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

Details

Stereochemistry ACHIRAL
Molecular Formula C2HCl3O2
Molecular Weight 163.387
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Trichloroacetic acid

SMILES

OC(=O)C(Cl)(Cl)Cl

InChI

InChIKey=YNJBWRMUSHSURL-UHFFFAOYSA-N
InChI=1S/C2HCl3O2/c3-2(4,5)1(6)7/h(H,6,7)

HIDE SMILES / InChI
Trichloroacetic acid (TCA; TCAA) is a chemical used in skin peel formulations. It is more frequently used for lighter skin and is less used on darker skin because of the higher risks of scarring, as well as post-peel dyschromias. Low concentrations, 10-35% is preferred for skin peel formulations so that it only reaches the upper papillary dermis. Topical TCA is an efficacious treatment of internal anal high-grade squamous intraepithelial lesions (HSIL). Advantages of TCA for this recurrent disease process include low cost, no requirement for special equipment beyond that for high-resolution anoscopy, and painless application procedure.

Originator

Curator's Comment: in 1839 by Jean-Baptiste Dumas

Approval Year

Conditions

Conditions

PubMed

PubMed

TitleDatePubMed
trans-Activation of PPARalpha and PPARgamma by structurally diverse environmental chemicals.
1999 Dec 1
Effect of trichloroethylene and its metabolites, dichloroacetic acid and trichloroacetic acid, on the methylation and expression of c-Jun and c-Myc protooncogenes in mouse liver: prevention by methionine.
2000 Apr
Phenotypic silencing of cytoplasmic genes using sequence-specific double-stranded short interfering RNA and its application in the reverse genetics of wild type negative-strand RNA viruses.
2001
Regulation by gonadal steroids of estrogen and progesterone receptors along the reproductive tract in female lambs.
2001
Deproteinization of serum: another best approach to eliminate all forms of bilirubin interference on serum creatinine by the kinetic Jaffe reaction.
2001
Simultaneous determination of flucytosine and fluorouracil in human plasma by high-performance liquid chromatography.
2001 Apr
Haloacetates in fog and rain.
2001 Apr 1
Effects of the matrix and sample preparation on the determination of fluoroquinolone residues in animal tissues.
2001 Apr 20
Production of hyaluronan and chondroitin sulphate proteoglycans from human arterial smooth muscle--the effect of glucose, insulin, IGF-I or growth hormone.
2001 Aug
Kinetics in the pre-steady state of the formation of cystines in ribonucleoside diphosphate reductase: evidence for an asymmetric complex.
2001 Aug 14
Factors involved in clearance of genital warts.
2001 Dec
Trichloroethylene oxidative metabolism in plants: the trichloroethanol pathway.
2001 Dec
A novel method to analyze betaine in chicken liver: effect of dietary betaine and choline supplementation on the hepatic betaine concentration in broiler chicks.
2001 Feb
Purification and structure elucidation of the N-acetylbacillosamine-containing polysaccharide from Bacillus licheniformis ATCC 9945.
2001 Feb
Two-iron rubredoxin of Pseudomonas oleovorans: production, stability and characterization of the individual iron-binding domains by optical, CD and NMR spectroscopies.
2001 Feb 15
Simple and rapid determination of nevirapine in human serum by reversed-phase high-performance liquid chromatography.
2001 Feb 25
Isolation of antidiabetic components from white-skinned sweet potato (Ipomoea batatas L.).
