CAFFEIC ACID

Possibly Marketed Outside US

First approved in 2018

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21116690 | https://www.ncbi.nlm.nih.gov/pubmed/25498895 | https://www.ncbi.nlm.nih.gov/pubmed/25778883 | https://www.ncbi.nlm.nih.gov/pubmed/28911606

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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Apoptosis 155 Target ID: WP254 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21116690	Activator 1430
Oxidative Stress 160 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25498895 \| https://www.ncbi.nlm.nih.gov/pubmed/26098639 \| https://www.ncbi.nlm.nih.gov/pubmed/28911606	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Fibrosarcoma 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21116690	Primary	Basic research	Unknown Approved Use Unknown
Esophageal cancer 12 Sources: https://clinicaltrials.gov/ct2/show/NCT03070262	Primary	Phase III 656	Unknown Approved Use Unknown
Immune thrombocytopenia 9 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25778883 https://clinicaltrials.gov/ct2/show/NCT02556814 https://clinicaltrials.gov/ct2/show/NCT02351622	Primary	Phase IV 63	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Selective inhibitory activity of polyhydroxycarboxylates derived from phenolic compounds against human immunodeficiency virus replication.	1991	1675677
Molecular mechanisms of tirapazamine (SR 4233, Win 59075)-induced hepatocyte toxicity under low oxygen concentrations.	1995 Apr	7710944
Dicaffeoylquinic acid inhibitors of human immunodeficiency virus integrase: inhibition of the core catalytic domain of human immunodeficiency virus integrase.	1996 Oct	8863829
Steroid hormone activity of flavonoids and related compounds.	2000 Jul	10989984
In vitro activity of polyhydroxycarboxylates against herpesviruses and HIV.	2001 Nov	12018678
Antiviral activity of Plantago major extracts and related compounds in vitro.	2002 Jul	12076751
Isolation, structure, and HIV-1-integrase inhibitory activity of structurally diverse fungal metabolites.	2003 Dec	14714192
The histone deacetylase inhibitor suberoylanilide hydroxamic acid induces apoptosis via induction of 15-lipoxygenase-1 in colorectal cancer cells.	2004 Dec 1	15574791
Protective effect of Mesona procumbens against tert-butyl hydroperoxide-induced acute hepatic damage in rats.	2004 Jun 30	15212457
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
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	20150427
Caffeic acid protects rat heart mitochondria against isoproterenol-induced oxidative damage.	2010 Nov	20376586
Interaction of cinnamic acid derivatives with commercial hypoglycemic drugs on 2-deoxyglucose uptake in 3T3-L1 adipocytes.	2011 Sep 28	21870829
Differentiation between stoichiometric and anticatalytic antioxidant properties of benzoic acid analogues: a structure/redox potential relationship study.	2013 Nov 25	24060682
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	25130191

Patents

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.

Name

Type

Language

CAFFEIC ACID

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