Massoia lactone

Massoia lactone

Names
IUPAC name (R)-5,6-Dihydro-6-pentyl-2H-pyran-2-one
Other names (R)-5-hydroxy-2-decenoic acid lactone Cocolactone 5-Pentylpent-2-en-5-olide C-10 massoia lactone
Identifiers
CAS Number	51154-96-2 Y
3D model (JSmol)	Interactive image
EC Number	259-359-9
PubChem CID	39914
UNII	847O2V0IOA Y
SMILES CCCCCC1CC=CC(=O)O1
Properties
Chemical formula	C10H16O2
Molar mass	168.24 g/mol
Density	0.982 g/cm3
Melting point	−95.2 °C (−139.4 °F; 178.0 K)
Boiling point	286–287 °C (547–549 °F; 559–560 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Massoia lactone is an alkyl lactone derived from the bark of the Massoia tree (Cryptocaria massoia)^[1] which is found in Papua, Indonesia though the compound can also be found as a component of cane sugar molasses, cured tobacco, and the essential oil of Sweet Osmanthus (Osmanthus fragrans). Chemically, massoia lactone can be obtained as a minor product in transfer hydrogenation of 6-amyl-α-pyrone.^[2]

Known in the late 18th and early 19th centuries as massoy bark, massoia essential oil was once widely used as a natural coconut flavouring. Natural massoia lactone has been largely superseded by a synthetic alternative because the extraction process is expensive and the process of removing the bark kills the tree.

Massoia lactone has an odour that is described as sweet, coconut meat, lactonic, creamy, milky and waxy^[3] and, at a dilution of 20 ppm, a taste described as creamy, coconut, green, and slightly fruity.

References

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