8-Pentadecanone
[CAS# 818-23-5]

Identification

• Classification: Organic raw materials >> Ketone compound
• Name: 8-Pentadecanone
• Synonyms: pentadecan-8-one
• Molecular Formula: C₁₅H₃₀O
• Molecular Weight: 226.40
• CAS Registry Number: 818-23-5
• EC Number: 212-450-7
• SMILES: CCCCCCCC(=O)CCCCCCC

Properties

• Density: 0.8±0.1 g/cm³ Calc.^*
• Melting point: 43 ºC (Expl.)
• Boiling point: 292.6±8.0 ºC 760 mmHg (Calc.)^*
• Flash point: 83.1±14.0 ºC (Calc.)^*
• Index of refraction: 1.437 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413

Discovory and Applicatios

8-Pentadecanone is a long-chain aliphatic ketone with the molecular formula C₁₅H₃₀O. Structurally, it consists of a linear 15-carbon hydrocarbon chain with a carbonyl group located at the eighth carbon, placing the ketone near the middle of the chain. This mid-chain positioning influences its physical properties, giving it characteristics typical of long-chain ketones: it is waxy or solid at room temperature, hydrophobic, and soluble in nonpolar organic solvents while poorly soluble in water.

Compounds such as 8-Pentadecanone are commonly found as minor components of plant waxes and insect cuticular lipids. In plants, mid-chain ketones contribute to the epicuticular wax layer that protects leaves and fruits by reducing water loss, reflecting ultraviolet light, and providing a barrier against microbial pathogens. In insects, similar long-chain ketones may contribute to desiccation resistance and, in some cases, chemical signaling, although the specific biological role of 8-Pentadecanone is less studied than more common ketones.

From a synthetic perspective, 8-Pentadecanone can be prepared in the laboratory via oxidation of the corresponding secondary alcohol or by carbon–carbon bond-forming reactions followed by introduction of the ketone group. Its defined structure and stability make it a useful reference compound in analytical chemistry, particularly for gas chromatography and mass spectrometry, where it can serve as a standard for identifying mid-chain ketones in natural waxes and lipid extracts.

Applications of 8-Pentadecanone are primarily research-oriented. It is used to study the physical and chemical properties of long-chain ketones, their behavior in biological waxes, and their role in surface chemistry. It also serves as a model compound for bio-based chemical studies, where mid-chain ketones may act as intermediates in the synthesis of waxes, surfactants, or other hydrophobic materials.

Overall, 8-Pentadecanone is a mid-chain long-chain ketone with significance in natural wax chemistry and analytical research. Its combination of a central carbonyl group and an extended hydrocarbon chain exemplifies the typical properties of mid-chain aliphatic ketones, influencing melting point, solubility, and chemical reactivity in both natural and synthetic contexts.

References

2023. The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata). Zenodo.
DOI: 10.5281/zenodo.5794106

2021. Multitudinous Potential of Trichoderma Species in Imparting Resistance Against F. oxysporum f. sp. cucumerinum and Meloidogyne incognita Disease Complex. Journal of Plant Growth Regulation.
DOI: 10.1007/s00344-021-10372-9

2019. Chemical composition of fennel seed extract and determination of fenchone in commercial formulations by GC�MS method. Journal of Food Science and Technology.
DOI: 10.1007/s13197-019-03695-9