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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

Description

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

2017
414
Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Lipid digestive enzymes
Inhibitor
8146
Angiotensin-converting enzyme
96
Target ID: P12821
Gene ID: 1636.0
Gene Symbol: ACE
Target Organism: Homo sapiens (Human)
Inhibitor
8146
Dipeptidyl peptidase 4
8
Target ID: P27487
Gene ID: 1803.0
Gene Symbol: DPP4
Target Organism: Homo sapiens (Human)
Inhibitor
8146
Tyrosine-protein phosphatase non-receptor type 1
4
Target ID: P18031
Gene ID: 5770.0
Gene Symbol: PTPN1
Target Organism: Homo sapiens (Human)
Inhibitor
8146
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
Selective growth inhibitor toward human intestinal bacteria derived from Pulsatilla cernua root.
2001 Oct
Cinnamic acid based thiazolidinediones inhibit human P450c17 and 3beta-hydroxysteroid dehydrogenase and improve insulin sensitivity independent of PPARgamma agonist activity.
2004 Apr
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
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
Interaction of cinnamic acid derivatives with commercial hypoglycemic drugs on 2-deoxyglucose uptake in 3T3-L1 adipocytes.
2011 Sep 28
Comparative study of the possible protective effects of cinnamic acid and cinnamaldehyde on cisplatin-induced nephrotoxicity in rats.
2013 Dec
Patents

Patents

JP1033117A
2
JP1056654A
2
JP1075414A
2
JP1075416A
2
JP2000072761A
2
JP2000086603A
2
JP2000095688A
2
JP2000095689A
2
JP2000095690A
2
JP2000136121A
2
JP2000136313A
2
JP2000159857A
2
JP2000204397A
3
JP2000226313A
2
JP2000229912A
2
JP2000256108A
2
JP2000256462A
2
JP2000264868A
2
JP2000319154A
18
JP2000319202A
2
JP2000507091A
5
JP2000517348A
2
JP2001013110A
2
JP2001048764A
4
JP2001086966A
4
JP2001114742A
2
JP2001136957A
3
JP2001245629A
4
JP2001278774A
7
JP2001501449A
4
JP2001525340A
2
JP2001527517A
8
JP2002029916A
2
JP2002037759A
2
JP2002053728A
2
JP2002060395A
2
JP2002131534A
2
JP2002241213A
5
JP2002363195A
2
JP2002371039A
2
JP2002503693A
5
JP2002524505A
3
JP2002533379A
53
JP2002542363A
3
JP2002543243A
3
JP2003000294A
2
JP2003002805A
2
JP2003012412A
2
JP2003033196A
7
JP2003073392A
2
JP2003113005A
2

