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EC / List no.: 201-206-5
CAS no.: 79-42-5
Mol. formula: C3H6O2S
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.
Thiolactic acid was once widely used in hair permanent waving formulations, but has been displaced by formulations based on thioglycolic acid.
Instead of using the acid itself, its salts are used.
It is now mainly used for depilation.
Thiolactic acid (TLA) can be used as a building block in the synthesis of:
Thiolactomycin via oxathiolanone intermediate.
4-Thiazolidinones by reacting various Schiff bases with thioglycolic acid.
1,4-Naphthoquinone derivatives containing sulfur atom for antibacterial and antiviral activity studies.
It can also be used as a bidental chelating agent for the surface modification of titanium dioxide (TiO2) nanoparticles for the removal of cadmium from waste water.
Thiolactic acid appears as an oily liquid with an unpleasant odor.
Toxic by ingestion and skin absorption. Used as a depilatory and in hair waving preparations.
Uses:
Thiolactic acid is an important raw material for organic synthesis, mainly used in the preparation of herbicides, plasticized heat stabilizers and antioxidants, as well as the deployment of daily spices.
Depilatory, hair-waving preparations.
Preparation
It is prepared from the electrolysis of the corresponding sulfide S (SCHMeCO2H) Alternatively, it can be prepared from the reaction between pyruvate and hydrogen sulfide.
Hydrogen sulfide is added to 50% pyruvic acid to make it saturated at 60-70 DEG C; add hydrochloric acid to until turbidity is formed; dilute sulfuric acid is added to make it weakly acidic, and 2.5% sodium amalgam is added to the precipitated compound for reduction.
Cool it till hydrogen sulfide is completed released.
Then add ether the acidic medium, extract the lactic acid, remove the ether by distillation, here thiolactic acid is finally obtained.
Chemical Properties
Clear colorless to slightly yellow liquid.
Oily liquid;
Melting point 10 ℃;
Boiling point d-95 ~ 100 ℃ / 2133Pa, dl- 98.5 ~ 99.0 ℃ / 1866Pa;
Density I-D19.24 1.193;
Refractive index dl-nD: 1.4823;
Optical rotation[α] D-45.47;
soluble in water, ethanol and ether.
Thiolactic acid has a roasted, meaty odor.
Preparation
By electrolysis of the corresponding sulfide, S(SCHMeCO2H)2.
Use: Thiolactic acid's unique reducing properties make it acceptable for use in a wide variety of chemical reactions including addition, elimination, or cyclization reactions.
TGA's sulfur group (-SH) will react in the presence of bases, acids, ketone groups or organic halogens.
In the presence of alcohols or amines, the carboxylic group will react preferentially.
Odor: Meaty, sulphurous, brothy, brown notes
Flavor: meaty, sulphurous, brothy, brown
Used in smoke, meat and bacon flavours.
Normal use levels in finished consumer product: 0.5-50 ppm.
Its functions (INCI)
Antioxidant : Inhibits reactions favored by oxygen, thus avoiding oxidation and rancidity
Depilatory : Removes unwanted hair
Hair waving or straightening : Modifies the chemical structure of the hair, to style it in the required style
Masking : Reduces or inhibits the odor or basic taste of the product
Reducing : Changes the chemical nature of another substance by adding hydrogen or removing oxygen
THIOLACTIC ACID is classified as :
Antioxidant
Depilatory
Hair waving or straightening
Masking
Reducing
Category
Depilatory Agents
Restructuring / Replenishing Agents
Application/Recommended for
Hair care (Shampoos, Conditioners & Styling)
Toiletries (Shower & Bath, Oral care...)
Thiolactic acid is used as a monodentate thiol ligands that has an influence on the colloidal stability, photoluminescence quantum yield and decay behavior of a set of CdTe nanocrystal colloids.
Thiolactic acid, containing-COOH and -SH groups, belonging to a physiologically important class of compounds called mercaptans, has gained sufficient importance in the fields of pharmaceutical, synthetic and analytical chemistry in recent years.
