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
Inhibition of HIV-1 proteinase by non-peptide carboxylates.	1991 Apr 15	2018518
Steroid hormone activity of flavonoids and related compounds.	2000 Jul	10989984
Molecular mechanisms controlling the rate and specificity of catechol O-methylation by human soluble catechol O-methyltransferase.	2001 Feb	11160877
Isolation, structure, and HIV-1-integrase inhibitory activity of structurally diverse fungal metabolites.	2003 Dec	14714192
A blend of polyphenolic compounds explains the stimulatory effect of red wine on human endothelial NO synthase.	2005 Mar	15740983
Activation of rat liver microsomal glutathione S-transferase by gallic acid.	2005 Nov 19	16125204
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Synthesis of trans-caffeate analogues and their bioactivities against HIV-1 integrase and cancer cell lines.	2008 Dec 15	18952420
The genome-wide expression profile of Scrophularia ningpoensis-treated thapsigargin-stimulated U-87MG cells.	2009 May	19442820
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
Antifungal efficacy of some natural phenolic compounds against significant pathogenic and toxinogenic filamentous fungi.	2013 Oct	23800587
Inhibitors of the glyoxylate cycle enzyme ICL1 in Candida albicans for potential use as antifungal agents.	2014	24781056

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