2-[1-(Mercaptomethyl)cyclopropyl]acetic acid
[CAS# 162515-68-6]

Identification

• Classification: Organic raw materials >> Organic sulfur compound
• Name: 2-[1-(Mercaptomethyl)cyclopropyl]acetic acid
• Synonyms: 2-[1-(sulfanylmethyl)cyclopropyl]acetic acid
• Molecular Formula: C₆H₁₀O₂S
• Molecular Weight: 146.21
• CAS Registry Number: 162515-68-6
• EC Number: 420-240-3
• SMILES: C1CC1(CC(=O)O)CS

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Melting point: 42-45 °C
• Index of Refraction: 1.538, Calc.^*
• Boiling Point: 290.1±13.0 °C (760 mmHg), Calc.^*
• Flash Point: 129.2±19.8 °C, Calc.^*, 110 °C

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

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS09 Danger
• Risk Statements: H312-H302-H314-H317-H411
• Safety Statements: P260-P261-P264-P270-P272-P273-P280-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P321-P330-P333+P317-P362+P364-P363-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Skin sensitization	Skin Sens.	1	H317
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	3	H311
Skin sensitization	Skin Sens.	1A	H317
Specific target organ toxicity - single exposure	STOT SE	3	H335
Serious eye damage	Eye Dam.	1	H318

Discovery and Applications

2-[1-(Mercaptomethyl)cyclopropyl]acetic acid is a unique compound that belongs to a class of organic molecules known for their potential therapeutic applications and structural diversity. This compound features a cyclopropyl group, which contributes to its distinct properties, and a mercaptomethyl substituent that enhances its reactivity and interaction with biological systems. The synthesis and study of this compound highlight the ongoing research in medicinal chemistry aimed at discovering new agents with specific biological activities.

The discovery of 2-[1-(mercaptomethyl)cyclopropyl]acetic acid is rooted in the exploration of cyclopropyl-containing compounds, which have garnered interest due to their presence in numerous natural products and pharmaceuticals. Cyclopropyl groups can significantly influence the pharmacological properties of a compound, providing a scaffold that enhances binding affinity to biological targets. The introduction of the mercaptomethyl group further diversifies the compound's chemical reactivity, potentially allowing it to participate in various biochemical interactions.

Synthesis of 2-[1-(mercaptomethyl)cyclopropyl]acetic acid typically involves several steps, beginning with the formation of the cyclopropyl framework followed by the incorporation of the mercaptomethyl group. One common method for synthesizing this compound involves the reaction of cyclopropyl derivatives with thiol-containing reagents. This synthetic pathway not only allows for the generation of the desired product but also provides opportunities for further functionalization, which can be essential for exploring the compound's biological properties.

The applications of 2-[1-(mercaptomethyl)cyclopropyl]acetic acid are primarily focused on its potential as a pharmaceutical agent. Its structural characteristics may confer various biological activities, including antimicrobial, anti-inflammatory, and anticancer properties. The mercaptomethyl group can facilitate interactions with cysteine residues in proteins, a common target for drug design. This interaction is particularly relevant in the context of enzyme inhibition, where compounds can act as inhibitors by binding to the active sites of enzymes and modulating their activities.

Research into the biological activities of 2-[1-(mercaptomethyl)cyclopropyl]acetic acid has been encouraged by the broader interest in thiol-containing compounds, which are known to exhibit a range of pharmacological effects. The potential for this compound to act as a modulator of cellular pathways makes it a candidate for further investigation in the field of drug discovery. Furthermore, the ability to modify its structure can lead to derivatives with enhanced selectivity and potency, expanding its applicability in therapeutic contexts.

The safety profile of 2-[1-(mercaptomethyl)cyclopropyl]acetic acid, like many sulfur-containing compounds, should be carefully evaluated. While many thiol-containing compounds are considered to have low toxicity, proper safety measures must be observed when handling any chemical substances in the laboratory setting, including personal protective equipment and adherence to standard laboratory protocols.

In conclusion, 2-[1-(mercaptomethyl)cyclopropyl]acetic acid represents an intriguing compound with potential applications in medicinal chemistry. Its unique structural features and reactivity make it a promising candidate for further research aimed at discovering new therapeutic agents. Ongoing investigations into its synthesis and biological properties may reveal important insights into its role in drug development and its potential impact on treating various diseases.

References

2016. Asymmetric Catalysis with Iron-Salen Complexes. Synthesis, 48(19), 3121-3136.
DOI: 10.1055/s-0035-1562103

2003. Montelukast sodium. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-13-0175