The polarographic behaviour of this compound has already been studied by the authors but there is hardly any reference in the literature reporting its dissociation constants.
A knowledge of the acid dissociation constants of simple mercaptans is fundamental to an understanding of the chemistry of these compounds for two reasons; firstly be-cause many important reactions of mercaptans may proceed through the mercaptide ions, and secondly because the acid dissociation constants can give important information about the distribution of electrons in mercaptans.
Moreover, these values are essential for investigating the complexing tendency of such compounds with metals.
In view of its importance and in the absence of any literature on the subject, it was considered worthwhile to determine the acid dissociation constants of -COOH and -SH groups in thiolactic acid at different temperatures, viz., 20°, 30° and 40°C, using potentiometric and polarographic techniques.
Thiolactic acid is a synthetic flavor and skin sensitizer used in cosmetics, food and household care products.
Thiolactic acid, containing a reactive sulphydryl group, has been shown to easily reduce Cr(VI) and yield disulfide as oxidation product.
The reaction was studied by the use of spectrophotometry.
The spectral data as well as the kinetic information showed distinct evidence of the formation of an Sbonded Cr(VI)-thiolactate intermediate that was subsequently followed by a somewhat slower, bimolecular redox process leading to the formation of the final products.
The rate laws for these two stages have been determined, showing a complex dependence on substrate and hydrogen ion concentration.
Small experimental Arrhenius activation energies for the two successive steps were also obtained.
The involvement of paramagnetic Cr(V) species and that of some organic free radicals were evidenced by ESR and, the latter, also by initialization of polymerization.
A reaction mechanism has been proposed, that leads to a rate law in convincing agreement with the experimental one.
Thiolactic Acid is a colorless to pale yellow liquid with a roasted, meaty odor.
It is miscible in water, alcohol, ether and acetone.
This product differs from other flavors by having a specific gravity of 1.192 - 1.200.
The functions of the cosmetic ingredient
ANTIOXIDANT : inhibiting reactions promoted by oxygen, thus avoiding oxidation and rancidity.
DEPILATORY : breaking down the the mechanical strength of hair fibers so that they can be removed by mild scraping/rubbing.
FRAGRANCE : imparting an odour or taste.
creating a perceivable pleasant smell and/or masking a bad smell.
HAIR WAVING OR STRAIGHTENING : modifying the chemical structure of the hair, allowing it to be set in the style required (permanent waves or hair straightening).
REDUCING : changing the chemical nature of another ingredient by adding hydrogen (or removing oxygen).
Thiolactic Acid - also is an organic- chemical compound , the synthesis of herbicides is needed and also in depilatory creams is used.
The ammonium salt of thiolactic ammonium thiolactate.
Chemical properties
Molecular weight:106.14
Formula:C3H6O2S
Purity:97%
MDL:MFCD00004862
Melting point:10-14°
Boiling point:217°
Flash point:107°(225°F)
Density:1.196
EINECS:201-206-5
Merck:14,9340
SMILES:C-C(-S)-C(=O)-O
Molecular Formula: C4H8O2S;
Molecular Weight: 120.17
About Thiolactic Acid
Helpful information
Thiolactic Acid is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 to < 100 tonnes per annum.
Thiolactic Acid is used by consumers, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.
Consumer Uses
Thiolactic Acid is used in the following products: cosmetics and personal care products.
Other release to the environment of Thiolactic Acid is likely to occur from: indoor use as reactive substance.
Article service life
ECHA has no public registered data on the routes by which Thiolactic Acid is most likely to be released to the environment. ECHA has no public registered data indicating whether or into which articles the substance might have been processed.
Widespread uses by professional workers
Thiolactic Acid is used in the following products: metal surface treatment products, laboratory chemicals and cosmetics and personal care products.
Thiolactic Acid is used for the manufacture of: chemicals and electrical, electronic and optical equipment.
Other release to the environment of Thiolactic Acid is likely to occur from: indoor use as reactive substance.
