Thioglycolic acid

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Thioglycolic acid [1]
2-mercaptoacetic acid 200.svg
Thioglycolic-acid-van-der-waals.png
Names
Preferred IUPAC name
Sulfanylacetic acid
Other names
2-Sulfanylacetic acid
2-Mercaptoacetic acid
Acetyl mercaptan
Mercaptoacetate
Mercaptoacetic acid
Thioglycolic acid
Thiovanic acid [2]
Identifiers
3D model (JSmol)
506166
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.616 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-677-4
101048
KEGG
PubChem CID
RTECS number
  • AI5950000
UNII
  • InChI=1S/C2H4O2S/c3-2(4)1-5/h5H,1H2,(H,3,4) Yes check.svgY
    Key: CWERGRDVMFNCDR-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C2H4O2S/c3-2(4)1-5/h5H,1H2,(H,3,4)
    Key: CWERGRDVMFNCDR-UHFFFAOYAP
  • C(C(=O)O)S
Properties
C2H4O2S
Molar mass 92.11 g·mol−1
Appearancecolorless, clear liquid [3]
Odor strong, disagreeable [3]
Density 1.32 g/cm3
Melting point −16 °C (3 °F; 257 K)
Boiling point 96 °C (205 °F; 369 K) at 5 mmHg
miscible [3]
Vapor pressure 10 mmHg (17.8 °C) [3]
−50.0·10−6 cm3/mol
Hazards
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-skull.svg
H301+H311+H331, H314
P260, P261, P262, P264, P264+P265, P270, P271, P272, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P320, P321, P330, P333+P317, P361+P364, P362+P364, P363, P403+P233, P405, P501
Flash point >110 °C; 230 °F; 383 K [3]
Explosive limits 5.9% [3]
NIOSH (US health exposure limits):
PEL (Permissible)
none [3]
REL (Recommended)
TWA 1 ppm (4 mg/m3) [skin] [3]
IDLH (Immediate danger)
N.D. [3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Thioglycolic acid (TGA) is the organic compound HSCH2CO2H. TGA is often called mercaptoacetic acid (MAA). It contains both a thiol (mercaptan) and carboxylic acid functional groups. It is a colorless liquid with a strongly unpleasant odor. [4] [5] TGA is miscible with polar organic solvents. [6] [7]

Uses

TGA is used as a chemical depilatory and is still used as such, especially in salt forms, including calcium thioglycolate and sodium thioglycolate. TGA is the precursor to ammonium thioglycolate, which is used for permanents. TGA and its derivatives break the disulfide 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, as is done commonly in leather processing. It is also used as an acidity indicator, manufacturing of thioglycolates, and in bacteriology for preparation of thioglycolate media. [7] Thioglycolysis reactions are used on condensed tannins to study their structure. [8] [9] [10] [11]

TGA has also been used to soften nails, either to reshape pincer nails into the correct position [12] or to help the topical antifungal agent terbinafine penetrate the nail. [13]

Organotin derivatives of thioglycolic acid isooctyl esters are widely used as stabilizers for PVC. These species have the formula R2Sn(SCH2CO2C8H17)2. [7]

Sodium thioglycolate is a component of thioglycolate broth, a special bacterial growth media. It is also used in so-called "fallout remover" [14] or "wheel cleaner" to remove iron oxide residue from wheels. [15] Ferrous iron combines with thioglycolate to form red-violet [16] ferric thioglycolate. [17] [18]

Production

Thioglycolic acid is prepared by reaction of sodium or potassium chloroacetate with alkali metal hydrosulfide in aqueous medium. [19] It can be also prepared via the Bunte salt obtained by reaction of sodium thiosulfate with chloroacetic acid: [7] [20]

ClCH2CO2H + Na2S2O3 → Na[O3S2CH2CO2H] + NaCl
Na[O3S2CH2CO2H] + H2O → HSCH2CO2H + NaHSO4

Reactions

Thioglycolic acid with a pKa of 3.83 [7] is an acid about 8.5 times stronger 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 (2-[(carboxymethyl)disulfanyl]acetic acid or dithiodiglycolic acid):

2 HSCH2CO2H + "O" → [SCH2CO2H]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, molybdenum, silver, and tin. Thioglycolic acid reacts with diethyl acetylmalonate to form acetylmercaptoacetic acid and diethyl malonate, the reducing agent in the conversion of Fe(III) to Fe(II). [21]

History

Scientist David R. Goddard, in the early 1930s, identified TGA as a useful reagent for reducing the disulfide bonds in proteins, including keratin (hair protein), while studying why protease 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. [22] TGA was developed in the 1940s for use as a chemical depilatory.

