10-Nonadecanone
[CAS# 504-57-4]

Identification

• Classification: Organic raw materials >> Ketone compound
• Name: 10-Nonadecanone
• Synonyms: nonadecan-10-one
• Molecular Formula: C₁₉H₃₈O
• Molecular Weight: 282.50
• CAS Registry Number: 504-57-4
• EC Number: 207-994-7
• SMILES: CCCCCCCCCC(=O)CCCCCCCCC

Properties

• Density: 0.8±0.1 g/cm³ Calc.^*
• Melting point: 58 °C (Expl.)
• Boiling point: 351.2±10.0 °C 760 mmHg (Calc.)^*, 412.7 °C (Expl.)
• Flash point: 81.6±14.6 °C (Calc.)^*
• Index of refraction: 1.444 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315
• Safety Statements: P264-P280-P302+P352-P321-P332+P317-P362+P364

Hazard Classification

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

Discovery and Applications

10-Nonadecanone is a long-chain aliphatic ketone with the molecular formula C₁₉H₃₈O. Structurally, it consists of a linear 19-carbon hydrocarbon chain with a carbonyl group located at the tenth carbon, placing the ketone roughly in the center of the molecule. This mid-chain position of the carbonyl group influences the physical properties of the compound, giving it characteristics typical of long-chain ketones: it is solid or waxy at room temperature, relatively hydrophobic, and soluble in nonpolar organic solvents but poorly soluble in water.

Compounds such as 10-Nonadecanone are commonly found as minor constituents of plant waxes, insect cuticular lipids, and other biological lipid mixtures. In plants, mid-chain ketones contribute to the composition of epicuticular waxes, which serve protective roles including reducing water loss, shielding against ultraviolet radiation, and providing a barrier to pathogens. In insects, similar long-chain ketones can influence desiccation resistance and may function in chemical communication, although the specific role of 10-Nonadecanone in these systems is less well documented than for shorter or more common ketones.

From a synthetic perspective, 10-Nonadecanone can be prepared in the laboratory via oxidation of the corresponding secondary alcohol or by constructing the carbon chain through controlled carbon–carbon bond-forming reactions followed by introduction of the ketone functionality. Its structure and properties make it a useful reference compound in analytical chemistry, particularly for gas chromatography and mass spectrometry, where it serves as a standard for identifying mid-chain aliphatic ketones in natural waxes and lipid extracts.

Applications of 10-Nonadecanone are mainly research-oriented. It is used to study the physical and chemical properties of long-chain ketones, their behavior in biological systems, and their role in surface chemistry. Additionally, it can serve as a model compound in the exploration of bio-based chemicals derived from fatty acids, where such ketones may be intermediates in the production of waxes, surfactants, or other hydrophobic materials.

Overall, 10-Nonadecanone is a long-chain mid-ketone whose significance lies in its presence in natural waxes, its utility as a reference standard, and its role as a model compound in research on long-chain lipids and bio-based chemical materials. Its combination of a central carbonyl group and a long hydrocarbon chain exemplifies the properties of mid-chain aliphatic ketones, influencing melting point, solubility, and reactivity in both natural and synthetic contexts.

References

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DOI: 10.5281/zenodo.5794106

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DOI: 10.1007/s00344-021-10372-9

2012. Volatile Mediated Interactions Between Bacteria and Fungi in the Soil. Journal of Chemical Ecology, 38(6).
DOI: 10.1007/s10886-012-0135-5