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
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+
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
Primary Target | Pharmacology | Condition | Potency |
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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 |
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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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Synergistic activities of antituberculous drugs with cerulenin and trans-cinnamic acid against Mycobacterium tuberculosis. | 1998 Jun |
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A different approach to treatment of phenylketonuria: phenylalanine degradation with recombinant phenylalanine ammonia lyase. | 1999 Mar 2 |
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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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Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens. | 2001 Mar |
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Selective growth inhibitor toward human intestinal bacteria derived from Pulsatilla cernua root. | 2001 Oct |
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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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Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
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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 |
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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
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Record UNII |
U14A832J8D
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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DSLD |
2727 (Number of products:1)
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FDA ORPHAN DRUG |
782820
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CFR |
21 CFR 172.515
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FDA ORPHAN DRUG |
802320
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FDA ORPHAN DRUG |
783920
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JECFA EVALUATION |
CINNAMIC ACID
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210-708-3
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35697
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1368650
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140-10-3
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1368649
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623441
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444539
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23248
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M3569
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44010
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27386
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CINNAMIC ACID
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U14A832J8D
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DTXSID5022489
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SUB29136
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1133933
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9189
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C029010
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U14A832J8D
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205-398-1
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621-82-9
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NON-SPECIFIC STEREOCHEMISTRY |
Related Record | Type | Details | ||
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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.
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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Related Record | Type | Details | ||
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PARENT -> METABOLITE | |||
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METABOLITE -> PARENT |
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ACTIVE MOIETY |