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{{chembox |
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{{chembox |
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| verifiedrevid = 405927831 |
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| verifiedrevid = 428850586 |
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| ImageFile = Massoialactone.png |
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| ImageFile = Massoialactone.png |
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| ImageSize = 200px |
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| ImageSize = |
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| IUPACName = (''R'')-5,6-Dihydro-6-pentyl-2''H''-pyran-2-one |
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| IUPACName = (''R'')-5,6-Dihydro-6-pentyl-2''H''-pyran-2-one |
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| OtherNames = (''R'')-5-hydroxy-2-decenoic acid lactone<br/>Cocolactone<br/>5-Pentylpent-2-en-5-olide<br />C-10 massoia lactone |
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| OtherNames = (''R'')-5-hydroxy-2-decenoic acid lactone<br/>Cocolactone<br/>5-Pentylpent-2-en-5-olide<br />C-10 massoia lactone |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 51154-96-2 |
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| PubChem = 39914 |
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| CASNo = 51154-96-2 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| EINECS = 259-359-9 |
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| UNII = 847O2V0IOA |
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| SMILES = CCCCCC1CC=CC(=O)O1 |
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| PubChem = 39914 |
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| EINECS = 259-359-9 |
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| SMILES = CCCCCC1CC=CC(=O)O1 |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>10</sub>H<sub>16</sub>O<sub>2</sub> |
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| Formula = C<sub>10</sub>H<sub>16</sub>O<sub>2</sub> |
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| MolarMass = 168.24 g/mol |
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| MolarMass = 168.24 g/mol |
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| Appearance = |
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| Appearance = |
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| Density = 0.982 g/cm<sup>3</sup> |
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| Density = 0.982 g/cm<sup>3</sup> |
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| MeltingPtC = -95.2 |
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| MeltingPtC = -95.2 |
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| BoilingPt = 170-174 °C |
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| BoilingPtC = 286-287 |
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| Section3 = {{Chembox Hazards |
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| FlashPt = |
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|Section3={{Chembox Hazards |
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| FlashPt = |
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'''Massoia lactone''' is an ] ] derived from the bark of the ] (''Cryptocaria massoia'')<ref>throughout Malaysia though the compound can also be found as a component of cane sugar ], cured ] and the essential oil of Sweet ] ('']''). |
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'''Massoia lactone''' is an ] ] derived from the bark of the ] (''Cryptocaria massoia'')<ref>T. Rali, S. W. Wossa and D. N. Leach (2007) ''Molecules'' '''12''' 149-154.</ref> which is found in Papua, Indonesia though the compound can also be found as a component of cane sugar ], cured ], and the essential oil of Sweet ] ('']''). Chemically, massoia lactone can be obtained as a minor product in transfer hydrogenation of 6-amyl-α-pyrone.<ref>Alam, Md. Imteyaz; Khan, Tuhin S.; Haider, M. Ali (2019). "Alternate Biobased Route to Produce δ-Decalactone: Elucidating the Role of Solvent and Hydrogen Evolution in Catalytic Transfer Hydrogenation". ACS Sustainable Chemistry & Engineering. 7 (3): 2894–2898. doi:10.1021/acssuschemeng.8b05014</ref> |
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Once widely used as a natural ] flavouring, natural massoia lactone has been largely superseded by a synthetic alternative because the extraction process is expensive and the tree is killed during the process of removing the bark. |
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Known in the late 18th and early 19th centuries as massoy bark, massoia essential oil was once widely used as a natural ] 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. |
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Massoia lactone has an odour that is described as sweet, coconut meat, ], creamy, milky and waxy<ref></ref> and, at a dilution of 20 ppm, a taste described as creamy, coconut, green and slightly fruity. |
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Massoia lactone has an odour that is described as sweet, coconut meat, ], creamy, milky and waxy<ref></ref> and, at a dilution of 20 ppm, a taste described as creamy, coconut, green, and slightly fruity. |
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== References == |
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== References == |
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{{reflist|30em}} |
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<references/> |
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] |