Glyceryl monothioglycolate
[CAS# 30618-84-9]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Glyceryl monothioglycolate
• Synonyms: Glycerol monomercaptoacetate; Mercaptoacetic acid monoester with 1,2,3-propanetriol
• Molecular Formula: C₅H₁₀O₄S
• Molecular Weight: 166.19
• CAS Registry Number: 30618-84-9
• EC Number: 250-264-8
• SMILES: C(C(COC(=O)CS)O)O

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.524, Calc.^*
• Boiling Point: 359.8±27.0 °C (760 mmHg), Calc.^*
• Flash Point: 171.4±23.7 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS06;GHS07 Danger
• Risk Statements: H301-H312-H317
• Safety Statements: P261-P264-P270-P272-P280-P301+P316-P302+P352-P317-P321-P330-P333+P317-P362+P364-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	4	H312
Skin sensitization	Skin Sens.	1	H317
Skin sensitization	Skin Sens.	1B	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

Glyceryl monothioglycolate, with the chemical formula C₅H₁₀O₄S, is an organic compound notable for its unique chemical structure and diverse applications. This compound is a thiol derivative of glycerol, where a thioglycolic acid moiety is attached to a glycerol backbone. The discovery and subsequent applications of glyceryl monothioglycolate have made it a significant substance in several industrial and research fields.

The compound was first synthesized as part of research into new thiol-based reagents and intermediates. Thioglycolic acid, a precursor, is known for its role in organic synthesis due to its thiol group, which can form strong bonds with various metals and organic molecules. By attaching this moiety to glycerol, researchers developed glyceryl monothioglycolate as a versatile reagent with improved properties over simpler thioglycolic acid derivatives.

Glyceryl monothioglycolate is primarily used in the field of polymer chemistry and material science. It acts as a chain transfer agent in radical polymerization processes. Its thiol group can react with growing polymer chains, allowing for controlled polymerization and modification of polymer properties. This application is crucial for producing polymers with specific characteristics, such as desired molecular weights and functional groups. The ability to control polymer chain lengths and branching enhances the performance of polymers in various applications, including coatings, adhesives, and specialty materials.

In addition to its role in polymer chemistry, glyceryl monothioglycolate is utilized in the production of thiol-functionalized compounds. Its chemical structure allows it to serve as a building block for creating complex molecules with thiol groups. These thiol-functionalized compounds are valuable in diverse fields, including pharmaceuticals and agrochemicals, where thiol groups can influence the activity and stability of drugs and pesticides.

The compound also finds use in cosmetic formulations. Glyceryl monothioglycolate is incorporated into some cosmetic products as a conditioning agent and skin treatment ingredient. Its ability to form stable bonds with proteins and other molecules makes it useful in enhancing the texture and efficacy of cosmetic products.

Research continues to explore new applications and improvements for glyceryl monothioglycolate. Innovations in polymer chemistry, materials science, and cosmetics are likely to expand its use further. The compound's versatility and effectiveness in forming thiol-based bonds make it a valuable tool for developing new materials and products across various industries.

In summary, glyceryl monothioglycolate is a significant compound in the realms of polymer chemistry, materials science, and cosmetics. Its unique chemical properties allow it to act as a chain transfer agent in polymerization, a building block for thiol-functionalized compounds, and a conditioning agent in cosmetic products. The ongoing research into its applications underscores its importance in advancing both industrial processes and consumer products.

References

1985. Human sensitization testing with commercial permanent waving lotions containing glyceryl monothioglycolate. Contact Dermatitis, 13(2).
DOI: 10.1111/j.1600-0536.1985.tb02549.x

1988. Persistence of an allergen in hair after glyceryl monothioglycolate-containing permanent wave solutions. Journal of the American Academy of Dermatology, 19(1 Pt 1).
DOI: 10.1016/s0190-9622(88)70151-6

2014. Contact allergy to ingredients of hair cosmetics - a comparison of female hairdressers and clients based on IVDK 2007-2012 data. Contact Dermatitis, 71(1).
DOI: 10.1111/cod.12196