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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
Structure of CAFFEIC ACID

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+

HIDE SMILES / InChI

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

Sources: DOI: 10.1021/jf60107a016

Approval Year

PubMed

PubMed

TitleDatePubMed
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

Sample Use Guides

300mg three times a day
Route of Administration: Oral
Caffeic acid treatment significantly increased ROS level in HT-1080 cells. Among all the doses tested, 50 ug/ml of Caffeic acid showed the maximum generation of ROS (95%) in HT-1080 cells.
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:27:37 UTC 2021
Edited
by admin
on Fri Jun 25 21:27:37 UTC 2021
Record UNII
U2S3A33KVM
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CAFFEIC ACID
DSC   HSDB   INCI   MI   USP-RS  
INCI  
Official Name English
3,4-DIHYDROXYBENZENEACRYLIC ACID
Systematic Name English
CAFFEIC ACID [DSC]
Common Name English
2-PROPENOIC ACID, 3-(3,4-DIHYDROXYPHENYL)-, (2E)-
Code English
4-(2-CARBOXYETHENYL)-1,2-DIHYDROXYBENZENE
Systematic Name English
CAFFEIC ACID [INCI]
Common Name English
CAFFEIC ACID (CONSTITUENT OF BLACK COHOSH) [DSC]
Common Name English
3-(3,4-DIHYDROXYPHENYL)-2-PROPENOIC ACID
Systematic Name English
CAFFEIC ACID [IARC]
Common Name English
CINNAMIC ACID, 3,4-DIHYDROXY-
Common Name English
CAFFEIC ACID [WHO-DD]
Common Name English
CAFFEIC ACID [HSDB]
Common Name English
NSC-57197
Code English
NSC-623438
Code English
CAFFEIC ACID [MI]
Common Name English
TRANS-3,4-DIHYDROXYCINNAMIC ACID
Common Name English
TRANS-CAFFEIC ACID
Common Name English
2-PROPENOIC ACID, 3-(3,4-DIHYDROXYPHENYL)-
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
NCI_THESAURUS
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
ECHA (EC/EINECS)
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
MESH
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
PUBCHEM
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
WIKIPEDIA
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
CAS
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
RXCUI
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
MERCK INDEX
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
HSDB
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
CAS
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
EPA CompTox
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
FDA UNII
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
DRUG BANK
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
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