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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
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
Fifty years of dysentery research at the Pécs University.
2001
The [15N]methacetin liver function test characterizes multicomponent exposure of children in industrially polluted regions.
2001
Exogenous ochronosis. An update on clinical features, causative agents and treatment options.
2001
Synthesis of disaccharides related to the mycobacterial arabinogalactan.
2001
A multi media load model for the Baltic Sea.
2001
Site-specific mutations of FtsZ--effects on GTPase and in vitro assembly.
2001
Deproteinization of serum: another best approach to eliminate all forms of bilirubin interference on serum creatinine by the kinetic Jaffe reaction.
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
Haloacetates in fog and rain.
2001 Apr 1
Effect of the eluent pH and acidic modifiers in high-performance liquid chromatography retention of basic analytes.
2001 Apr 13
Effects of the matrix and sample preparation on the determination of fluoroquinolone residues in animal tissues.
2001 Apr 20
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
Molluscum contagiosum in herpes zoster scars.
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
Factors involved in clearance of genital warts.
2001 Dec
Diagnosis and management of cervical intraepithelial neoplasia.
2001 Dec
Trichloroethylene oxidative metabolism in plants: the trichloroethanol pathway.
2001 Dec
Application of quantitative ethanol detector (QED) test kit to measure ethanol concentration in blood samples.
2001 Dec 27
Feasibility of iodine-125 labeled anti-human hemoglobin antibody in the detection of bleeding sites from the large bowel-A preliminary study.
2001 Jul
Medium-depth chemical peels.
2001 Jul
A new glycogen synthase activity ratio in skeletal muscle: effects of exercise and insulin.
2001 Jul 13
Isolation and specific detection of two major schistosoma gut-associated circulating antigens.
2001 Jun
Reduction of haloacetic acids by Fe0: implications for treatment and fate.
2001 Jun 1
Direct electrochemistry of hemoglobin in layer-by-layer films with poly(vinyl sulfonate) grown on pyrolytic graphite electrodes.
2001 Mar
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
Tethered dithiacyclopropenones. syntheses and structural properties of tetrathiacyclopropenonophanes.
2001 May 18
A facile and effective synthesis of alpha-(1-->6)-linked mannose di-, tri-, tetra-, hexa-, octa-, and dodecasaccharides, and beta-(1-->6)-linked glucose di-, tri-, tetra-, hexa-, and octasaccharides using sugar trichloroacetimidates as the donors and unprotected or partially protected glycosides as the acceptors.
2001 May 8
Outcome of 22 cases of perforated tympanic membrane caused by otomycosis.
2001 Nov
Differences in yields of microbial crude protein from in vitro fermentation of carbohydrates.
2001 Nov
Improved radioiodination of biomolecules using exhaustive Chloramine-T oxidation.
2001 Nov
Antibodies against Streptococcus agalactiae proteins c(alpha) and R4 in sera from pregnant women from Norway and Zimbabwe.
2001 Nov
Antiparallel pleated beta-sheets observed in crystal structures of N,N-bis(trichloroacetyl) and N,N-bis(m-bromobenzoyl) gramicidin S.
2001 Nov 1
Redundancy of mammalian proteasome beta subunit function during endoplasmic reticulum associated degradation.
2001 Nov 6
An immunohistological study of the localization characteristics of thymus and activation-regulated chemokine in the allergic inferior turbinate mucosa with reference to the effectiveness of trichloroacetic acid treatment.
2001 Nov-Dec
New method for exopolysaccharide determination in culture broth using stirred ultrafiltration cells.
2001 Oct
The application of physiologically based pharmacokinetic modelling in the analysis of occupational exposure to perchloroethylene.
2001 Oct 15
Estimating internal phosphorus pools in macroalgae using radioactive phosphorus and trichloroacetic acid extracts.
2001 Oct 15
Trace determination of 1-octacosanol in rat plasma by solid-phase extraction with Tenax GC and capillary gas chromatography.
2001 Oct 5
Synthesis of a set of di- and tri-sulfated galabioses.
2001 Oct 8
Trichloroethylene, trichloroacetic acid, and dichloroacetic acid: do they affect fetal rat heart development?
2001 Sep-Oct
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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:03:06 GMT 2023
Edited
by admin
on Fri Dec 15 15:03:06 GMT 2023
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 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
IARC Trichloroacetic acid
Code System Code Type Description
SMS_ID
100000077252
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
RXCUI
10773
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
MERCK INDEX
m11062
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY Merck Index
ALANWOOD
TCA
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
FDA UNII
5V2JDO056X
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
MESH
D014238
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
DAILYMED
5V2JDO056X
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
PUBCHEM
6421
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
WIKIPEDIA
TRICHLOROACETIC ACID
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
EPA CompTox
DTXSID1021378
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
RXCUI
618564
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
ALTERNATIVE
ChEMBL
CHEMBL14053
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
EVMPD
SUB15604MIG
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
CHEBI
27455
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
NSC
215204
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
CHEBI
30956
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
CAS
76-03-9
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
DRUG BANK
DB11152
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
DRUG CENTRAL
3627
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
LACTMED
Trichloroacetic Acid
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-927-2
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
HSDB
1779
Created by admin on Fri Dec 15 15:03:06 GMT 2023 , Edited by admin on Fri Dec 15 15:03:06 GMT 2023
PRIMARY
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