6-Amyl-α-pyrone
{{Chembox
| ImageFile = 6-Amyl-alpha-pyrone.svg
| ImageSize =
| ImageAlt =
| PIN = 6-Pentyl-2H-pyran-2-one
| OtherNames = 5-Hydroxy-2,4-decadienoic acid δ-lactone
| Section1 = {{Chembox Identifiers
| CASNo = 27593-23-3
| PubChem = 33960
| ChemSpiderID = 31302
| EC_number = 248-552-3
| UNII = 8JTW8HL4PJ
| ChEBI = 66729
| ChEMBL = 503899
| SMILES = CCCCCC1=CC=CC(=O)O1
| StdInChIKey = MAUFTTLGOUBZNA-UHFFFAOYSA-N
| StdInChI=1S/C10H14O2/c1-2-3-4-6-9-7-5-8-10(11)12-9/h5,7-8H,2-4,6H2,1H3
}}
| Section2 = {{Chembox Properties
| C=10|H=14|O=2
| Appearance =
| Density = 1.004 g/cm3
| MeltingPt =
| BoilingPtC = 287.6
| Solubility =
}}
| Section7 = {{Chembox Hazards
| MainHazards =
| NFPA-F =
| NFPA-H =
| NFPA-R =
| NFPA-S =
| ExternalSDS = [https://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=IN&language=en&productNumber=W369608&brand=ALDRICH&PageToGoToURL=https%3A%2F%2Fwww.sigmaaldrich.com%2Fcatalog%2Fproduct%2Faldrich%2Fw369608%3Flang%3Den MSDS]
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335}}
| PPhrases = {{P-phrases|261|305+351+338}}
| FlashPtC = 113
| FlashPt_notes = closed cup
| AutoignitionPt =
| ExploLimits =
| LD50 =
| PEL =
}}
}}
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.{{cite web|url=http://webbook.nist.gov/cgi/cbook.cgi?ID=27593-23-3#|title=2H-Pyran-2-one, 6-pentyl-|website=webbook.nist.gov}} It is a colorless liquid which possesses characteristic coconut aroma, produced biologically by Trichoderma species.{{cite journal|last1=Kalyani|first1=A|last2=Prapulla|first2=SG|last3=Karanth|first3=NG|title=Study on the production of 6-pentyl-alpha-pyrone using two methods of fermentation.|journal=Appl Microbiol Biotechnol|date=May 2000|volume=53|issue=5|pages=610–2|pmid=10855724|doi=10.1007/s002530051665|s2cid=32910}}{{cite journal|last1=Prapulla|first1=S. G.|last2=Karanth|first2=N. G.|last3=Engel|first3=K. H.|last4=Tressl|first4=R.|title=Production of 6-pentyl-α-pyrone byTrichoderma viride|journal=Flavour and Fragrance Journal|date=August 1992|volume=7|issue=4|pages=231–234|doi=10.1002/ffj.2730070412}} It is found in animal foods, peach (Prunus persica), and heated beef.{{cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/6-Pentyl-2H-pyran-2-one#section=Top|title=6-Pentyl-2H-pyran-2-one|last=Pubchem|website=pubchem.ncbi.nlm.nih.gov}}
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.{{Cite journal | doi = 10.1039/C6GC02528E | title = Development of 6-amyl-α-pyrone as a potential biomass-derived platform molecule | journal = Green Chemistry | volume = 18 | issue = 24 | pages = 6431–6435 | year = 2016 | last1 = Alam | first1 = Md. Imteyaz | last2 = Gupta | first2 = Shelaka | last3 = Bohre | first3 = Ashish | last4 = Ahmad | first4 = Ejaz | last5 = Khan | first5 = Tuhin S. | last6 = Saha | first6 = Basudeb | last7 = Haider | first7 = M. Ali | doi-access = free }} 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.{{Cite journal | doi = 10.1021/acssuschemeng.8b05014 | title = Alternate Biobased Route to Produce δ-Decalactone: Elucidating the Role of Solvent and Hydrogen Evolution in Catalytic Transfer Hydrogenation | journal = ACS Sustainable Chemistry & Engineering | volume = 7 | issue = 3 | pages = 2894–2898 | year = 2019 | last1 = Alam | first1 = Md. Imteyaz | last2 = Khan | first2 = Tuhin S. | last3 = Haider | first3 = M. Ali | s2cid = 104343740 }} 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.{{Cite journal|last1=Alam|first1=Md. Imteyaz|last2=Kumar|first2=Pramod|last3=Bohre|first3=Ashish|last4=Ali Haider|first4=M.|date=2022-01-01|title=Renewable synthesis of branched diols as polymer precursors from biomass-derived lactones and 2-pyrones|journal=Materials Science for Energy Technologies|language=en|volume=5|pages=1–5|doi=10.1016/j.mset.2021.10.002|s2cid=243467639 |issn=2589-2991|doi-access=free|bibcode=2022MSET....5....1A }}
References
{{reflist}}
External links
- [https://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=IN&language=en&productNumber=W369608&brand=ALDRICH&PageToGoToURL=https%3A%2F%2Fwww.sigmaaldrich.com%2Fcatalog%2Fproduct%2Faldrich%2Fw369608%3Flang%3Den Safety Data Sheet]
{{DEFAULTSORT:Amyl-α-pyrone, 6-}}