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Details

Stereochemistry ACHIRAL
Molecular Formula C9H8O2
Molecular Weight 148.1586
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CINNAMIC ACID

SMILES

OC(=O)\C=C\C1=CC=CC=C1

InChI

InChIKey=WBYWAXJHAXSJNI-VOTSOKGWSA-N
InChI=1S/C9H8O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7H,(H,10,11)/b7-6+

HIDE SMILES / InChI

Molecular Formula C9H8O2
Molecular Weight 148.1586
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P12821
Gene ID: 1636.0
Gene Symbol: ACE
Target Organism: Homo sapiens (Human)
Target ID: P27487
Gene ID: 1803.0
Gene Symbol: DPP4
Target Organism: Homo sapiens (Human)
Target ID: P18031
Gene ID: 5770.0
Gene Symbol: PTPN1
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Inhibition of rat liver mevalonate pyrophosphate decarboxylase and mevalonate phosphate kinase by phenyl and phenolic compounds.
1979 Jul 1
An extracorporeal hollow-fiber reactor for phenylketonuria using immobilized phenylalanine ammonia lyase.
1986
Synergistic activities of antituberculous drugs with cerulenin and trans-cinnamic acid against Mycobacterium tuberculosis.
1998 Jun
A different approach to treatment of phenylketonuria: phenylalanine degradation with recombinant phenylalanine ammonia lyase.
1999 Mar 2
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
Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens.
2001 Mar
Genetically engineered Pseudomonas: a factory of new bioplastics with broad applications.
2001 Oct
Selective growth inhibitor toward human intestinal bacteria derived from Pulsatilla cernua root.
2001 Oct
Organic acids in the second morning urine in a healthy Swiss paediatric population.
2003 Dec
Recombinant Saccharomyces cerevisiae expressing P450 in artificial digestive systems: a model for biodetoxication in the human digestive environment.
2003 May
Cinnamic acid based thiazolidinediones inhibit human P450c17 and 3beta-hydroxysteroid dehydrogenase and improve insulin sensitivity independent of PPARgamma agonist activity.
2004 Apr
Gastrointestinally distributed UDP-glucuronosyltransferase 1A10, which metabolizes estrogens and nonsteroidal anti-inflammatory drugs, depends upon phosphorylation.
2004 Jul 2
Esters, amides and substituted derivatives of cinnamic acid: synthesis, antimicrobial activity and QSAR investigations.
2004 Oct
A blend of polyphenolic compounds explains the stimulatory effect of red wine on human endothelial NO synthase.
2005 Mar
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Phenolic acids suppress adipocyte lipolysis via activation of the nicotinic acid receptor GPR109A (HM74a/PUMA-G).
2009 May
Influence of cinnamaldehyde on viral myocarditis in mice.
2010 Aug
Biochemical mechanism of caffeic acid phenylethyl ester (CAPE) selective toxicity towards melanoma cell lines.
2010 Oct 6
Structure-activity relationships of trans-substituted-propenoic acid derivatives on the nicotinic acid receptor HCA2 (GPR109A).
2011 May 1
Interaction of cinnamic acid derivatives with commercial hypoglycemic drugs on 2-deoxyglucose uptake in 3T3-L1 adipocytes.
2011 Sep 28
Design, synthesis, and molecular hybrids of caudatin and cinnamic acids as novel anti-hepatitis B virus agents.
2012 Aug
Amelioration of cyclophosphamide induced myelosuppression and oxidative stress by cinnamic acid.
2012 Feb 5
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:46:44 GMT 2023
Edited
by admin
on Fri Dec 15 16:46:44 GMT 2023
Record UNII
U14A832J8D
Record Status Validated (UNII)
Record Version
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Name Type Language
CINNAMIC ACID
FCC   FHFI   INCI   MART.   MI   USP-RS   WHO-DD  
INCI  
Official Name English
NSC-44010
Code English
3-PHENYLACRYLIC ACID
Systematic Name English
NSC-623441
Code English
FEMA NO. 2288
Code English
CINNAMIC ACID [FCC]
Common Name English
CINNAMIC ACID [INCI]
Common Name English
CINNAMIC ACID [MART.]
Common Name English
CINNAMIC ACID [USP-RS]
Common Name English
2-PROPENOIC ACID, 3-PHENYL-, (2E)-
Common Name English
2-PROPENOIC ACID, 3-PHENYL-, (E)-
Common Name English
CINNAMIC ACIDUM
Common Name English
CINNAMIC ACID [FHFI]
Common Name English
TRANS-CINNAMIC ACID
Systematic Name English
CINNAMIC ACID (CONSTITUENT OF CINNAMOMUM VERUM BARK) [DSC]
Common Name English
3-PHENYL-2-PROPENOIC ACID
Systematic Name English
3-PHENYLPROPENOIC ACID
Systematic Name English
NSC-9189
Code English
CINNAMIC ACID [MI]
Common Name English
2-PROPENOIC ACID, 3-PHENYL-
Common Name English
CINNAMIC ACID, (E)-
