thioglycolic acid
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Thioglycolic acid (TGA) is the
organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. T ...
HSCH2CO2H. TGA is often called mercaptoacetic acid (MAA). It contains both a
thiol In organic chemistry, a thiol (; ), or thiol derivative, is any organosulfur compound of the form , where R represents an alkyl or other organic substituent. The functional group itself is referred to as either a thiol group or a sulfhydryl gro ...
( mercaptan) and carboxylic acid functional groups. It is a colorless liquid with a strongly
unpleasant odor An odor (American English) or odour (Commonwealth English; see spelling differences) is caused by one or more volatilized chemical compounds that are generally found in low concentrations that humans and animals can perceive via their sense ...
. TGA is miscible with polar organic solvents.''The Merck index'', 14th ed.; O’Neil, Maryadele J., Ed.; Merck & Co., Inc.: Whitehouse Station, NJ, 2006; p. 9342.Robert Rippel "Mercaptoacetic Acid and Derivatives" in ''Ullmann's Encyclopedia of Industrial Chemistry'', 2012, Wiley-VCH, Weinheim. .


Uses

TGA is used as a chemical
depilatory Hair removal, also known as epilation or depilation, is the deliberate removal of body hair or head hair. Hair typically grows all over the human body and can vary in thickness and length across human populations. Hair can become more visible d ...
and is still used as such, especially in salt forms, including calcium thioglycolate and sodium thioglycolate. TGA is the precursor to
ammonium thioglycolate Ammonium thioglycolate, also known as perm salt, is the salt of thioglycolic acid and ammonia. It has the formula HSCH2CO2NH4 and has use in perming hair. Chemistry Being the salt of a weak acid and weak base, ammonium thioglycolate exists in ...
, which is used for permanents. TGA and its derivatives break the
disulfide In biochemistry, a disulfide (or disulphide in British English) refers to a functional group with the structure . The linkage is also called an SS-bond or sometimes a disulfide bridge and is usually derived by the coupling of two thiol groups. In ...
bonds in the cortex of hair. One reforms these broken bonds in giving hair a "perm". Alternatively and more commonly, the process leads to
depilation Hair removal, also known as epilation or depilation, is the deliberate removal of body hair or head hair. Hair typically grows all over the human body and can vary in thickness and length across human populations. Hair can become more visible ...
, as is done commonly in
leather Leather is a strong, flexible and durable material obtained from the tanning, or chemical treatment, of animal skins and hides to prevent decay. The most common leathers come from cattle, sheep, goats, equine animals, buffalo, pigs and hog ...
processing. It is also used as an acidity indicator, manufacturing of thioglycolates, and in bacteriology for preparation of thioglycolate media. In fact thioglycolysis reactions used on condensed tannins to study their structure. Organotin derivatives of thioglycolic acid isooctyl esters are widely used as stabilizers for PVC. These species have the formula R2Sn(SCH2CO2C8H17)2. Applying TGA can soften nails and then fix pincer nails in the correct position. Sodium thioglycolate is a component of
thioglycolate broth Thioglycolate broth is a multipurpose, enrichment, differential medium used primarily to determine the oxygen requirements of microorganisms. Sodium thioglycolate in the medium consumes oxygen and permits the growth of obligate anaerobes. This, co ...
, a special bacterial growth media. It is also used in so-called "fallout remover" or "wheel cleaner" to remove iron oxide residue from
wheels A wheel is a circular component that is intended to rotate on an axle bearing. The wheel is one of the key components of the wheel and axle which is one of the six simple machines. Wheels, in conjunction with axles, allow heavy objects to b ...
.
Ferrous In chemistry, the adjective Ferrous indicates a compound that contains iron(II), meaning iron in its +2 oxidation state, possibly as the divalent cation Fe2+. It is opposed to " ferric" or iron(III), meaning iron in its +3 oxidation state, suc ...
iron combines with thioglycolate to form red-violet ferric thioglycolate.


Production

Thioglycolic acid is prepared by reaction of sodium or potassium chloracetate with alkali metal hydrosulfide in aqueous medium.Cosmetic, Toiletry, and Fragrance Association (CTFA). Thioglycolic Acid. 1987;(1987a). Submission of unpublished data by CTFA Code No. 3-25-2 It can be also prepared via the Bunte salt obtained by reaction of
sodium thiosulfate Sodium thiosulfate (sodium thiosulphate) is an inorganic compound with the formula . Typically it is available as the white or colorless pentahydrate, . The solid is an efflorescent (loses water readily) crystalline substance that dissolves well in ...
with
chloroacetic acid Chloroacetic acid, industrially known as monochloroacetic acid (MCA), is the organochlorine compound with the formula ClCH2CO2H. This carboxylic acid is a useful building block in organic synthesis. It is a colorless solid. Related compounds a ...
:Saeed M. Hameed N. Madan V. Mansoor S. Preparation and Mechanisms studies of Thioglycolic Acid. ''Pak. J. Sci. Ind. Res.'' 1992, 35: 131-132 :ClCH2CO2H + Na2S2O3 → Na 3S2CH2CO2H+ NaCl :Na 3S2CH2CO2H+ H2O → HSCH2CO2H + NaHSO4


Reactions

Thioglycolic acid with a pKa of 3.83 is about 10 times stronger an acid than acetic acid (pKa 4.76): :HSCH2CO2H → HSCH2CO2 + H+ The second ionization has a pKa of 9.3: : HSCH2CO2SCH2CO2 + H+ Thioglycolic acid is a reducing agent, especially at higher pH. It oxidizes to the corresponding
disulfide In biochemistry, a disulfide (or disulphide in British English) refers to a functional group with the structure . The linkage is also called an SS-bond or sometimes a disulfide bridge and is usually derived by the coupling of two thiol groups. In ...
(2- carboxymethyl)disulfanylcetic acid or dithiodiglycolic acid): :2 HSCH2CO2H + "O" → CH2CO2Hsub>2 + H2O


