U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

Description

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.

CNS Activity

Originator

Wolfrom, M.L. et al.
1
Sources: DOI: 10.1021/jf60107a016

Approval Year

2020
842
Targets

Targets

Primary TargetPharmacologyConditionPotency
Activator
1410
Inhibitor
8228
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Phase III
663
Unknown

Approved Use

Unknown
Primary
Phase IV
63
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
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
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
Nonsteroidal anti-inflammatory drugs induce apoptosis in esophageal cancer cells by restoring 15-lipoxygenase-1 expression.
2001 Jun 15
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
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
Transcriptional regulation of deoxynivalenol-induced IL-8 expression in human monocytes.
2007 Oct
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
Preventive effect of caffeic acid on lysosomal dysfunction in isoproterenol-induced myocardial infarcted rats.
2010 Mar-Apr
Caffeic acid protects rat heart mitochondria against isoproterenol-induced oxidative damage.
2010 Nov
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
Activity of caffeic acid derivatives against Candida albicans biofilm.
2014 Mar 15
Patents

Patents

04521438
1
07074620
1
07273920
1
JP2001240527A
1
JP2002080360A
2
JP2002155017A
1
JP2002541233A
397
JP2005089676A
2
JP2007297296A
1
JP2008106013A
5
JP2008278780A
2
JP2009029657A
1
JP2009100760A
1
JP2009526755A
442
JP2010120908A
1
JP2011057687A
1
JPH01132344A
1
JPH02235852A
1
JPH05286835A
4
JPH05311472A
1
JPH0616537A
1
JPH08208419A
1
JPH08259453A
1
JPH08337516A
2
JPH09151130A
1
JPH10117680A
4
JPH10179079A
1
JPH10183164A
1
JPH10262547A
2
JPH10273404A
1
JPS59155314A
2
JPS63168464A
1

Sample Use Guides

In Vivo Use Guide
300mg three times a day
Route of Administration: Oral
In Vitro Use Guide
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 Thu Jul 06 00:51:19 UTC 2023
Edited
by admin
on Thu Jul 06 00:51:19 UTC 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 Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
DSLD 1678 (Number of products:14)
Created by admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
Code System Code Type Description
DAILYMED
U2S3A33KVM
Created by admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
PRIMARY
CHEBI
16433
Created by admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
PRIMARY
NCI_THESAURUS
C68540
Created by admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
PRIMARY
ECHA (EC/EINECS)
206-361-2
Created by admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
PRIMARY
MESH
C040048
Created by admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
PRIMARY
NSC
57197
Created by admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
PRIMARY
SMS_ID
100000174372
Created by admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
PRIMARY
PUBCHEM
689043
Created by admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
PRIMARY
WIKIPEDIA
CAFFEIC ACID
Created by admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
PRIMARY
CAS
331-39-5
Created by admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
NON-SPECIFIC STEREOCHEMISTRY
RXCUI
1311397
Created by admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
PRIMARY RxNorm
MERCK INDEX
M2908
Created by admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
PRIMARY Merck Index
HSDB
331-39-5
Created by admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
PRIMARY
CAS
501-16-6
Created by admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
PRIMARY
FDA UNII
U2S3A33KVM
Created by admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
PRIMARY
DRUG BANK
DB01880
Created by admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
PRIMARY
CHEBI
17395
Created by admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
PRIMARY
NSC
623438
Created by admin on Thu Jul 06 00:51:19 UTC 2023 , Edited by admin on Thu Jul 06 00:51:19 UTC 2023
PRIMARY
Related Record Type Details
CENTAURIUM ERYTHRAEA WHOLE
PARENT -> CONSTITUENT ALWAYS PRESENT
GALIUM APARINE WHOLE
PARENT -> CONSTITUENT ALWAYS PRESENT
VACCINIUM MYRTILLUS LEAF
PARENT -> CONSTITUENT ALWAYS PRESENT
IPOMOEA AQUATICA LEAF
PARENT -> CONSTITUENT ALWAYS PRESENT
19.2% reaction on PG synthase w/10.0 mM conc. of compound
COMFREY ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
BLACK COHOSH
PARENT -> CONSTITUENT ALWAYS PRESENT
CYNARA SCOLYMUS LEAF
PARENT -> CONSTITUENT ALWAYS PRESENT
COMFREY LEAF
PARENT -> CONSTITUENT ALWAYS PRESENT
MENYANTHES TRIFOLIATA LEAF
PARENT -> CONSTITUENT ALWAYS PRESENT
ARCTIUM LAPPA ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
Structure of 3-(3,4-DIHYDROXYPHENYL) PROPIONIC ACID
METABOLITE -> PARENT
Related Record Type Details
Structure of CAFFEIC ACID
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966