Gamma-undecalactone, also known as γ-undecalactone, is a lactone with a fruity, peach-like odor. It is a cyclic ester formed from the condensation of undecanoic acid. This compound is commonly used in the fragrance industry due to its pleasant aroma, which resembles ripe peaches and apricots. It is used in perfumes, personal care products, and flavorings.

Chemical Composition and Structure

The chemical composition of gamma-undecalactone includes:

Undecanoic Acid: A fatty acid with a molecular formula of C11H22O2.
Lactone Ring: A cyclic ester formed from the reaction of undecanoic acid.

The structure of gamma-undecalactone is characterized by:

Lactone Ring: A 10-membered ring structure with a five-membered oxygen-containing ring, where the ester bond forms a closed loop.
Molecular Formula: C11H20O2. The structure includes a lactone ring with an oxygen atom and a long hydrocarbon chain.
Structure: CH3(CH2)8COO-CH2-CH3. This structure includes a lactone ring with an alkyl chain that imparts its characteristic fruity aroma.

Physical Properties

Gamma-undecalactone is typically a colorless or pale yellow liquid. Its physical properties include:

Boiling Point: Approximately 240°C (464°F).
Melting Point: Around 12°C (54°F).
Solubility: It is soluble in organic solvents like ethanol, oils, and fats but has limited solubility in water.

Production Process

The production process for gamma-undecalactone involves:

Synthesis: The lactone is synthesized through the cyclization of undecanoic acid. This is typically achieved by heating the acid in the presence of a catalyst or under specific conditions to promote ring formation.
Purification: After synthesis, the product is purified using techniques such as distillation or extraction to remove impurities and unreacted materials.
Characterization: The purified gamma-undecalactone is characterized using analytical methods such as gas chromatography and spectroscopy to confirm its purity and structure.

Applications

Gamma-undecalactone is used in:

Fragrances: As a key component in perfumes and scented products to provide a fruity, peach-like note.
Personal Care Products: Incorporated into lotions, shampoos, and other cosmetic products for its pleasant aroma.
Flavorings: Used in food products to impart a fruity, sweet flavor.
Aromatherapy: Included in essential oil blends for its aromatic properties.

Safety

Gamma-undecalactone is generally considered safe for use in fragrances and personal care products when used in appropriate concentrations. It is important to follow recommended usage levels to avoid potential skin irritation. Proper handling and storage are essential to ensure safety.

Environmental and Safety Considerations

The production of gamma-undecalactone should follow environmentally responsible practices to minimize ecological impact. Efficient synthesis and purification processes should be employed to reduce waste. Proper labeling and handling are crucial to ensure safe use in its various applications.

INCI


Perfuming. Unlike fragrance, which can also contain slightly less pleasant or characteristic odours, the term perfume indicates only very pleasant fragrances. Used for perfumes and aromatic raw materials.

Skin conditioning agent. It is the mainstay of topical skin treatment as it has the function of restoring, increasing or improving skin tolerance to external factors, including melanocyte tolerance. The most important function of the conditioning agent is to prevent skin dehydration, but the subject is rather complex and involves emollients and humectants that can be added in the formulation.
Synonyms:

CAS: 104-67-6 EC number 203-225-4