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+;

HIDE SMILES / InChI

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

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
A different approach to treatment of phenylketonuria: phenylalanine degradation with recombinant phenylalanine ammonia lyase.	1999 Mar 2	10051643
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	11486831
Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens.	2001 Mar	11258977
Organic acids in the second morning urine in a healthy Swiss paediatric population.	2003 Dec	14708889
Recombinant Saccharomyces cerevisiae expressing P450 in artificial digestive systems: a model for biodetoxication in the human digestive environment.	2003 May	12732562
Cinnamic acid based thiazolidinediones inhibit human P450c17 and 3beta-hydroxysteroid dehydrogenase and improve insulin sensitivity independent of PPARgamma agonist activity.	2004 Apr	15072549
Gastrointestinally distributed UDP-glucuronosyltransferase 1A10, which metabolizes estrogens and nonsteroidal anti-inflammatory drugs, depends upon phosphorylation.	2004 Jul 2	15117964
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Phenolic acids suppress adipocyte lipolysis via activation of the nicotinic acid receptor GPR109A (HM74a/PUMA-G).	2009 May	19136666
Influence of cinnamaldehyde on viral myocarditis in mice.	2010 Aug	20460981
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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:00:19 GMT 2023` Edited by `admin` on `Fri Dec 15 16:00:19 GMT 2023`
Record UNII	1DKD3Z3E4Y
Record Status	`Validated (UNII)`
Record Version

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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