With metal ions

Thioglycolic acid, usually as its dianion, forms complexes with metal ions. Such complexes have been used for the detection of
iron Iron () is a chemical element with Symbol (chemistry), symbol Fe (from la, Wikt:ferrum, ferrum) and atomic number 26. It is a metal that belongs to the first transition series and group 8 element, group 8 of the periodic table. It is, Abundanc ...
, molybdenum,
silver Silver is a chemical element with the symbol Ag (from the Latin ', derived from the Proto-Indo-European ''h₂erǵ'': "shiny" or "white") and atomic number 47. A soft, white, lustrous transition metal, it exhibits the highest electrical ...
, and
tin Tin is a chemical element with the symbol Sn (from la, stannum) and atomic number 50. Tin is a silvery-coloured metal. Tin is soft enough to be cut with little force and a bar of tin can be bent by hand with little effort. When bent, t ...
. Thioglycolic acid reacts with diethyl acetylmalonate to form acetylmercaptoacetic acid and diethyl malonate, the reducing agent in conversion of Fe(III) to Fe(II).Lee CW, Phil M. The detection of iron traces on hands by ferrozine sparys: a report on the sensitivity and interference of the method and recommended procedure in forensic science investigation. ''J Forensic Sci.'' 1986, 31:920-930.


History

Scientist David R. Goddard, in the early 1930s, identified TGA as a useful reagent for reducing the
disulfide bond In biochemistry, a disulfide (or disulphide in British English) refers to a functional group with the structure . The linkage is also called an SS-bond or sometimes a disulfide bridge and is usually derived by the coupling of two thiol groups. In ...
s in
protein Proteins are large biomolecules and macromolecules that comprise one or more long chains of amino acid residues. Proteins perform a vast array of functions within organisms, including catalysing metabolic reactions, DNA replication, res ...
s, including
keratin Keratin () is one of a family of structural fibrous proteins also known as ''scleroproteins''. Alpha-keratin (α-keratin) is a type of keratin found in vertebrates. It is the key structural material making up scales, hair, nails, feathers, ho ...
(hair protein), while studying why
protease A protease (also called a peptidase, proteinase, or proteolytic enzyme) is an enzyme that catalyzes (increases reaction rate or "speeds up") proteolysis, breaking down proteins into smaller polypeptides or single amino acids, and spurring the ...
enzymes could not easily digest hair, nails, feathers, and such. He realized that while the disulfide bonds, which stabilize proteins by cross-linking, were broken, the structures containing these proteins could be reshaped easily, and that they would retain this shape after the disulfide bonds were allowed to re-form.National Academies Press:Biographical Memoirs:David Rockwell Goddard:by Ralph O. Erickson
/ref> TGA was developed in the 1940s for use as a chemical
depilatory Hair removal, also known as epilation or depilation, is the deliberate removal of body hair or head hair. Hair typically grows all over the human body and can vary in thickness and length across human populations. Hair can become more visible d ...
.


Safety and detection

The LD50 (oral, rat) is 261 mg/kg, LC50 inhalation for rat is 21 mg/m3 for 4 h, and LD50 dermal for rabbit is 848 mg/kg.Sigma-Aldrich MSDS. http://www.sigmaaldrich.com/safety-center.html?cm_sp=Search-_-MSDS-_-MSDS1 (accessed Nov 10, 2013). Product Number – T3758 Mercaptoacetic acid in hair waving and depilatory products containing other mercapto acids can be identified by using thin-layer chromatography and gas chromatography.Goetz N, Gataud P, Bore P. Determination of mercaptoacetic acid in hair waving and depilatory products. ''Analyst.'' 1979,104:1062-1069Goetz N, Gataud P, Bore P. Gas-chromatographic determination of mercaptoacetic acid in hair-waving and diplatory products. ''Cosmet Sci Technol Ser.'' 1985, 4:65-79. MAA also has been identified by using potentiometric titration with silver nitrate solution.Vandeputte M, Dryon L, Van Den Winkel P, Mertens J, Massart DL. Determination of thioglycolic acid using a silver sulfide single crystal electrode. ''Analysis.'' 1975,3:500-504.


See also

*
Glycolic acid Glycolic acid (or hydroxyacetic acid; chemical formula HOCH2CO2H) is a colorless, odorless and hygroscopic crystalline solid, highly soluble in water. It is used in various skin-care products. Glycolic acid is widespread in nature. A glycolate (s ...
*
Ammonium thioglycolate Ammonium thioglycolate, also known as perm salt, is the salt of thioglycolic acid and ammonia. It has the formula HSCH2CO2NH4 and has use in perming hair. Chemistry Being the salt of a weak acid and weak base, ammonium thioglycolate exists in ...
*
Thiolactic acid Thiolactic acid is the organosulfur compound with the formula HSCH2CO2H. The molecule contains both carboxylic acid and thiol functional groups. It is structurally related to lactic acid by the interchange of SH for OH. It is a colorless oil. T ...


References


Further reading

*Okada K, Okada E. Novel treatment using thioglycolic acid for pincer nails. ''J. Dermatol.'' 2012, volume 39, pp. 996-999. {{Authority control Thiols Acetic acids Chelating agents Foul-smelling chemicals