6-Amyl-α-pyrone

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
CAS Number	27593-23-3;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:66729;
ChEMBL	ChEMBL503899;
ChemSpider	31302;
ECHA InfoCard	100.044.124
EC Number	248-552-3;
PubChem CID	33960;
UNII	8JTW8HL4PJ;
CompTox Dashboard (EPA)	DTXSID0047589 ;
	InChI 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;
	SMILES CCCCCC1=CC=CC(=O)O1;
Properties
Chemical formula	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:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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

^ "2H-Pyran-2-one, 6-pentyl-". webbook.nist.gov.
^ 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.
^ 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.
^ Pubchem. "6-Pentyl-2H-pyran-2-one". pubchem.ncbi.nlm.nih.gov.
^ 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.
^ 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.
^ 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.

External links

Safety Data Sheet

[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.

[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.

[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.

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