Recombinant Saccharomyces cerevisiae expressing P450 in artificial digestive systems: a model for biodetoxication in the human digestive environment. | 2003 May |
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| Cinnamic acid based thiazolidinediones inhibit human P450c17 and 3beta-hydroxysteroid dehydrogenase and improve insulin sensitivity independent of PPARgamma agonist activity. | 2004 Apr |
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| Gastrointestinally distributed UDP-glucuronosyltransferase 1A10, which metabolizes estrogens and nonsteroidal anti-inflammatory drugs, depends upon phosphorylation. | 2004 Jul 2 |
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| Esters, amides and substituted derivatives of cinnamic acid: synthesis, antimicrobial activity and QSAR investigations. | 2004 Oct |
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| A blend of polyphenolic compounds explains the stimulatory effect of red wine on human endothelial NO synthase. | 2005 Mar |
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| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
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| Phenolic acids suppress adipocyte lipolysis via activation of the nicotinic acid receptor GPR109A (HM74a/PUMA-G). | 2009 May |
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| Influence of cinnamaldehyde on viral myocarditis in mice. | 2010 Aug |
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| Biochemical mechanism of caffeic acid phenylethyl ester (CAPE) selective toxicity towards melanoma cell lines. | 2010 Oct 6 |
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| Transformation of cinnamic acid from trans- to cis-form raises a notable bactericidal and synergistic activity against multiple-drug resistant Mycobacterium tuberculosis. | 2011 Jun 14 |
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| Enhanced activity of antifungal drugs using natural phenolics against yeast strains of Candida and Cryptococcus. | 2011 May |
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| Structure-activity relationships of trans-substituted-propenoic acid derivatives on the nicotinic acid receptor HCA2 (GPR109A). | 2011 May 1 |
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| Interaction of cinnamic acid derivatives with commercial hypoglycemic drugs on 2-deoxyglucose uptake in 3T3-L1 adipocytes. | 2011 Sep 28 |
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| Design, synthesis, and molecular hybrids of caudatin and cinnamic acids as novel anti-hepatitis B virus agents. | 2012 Aug |
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| Amelioration of cyclophosphamide induced myelosuppression and oxidative stress by cinnamic acid. | 2012 Feb 5 |
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| Comparative study of the possible protective effects of cinnamic acid and cinnamaldehyde on cisplatin-induced nephrotoxicity in rats. | 2013 Dec |
Patents
Sample Use Guides
In a preclinical study cinnamic acid was administered orally to rats at a dose of 5 and 10 mg/kg (diabetes model). In a preclinical model of obesity/hypertension cinnamic acid was given at 30 mg/kg/day.
Route of Administration:
Oral
To determine the effect of cinnamic acid on glucose uptake FL83B cells were suspended in HBSS
containing 5 mM glucose and 5.0 ug/mL insulin. Each 20 uL aliquot of the cell suspension was incubated with the mixture of 20 uL of 12.5 uM cinnamic acid and 20 uL of HBSS at 37 celsius degrees for 30 min with constant shaking. Glucose uptake in mouse liver FL83B cells treated with cinnamic acid (472.8 (8.9 cpm/mg of protein) is
2.3 and 2.0 times of the basal uptake value (240.6 (20.2 cpm/mg of protein), respectively.
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1DKD3Z3E4Y
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Sodium cinnamate
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DTXSID5060223
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538-42-1
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5462638
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208-691-2
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C029010
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ACTIVE MOIETY
SUBSTANCE RECORD
