m →Derivatives: Journal cites:, added 1 PMC
|
→Derivatives: Import from Pyrone
|
||
Line 48: | Line 48: | ||
6-Amyl-α-pyrone (6PP) is a derivative of 2-pyrone, found in animal foods and heated beef.<ref>{{PubChem|33960}}</ref> Due to its good organoleptic properties with coconut aroma, it is used as flavor enhancer in the food industry. Biologically, it is produced by ''[[Trichoderma]]'' species via solid state fermentation.<ref>{{Cite journal | doi = 10.1590/S1517-83822008000400022| pmid = 24031295| title = Production of 6-pentyl-α-pyrone by trichoderma harzianum in solid-state fermentation| journal = Brazilian Journal of Microbiology| volume = 39| issue = 4| pages = 712| year = 2008| last1 = Ramos| first1 = Aline de Souza| last2 = Fiaux| first2 = Sorele Batista| last3 = Leite| first3 = Selma Gomes Ferreira| pmc=3768464}}</ref> |
6-Amyl-α-pyrone (6PP) is a derivative of 2-pyrone, found in animal foods and heated beef.<ref>{{PubChem|33960}}</ref> Due to its good organoleptic properties with coconut aroma, it is used as flavor enhancer in the food industry. Biologically, it is produced by ''[[Trichoderma]]'' species via solid state fermentation.<ref>{{Cite journal | doi = 10.1590/S1517-83822008000400022| pmid = 24031295| title = Production of 6-pentyl-α-pyrone by trichoderma harzianum in solid-state fermentation| journal = Brazilian Journal of Microbiology| volume = 39| issue = 4| pages = 712| year = 2008| last1 = Ramos| first1 = Aline de Souza| last2 = Fiaux| first2 = Sorele Batista| last3 = Leite| first3 = Selma Gomes Ferreira| pmc=3768464}}</ref> |
||
In July 2013, derivatives of 2-pyrone were identified as a new class of signalling molecule in bacterial communication, similar to [[quorum sensing]]. Cells with LuxR-type receptors, but lacking its homolog LuxI (and thus unable to produce [[N-Acyl Homoserine Lactone|''N''-acylhomoserine lactone]] QS signaling molecules) are known as LuxR "solos", to which pyrones bind as ligands facilitating cell-cell communication.<ref>{{cite journal |
|||
|last = Brachmann |first = Alexander |author2=Brameyer, S. |author3=Kresovic, D. |author4=Hitkova, I. |author5=Kopp, Y. |author6=Manske, C. |author7=Schubert, K. |author8=Bode, H. B. |author9=Heermann, R. |title = Pyrones as bacterial signaling molecules |journal=[[Nature Chemical Biology]] |volume = 9 |issue = 9 |pages = 573–578 | publisher=[[Nature Publishing Group]] |date=14 July 2013 |doi=10.1038/nchembio.1295 |pmid = 23851573 }}</ref> |
|||
==See also== |
==See also== |
Names | |
---|---|
IUPAC name
Pyran-2-one | |
Other names
α-Pyrone | |
Identifiers | |
| |
3D model (JSmol) |
|
ChEBI | |
ChemSpider |
|
ECHA InfoCard | 100.007.264 |
PubChem CID |
|
CompTox Dashboard (EPA) |
|
| |
| |
Properties | |
C5H4O2 | |
Molar mass | 96.085 g·mol−1 |
Density | 1.197 g/mL |
Boiling point | 102 to 103 °C (216 to 217 °F; 375 to 376 K) at 20 mmHg |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
2-Pyrone (α-pyroneorpyran-2-one) is an unsaturated cyclic chemical compound with the molecular formula C5H4O2. It is isomeric with 4-pyrone.
2-Pyrone is used in organic synthesis as a building block for more complex chemical structures because it may participate in a variety of cycloaddition reactions to form bicyclic lactones. For example, it readily undergoes Diels-Alder reactions with alkynes producing, upon loss of carbon dioxide, substituted benzenes.[2] The Gogte Synthesis (1938) is a method for the alkylation of certain pyrones with acid chlorides.[citation needed]
The most common natural products containing a 2-pyrone are the bufanolides and kavalactones. Oxovitisin A, a pyranoanthocyanin found in wine, also contains a 2-pyrone element.
6-Amyl-α-pyrone (6PP) is a derivative of 2-pyrone, found in animal foods and heated beef.[3] Due to its good organoleptic properties with coconut aroma, it is used as flavor enhancer in the food industry. Biologically, it is produced by Trichoderma species via solid state fermentation.[4]
In July 2013, derivatives of 2-pyrone were identified as a new class of signalling molecule in bacterial communication, similar to quorum sensing. Cells with LuxR-type receptors, but lacking its homolog LuxI (and thus unable to produce N-acylhomoserine lactone QS signaling molecules) are known as LuxR "solos", to which pyrones bind as ligands facilitating cell-cell communication.[5]