Massoia lactone

The dianion derived from but-2-ynoic acid reacts with aldehydes to give 5-hydroxyalk-2-ynoates (539). Partial reduction over a Lindlar catalyst and acid-catalyzed cyclization of the resulting enoate gives the dihydropyran-2-one (78LA337). The route is exemplified by the synthesis of the naturally occurring massoia lactone (Scheme 200). In previous work (46JCS954) the hydroxyalkynoic acids themselves, obtained from epoxides and acetylene, were used. 

Massoia lactone Coconut Massoia tree (Cryptocaria massoia)... 

Decalactone Ricinolic acid, cor-rolic acid, Massoia lactone or 11-hydroxy hexadecanoic acid Candida species, Clador-sporium sua-volens, baker s yeast Peach, buttery... 

Geranyl propionate Glycyrrhizin Linalyl propionate Massoia lactone... 

Massoia bark essential oil, raw material to make Massoia lactone, which suffered from considerable quality variations. Sourcing a reliable supplier required numerous analyses and laboratory distillations of different barks. 

In 1940, Meijer (4) isolated Massoia lactone, 5.6-Dihydro-6-pentyl (2H)pyran-2-one (Dec-2-en-5-olide), C10HI6O2, from true massoia oil. In 1954, Abe and Sato (5) confirmed the structure. In 1968, Cavill al. (6) isolated a... 

The massoia tree occurs in a few varieties, distinguished by those with thin bark and those with thick bark. Working with selected producers who provided oils of the right composition, i.e. a high percentage of massoia lactone along with the right enantiomeric ratio, yielded different types of barks that were subjected to lab scale extraction and analysis in the laboratory. 

From the data in Table I, we confirm that the Lawang bark essential oil is really different from massoia bark oil, containing mostly a mixture of eugenol mid methyleugenol and no massoia lactone. Ibese first analyses made after distillation of actual barks, also confirmed that the real massoia essential oils are very different from one collection town to another. Oil obtained fi om bark purchased fi om a broker in Europe is different again. The variations occur in both the massoia lactone content and in its stereochemistry. No quality consistency was found with these purchased barks or their essential oils. 

The oil prepared from bark obtained from Jaya-Pura origin during this second sourcing attempt is very different from that obtained previously. Its chirality is also different, rich in S(+) massoia lactone. Investigation of this oil continues. 

Bemreuther A., Lander V., Huffer M., Schreir P., Enantioselective Analysis of Dec-2-en-5-olide (Massoia Lactone) From Natural Sources by Multidimensional Capillary Gas Chromatography, Flavour and Fragrance Journal 1990,5, 71-73. 

Synthesis of goniothalamin, massoia lactone, and parasorbic acid... 

Benoni H, Hardebeck K 1964 Zur Isolierung und pharmakologischen Untersuchung von natiirlichem linksdrehenden Massoia-Lacton. Arzneim Forsch 14 40-42... 

Next to these fatty acids, hydroxy fatty acids can be used as substrates for 8-lactone synthesis via biotransformation in bacterial cells. Clostridium tyrobutyricum uses 5-hydroxy-2-decenoic acid or 5-hydroxy-2-dodecenoic acid to produce 8-decalactone (5.95 gL ) or 8-dodecalactone (13 gL ) (Pichersky 1998). Bacillus subtilis and Pseudomonas sp. transform massoia lactone to 8-decalactone (Gocho et al. 1998). Therefore, in case of y-DL, 8-decalactone, and 8-dodecalactone, the hurdle to achieve product concentrations far above 100 mg can be overcome by screening and choice of appropriate... 

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