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 16 20:59:48 UTC 2022
Edited
by admin
on Fri Dec 16 20:59:48 UTC 2022
Record UNII
U14A832J8D
Record Status Validated (UNII)
Record Version
  • Download
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 16 20:59:48 UTC 2022 , Edited by admin on Fri Dec 16 20:59:48 UTC 2022
FDA ORPHAN DRUG 782820
Created by admin on Fri Dec 16 20:59:48 UTC 2022 , Edited by admin on Fri Dec 16 20:59:48 UTC 2022
CFR 21 CFR 172.515
Created by admin on Fri Dec 16 20:59:48 UTC 2022 , Edited by admin on Fri Dec 16 20:59:48 UTC 2022
FDA ORPHAN DRUG 802320
Created by admin on Fri Dec 16 20:59:48 UTC 2022 , Edited by admin on Fri Dec 16 20:59:48 UTC 2022
FDA ORPHAN DRUG 783920
Created by admin on Fri Dec 16 20:59:48 UTC 2022 , Edited by admin on Fri Dec 16 20:59:48 UTC 2022
JECFA EVALUATION CINNAMIC ACID
Created by admin on Fri Dec 16 20:59:48 UTC 2022 , Edited by admin on Fri Dec 16 20:59:48 UTC 2022
Code System Code Type Description
ECHA (EC/EINECS)
210-708-3
Created by admin on Fri Dec 16 20:59:48 UTC 2022 , Edited by admin on Fri Dec 16 20:59:48 UTC 2022
ALTERNATIVE
CHEBI
35697
Created by admin on Fri Dec 16 20:59:48 UTC 2022 , Edited by admin on Fri Dec 16 20:59:48 UTC 2022
PRIMARY
RXCUI
1368650
Created by admin on Fri Dec 16 20:59:48 UTC 2022 , Edited by admin on Fri Dec 16 20:59:48 UTC 2022
PRIMARY
CAS
140-10-3
Created by admin on Fri Dec 16 20:59:48 UTC 2022 , Edited by admin on Fri Dec 16 20:59:48 UTC 2022
PRIMARY
RXCUI
1368649
Created by admin on Fri Dec 16 20:59:48 UTC 2022 , Edited by admin on Fri Dec 16 20:59:48 UTC 2022
PRIMARY RxNorm
NSC
623441
Created by admin on Fri Dec 16 20:59:48 UTC 2022 , Edited by admin on Fri Dec 16 20:59:48 UTC 2022
PRIMARY
PUBCHEM
444539
Created by admin on Fri Dec 16 20:59:48 UTC 2022 , Edited by admin on Fri Dec 16 20:59:48 UTC 2022
PRIMARY
CHEBI
23248
Created by admin on Fri Dec 16 20:59:48 UTC 2022 , Edited by admin on Fri Dec 16 20:59:48 UTC 2022
PRIMARY
MERCK INDEX
M3569
Created by admin on Fri Dec 16 20:59:48 UTC 2022 , Edited by admin on Fri Dec 16 20:59:48 UTC 2022
PRIMARY Merck Index
NSC
44010
Created by admin on Fri Dec 16 20:59:48 UTC 2022 , Edited by admin on Fri Dec 16 20:59:48 UTC 2022
PRIMARY
CHEBI
27386
Created by admin on Fri Dec 16 20:59:48 UTC 2022 , Edited by admin on Fri Dec 16 20:59:48 UTC 2022
PRIMARY
WIKIPEDIA
CINNAMIC ACID
Created by admin on Fri Dec 16 20:59:48 UTC 2022 , Edited by admin on Fri Dec 16 20:59:48 UTC 2022
PRIMARY
FDA UNII
U14A832J8D
Created by admin on Fri Dec 16 20:59:48 UTC 2022 , Edited by admin on Fri Dec 16 20:59:48 UTC 2022
PRIMARY
EPA CompTox
DTXSID5022489
Created by admin on Fri Dec 16 20:59:48 UTC 2022 , Edited by admin on Fri Dec 16 20:59:48 UTC 2022
PRIMARY
EVMPD
SUB29136
Created by admin on Fri Dec 16 20:59:48 UTC 2022 , Edited by admin on Fri Dec 16 20:59:48 UTC 2022
PRIMARY
RS_ITEM_NUM
1133933
Created by admin on Fri Dec 16 20:59:48 UTC 2022 , Edited by admin on Fri Dec 16 20:59:48 UTC 2022
PRIMARY
NSC
9189
Created by admin on Fri Dec 16 20:59:48 UTC 2022 , Edited by admin on Fri Dec 16 20:59:48 UTC 2022
PRIMARY
MESH
C029010
Created by admin on Fri Dec 16 20:59:48 UTC 2022 , Edited by admin on Fri Dec 16 20:59:48 UTC 2022
PRIMARY
DAILYMED
U14A832J8D
Created by admin on Fri Dec 16 20:59:48 UTC 2022 , Edited by admin on Fri Dec 16 20:59:48 UTC 2022
PRIMARY
ECHA (EC/EINECS)
205-398-1
Created by admin on Fri Dec 16 20:59:48 UTC 2022 , Edited by admin on Fri Dec 16 20:59:48 UTC 2022
PRIMARY
CAS
621-82-9
Created by admin on Fri Dec 16 20:59:48 UTC 2022 , Edited by admin on Fri Dec 16 20:59:48 UTC 2022
NON-SPECIFIC STEREOCHEMISTRY
Related Record Type Details
STEVIA REBAUDIUNA LEAF
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.
CINNAMOMUM CASSIA TWIG
PARENT -> CONSTITUENT ALWAYS PRESENT
CINNAMON
PARENT -> CONSTITUENT ALWAYS PRESENT
Structure of SODIUM CINNAMATE
SALT/SOLVATE -> PARENT
CHINESE CINNAMON
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
Related Record Type Details
Structure of PHENYLALANINE
PARENT -> METABOLITE
Structure of 5-P-COUMAROYLQUINIC ACID
METABOLITE -> PARENT
Related Record Type Details
Structure of CINNAMIC ACID
ACTIVE MOIETY
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