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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
Structure of CAFFEIC ACID

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+

HIDE SMILES / InChI

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

Sources: DOI: 10.1021/jf60107a016

Approval Year

PubMed

PubMed

TitleDatePubMed
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
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
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
15-LOX-1: a novel molecular target of nonsteroidal anti-inflammatory drug-induced apoptosis in colorectal cancer cells.
2000 Jul 19
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
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
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
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Novel screening assay for antioxidant protection against peroxyl radical-induced loss of protein function.
2007 Nov
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
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
Antifungal efficacy of some natural phenolic compounds against significant pathogenic and toxinogenic filamentous fungi.
2013 Oct
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 Dec 15 17:32:10 GMT 2023
Edited
by admin
on Fri Dec 15 17:32:10 GMT 2023
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
Caffeic acid [WHO-DD]
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 [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 Dec 15 17:32:11 GMT 2023 , Edited by admin on Fri Dec 15 17:32:11 GMT 2023
DSLD 1678 (Number of products:14)
Created by admin on Fri Dec 15 17:32:11 GMT 2023 , Edited by admin on Fri Dec 15 17:32:11 GMT 2023
Code System Code Type Description
DAILYMED
U2S3A33KVM
Created by admin on Fri Dec 15 17:32:11 GMT 2023 , Edited by admin on Fri Dec 15 17:32:11 GMT 2023
PRIMARY
CHEBI
16433
Created by admin on Fri Dec 15 17:32:11 GMT 2023 , Edited by admin on Fri Dec 15 17:32:11 GMT 2023
PRIMARY
NCI_THESAURUS
C68540
Created by admin on Fri Dec 15 17:32:11 GMT 2023 , Edited by admin on Fri Dec 15 17:32:11 GMT 2023
PRIMARY
ECHA (EC/EINECS)
206-361-2
Created by admin on Fri Dec 15 17:32:11 GMT 2023 , Edited by admin on Fri Dec 15 17:32:11 GMT 2023
PRIMARY
MESH
C040048
Created by admin on Fri Dec 15 17:32:11 GMT 2023 , Edited by admin on Fri Dec 15 17:32:11 GMT 2023
PRIMARY
NSC
57197
Created by admin on Fri Dec 15 17:32:11 GMT 2023 , Edited by admin on Fri Dec 15 17:32:11 GMT 2023
PRIMARY
SMS_ID
100000174372
Created by admin on Fri Dec 15 17:32:11 GMT 2023 , Edited by admin on Fri Dec 15 17:32:11 GMT 2023
PRIMARY
PUBCHEM
689043
Created by admin on Fri Dec 15 17:32:11 GMT 2023 , Edited by admin on Fri Dec 15 17:32:11 GMT 2023
PRIMARY
WIKIPEDIA
CAFFEIC ACID
Created by admin on Fri Dec 15 17:32:11 GMT 2023 , Edited by admin on Fri Dec 15 17:32:11 GMT 2023
PRIMARY
CAS
331-39-5
Created by admin on Fri Dec 15 17:32:11 GMT 2023 , Edited by admin on Fri Dec 15 17:32:11 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
RXCUI
1311397
Created by admin on Fri Dec 15 17:32:11 GMT 2023 , Edited by admin on Fri Dec 15 17:32:11 GMT 2023
PRIMARY RxNorm
MERCK INDEX
m2908
Created by admin on Fri Dec 15 17:32:11 GMT 2023 , Edited by admin on Fri Dec 15 17:32:11 GMT 2023
PRIMARY Merck Index
HSDB
331-39-5
Created by admin on Fri Dec 15 17:32:11 GMT 2023 , Edited by admin on Fri Dec 15 17:32:11 GMT 2023
PRIMARY
CAS
501-16-6
Created by admin on Fri Dec 15 17:32:11 GMT 2023 , Edited by admin on Fri Dec 15 17:32:11 GMT 2023
PRIMARY
FDA UNII
U2S3A33KVM
Created by admin on Fri Dec 15 17:32:11 GMT 2023 , Edited by admin on Fri Dec 15 17:32:11 GMT 2023
PRIMARY
DRUG BANK
DB01880
Created by admin on Fri Dec 15 17:32:11 GMT 2023 , Edited by admin on Fri Dec 15 17:32:11 GMT 2023
PRIMARY
CHEBI
17395
Created by admin on Fri Dec 15 17:32:11 GMT 2023 , Edited by admin on Fri Dec 15 17:32:11 GMT 2023
PRIMARY
NSC
623438
Created by admin on Fri Dec 15 17:32:11 GMT 2023 , Edited by admin on Fri Dec 15 17:32:11 GMT 2023
PRIMARY
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