16400-72-9

Basic information

• Product Name: massoialactone
• Synonyms: 2H-Pyran-2-one, 6-heptyl-5,6-dihydro-; 5-Heptyl-2-pentene-5-olide; 5-Hydroxy-2-dodecenoic acid lactone; 6-Heptyl-5,6-dihydro-2-pyrone; 6-Heptyl-5,6-dihydro-2H-pyran-2-one; 6-Heptyl-5,6-dihydropyran-2-one; delta-2-Dodecenolactone; 5-Hydroxy-2-dodecenoic acid delta-lactone
• CAS NO: 16400-72-9
• Molecular Formula: C₁₂H₂₀O₂
• Molecular Weight: 196.286
• EINECS: 240-453-3
• Mol File: 16400-72-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 318.1°C at 760 mmHg
• Flash Point: 130.8°C
• Density: 0.946g/cm³
• Vapor Pressure: 0.000368mmHg at 25°C
• Refractive Index: 1.46
• CAS DataBase Reference: massoialactone(CAS DataBase Reference)
• NIST Chemistry Reference: massoialactone(16400-72-9)
• EPA Substance Registry System: massoialactone(16400-72-9)

Safety Data

• Hazardous Substances Data: 16400-72-9(Hazardous Substances Data)

Usage

General Description

Massoialactone is a naturally occurring lactone compound found in various food and beverage products, including apricots, peaches, and strawberries. It contributes to the sweet, fruity aroma of these fruits and is commonly used as a flavoring agent in the food industry. Massoialactone has been isolated and identified in research studies on the flavor compounds of different fruits and is known for its pleasant, creamy, and coconut-like scent. Its aroma is often described as sweet, tropical, and reminiscent of coconut, and it is used in the production of flavorings and fragrances. Additionally, massoialactone may have potential pharmacological and therapeutic properties, as research has shown its inhibitory effects on the growth of certain cancer cells. Overall, massoialactone is a versatile and intriguing compound with various applications in the food, fragrance, and potential pharmaceutical industries.

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Relevant articles and documents

2H-pyran-2-ones from trichoderma viride and trichoderma asperellum

Volatiles emitted by the soil fungi Trichoderma viride 272 and Trichoderma asperellum 328 were collected by using the closed loop stripping analysis (CLSA) headspace technique, and the obtained extracts were analysed by GC/MS. Several alkyl- and alkenyl-2H-pyran-2-ones, including known compounds 6-pentyl-2H-pyran-2-one and (E)-6-(pent-1-en-1-yl)-2H-pyran-2-one, and the new derivatives (E)-6-(pent-2-en-1-yl)-2H-pyran-2-one, 6-propyl-2H-pyran-2-one, and 6-heptyl-2H-pyran-2-one were found. The alkenyl derivative (E)-6-(hept-1-en-1- yl)-2H-pyran-2-one, previously tentatively identified from a marine Botrytis by MS analysis, was also detected. All alkenyl pyrones were synthesised by using a reported Stille coupling followed by lactonisation, whereas the alkylated pyrones were obtained through a reported synthetic approach by radical bromination of 5-alkylpent-2-en-5-olides and dehydrobromination. Because the yields in both cases were not satisfactory and fell a long way short of the yields reported for similar compounds, all compounds were synthesised again using a gold-catalysed coupling of terminal alkynes with propiolic acid recently developed by Schreiber and co-workers, giving high yields in all cases. A comparison of the synthetic methods is given. Copyright

A NEW SYNTHESIS OF α,β-UNSATURATED γ- AND δ-LACTONS VIA INTRAMOLECULAR ACYLATION OF α-SULFINYL CARBANION

A new synthesis of α,β-unsaturated γ- and δ-lactones involving the intramolecular acylation of α-sulfinyl carbanion followed by pyrolisis is described.