Massoia lactone: Difference between revisions

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 {{chembox
+| Watchedfields = changed
-| verifiedrevid = 405927831
+| verifiedrevid = 428850586
 | ImageFile = Massoialactone.png
-| ImageSize = 200px
+| ImageSize =
 | IUPACName = (''R'')-5,6-Dihydro-6-pentyl-2''H''-pyran-2-one
 | OtherNames = (''R'')-5-hydroxy-2-decenoic acid lactone<br/>Cocolactone<br/>5-Pentylpent-2-en-5-olide<br />C-10 massoia lactone
-| Section1 = {{Chembox Identifiers
+|Section1={{Chembox Identifiers
+| CASNo_Ref = {{cascite|correct|??}}
-|   CASNo = 51154-96-2
-|   PubChem = 39914
+| CASNo = 51154-96-2
+| UNII_Ref = {{fdacite|correct|FDA}}
-|   EINECS = 259-359-9
+| UNII = 847O2V0IOA
-|   SMILES = CCCCCC1CC=CC(=O)O1
+| PubChem = 39914
+| EINECS = 259-359-9
+| SMILES = CCCCCC1CC=CC(=O)O1
   }}
-| Section2 = {{Chembox Properties
+|Section2={{Chembox Properties
-|   Formula = C<sub>10</sub>H<sub>16</sub>O<sub>2</sub>
+| Formula = C<sub>10</sub>H<sub>16</sub>O<sub>2</sub>
-|   MolarMass = 168.24 g/mol
+| MolarMass = 168.24 g/mol
-|   Appearance =
+| Appearance =
-|   Density = 0.982 g/cm<sup>3</sup>
+| Density = 0.982 g/cm<sup>3</sup>
-|   MeltingPtC = -95.2
+| MeltingPtC = -95.2
-|   BoilingPt = 170-174 °C
+| BoilingPtC = 286-287
-|   Solubility =
+| BoilingPt_notes =
+| Solubility =
-  }}
-| Section3 = {{Chembox Hazards
-|   MainHazards =
-|   FlashPt =
-|   Autoignition =
   }}
+|Section3={{Chembox Hazards
+| MainHazards =
+| FlashPt =
+| AutoignitionPt =
+ }}
 }}
-'''Massoia lactone''' is an [[alkyl]] [[lactone]] derived from the bark of the [[Cryptocarya|Massoia tree]] (''Cryptocaria massoia'')<ref>[http://works.bepress.com/cgi/viewcontent.cgi?article=1016&context=david_leach "Molecules 2007, 12, 149-154"]</ref> which is found throughout Malaysia 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]]'').
+'''Massoia lactone''' is an [[alkyl]] [[lactone]] derived from the bark of the [[Cryptocarya|Massoia tree]] (''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 [[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.<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>
-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 tree is killed during the process of removing the bark.
+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<ref>[http://www.thegoodscentscompany.com/data/rw1031001.html "Good Scents Company product page for Massoia Lactone"]</ref> and, at a dilution of 20 ppm, a taste described as creamy, coconut, green and slightly fruity.
+Massoia lactone has an odour that is described as sweet, coconut meat, [[lactonic]], creamy, milky and waxy<ref>[http://www.thegoodscentscompany.com/data/rw1031001.html "Good Scents Company product page for Massoia Lactone"]</ref> and, at a dilution of 20 ppm, a taste described as creamy, coconut, green, and slightly fruity.
 == References ==
+{{reflist|30em}}
-<references/>
 [[Category:Lactones]]