2001 Jan
[Clinical aspects and therapy of anogenital warts and papillomavirus-associated lesions].
2001 Jan
Insulin receptor antibodies inhibit insulin uptake by the liver: in vivo 123I-insulin scintigraphic scanning and in vitro characterization in autoimmune hypoglycemia.
2001 Jan
Quantitative and qualitative effects of chemical peeling on photo-aged skin: an experimental study.
2001 Jan
The fate and persistence of trifluoroacetic and chloroacetic acids in pond waters.
2001 Jan
Medium-depth chemical peels.
2001 Jul
Dermal peels.
2001 Jul
Possible explanation of the disparity between the in vitro and in vivo measurements of Rubisco activity: a study in loblolly pine grown in elevated pCO2.
2001 Jul
Isolation and specific detection of two major schistosoma gut-associated circulating antigens.
2001 Jun
Study on the cytochrome P-450- and glutathione-dependent biotransformation of trichloroethylene in humans.
2001 Mar
Direct medical costs for surgical and medical treatment of condylomata acuminata.
2001 Mar
Fast, simple and cost-effective determination of thiopental in human plasma by a new HPLC technique.
2001 Mar
Urinary concentrations of trichloroacetic acid in Danish workers exposed to trichloroethylene, 1947-1985.
2001 Mar
Mediated efflux of IgG molecules from brain to blood across the blood-brain barrier.
2001 Mar 1
Inositol phosphates from barley low-phytate grain mutants analysed by metal-dye detection HPLC and NMR.
2001 Mar 1
Leptin transport at the blood--cerebrospinal fluid barrier using the perfused sheep choroid plexus model.
2001 Mar 23
Differential effects of dihalogenated and trihalogenated acetates in the liver of B6C3F1 mice.
2001 Mar-Apr
How Ala-->Gly mutations in different helices affect the stability of the apomyoglobin molten globule.
2001 May 1
Synthesis of a set of di- and tri-sulfated galabioses.
2001 Oct 8
Effect of chloroform on dichloroacetic acid and trichloroacetic acid-induced hypomethylation and expression of the c-myc gene and on their promotion of liver and kidney tumors in mice.
2001 Sep
The immunosuppressive activity of chemically modified lipopolysaccharide of Shigella sonnei.
2002 Jan 1
Sources, pathways, and relative risks of contaminants in surface water and groundwater: a perspective prepared for the Walkerton inquiry.
2002 Jan 11
Study of competitive binding of enantiomers to protein by affinity capillary electrochromatography.
2002 Jan 15
Succinate dehydrogenase and fumarate reductase from Escherichia coli.
2002 Jan 17
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: http://www.ncbi.nlm.nih.gov/pubmed/24922100
for melasma: 15% TCA peel for anal high-grade squamous intraepithelial lesions: 80% TCA
Route of Administration: Topical
In Vitro Use Guide
Lymphocytes obtained from three healthy donors were exposed to 25, 50, and 100 μg/ml concentration of TCA separately. TCA exposure resulted in chromosomal anomalies and the formation of micronuclei in lymphocytes. Chromosome analysis revealed the dose-dependent and significant induction of Chromosomal aberration (CA).
Name Type Language
Trichloroacetic acid
EP   HSDB   MART.   MI   VANDF   WHO-DD  
Systematic Name English
NSC-215204
Code English
ACETIC ACID, TRICHLORO-
Common Name English
TCA
ISO  
Common Name English
TRICHLOROACETATE
Systematic Name English
