Massoia oil

Massoia oil (bark of Cryptocaria massoia (Lauraceae)). The oil possesses a coconut-peach flavour. 

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... 

Table I. Compositional Analysis of Massoia Oils, First Sampling...

Production of Natural Flavor and Fragrance Ingredients in 2003 Massoia, Orris, and Vetiver Oils... 

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. 

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. 

Initial Work to Differentiate Massoia Bark Oils by Origin... 

Massoia essential oils prepared from barks of various origins were analyzed after laboratory extraction. Table I summarizes the compositional analysis... 

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. 

Continuing the sourcing search finally a yielded a consistent supplier of authentic massoia bark oil. This supplier provided two qualities of barks, again... 

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. 

An intensive massoia sourcing and R D program overcame raw material inconsistency problems encountered previously. The improved knowledge of this item combined with the identification of a reliable source has permitted an increase in the sales of massoia bark oil. 

Gamero J., Joulain D., Massoia Essential Oil, 9th International Congress of Essential Oils, Singapore (1983). 

It is interesting that the 8-decalactone is formed by an entirely different biotrans-fonnation. This lactone is formed by the miCTobial reduction of an a,P-unsaturated lactone found in Massoia bark oil. Massoia bark oil contains about 80% 2-decen-5-ohde, 1% 2-dodecen-5-olide and 6% benzyl benzoate. Several microorganisms... 

Massoilactone (45) is the major component of the bark oil of Cryptocarya massoia (Lauraceae) (1, 74). The absolute configuration of (-)-massoilactone is (R) at C-5, which is enantiomeric to parasorbic acid (29, 78). An analogous lactone (46) was also isolated from the same plant (22). Massoi bark has been used for many centuries as a constituent of native medicines. The sedative action expected from the structural similarity between massoilactone and active Kawa-type lactones is dubious (9). (-)-Massoilactone has been isolated from cane molasses as one of, and the most characteristic, sugary-flavor substances (48). This compound was also obtained from two species of formicine ants of the genus Cam-ponotus (22). This powerful skin-irritating compound might be responsible for the defensive factor secreted by the ants. 

Cavill G W K, Clark D V, Whitefield F B 1968 Insect venoms, attractants, and repellents. XL Massoilactone from two species of formicine ants, and some observations on constituents of the bark oil of Cryptocarya massoia. Aust J Chem 21 1819-1823... 

This oil is distilled from the bark of Massoia aromatica, a tree found in New Guinea, in which it occurs to the extent of 6 to 8 per cent Woy, who investigated the oil, states that it contains a considerable quantity of eugenol, with some safrol, a body resembling creosote, and traces of free acetic acid. It is however, doubtful, whether the so-called massoi bark of commerce ever consists of one kind of bark only. It is possible that the principal compound of the commercial bark is that of a species of cinnamon. He also claimed that it contains a terpene not identical with any already known hydrocarbon. Wallach has, however, shown that this body is a mixture of the terpenes pinene and limonene, with perhaps, some dipentene. The oil is a clear yellow liquid of dove-like odour of specific gravity 1 040 to 1 065, and refractive index about 1 5400. 

Massoialactone is a cyclic natural alkyl lactone with a sweet, coconut meat odor and taste that was first isolated in 1937 from the bark oil of the Massoia tree Crypto-carya massoia) It also was found and isolated from... 

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