9-Heptadecanone
[CAS# 540-08-9]

Identification

• Classification: Organic raw materials >> Ketone compound
• Name: 9-Heptadecanone
• Synonyms: heptadecan-9-one
• Molecular Formula: C₁₇H₃₄O
• Molecular Weight: 254.45
• CAS Registry Number: 540-08-9
• EC Number: 208-734-5
• SMILES: CCCCCCCCC(=O)CCCCCCCC

Properties

• Density: 0.8±0.1 g/cm³ Calc.^*
• Melting point: 51 - 53 ºC (Expl.)
• Boiling point: 322.7±10.0 ºC 760 mmHg (Calc.)^*, 250 - 253 ºC (Expl.)
• Flash point: 83.6±14.6 ºC (Calc.)^*
• Index of refraction: 1.441 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

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

Discovory and Applicatios

9-Heptadecanone is a long-chain aliphatic ketone with the molecular formula C₁₇H₃₄O. The compound consists of a linear 17-carbon hydrocarbon chain with a carbonyl group located at the ninth carbon, placing the ketone roughly at the midpoint of the chain. This central position of the carbonyl group influences the physical properties of the molecule, giving it characteristics typical of mid-chain ketones: it is solid or waxy at room temperature, hydrophobic, and soluble in organic solvents but poorly soluble in water.

Compounds like 9-Heptadecanone are commonly found as components of plant waxes and insect cuticular lipids. In plants, mid-chain ketones are part of the epicuticular wax layer that protects leaves and fruits by reducing water loss, reflecting ultraviolet light, and providing a barrier against pathogens. In insects, similar long-chain ketones can contribute to desiccation resistance and occasionally participate in chemical signaling, although the specific biological role of 9-Heptadecanone is less well characterized than for some shorter or more abundant ketones.

From a synthetic standpoint, 9-Heptadecanone can be prepared by oxidation of the corresponding secondary alcohol or through carbon–carbon bond-forming reactions followed by introduction of the ketone group. Its structural simplicity and well-defined properties make it useful as a reference standard in analytical chemistry, particularly for gas chromatography and mass spectrometry, where it is used to identify and quantify mid-chain aliphatic ketones in natural wax and lipid extracts.

Research applications of 9-Heptadecanone focus on understanding the physical and chemical behavior of long-chain ketones, studying their roles in natural waxes and surface lipids, and exploring their potential as intermediates in bio-based chemicals. Its long hydrocarbon chain and central carbonyl group make it a suitable model compound for investigating melting points, solubility, hydrophobicity, and reactivity of mid-chain ketones.

Overall, 9-Heptadecanone is a long-chain mid-ketone with significance in natural wax chemistry and analytical research. Its combination of a central carbonyl group and an extended hydrocarbon chain exemplifies the properties of mid-chain aliphatic ketones, influencing thermal behavior, 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

2011. Nonpolar compounds and free fatty acids from marine fungi Aspergillus ustus. Chemistry of Natural Compounds, 47(5).
DOI: 10.1007/s10600-011-0066-3

1988. Lipid constituents of Tridax procumbens. Phytochemistry, 27(1).
DOI: 10.1016/0031-9422(88)83120-0