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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

Molecular Formula C2HCl3O2
Molecular Weight 163.387
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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
Fifty years of dysentery research at the Pécs University.
2001
Exogenous ochronosis. An update on clinical features, causative agents and treatment options.
2001
Regulation by gonadal steroids of estrogen and progesterone receptors along the reproductive tract in female lambs.
2001
Site-specific mutations of FtsZ--effects on GTPase and in vitro assembly.
2001
Thyroxine signal transduction in liver cells involves phospholipase C and phospholipase D activation. Genomic independent action of thyroid hormone.
2001
The effects of alpha-lactabumin and whey protein concentrate on dry matter recovery, TCA soluble protein levels, and peptide distribution in the rat gastrointestinal tract.
2001 Apr
Trimethylamine and total volatile basic nitrogen determination by flow injection/gas diffusion in Mediterranean hake (Merluccius merluccius).
2001 Apr
Sample preparation for residue determination of gentamicin and neomycin by liquid chromatography.
2001 Apr 20
High-performance liquid chromatographic determination of cefepime in human plasma and in urine and dialysis fluid using a column-switching technique.
2001 Apr 25
[Endogenic intoxication markers: data from capillary electrophoresis of trichloroacetic acid supernatant].
2001 Aug
Photosonochemical degradation of trichloroacetic acid in aqueous solution.
2001 Aug
Stability of a cisplatin-chondroitin sulfate A complex in plasma and kidney in terms of protein binding.
2001 Aug
Assay of 2,3-dihydroxybenzoic acid and related compounds in plant materials by high-performance liquid chromatography.
2001 Aug 24
Factors involved in clearance of genital warts.
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
Isolation of antidiabetic components from white-skinned sweet potato (Ipomoea batatas L.).
2001 Jan
Quantitative and qualitative effects of chemical peeling on photo-aged skin: an experimental study.
2001 Jan
Medium-depth chemical peels.
2001 Jul
A simple HPLC method for the determination of the mycotoxins ochratoxin A and B in blood serum of swine.
2001 Jul
Investigation of uptake, translocation and fate of trichloroacetic acid in Norway spruce (Picea abies/L./Karst.) using 14C-labelling.
2001 Jul
Simplified analysis of contaminant rejection during ground- and surface water nanofiltration under the information collection rule.
2001 Jul
Sensitive and simple determination of mannitol in human brain tissues by gas chromatography-mass spectrometry.
2001 Jul 5
Factors influencing attachment of thermophilic bacilli to stainless steel.
2001 Jun
Study on the cytochrome P-450- and glutathione-dependent biotransformation of trichloroethylene in humans.
2001 Mar
Determination of 226Ra in biological samples by adsorption on specific adsorbers.
2001 Mar
Fast, simple and cost-effective determination of thiopental in human plasma by a new HPLC technique.
2001 Mar
Inositol phosphates from barley low-phytate grain mutants analysed by metal-dye detection HPLC and NMR.
2001 Mar 1
The treatment of eruptive syringomas in an African American patient with a combination of trichloroacetic acid and CO2 laser destruction.
2001 May
How Ala-->Gly mutations in different helices affect the stability of the apomyoglobin molten globule.
2001 May 1
Lamotrigine analysis in blood and brain by high-performance liquid chromatography.
2001 May 5
Outcome of 22 cases of perforated tympanic membrane caused by otomycosis.
2001 Nov
Redundancy of mammalian proteasome beta subunit function during endoplasmic reticulum associated degradation.
2001 Nov 6
Aerobic dehalogenation potentials of four bacterial species isolated from soil and sewage sludge.
2001 Oct
Atomic emission method for total boron in blood during neutron-capture therapy.
2001 Oct
Determining optimal surface roughness of TiO(2) blasted titanium implant material for attachment, proliferation and differentiation of cells derived from human mandibular alveolar bone.
2001 Oct
The application of physiologically based pharmacokinetic modelling in the analysis of occupational exposure to perchloroethylene.
2001 Oct 15
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
Determination of D- and L-aspartate in cell culturing medium, within cells of MPT1 cell line and in rat blood by a column-switching high-performance liquid chromatogrpahic method.
2001 Sep 15
Spectra interference between diquat and paraquat by second derivative spectrophotometry.
2001 Sep 15
The immunosuppressive activity of chemically modified lipopolysaccharide of Shigella sonnei.
2002 Jan 1
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).
