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Undecanoic acid

Catalog Number: BT-284988

CAS Number: 112-37-8

Molecular Formula: C11H22O2

Molecular Weight: 186.29 g/mol

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Product Introduction

Description

Undecanoic acid, also known as undecylic acid, is a saturated fatty acid with the chemical formula C11H22O2. It is a colorless to pale yellow liquid with a characteristic odor and is insoluble in water but soluble in organic solvents. Undecanoic acid is widely used in various industries, including pharmaceuticals, cosmetics, and food, due to its unique chemical and biological properties.

Properties

CAS Number

112-37-8

Product Name

Undecanoic acid

IUPAC Name

undecanoic acid

Molecular Formula

C11H22O2

Molecular Weight

186.29 g/mol

InChI

InChI=1S/C11H22O2/c1-2-3-4-5-6-7-8-9-10-11(12)13/h2-10H2,1H3,(H,12,13)

InChI Key

ZDPHROOEEOARMN-UHFFFAOYSA-N

SMILES

CCCCCCCCCCC(=O)O

Solubility

2.80e-04 M
0.0522 mg/mL at 30 °C
0.0522 mg/mL
Insoluble in water; very soluble in alcohol, chloroform, acetone

Synonyms

Undecanoate; NSC 7885; NSC-7885; NSC7885

Canonical SMILES

CCCCCCCCCCC(=O)O

Method of Synthesis or Extraction

Undecanoic acid can be synthesized by various methods, including oxidation of undecanol, hydrolysis of undecenyl cyanide, and decarboxylation of undecenoic acid. The efficiency and yield of each method depend on the starting material, reaction conditions, and purification methods. For example, the oxidation of undecanol using potassium permanganate as an oxidizing agent can yield up to 90% of undecanoic acid. However, this method requires careful control of reaction conditions and can produce hazardous waste. On the other hand, the hydrolysis of undecenyl cyanide using hydrochloric acid can yield up to 95% of undecanoic acid, but it requires a high-temperature reaction and careful handling of toxic cyanide compounds. The decarboxylation of undecenoic acid using sodium hydroxide can yield up to 80% of undecanoic acid, but it requires a high-temperature reaction and careful control of reaction conditions. Environmental and safety considerations should be taken into account when choosing the method of synthesis or extraction of undecanoic acid.

Chemical Structure and Biological Activity

Undecanoic acid has a straight-chain structure with a carboxylic acid group at one end and a methyl group at the other end. It has a molecular weight of 186.3 g/mol and a melting point of 28-30°C. Undecanoic acid has been shown to have antimicrobial, antifungal, and anti-inflammatory properties. It can inhibit the growth of various bacteria, including Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa. Undecanoic acid can also inhibit the growth of fungi, including Candida albicans and Aspergillus niger. The mechanism of action of undecanoic acid is not fully understood, but it is believed to disrupt the cell membrane and interfere with the energy metabolism of microorganisms.

Biological Effects

Undecanoic acid has been shown to have various biological effects on cell function and signal transduction. It can modulate the activity of various enzymes, including lipases, proteases, and phospholipases. Undecanoic acid can also affect the expression of various genes involved in inflammation, oxidative stress, and cell proliferation. Undecanoic acid has been investigated for its potential therapeutic and toxic effects. It has been shown to have anti-inflammatory and analgesic effects in animal models of arthritis and neuropathic pain. Undecanoic acid has also been investigated for its potential use in cancer therapy, as it can induce apoptosis and inhibit cell proliferation in various cancer cell lines. However, the toxic effects of undecanoic acid on human cells and organs are not fully understood and require further investigation.

Applications

Undecanoic acid has various applications in medical research, environmental research, and industrial research. In medical research, undecanoic acid has been investigated for its role in drug development, clinical trials, and findings. Undecanoic acid has been used as a topical antifungal agent in the treatment of skin infections. Undecanoic acid has also been investigated for its potential use in the treatment of Alzheimer's disease, as it can inhibit the activity of acetylcholinesterase, an enzyme involved in the degradation of acetylcholine. In environmental research, undecanoic acid has been investigated for its effects on ecosystems, role in pollution management, and sustainability and environmental impact. Undecanoic acid has been shown to have low toxicity to aquatic organisms and can be used as a biodegradable surfactant in cleaning products. In industrial research, undecanoic acid has been used in manufacturing processes to improve product quality and efficiency. Undecanoic acid has been used as a plasticizer in the production of polyvinyl chloride and as a lubricant in metalworking fluids.

Future Perspectives and Challenges

Undecanoic acid has great potential for various applications in scientific research, but there are still limitations in its use and study. The toxicity and safety of undecanoic acid on human cells and organs require further investigation. The mechanism of action of undecanoic acid on microorganisms and cells needs to be elucidated to develop more effective and specific therapeutic agents. The development of new and efficient methods of synthesis or extraction of undecanoic acid is also needed to reduce the environmental impact and increase the yield and purity of the product. The future trends and prospects of undecanoic acid in scientific research depend on the progress in these areas and the discovery of new applications and uses.
Conclusion:
Undecanoic acid is a versatile and promising compound with various applications in medical research, environmental research, and industrial research. The methods of synthesis or extraction, chemical structure, biological activity, biological effects, applications, future perspectives, and challenges of undecanoic acid have been discussed in this paper. Further research is needed to fully understand the potential of undecanoic acid and to develop new and efficient methods of synthesis or extraction and therapeutic agents.

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