Masoja

Cryptocarya massoy (Oken) Kosterm. is a tree of the Lauraceae family, endemic to the island of New Guinea. Its bark was traded across the Indonesian archipelago. The tree is classed as Near Threatened.

The major components of the bark oil are the C-10 and C-12 massoia lactones. In one analysis the bark oil held 64.8 area % of C-10 massoia lactone, 17.4 % of C-12 massoia lactone and 13.4 % of benzyl benzoate. The heartwood and bark oils are the main natural sources of the C-10 and C-12 massoia lactones. The fruit oil is composed predominantly of benzyl benzoate. The C-10 massoia lactone is 5,6-dihydro-6-pentyl-2H-pyran-2-one. The massoia lactones are compounds with 10, 12 and 14 carbon chains, and in nature they are rare essential oil components. The C-14 massoia lactone and δ-decalactone occur as minor constituents in the heartwood oil.

Massoia lactone is an alkyl lactone derived from the bark of the massoia tree. It can also be found as a component of cane sugar molasses, cured tobacco and the essential oil of sweet osmanthus (Osmanthus fragrans). An ene-reductase can reduce massoia lactone to δ-decalactone, and the highest conversion, above 99%, was reached with the enzyme OYE3.

Composition of the oils

They gave pale yellow oils in yields of 0.7, 1.2 and 1.0 %. The C-10 massoia lactone is the major compound, present in similar amounts in bark oil and heartwood oil (68.4 % in the heartwood) and only as a trace in the fruit oil (1.4 %). The heartwood oil holds more C-12 massoia lactone (27.7 %) than the bark oil or the fruit oil (0.2 %). It also holds 1.4 % of C-14 massoia lactone and 2.5 % of δ-decalactone. The C-14 lactone is the main constituent of the leaf oil of Cryptocarya cunninghamii.

Benzyl benzoate is the main compound of the fruit oil (68.3 %). It is present to a lesser extent in the bark oil and absent from the heartwood oil.

The massoia lactones

The genus Cryptocarya comprises more than 350 species distributed through the tropics, subtropics and temperate regions of the world. The massoia lactones share an α,β-unsaturated δ-lactone ring, with a chain of five, seven or nine carbons at the C6 position. The same ring is a common feature of other natural products such as goniothalamin, callystatin A, canolide A and the kava lactones.

Massoia lactone, C₁₀H₁₆O₂, has a molar mass of about 168.24 g/mol, a density of 0.982 g/cm³, a melting point of −95.2 °C and a boiling point of 286–287 °C. Chemically, it can be obtained as a minor product of the transfer hydrogenation of 6-amyl-α-pyrone. The saturated δ-decalactone has the formula C₁₀H₁₈O₂ and a molecular weight of 170.25.

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