Safety and detection

The LD50 (oral, rat) is 261 mg/kg, [7] LC50 inhalation for rat is 21 mg/m3 for 4 h, and LD50 dermal for rabbit is 848 mg/kg. [23] Mercaptoacetic acid in hair waving and depilatory products containing other mercapto acids can be identified by using thin-layer chromatography and gas chromatography. [24] [25] MAA also has been identified by using potentiometric titration with silver nitrate solution. [26]

See also

Related Research Articles

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Cysteine is a semiessential proteinogenic amino acid with the formula HOOC−CH(−NH2)−CH2−SH. The thiol side chain in cysteine enables the formation of disulfide bonds, and often participates in enzymatic reactions as a nucleophile. Cysteine is chiral, but both D and L-cysteine are found in nature. L‑Cysteine is a protein monomer in all biota, and D-cysteine acts as a signaling molecule in mammalian nervous systems. Cysteine is named after its discovery in urine, which comes from the urinary bladder or cyst, from Greek κύστη kýsti, "bladder".

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2
anion. The linkage is also called an SS-bond or sometimes a disulfide bridge and usually derived from two thiol groups.

<span class="mw-page-title-main">Thiol</span> Any organic compound having a sulfanyl group (–SH)

In organic chemistry, a thiol, or thiol derivative, is any organosulfur compound of the form R−SH, where R represents an alkyl or other organic substituent. The −SH functional group itself is referred to as either a thiol group or a sulfhydryl group, or a sulfanyl group. Thiols are the sulfur analogue of alcohols, and the word is a blend of "thio-" with "alcohol".

<span class="mw-page-title-main">Tanning (leather)</span> Process of treating animal skin to produce leather

Tanning, or hide tanning, is the process of treating skins and hides of animals to produce leather. A tannery is the place where the skins are processed.

<span class="mw-page-title-main">Perm (hairstyle)</span> Hairstyle featuring artificial curls

A permanent wave, commonly called a perm or permanent, is a hairstyle consisting of waves or curls set into the hair. The curls may last a number of months, hence the name.

<span class="mw-page-title-main">Cross-link</span> Bonds linking one polymer chain to another

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<span class="mw-page-title-main">Methylamine</span> Organic chemical compound

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<span class="mw-page-title-main">Sodium thiosulfate</span> Chemical compound

Sodium thiosulfate is an inorganic compound with the formula Na2S2O3·(H2O)x. Typically it is available as the white or colorless pentahydrate, which is a white solid that dissolves well in water. The compound is a reducing agent and a ligand, and these properties underpin its applications.

A relaxer is a type of lotion or cream generally used by people with tight curls or very curly hair which makes hair easier to straighten by chemically "relaxing" the natural curls. The active agent is usually a strong alkali, although some formulations are based on ammonium thioglycolate or formaldehyde.

<span class="mw-page-title-main">Ammonium thioglycolate</span> Chemical compound

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.

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A chemical depilatory is a cosmetic preparation used to remove hair from the skin. Common active ingredients are salts of thioglycolic acid and thiolactic acids. These compounds break the disulfide bonds in keratin and also hydrolyze the hair so that it is easily removed. Formerly, sulfides such as strontium sulfide were used, but due to their unpleasant odor, they have been replaced by thiols.

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<span class="mw-page-title-main">Veet</span> Canadian brand of chemical depilatory

Veet, formerly called Neet and Immac, is a Canadian brand of chemical depilatory products manufactured by the British-Dutch company Reckitt Benckiser. Hair removal cream, Lotions, gel, mousse, and wax products are produced under this brand, with differing variants being sold internationally. Previous products produced under the Neet and Immac brands were similar to those produced today.

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<span class="mw-page-title-main">Condensed tannin</span> Polymers formed by the condensation of flavans.

Condensed tannins are polymers formed by the condensation of flavans. They do not contain sugar residues.

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Further reading