6-Amyl-α-pyrone explained

6-Amyl-α-pyrone, also 6-pentyl-2-pyrone or 6PP, is an unsaturated lactone molecule. It contains two double bonds in the ring and a pentyl substituent at carbon adjacent to the ring oxygen.[1] It is a colorless liquid which possesses characteristic coconut aroma, produced biologically by Trichoderma species.[2] [3] It is found in animal foods, peach (Prunus persica), and heated beef.[4]

Reactivity

Chemically, 6PP is converted into a linear ketone via ring opening and decarboxylation in presence of water, which subsequently undergoes solid base catalyzed aldol condensation reaction into C14/C15 hydrocarbon precursor.[5] Upon heating in presence of Pd/C catalyst with formic acid, the double bonds of the 6PP get reduced to yield the flavoring compound δ-decalactone.[6] In presence of strong reducing agent like lithium aluminium hydride, the double bonds of the ring get saturated and transformed into 1,5-decanediol via sequential hydrogenation steps.[7]

External links

Notes and References

  1. Web site: 2H-Pyran-2-one, 6-pentyl-. webbook.nist.gov.
  2. Kalyani. A. Prapulla. SG. Karanth. NG. Study on the production of 6-pentyl-alpha-pyrone using two methods of fermentation.. Appl Microbiol Biotechnol. May 2000. 53. 5. 610–2. 10855724. 10.1007/s002530051665. 32910.
  3. Prapulla. S. G.. Karanth. N. G.. Engel. K. H.. Tressl. R.. Production of 6-pentyl-α-pyrone byTrichoderma viride. Flavour and Fragrance Journal. August 1992. 7. 4. 231–234. 10.1002/ffj.2730070412.
  4. Web site: 6-Pentyl-2H-pyran-2-one. Pubchem. pubchem.ncbi.nlm.nih.gov.
  5. 10.1039/C6GC02528E . Development of 6-amyl-α-pyrone as a potential biomass-derived platform molecule . Green Chemistry . 18 . 24 . 6431–6435 . 2016 . Alam . Md. Imteyaz . Gupta . Shelaka . Bohre . Ashish . Ahmad . Ejaz . Khan . Tuhin S. . Saha . Basudeb . Haider . M. Ali . free .
  6. 10.1021/acssuschemeng.8b05014 . 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 . 2019 . Alam . Md. Imteyaz . Khan . Tuhin S. . Haider . M. Ali . 104343740 .
  7. Alam. Md. Imteyaz. Kumar. Pramod. Bohre. Ashish. Ali Haider. M.. 2022-01-01. Renewable synthesis of branched diols as polymer precursors from biomass-derived lactones and 2-pyrones. Materials Science for Energy Technologies. en. 5. 1–5. 10.1016/j.mset.2021.10.002. 243467639 . 2589-2991. free. 2022MSET....5....1A .

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