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

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
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
Influence of twenty potentially antiviral substances on in vitro multiplication of hepatitis A virus.	1986 Mar	3010855
Selective inhibitory activity of polyhydroxycarboxylates derived from phenolic compounds against human immunodeficiency virus replication.	1991	1675677
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	8340025
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	9986720
Nonsteroidal anti-inflammatory drugs induce apoptosis in esophageal cancer cells by restoring 15-lipoxygenase-1 expression.	2001 Jun 15	11406566
In vitro activity of polyhydroxycarboxylates against herpesviruses and HIV.	2001 Nov	12018678
Urinary flavonoids and phenolic acids as biomarkers of intake for polyphenol-rich foods.	2006 Jul	16870009
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Caffeic acid attenuates 12-O-tetradecanoyl-phorbol-13-acetate (TPA)-induced NF-κB and COX-2 expression in mouse skin: abrogation of oxidative stress, inflammatory responses and proinflammatory cytokine production.	2012 Feb	22036979

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.

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

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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