TRICHLOROACETIC ACID [EP IMPURITY]
Common Name English
TRICHLOROACETIC ACID [MART.]
Common Name English
TRICHLOROACETIC ACID [VANDF]
Common Name English
TRICHLOROACETIC ACID [HSDB]
Common Name English
TRICHLOROACETIC ACID [EP MONOGRAPH]
Common Name English
TRICHLOROACETIC ACID [MI]
Common Name English
Trichloroacetic acid [WHO-DD]
Common Name English
TCA [ISO]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 81002
Created by admin on Wed Jul 05 22:35:14 UTC 2023 , Edited by admin on Wed Jul 05 22:35:14 UTC 2023
IARC Trichloroacetic acid
Code System Code Type Description
SMS_ID
100000077252
Created by admin on Wed Jul 05 22:35:14 UTC 2023 , Edited by admin on Wed Jul 05 22:35:14 UTC 2023
PRIMARY
RXCUI
10773
Created by admin on Wed Jul 05 22:35:14 UTC 2023 , Edited by admin on Wed Jul 05 22:35:14 UTC 2023
PRIMARY
MERCK INDEX
M11062
Created by admin on Wed Jul 05 22:35:14 UTC 2023 , Edited by admin on Wed Jul 05 22:35:14 UTC 2023
PRIMARY Merck Index
ALANWOOD
TCA
Created by admin on Wed Jul 05 22:35:14 UTC 2023 , Edited by admin on Wed Jul 05 22:35:14 UTC 2023
PRIMARY
FDA UNII
5V2JDO056X
Created by admin on Wed Jul 05 22:35:14 UTC 2023 , Edited by admin on Wed Jul 05 22:35:14 UTC 2023
PRIMARY
MESH
D014238
Created by admin on Wed Jul 05 22:35:14 UTC 2023 , Edited by admin on Wed Jul 05 22:35:14 UTC 2023
PRIMARY
DAILYMED
5V2JDO056X
Created by admin on Wed Jul 05 22:35:14 UTC 2023 , Edited by admin on Wed Jul 05 22:35:14 UTC 2023
PRIMARY
PUBCHEM
6421
Created by admin on Wed Jul 05 22:35:14 UTC 2023 , Edited by admin on Wed Jul 05 22:35:14 UTC 2023
PRIMARY
WIKIPEDIA
TRICHLOROACETIC ACID
Created by admin on Wed Jul 05 22:35:14 UTC 2023 , Edited by admin on Wed Jul 05 22:35:14 UTC 2023
PRIMARY
EPA CompTox
DTXSID1021378
Created by admin on Wed Jul 05 22:35:14 UTC 2023 , Edited by admin on Wed Jul 05 22:35:14 UTC 2023
PRIMARY
RXCUI
618564
Created by admin on Wed Jul 05 22:35:14 UTC 2023 , Edited by admin on Wed Jul 05 22:35:14 UTC 2023
ALTERNATIVE
ChEMBL
CHEMBL14053
Created by admin on Wed Jul 05 22:35:14 UTC 2023 , Edited by admin on Wed Jul 05 22:35:14 UTC 2023
PRIMARY
EVMPD
SUB15604MIG
Created by admin on Wed Jul 05 22:35:14 UTC 2023 , Edited by admin on Wed Jul 05 22:35:14 UTC 2023
PRIMARY
CHEBI
27455
Created by admin on Wed Jul 05 22:35:14 UTC 2023 , Edited by admin on Wed Jul 05 22:35:14 UTC 2023
PRIMARY
NSC
215204
Created by admin on Wed Jul 05 22:35:14 UTC 2023 , Edited by admin on Wed Jul 05 22:35:14 UTC 2023
PRIMARY
CHEBI
30956
Created by admin on Wed Jul 05 22:35:14 UTC 2023 , Edited by admin on Wed Jul 05 22:35:14 UTC 2023
PRIMARY
CAS
76-03-9
Created by admin on Wed Jul 05 22:35:14 UTC 2023 , Edited by admin on Wed Jul 05 22:35:14 UTC 2023
PRIMARY
DRUG BANK
DB11152
Created by admin on Wed Jul 05 22:35:14 UTC 2023 , Edited by admin on Wed Jul 05 22:35:14 UTC 2023
PRIMARY
DRUG CENTRAL
3627
Created by admin on Wed Jul 05 22:35:14 UTC 2023 , Edited by admin on Wed Jul 05 22:35:14 UTC 2023
PRIMARY
LACTMED
Trichloroacetic Acid
Created by admin on Wed Jul 05 22:35:14 UTC 2023 , Edited by admin on Wed Jul 05 22:35:14 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-927-2
Created by admin on Wed Jul 05 22:35:14 UTC 2023 , Edited by admin on Wed Jul 05 22:35:14 UTC 2023
PRIMARY
HSDB
1779
Created by admin on Wed Jul 05 22:35:14 UTC 2023 , Edited by admin on Wed Jul 05 22:35:14 UTC 2023
PRIMARY