SODIUM CINNAMATE

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

Structure Search

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+;

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Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28230764 | https://www.ncbi.nlm.nih.gov/pubmed/25765836 | https://www.ncbi.nlm.nih.gov/pubmed/26139902

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
Lipid digestive enzymes 2 Target ID: Lipid digestive enzymes Sources: https://www.ncbi.nlm.nih.gov/pubmed/26139902	Inhibitor 8297
Angiotensin-converting enzyme 97 Target ID: P12821 Gene ID: 1636.0 Gene Symbol: ACE Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26139902	Inhibitor 8297
Dipeptidyl peptidase 4 8 Target ID: P27487 Gene ID: 1803.0 Gene Symbol: DPP4 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/28230764	Inhibitor 8297
Tyrosine-protein phosphatase non-receptor type 1 4 Target ID: P18031 Gene ID: 5770.0 Gene Symbol: PTPN1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26139902	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Obesity 203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26139902	Primary	Preclinical	Unknown Approved Use Unknown
Diabetes mellitus 91 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25765836	Primary	Preclinical	Unknown Approved Use Unknown
Hypertension 567 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26139902	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Inhibition of rat liver mevalonate pyrophosphate decarboxylase and mevalonate phosphate kinase by phenyl and phenolic compounds.	1979 Jul 1	226078
An extracorporeal hollow-fiber reactor for phenylketonuria using immobilized phenylalanine ammonia lyase.	1986	3956347
Synergistic activities of antituberculous drugs with cerulenin and trans-cinnamic acid against Mycobacterium tuberculosis.	1998 Jun	9685005
Genetically engineered Pseudomonas: a factory of new bioplastics with broad applications.	2001 Oct	11722541
Selective growth inhibitor toward human intestinal bacteria derived from Pulsatilla cernua root.	2001 Oct	11600003
Recombinant Saccharomyces cerevisiae expressing P450 in artificial digestive systems: a model for biodetoxication in the human digestive environment.	2003 May	12732562
A blend of polyphenolic compounds explains the stimulatory effect of red wine on human endothelial NO synthase.	2005 Mar	15740983
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	21536127
Interaction of cinnamic acid derivatives with commercial hypoglycemic drugs on 2-deoxyglucose uptake in 3T3-L1 adipocytes.	2011 Sep 28	21870829
Design, synthesis, and molecular hybrids of caudatin and cinnamic acids as novel anti-hepatitis B virus agents.	2012 Aug	22687441
Amelioration of cyclophosphamide induced myelosuppression and oxidative stress by cinnamic acid.	2012 Feb 5	22285266
Comparative study of the possible protective effects of cinnamic acid and cinnamaldehyde on cisplatin-induced nephrotoxicity in rats.	2013 Dec	23959918

Patents

Sample Use Guides

In Vivo Use Guide

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

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.

Name

Type

Language

SODIUM CINNAMATE

Systematic Name

English

SODIUM (E)-3-PHENYLPROP-2-ENOATE

Systematic Name

English

SODIUM CINNAMATE [INCI]

Common Name

English

CINNAMIC ACID, SODIUM SALT

Common Name

English

CINNAMATE SODIUM

Systematic Name

English

Code System Code Type Description

FDA UNII

1DKD3Z3E4Y