Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C9H8O4 |
| Molecular Weight | 180.1574 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)\C=C\C1=CC(O)=C(O)C=C1
InChI
InChIKey=QAIPRVGONGVQAS-DUXPYHPUSA-N
InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+
| Molecular Formula | C9H8O4 |
| Molecular Weight | 180.1574 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Optical Activity | NONE |
Caffeic acid is an organic compound that is classified as a hydroxycinnamic acid. Caffeic acid is naturally found in many agricultural products, such as fruit, vegetables, wine, olive oil, and coffee, and therefore, significantly present in human diet. Caffeic acid has been reported to have a wide variety of biological activities, including antioxidants, antithrombosis, antihypertensive, antifibrosis, antiviral and anti-tumor properties. Caffeic acid can be effectively employed as a natural antioxidant in various food products such as oils. Caffeic acid exhibits potent anticancer effect in HT-1080 cell line and that it may be used as an anticancer agent. Caffeic acid showed neuroprotective action against oxidative and DNA damage produced in the kindling epilepsy model, although they did not produce antiepileptogenic effect in vivo. Caffeic acid was effective in patients with primary immune thrombocytopenia. Detected in clinical trial caffeic acid-related adverse events were: mild nausea and elevation of liver enzymes.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Influence of twenty potentially antiviral substances on in vitro multiplication of hepatitis A virus. | 1986 Mar |
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| Inhibition of HIV replication by Hyssop officinalis extracts. | 1990 Dec |
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| Inhibition of HIV-1 proteinase by non-peptide carboxylates. | 1991 Apr 15 |
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| In vitro and in vivo reversible and irreversible inhibition of rat glutathione S-transferase isoenzymes by caffeic acid and its 2-S-glutathionyl conjugate. | 1993 Jul |
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| Molecular mechanisms of tirapazamine (SR 4233, Win 59075)-induced hepatocyte toxicity under low oxygen concentrations. | 1995 Apr |
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| Inhibitors of HIV-1 replication [corrected; erratum to be published] that inhibit HIV integrase. | 1996 Jun 25 |
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| Dicaffeoylquinic acid inhibitors of human immunodeficiency virus integrase: inhibition of the core catalytic domain of human immunodeficiency virus integrase. | 1996 Oct |
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| Dicaffeoylquinic and dicaffeoyltartaric acids are selective inhibitors of human immunodeficiency virus type 1 integrase. | 1998 Jan |
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| Structure-activity relationships: analogues of the dicaffeoylquinic and dicaffeoyltartaric acids as potent inhibitors of human immunodeficiency virus type 1 integrase and replication. | 1999 Feb 11 |
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| Nonsteroidal anti-inflammatory drugs induce apoptosis in esophageal cancer cells by restoring 15-lipoxygenase-1 expression. | 2001 Jun 15 |
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| In vitro activity of polyhydroxycarboxylates against herpesviruses and HIV. | 2001 Nov |
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| Antiviral activity of Plantago major extracts and related compounds in vitro. | 2002 Jul |
|
| Isolation, structure, and HIV-1-integrase inhibitory activity of structurally diverse fungal metabolites. | 2003 Dec |
|
| Protective effect of Mesona procumbens against tert-butyl hydroperoxide-induced acute hepatic damage in rats. | 2004 Jun 30 |
|
| Activation of rat liver microsomal glutathione S-transferase by gallic acid. | 2005 Nov 19 |
|
| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
|
| Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines. | 2008 Dec 15 |
|
| Oxygen-glucose deprivation activates 5-lipoxygenase mediated by oxidative stress through the p38 mitogen-activated protein kinase pathway in PC12 cells. | 2009 Mar |
|
| The genome-wide expression profile of Scrophularia ningpoensis-treated thapsigargin-stimulated U-87MG cells. | 2009 May |
|
| Preventive effect of caffeic acid on lysosomal dysfunction in isoproterenol-induced myocardial infarcted rats. | 2010 Mar-Apr |
|
| Entacapone and tolcapone, two catechol O-methyltransferase inhibitors, block fibril formation of alpha-synuclein and beta-amyloid and protect against amyloid-induced toxicity. | 2010 May 14 |
|
| Caffeic acid protects rat heart mitochondria against isoproterenol-induced oxidative damage. | 2010 Nov |
|
| Biochemical mechanism of caffeic acid phenylethyl ester (CAPE) selective toxicity towards melanoma cell lines. | 2010 Oct 6 |
|
| Protective effects of caffeic acid on lactate dehydrogenase isoenzymes, electrocardiogram, adenosine triphosphatases, and hematology on isoproterenol-induced myocardial infarcted rats. | 2011 Mar-Apr |
|
| 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 |
|
| Caffeic acid attenuates 12-O-tetradecanoyl-phorbol-13-acetate (TPA)-induced NF-κB and COX-2 expression in mouse skin: abrogation of oxidative stress, inflammatory responses and proinflammatory cytokine production. | 2012 Feb |
|
| Inhibitory effects of caffeic acid phenethyl ester derivatives on replication of hepatitis C virus. | 2013 |
|
| Novel phenolic inhibitors of small/intermediate-conductance Ca²⁺-activated K⁺ channels, KCa3.1 and KCa2.3. | 2013 |
|
| Oral administration of caffeic acid ameliorates the effect of cisplatin on brush border membrane enzymes and antioxidant system in rat intestine. | 2013 Jan |
|
| Differentiation between stoichiometric and anticatalytic antioxidant properties of benzoic acid analogues: a structure/redox potential relationship study. | 2013 Nov 25 |
|
| Antifungal efficacy of some natural phenolic compounds against significant pathogenic and toxinogenic filamentous fungi. | 2013 Oct |
|
| Inhibitors of the glyoxylate cycle enzyme ICL1 in Candida albicans for potential use as antifungal agents. | 2014 |
|
| Polyacetylenes and anti-hepatitis B virus active constituents from Artemisia capillaris. | 2014 Jun |
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| Activity of caffeic acid derivatives against Candida albicans biofilm. | 2014 Mar 15 |
|
| Investigation of the effects of some phenolic compounds on the activities of glucose-6-phosphate dehydrogenase and 6-phosphogluconate dehydrogenase from human erythrocytes. | 2014 Nov |
|
| Protective effects of caffeic acid against hypothalamic neuropeptides alterations induced by malathion in rat. | 2015 Apr |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 17:32:10 UTC 2023
by
admin
on
Fri Dec 15 17:32:10 UTC 2023
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| Record UNII |
U2S3A33KVM
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| Record Status |
Validated (UNII)
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NCI_THESAURUS |
C68539
Created by
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DSLD |
1678 (Number of products:14)
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| Code System | Code | Type | Description | ||
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U2S3A33KVM
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PRIMARY | |||
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16433
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PRIMARY | |||
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C68540
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206-361-2
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C040048
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57197
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100000174372
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689043
Created by
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CAFFEIC ACID
Created by
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331-39-5
Created by
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NON-SPECIFIC STEREOCHEMISTRY | |||
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1311397
Created by
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m2908
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331-39-5
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501-16-6
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U2S3A33KVM
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DB01880
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17395
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623438
Created by
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PARENT -> CONSTITUENT ALWAYS PRESENT |
19.2% reaction on PG synthase w/10.0 mM conc. of compound
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ACTIVE MOIETY |
