Nonanoic acid
[CAS# 112-05-0]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Acyclic carboxylic acid
• Name: Nonanoic acid
• Synonyms: Pelargonic acid
• Molecular Formula: C₉H₁₈O₂
• Molecular Weight: 158.24
• CAS Registry Number: 112-05-0
• EC Number: 203-931-2
• FEMA: 2784
• SMILES: CCCCCCCCC(=O)O

Properties

• Density: 0.906
• Melting point: 12.5 °C
• Boiling point: 254 °C
• Refractive index: 1.4299-1.4339
• Flash point: 114 °C
• Water solubility: NEGLIGIBLE

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H315-H319-H412
• Safety Statements: P260-P264-P264+P265-P273-P280-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P316-P317-P321-P332+P317-P337+P317-P362+P364-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1C	H314
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Skin sensitization	Skin Sens.	1B	H317
Skin sensitization	Skin Sens.	1	H317

• Transport Information: UN 3265

Discovery and Applications

Nonanoic acid, also known as pelargonic acid, is a nine-carbon fatty acid with the molecular formula C9H18O2. This compound belongs to the carboxylic acid family and is commonly found as a colorless, oily liquid with a mildly pungent odor. Nonanoic acid occurs naturally in some plants and oils, and it can also be synthesized for commercial purposes. Its discovery and applications are rooted in the agricultural and chemical industries, where its properties as a herbicide, antifungal agent, and intermediate in various syntheses are widely utilized.

Nonanoic acid was initially recognized for its occurrence in essential oils, particularly in pelargonium plants, from which its alternative name, pelargonic acid, is derived. This natural origin piqued the interest of researchers in the 19th century, who began studying its structure and potential applications in agriculture and industry. Since then, the compound has been synthesized chemically for use in broader applications, providing a more accessible route for industries requiring larger quantities.

In agriculture, nonanoic acid serves as an effective non-selective herbicide, targeting a broad range of weeds without the need for toxic or persistent chemicals. Due to its relatively low toxicity to animals and humans, nonanoic acid is often employed in organic farming and in environmentally conscious weed control strategies. When applied to plant foliage, nonanoic acid disrupts cell membranes, causing rapid desiccation and death in target weeds. This mechanism offers a biodegradable alternative to synthetic herbicides, reducing potential soil and water contamination.

Nonanoic acid is also used in pest control as a fungicide and insect repellent. It has demonstrated efficacy against common plant pathogens, and in formulations with other fatty acids, it can help manage fungal infections on crops. Additionally, its repellent properties are beneficial in protecting stored goods and crops from insects, especially in organic agricultural settings where synthetic pesticides are restricted. The use of nonanoic acid in this capacity capitalizes on its relatively low environmental persistence, aligning with sustainability practices in modern farming.

Another important application of nonanoic acid is as an intermediate in organic synthesis. It is frequently used as a building block for producing esters, salts, and other derivatives used in industrial processes. Nonanoic acid esters, for instance, are valued in the fragrance and flavor industries for their fruity, fatty scent and are often included in personal care products, lubricants, and food additives. In polymer chemistry, nonanoic acid derivatives serve as plasticizers and stabilizers, enhancing the flexibility and longevity of polymeric materials.

In recent years, nonanoic acid has gained interest as a renewable and biodegradable option in formulations for cleaning products, disinfectants, and solvents. Its fatty acid structure enables it to dissolve oils and organic compounds effectively, making it a useful ingredient in household and industrial cleaning solutions. Due to its non-persistent nature and low toxicity, nonanoic acid is particularly attractive in environmentally friendly product lines.

Nonanoic acid continues to be a subject of study, particularly in terms of its efficacy as a bio-based herbicide and its utility in biodegradable product development. Its applications across agriculture, industrial chemistry, and consumer goods underscore its versatility as a naturally derived, eco-friendly compound.

References

2019. Antimicrobial activity of a selection of organic acids, their salts and essential oils against swine enteropathogenic bacteria. Porcine Health Management.
DOI: 10.1186/s40813-019-0139-4

2020. Effects of the entomopathogenic fungus Metarhizium flavoviride on the fat body lipid composition of Zophobas morio larvae (Coleoptera: Tenebrionidae). Die Naturwissenschaften.
DOI: 10.1007/s00114-019-1662-5

2021. Volatile and semi-volatile organic compounds may help reduce pollinator-prey overlap in the carnivorous plant Drosophyllum lusitanicum (Drosophyllaceae). Journal of Chemical Ecology.
DOI: 10.1007/s10886-020-01235-w