6-Undecanone
[CAS# 927-49-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty ketone (including enol)
• Name: 6-Undecanone
• Synonyms: Undecan-6-one; Di-n-amyl ketone
• Molecular Formula: C₁₁H₂₂O
• Molecular Weight: 170.29
• CAS Registry Number: 927-49-1
• EC Number: 213-150-9
• SMILES: CCCCCC(=O)CCCCC

Properties

• Density: 0.8±0.1 g/cm³ Calc.^*, 0.831 g/mL (Expl.)
• Melting point: 14.6 ºC (Expl.)
• Boiling point: 226.6±8.0 ºC 760 mmHg (Calc.)^*, 228 ºC (Expl.)
• Flash point: 88.3 ºC (Calc.)^*, 88 ºC (Expl.)
• Index of refraction: 1.425 (Calc.)^*, 1.427 (Expl.)

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H227-H315
• Precautionary Statements: P210-P280-P370+P378-P403+P235-P501

Discovory and Applicatios

6-Undecanone is an aliphatic ketone with the molecular formula C₁₁H₂₂O. Structurally, it consists of an 11-carbon straight chain with a carbonyl group located at the sixth carbon, giving it a symmetrical arrangement within the chain. The compound typically appears as a colorless to pale yellow liquid with a characteristic fatty or fruity odor. It is soluble in most organic solvents such as ethanol, diethyl ether, and chloroform, but has limited solubility in water.

6-Undecanone is primarily used as a fragrance and flavoring agent. Its odor and taste characteristics resemble fatty or green notes, making it suitable for use in perfumes, personal care products, and food flavorings. In addition, it serves as a starting material or intermediate in the synthesis of other fragrance compounds and fine chemicals.

The compound also finds application as a biological agent in pest control. 6-Undecanone is known for its insect-repellent properties and is incorporated into formulations to deter mosquitoes, ticks, and other insects. Its relatively low toxicity to humans and animals, combined with its efficacy, makes it a preferred natural or semi-synthetic alternative to traditional repellents.

6-Undecanone can be synthesized by oxidation of the corresponding secondary alcohol, 6-undecanol, or through selective ketonization reactions of fatty acids or their derivatives. Industrial production typically relies on well-established chemical oxidation or ester cleavage methods to achieve high purity. Handling precautions include avoiding direct contact with eyes and skin, as it may cause irritation, and using it in well-ventilated areas due to its volatile nature.

Overall, 6-undecanone is a versatile medium-chain ketone valued for its odor, flavor, and biological activity. Its combination of a mid-chain carbonyl group and hydrocarbon chain imparts both olfactory properties and chemical reactivity, making it useful in the fragrance industry, as a synthetic intermediate, and as a biologically active agent.

References

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