Common Name English
TRANS-CINNAMIC ACID (CONSTITUENT OF CINNAMOMUM CASSIA BARK) [DSC]
Common Name English
CINNAMIC ACID, TRANS-
Common Name English
E-CINNAMIC ACID
Systematic Name English
Cinnamic acid [WHO-DD]
Common Name English
Classification Tree Code System Code
DSLD 2727 (Number of products:1)
Created by admin on Fri Dec 15 16:46:45 GMT 2023 , Edited by admin on Fri Dec 15 16:46:45 GMT 2023
FDA ORPHAN DRUG 782820
Created by admin on Fri Dec 15 16:46:45 GMT 2023 , Edited by admin on Fri Dec 15 16:46:45 GMT 2023
CFR 21 CFR 172.515
Created by admin on Fri Dec 15 16:46:45 GMT 2023 , Edited by admin on Fri Dec 15 16:46:45 GMT 2023
FDA ORPHAN DRUG 802320
Created by admin on Fri Dec 15 16:46:45 GMT 2023 , Edited by admin on Fri Dec 15 16:46:45 GMT 2023
FDA ORPHAN DRUG 783920
Created by admin on Fri Dec 15 16:46:45 GMT 2023 , Edited by admin on Fri Dec 15 16:46:45 GMT 2023
JECFA EVALUATION CINNAMIC ACID
Created by admin on Fri Dec 15 16:46:45 GMT 2023 , Edited by admin on Fri Dec 15 16:46:45 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
210-708-3
Created by admin on Fri Dec 15 16:46:45 GMT 2023 , Edited by admin on Fri Dec 15 16:46:45 GMT 2023
ALTERNATIVE
CHEBI
35697
Created by admin on Fri Dec 15 16:46:45 GMT 2023 , Edited by admin on Fri Dec 15 16:46:45 GMT 2023
PRIMARY
RXCUI
1368650
Created by admin on Fri Dec 15 16:46:45 GMT 2023 , Edited by admin on Fri Dec 15 16:46:45 GMT 2023
PRIMARY
CAS
140-10-3
Created by admin on Fri Dec 15 16:46:45 GMT 2023 , Edited by admin on Fri Dec 15 16:46:45 GMT 2023
PRIMARY
RXCUI
1368649
Created by admin on Fri Dec 15 16:46:45 GMT 2023 , Edited by admin on Fri Dec 15 16:46:45 GMT 2023
PRIMARY RxNorm
SMS_ID
100000090683
Created by admin on Fri Dec 15 16:46:45 GMT 2023 , Edited by admin on Fri Dec 15 16:46:45 GMT 2023
PRIMARY
NSC
623441
Created by admin on Fri Dec 15 16:46:45 GMT 2023 , Edited by admin on Fri Dec 15 16:46:45 GMT 2023
PRIMARY
PUBCHEM
444539
Created by admin on Fri Dec 15 16:46:45 GMT 2023 , Edited by admin on Fri Dec 15 16:46:45 GMT 2023
PRIMARY
CHEBI
23248
Created by admin on Fri Dec 15 16:46:45 GMT 2023 , Edited by admin on Fri Dec 15 16:46:45 GMT 2023
PRIMARY
JECFA MONOGRAPH
187
Created by admin on Fri Dec 15 16:46:45 GMT 2023 , Edited by admin on Fri Dec 15 16:46:45 GMT 2023
PRIMARY
MERCK INDEX
m3569
Created by admin on Fri Dec 15 16:46:45 GMT 2023 , Edited by admin on Fri Dec 15 16:46:45 GMT 2023
PRIMARY Merck Index
NSC
44010
Created by admin on Fri Dec 15 16:46:45 GMT 2023 , Edited by admin on Fri Dec 15 16:46:45 GMT 2023
PRIMARY
CHEBI
27386
Created by admin on Fri Dec 15 16:46:45 GMT 2023 , Edited by admin on Fri Dec 15 16:46:45 GMT 2023
PRIMARY
WIKIPEDIA
CINNAMIC ACID
Created by admin on Fri Dec 15 16:46:45 GMT 2023 , Edited by admin on Fri Dec 15 16:46:45 GMT 2023
PRIMARY
FDA UNII
U14A832J8D
Created by admin on Fri Dec 15 16:46:45 GMT 2023 , Edited by admin on Fri Dec 15 16:46:45 GMT 2023
PRIMARY
EPA CompTox
DTXSID5022489
Created by admin on Fri Dec 15 16:46:45 GMT 2023 , Edited by admin on Fri Dec 15 16:46:45 GMT 2023
PRIMARY
EVMPD
SUB29136
Created by admin on Fri Dec 15 16:46:45 GMT 2023 , Edited by admin on Fri Dec 15 16:46:45 GMT 2023
PRIMARY
RS_ITEM_NUM
1133933
Created by admin on Fri Dec 15 16:46:45 GMT 2023 , Edited by admin on Fri Dec 15 16:46:45 GMT 2023
PRIMARY
NSC
9189
Created by admin on Fri Dec 15 16:46:45 GMT 2023 , Edited by admin on Fri Dec 15 16:46:45 GMT 2023
PRIMARY
MESH
C029010
Created by admin on Fri Dec 15 16:46:45 GMT 2023 , Edited by admin on Fri Dec 15 16:46:45 GMT 2023
PRIMARY
DAILYMED
U14A832J8D
Created by admin on Fri Dec 15 16:46:45 GMT 2023 , Edited by admin on Fri Dec 15 16:46:45 GMT 2023
PRIMARY
ECHA (EC/EINECS)
205-398-1
Created by admin on Fri Dec 15 16:46:45 GMT 2023 , Edited by admin on Fri Dec 15 16:46:45 GMT 2023
PRIMARY
CAS
621-82-9
Created by admin on Fri Dec 15 16:46:45 GMT 2023 , Edited by admin on Fri Dec 15 16:46:45 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
PARENT -> CONSTITUENT ALWAYS PRESENT
Cinnamic acid content for water extract of plant leaf was 2.42+/-0.03 and plant callus was 0.76+/-0.59 as expressed as mg/100 g of dry base of extract. For the analysis of phenolic acids, a Nova pack C18 UG120 equipped with a Guard column, a JASCO HPLC system consisting of a column oven, a UV-Vis diode array detector set at 280 nm, a Liquid chromatography pump and a ChromNAV software program were used.
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> METABOLITE
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY