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+;
Molecular Formula | C9H7O2 |
Molecular Weight | 147.1507 |
Charge | -1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
Molecular Formula | Na |
Molecular Weight | 22.9898 |
Charge | 1 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26139902 |
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Target ID: P12821 Gene ID: 1636.0 Gene Symbol: ACE Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26139902 |
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Target ID: P27487 Gene ID: 1803.0 Gene Symbol: DPP4 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/28230764 |
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Target ID: P18031 Gene ID: 5770.0 Gene Symbol: PTPN1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26139902 |
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 |
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Inhibition of rat liver mevalonate pyrophosphate decarboxylase and mevalonate phosphate kinase by phenyl and phenolic compounds. | 1979 Jul 1 |
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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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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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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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Influence of cinnamaldehyde on viral myocarditis in mice. | 2010 Aug |
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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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Interaction of cinnamic acid derivatives with commercial hypoglycemic drugs on 2-deoxyglucose uptake in 3T3-L1 adipocytes. | 2011 Sep 28 |
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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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19685889
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:00:19 UTC 2023
by
admin
on
Fri Dec 15 16:00:19 UTC 2023
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Record UNII |
1DKD3Z3E4Y
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Record Status |
Validated (UNII)
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Record Version |
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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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