8-[(2-Hydroxybenzoyl)amino]octanoic acid
[CAS# 183990-46-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Carboxylic acid
• Name: 8-[(2-Hydroxybenzoyl)amino]octanoic acid
• Synonyms: Salcaprozic acid
• Molecular Formula: C₁₅H₂₁NO₄
• Molecular Weight: 279.34
• CAS Registry Number: 183990-46-7
• EC Number: 854-168-2
• SMILES: C1=CC=C(C(=C1)C(=O)NCCCCCCCC(=O)O)O

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.548, Calc.^*
• Boiling Point: 521.7±35.0 °C (760 mmHg), Calc.^*
• Flash Point: 269.3±25.9 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302+H312+H332-H302-H312-H315-H319-H332-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H312
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H332
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

8-[(2-Hydroxybenzoyl)amino]octanoic acid is a chemical compound that combines the structural features of an amino acid with a benzoyl group, specifically a 2-hydroxybenzoyl moiety. This compound contains an octanoic acid backbone, an amino group, and a hydroxybenzoyl group, which imparts significant chemical versatility. The presence of both a hydroxyl group on the benzene ring and an amino group on the octanoic acid backbone positions 8-[(2-hydroxybenzoyl)amino]octanoic acid as an interesting candidate for various biochemical and industrial applications. Its molecular structure allows it to interact with biological systems in a manner that could have therapeutic potential, as well as practical uses in chemical synthesis.

The discovery of 8-[(2-hydroxybenzoyl)amino]octanoic acid is part of the ongoing interest in creating new bioactive compounds with multifunctional properties. The synthesis of such compounds typically involves modifying the amino acid structure to achieve greater selectivity and potency in biological applications. The introduction of the 2-hydroxybenzoyl group into the structure is a strategic design to increase the compound's ability to interact with specific biological targets, such as enzymes or receptors. The hydroxy group can form hydrogen bonds and contribute to solubility in biological environments, while the benzoyl group can enhance lipophilicity, allowing better membrane penetration.

8-[(2-Hydroxybenzoyl)amino]octanoic acid has primarily been explored for its potential pharmacological properties. The combination of the amino acid backbone with the hydroxybenzoyl group may allow it to act as a ligand for specific receptors involved in metabolic processes. Its structure suggests that it may function as an inhibitor or modulator of enzymes in metabolic pathways, particularly those related to lipid metabolism or amino acid catabolism. The octanoic acid portion of the molecule may also influence its interaction with fatty acid pathways, potentially offering therapeutic effects in disorders related to metabolism, such as obesity, hyperlipidemia, or diabetes.

The hydroxybenzoyl group could also contribute to the compound’s antioxidant properties, allowing it to act as a free radical scavenger. This would make it a promising candidate in the development of compounds designed to combat oxidative stress, a common underlying factor in various chronic conditions, including cardiovascular diseases, neurodegenerative disorders, and cancer. Antioxidants like 8-[(2-hydroxybenzoyl)amino]octanoic acid may also have applications in skin care and anti-aging products, where they help to protect cells from oxidative damage caused by environmental stressors like UV radiation.

In addition to its biomedical applications, 8-[(2-hydroxybenzoyl)amino]octanoic acid holds potential in chemical synthesis. The functional groups present in the molecule allow it to serve as a building block for the synthesis of more complex compounds, such as peptides, drugs, and materials with specific properties. The amino acid structure, combined with the hydroxybenzoyl group, provides a versatile platform for creating derivatives that can target specific biological functions or participate in catalytic reactions. As a result, it is of interest in the fields of organic chemistry and materials science, where it can be used to develop novel materials with unique properties, such as drug delivery systems or bioactive coatings.

Furthermore, 8-[(2-hydroxybenzoyl)amino]octanoic acid may have applications in agricultural chemistry. Its potential role as a natural or synthetic pesticide or fungicide is being explored, due to the ability of the hydroxybenzoyl group to interact with certain biological targets. The compound’s ability to penetrate plant tissues or disrupt the function of pests could provide an environmentally friendly alternative to conventional agrochemicals.

In conclusion, 8-[(2-hydroxybenzoyl)amino]octanoic acid is a promising compound with a range of potential applications in medicine, chemical synthesis, and agriculture. Its unique structure, which incorporates both an amino acid backbone and a hydroxybenzoyl group, enables it to interact with various biological systems, offering opportunities for the development of new therapeutic agents, antioxidants, and chemical intermediates.

References

2012. Mitigating the Inhibition of Human Bile Salt Export Pump by Drugs: Opportunities Provided by Physicochemical Property Modulation, In Silico Modeling, and Structural Modification. Drug metabolism and disposition: the biological fate of chemicals.
DOI: 10.1124/dmd.112.047068

2009. Subchronic Oral Toxicity of Salcaprozate Sodium (SNAC) in Sprague-Dawley and Wistar Rats. International Journal of Toxicology.
DOI: 10.1177/1091581809337737

2000. Studies Directed at the Use of a Parallel Synthesis Matrix to Increase Throughput in an in Vivo Assay. Journal of Medicinal Chemistry.
DOI: 10.1021/jm990416r