Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C9H8O4 |
| Molecular Weight | 180.1578 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
c1cc(c(cc1/C(/[H])=C(\[H])/C(=O)O)O)O
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 | 180.1578 |
| 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 |
|
| Inhibition of HIV replication by Hyssop officinalis extracts. | 1990 Dec |
|
| Selective inhibitory activity of polyhydroxycarboxylates derived from phenolic compounds against human immunodeficiency virus replication. | 1991 |
|
| Inhibition of HIV-1 proteinase by non-peptide carboxylates. | 1991 Apr 15 |
|
| 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 |
|
| Molecular mechanisms of tirapazamine (SR 4233, Win 59075)-induced hepatocyte toxicity under low oxygen concentrations. | 1995 Apr |
|
| Inhibitors of HIV-1 replication [corrected; erratum to be published] that inhibit HIV integrase. | 1996 Jun 25 |
|
| Dicaffeoylquinic acid inhibitors of human immunodeficiency virus integrase: inhibition of the core catalytic domain of human immunodeficiency virus integrase. | 1996 Oct |
|
| Dicaffeoylquinic and dicaffeoyltartaric acids are selective inhibitors of human immunodeficiency virus type 1 integrase. | 1998 Jan |
|
| 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 |
|
| Steroid hormone activity of flavonoids and related compounds. | 2000 Jul |
|
| Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase. | 2001 Feb |
|
| Do wine polyphenols modulate p53 gene expression in human cancer cell lines? | 2001 Jul |
|
| Nonsteroidal anti-inflammatory drugs induce apoptosis in esophageal cancer cells by restoring 15-lipoxygenase-1 expression. | 2001 Jun 15 |
|
| In vitro activity of polyhydroxycarboxylates against herpesviruses and HIV. | 2001 Nov |
|
| 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 |
|
| The histone deacetylase inhibitor suberoylanilide hydroxamic acid induces apoptosis via induction of 15-lipoxygenase-1 in colorectal cancer cells. | 2004 Dec 1 |
|
| Gastrointestinally distributed UDP-glucuronosyltransferase 1A10, which metabolizes estrogens and nonsteroidal anti-inflammatory drugs, depends upon phosphorylation. | 2004 Jul 2 |
|
| Protective effect of Mesona procumbens against tert-butyl hydroperoxide-induced acute hepatic damage in rats. | 2004 Jun 30 |
|
| Anti-HIV activities of natural antioxidant caffeic acid derivatives: toward an antiviral supplementation diet. | 2005 |
|
| A blend of polyphenolic compounds explains the stimulatory effect of red wine on human endothelial NO synthase. | 2005 Mar |
|
| Activation of rat liver microsomal glutathione S-transferase by gallic acid. | 2005 Nov 19 |
|
| Urinary flavonoids and phenolic acids as biomarkers of intake for polyphenol-rich foods. | 2006 Jul |
|
| Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. | 2006 Nov |
|
| Anti-inflammatory and anti-atherogenic effects of cathechin, caffeic acid and trans-resveratrol in apolipoprotein E deficient mice. | 2007 Apr |
|
| Cigarette smoke toxicants as substrates and inhibitors for human cytosolic SULTs. | 2007 May 15 |
|
| Novel screening assay for antioxidant protection against peroxyl radical-induced loss of protein function. | 2007 Nov |
|
| Transcriptional regulation of deoxynivalenol-induced IL-8 expression in human monocytes. | 2007 Oct |
|
| Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines. | 2008 Dec 15 |
|
| Efficacy of caffeic acid in preventing nickel induced oxidative damage in liver of rats. | 2008 May 28 |
|
| Protection of mouse brain from aluminum-induced damage by caffeic acid. | 2008 Spring |
|
| 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 |
|
| 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 |
|
| Inhibitory effects of caffeic acid phenethyl ester derivatives on replication of hepatitis C virus. | 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 |
|
| 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 |
|
| 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 Jun 25 21:27:37 UTC 2021
by
admin
on
Fri Jun 25 21:27:37 UTC 2021
|
| Record UNII |
U2S3A33KVM
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Official Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C68539
Created by
admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
|
||
|
DSLD |
1678 (Number of products:14)
Created by
admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
C68540
Created by
admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
|
PRIMARY | |||
|
206-361-2
Created by
admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
|
PRIMARY | |||
|
C040048
Created by
admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
|
PRIMARY | |||
|
689043
Created by
admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
|
PRIMARY | |||
|
CAFFEIC ACID
Created by
admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
|
PRIMARY | |||
|
331-39-5
Created by
admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
|
NON-SPECIFIC STEREOCHEMISTRY | |||
|
1311397
Created by
admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
|
PRIMARY | RxNorm | ||
|
M2908
Created by
admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
|
PRIMARY | Merck Index | ||
|
331-39-5
Created by
admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
|
PRIMARY | |||
|
501-16-6
Created by
admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
|
PRIMARY | |||
|
331-39-5
Created by
admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
|
PRIMARY | |||
|
U2S3A33KVM
Created by
admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
|
PRIMARY | |||
|
DB01880
Created by
admin on Fri Jun 25 21:27:37 UTC 2021 , Edited by admin on Fri Jun 25 21:27:37 UTC 2021
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
19.2% reaction on PG synthase w/10.0 mM conc. of compound
|
||
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT | |||
|
PARENT -> CONSTITUENT ALWAYS PRESENT |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
METABOLITE -> PARENT |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |
