6-Amyl-α-pyrone
Names
Preferred IUPAC name
6-Pentyl-2H-pyran-2-one
Other names
5-Hydroxy-2,4-decadienoic acid δ-lactone
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.044.124
EC Number
  • 248-552-3
UNII
  • InChI=1S/C10H14O2/c1-2-3-4-6-9-7-5-8-10(11)12-9/h5,7-8H,2-4,6H2,1H3
    Key: MAUFTTLGOUBZNA-UHFFFAOYSA-N
  • CCCCCC1=CC=CC(=O)O1
Properties
C10H14O2
Molar mass 166.220 g·mol−1
Density 1.004 g/cm3
Boiling point 287.6 °C (549.7 °F; 560.8 K)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P305+P351+P338
Flash point 113 °C (235 °F; 386 K) closed cup
Safety data sheet (SDS) MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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]

References

  1. ↑ "2H-Pyran-2-one, 6-pentyl-". webbook.nist.gov.
  2. ↑ Kalyani, A; Prapulla, SG; Karanth, NG (May 2000). "Study on the production of 6-pentyl-alpha-pyrone using two methods of fermentation". Appl Microbiol Biotechnol. 53 (5): 610–2. doi:10.1007/s002530051665. PMID 10855724. S2CID 32910.
  3. ↑ Prapulla, S. G.; Karanth, N. G.; Engel, K. H.; Tressl, R. (August 1992). "Production of 6-pentyl-α-pyrone byTrichoderma viride". Flavour and Fragrance Journal. 7 (4): 231–234. doi:10.1002/ffj.2730070412.
  4. ↑ Pubchem. "6-Pentyl-2H-pyran-2-one". pubchem.ncbi.nlm.nih.gov.
  5. ↑ Alam, Md. Imteyaz; Gupta, Shelaka; Bohre, Ashish; Ahmad, Ejaz; Khan, Tuhin S.; Saha, Basudeb; Haider, M. Ali (2016). "Development of 6-amyl-α-pyrone as a potential biomass-derived platform molecule". Green Chemistry. 18 (24): 6431–6435. doi:10.1039/C6GC02528E.
  6. ↑ 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. S2CID 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. 5: 1–5. doi:10.1016/j.mset.2021.10.002. ISSN 2589-2991. S2CID 243467639.
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