Substance Class Chemical
Created
by admin
on Fri Dec 16 16:01:34 UTC 2022
Edited
by admin
on Fri Dec 16 16:01:34 UTC 2022
Record UNII
5V2JDO056X
Record Status Validated (UNII)
Record Version
  • Download
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 Fri Dec 16 16:01:34 UTC 2022 , Edited by admin on Fri Dec 16 16:01:34 UTC 2022
IARC Trichloroacetic acid
Code System Code Type Description
RXCUI
10773
Created by admin on Fri Dec 16 16:01:34 UTC 2022 , Edited by admin on Fri Dec 16 16:01:34 UTC 2022
PRIMARY
MERCK INDEX
M11062
Created by admin on Fri Dec 16 16:01:34 UTC 2022 , Edited by admin on Fri Dec 16 16:01:34 UTC 2022
PRIMARY Merck Index
ALANWOOD
TCA
Created by admin on Fri Dec 16 16:01:34 UTC 2022 , Edited by admin on Fri Dec 16 16:01:34 UTC 2022
PRIMARY
FDA UNII
5V2JDO056X
Created by admin on Fri Dec 16 16:01:34 UTC 2022 , Edited by admin on Fri Dec 16 16:01:34 UTC 2022
PRIMARY
MESH
D014238
Created by admin on Fri Dec 16 16:01:34 UTC 2022 , Edited by admin on Fri Dec 16 16:01:34 UTC 2022
PRIMARY
DAILYMED
5V2JDO056X
Created by admin on Fri Dec 16 16:01:34 UTC 2022 , Edited by admin on Fri Dec 16 16:01:34 UTC 2022
PRIMARY
PUBCHEM
6421
Created by admin on Fri Dec 16 16:01:34 UTC 2022 , Edited by admin on Fri Dec 16 16:01:34 UTC 2022
PRIMARY
WIKIPEDIA
TRICHLOROACETIC ACID
Created by admin on Fri Dec 16 16:01:34 UTC 2022 , Edited by admin on Fri Dec 16 16:01:34 UTC 2022
PRIMARY
EPA CompTox
DTXSID1021378
Created by admin on Fri Dec 16 16:01:34 UTC 2022 , Edited by admin on Fri Dec 16 16:01:34 UTC 2022
PRIMARY
RXCUI
618564
Created by admin on Fri Dec 16 16:01:34 UTC 2022 , Edited by admin on Fri Dec 16 16:01:34 UTC 2022
ALTERNATIVE
ChEMBL
CHEMBL14053
Created by admin on Fri Dec 16 16:01:34 UTC 2022 , Edited by admin on Fri Dec 16 16:01:34 UTC 2022
PRIMARY
EVMPD
SUB15604MIG
Created by admin on Fri Dec 16 16:01:34 UTC 2022 , Edited by admin on Fri Dec 16 16:01:34 UTC 2022
PRIMARY
CHEBI
27455
Created by admin on Fri Dec 16 16:01:34 UTC 2022 , Edited by admin on Fri Dec 16 16:01:34 UTC 2022
PRIMARY
NSC
215204
Created by admin on Fri Dec 16 16:01:34 UTC 2022 , Edited by admin on Fri Dec 16 16:01:34 UTC 2022
PRIMARY
CHEBI
30956
Created by admin on Fri Dec 16 16:01:34 UTC 2022 , Edited by admin on Fri Dec 16 16:01:34 UTC 2022
PRIMARY
CAS
76-03-9
Created by admin on Fri Dec 16 16:01:34 UTC 2022 , Edited by admin on Fri Dec 16 16:01:34 UTC 2022
PRIMARY
DRUG BANK
DB11152
Created by admin on Fri Dec 16 16:01:34 UTC 2022 , Edited by admin on Fri Dec 16 16:01:34 UTC 2022
PRIMARY
DRUG CENTRAL
3627
Created by admin on Fri Dec 16 16:01:34 UTC 2022 , Edited by admin on Fri Dec 16 16:01:34 UTC 2022
PRIMARY
LACTMED
Trichloroacetic Acid
Created by admin on Fri Dec 16 16:01:34 UTC 2022 , Edited by admin on Fri Dec 16 16:01:34 UTC 2022
PRIMARY
ECHA (EC/EINECS)
200-927-2
Created by admin on Fri Dec 16 16:01:34 UTC 2022 , Edited by admin on Fri Dec 16 16:01:34 UTC 2022
PRIMARY
HSDB
1779
Created by admin on Fri Dec 16 16:01:34 UTC 2022 , Edited by admin on Fri Dec 16 16:01:34 UTC 2022
PRIMARY
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