Formulation or re-packing
Thiolactic Acid is used in the following products: metal surface treatment products, laboratory chemicals and cosmetics and personal care products.
Release to the environment of Thiolactic Acid can occur from industrial use: formulation of mixtures.
Uses at industrial sites
Thiolactic Acid is used in the following products: metal surface treatment products and laboratory chemicals.
Thiolactic Acid is used for the manufacture of: chemicals and electrical, electronic and optical equipment.
Release to the environment of Thiolactic Acid can occur from industrial use: as processing aid and as processing aid.
Manufacture
Release to the environment of Thiolactic Acid can occur from industrial use: manufacturing of the substance.
Thiolactic Acid is a synthetic flavor and skin sensitizer used in cosmetics, food and household care products.
IUPAC NAMES:
2-MERCAPTOPROPIONIC ACID
2-Mercaptopropionic acid
2-mercaptopropionic acid
2-sulfanylpropanoic acid
Thiolactic Acid
Thiolactic acid, 2-Mercaptopropionic acid
SYNONYMS:
2-Mercaptopropionic acid
Thiolactic acid
79-42-5
2-Sulfanylpropanoic acid
2-Mercaptopropanoic acid
2-Thiolactic acid
2-Thiolpropionic acid
alpha-Mercaptopropionic acid
PROPANOIC ACID, 2-MERCAPTO-
alpha-Mercaptopropanoic acid
Propionic acid, 2-mercapto-
2-mercapto-propionic acid
CHEBI:47872
MFCD00004862
2-Mercaptopropionic acid, 95%
FEMA No. 3180
EINECS 201-206-5
UN2936
BRN 0506218
Rac-Thiolactic Acid
Thiolactic acid [UN2936] [Poison]
mercapto-propionic acid
Thiolactic acid, 95%
2-mercapto propionic acid
2-Mercapto-Propanoic acid
alpha -mercaptopropanoic acid
alpha -mercaptopropionic acid
SCHEMBL15864
4-03-00-00682 (Beilstein Handbook Reference)
.alpha.-Mercaptopropanoic acid
.alpha.-Mercaptopropionic acid
CHEMBL2158192
FEMA 3180
DTXSID80861636
STR01228
BBL011561
STL146731
AKOS000120478
AKOS017278454
MCULE-6944738352
UN 2936
2-Mercaptopropionic acid, >=95%, FG
Thiolactic acid [UN2936] [Poison]
N056
2-Mercaptopropionic acid, analytical standard
THIOLACTIC ACID
PROPANOIC ACID, 2-MERCAPTO-
2-mercapto-propanoicaci
2-mercaptopropanoicacid
α-Mercaptopropanoic acid
2-MERCAPTOPROPIONIC ACID 95+%
2-MERCAPTOPROPIONIC ACID 96+%
2-Mercaptopropionicacid,97%
MERCAPTOPROPIONSAEURE, 2-
Thiomilchsure
2-Mercaptopropionic acid, Thiolactic acid
Thiolactic acid,2-Mercaptopropionic acid
2-Mercaptopropionic acid,2-Mercaptopropionic acid, Thiolactic acid
2-Mercaptopropionic acid, 95% 100GR
Thiolactic acid 95%
Tiopronin Impurity 2
Tiopronin Impurity B
Tiopronin Impurity II
2-mercapto-Propanoicacid
2-mercapto-propionicaci
2-Sulfanylpropanoic acid
2-Thiolactic acid
2-thiolacticacid
alpha-Mercaptopropanoic acid
alpha-mercaptopropanoicacid
Propionic acid, 2-mercapto-
thiolactic
FEMA 3810
FEMA 3180
2-MERCAPTOPROPIONIC ACID
ALPHA-MERCAPTOPROPIONIC ACID
2-Mercaptopropanic Acid
Thiolacticacid,95%
ThiolacticAcid>
2-Mercaptopropionic acid ISO 9001：2015 REACH
