Decan-4-olide

• CAT Number: I025730
• CAS Number: 706-14-9
• Molecular Formula: C10H18O2
• Molecular Weight: 170.25
• Purity: 98%
• Synonyms: Decan-4-olide; 2-Decalactone; Decanolide-1,4; gamma-n-Decalactone; gamma-Decalactone; Decanolide-1,4.
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: 2(3H)-Furanone, 5-hexyldihydro-
• InChI: InChI=1S/C10H18O2/c1-2-3-4-5-6-9-7-8-10(11)12-9/h9H,2-8H2,1H3
• InChIKey: IFYYFLINQYPWGJ-UHFFFAOYSA-N
• SMILES: O=C1OC(CCCCCC)CC1

Decan-4-olide(CAT: I025730), also known as γ-Decalactone, is a lactone compound commonly found in various fruits and dairy products. It is responsible for the characteristic fruity aroma and flavor in these foods. Decan-4-olide has a pleasant peach-like odor and is used as a flavoring agent in the food and beverage industry. It can also be found in perfumes and other fragrances.

Reference

1: Xiao Z, Ma L, Zhao JY, Zhong H, Sun Y. 5-Hydroxy-γ-decalactone production by Bacillus sp. 1s-1 and its complete genome sequence. J Biotechnol. 2018 Nov 20;286:68-70. doi: 10.1016/j.jbiotec.2018.07.033. Epub 2018 Jul 24. PubMed PMID: 30053499.
2: Morales ML, Callejón RM, Ordóñez JL, Troncoso AM, García-Parrilla MC. Comparative assessment of software for non-targeted data analysis in the study of volatile fingerprint changes during storage of a strawberry beverage. J Chromatogr A. 2017 Nov 3;1522:70-77. doi: 10.1016/j.chroma.2017.09.056. Epub 2017 Sep 25. PubMed PMID: 28969903.
3: Pfluger P, Regner GG, Coelho VR, da Silva LL, Nascimento L, Viau CM, Zanette RA, Hoffmann C, Picada JN, Saffi J, Pereira P. Gamma-Decanolactone Improves Biochemical Parameters Associated with Pilocarpine-Induced Seizures in Male Mice. Curr Mol Pharmacol. 2018;11(2):162-169. doi: 10.2174/1874467210666171002114954. PubMed PMID: 28969582.
4: Marsol-Vall A, Balcells M, Eras J, Canela-Garayoa R. Development of a SBSE-TD method coupled to GC-MS and chemometrics for the differentiation of variety and processing conditions in peach juices. Food Chem. 2018 Jan 15;239:119-125. doi: 10.1016/j.foodchem.2017.06.070. Epub 2017 Jun 10. PubMed PMID: 28873539.
5: Zhang L, Li H, Gao L, Qi Y, Fu W, Li X, Zhou X, Gao Q, Gao Z, Jia H. Acyl-CoA oxidase 1 is involved in γ-decalactone release from peach (Prunus persica) fruit. Plant Cell Rep. 2017 Jun;36(6):829-842. doi: 10.1007/s00299-017-2113-4. Epub 2017 Feb 25. PubMed PMID: 28238071.
6: Soares GPA, Souza KST, Vilela LF, Schwan RF, Dias DR. γ-decalactone production by Yarrowia lipolytica and Lindnera saturnus in crude glycerol. Prep Biochem Biotechnol. 2017 Jul 3;47(6):633-637. doi: 10.1080/10826068.2017.1286601. Epub 2017 Feb 2. PubMed PMID: 28151056.
7: Braga A, Belo I. Biotechnological production of γ-decalactone, a peach like aroma, by Yarrowia lipolytica. World J Microbiol Biotechnol. 2016 Oct;32(10):169. doi: 10.1007/s11274-016-2116-2. Epub 2016 Aug 26. Review. PubMed PMID: 27565779.
8: Pflüger P, Viau CM, Coelho VR, Berwig NA, Staub RB, Pereira P, Saffi J. Gamma-decanolactone inhibits iNOS and TNF-alpha production by lipopolysaccharide-activated microglia in N9 cells. Eur J Pharmacol. 2016 Jun 5;780:38-45. doi: 10.1016/j.ejphar.2016.03.029. Epub 2016 Mar 21. PubMed PMID: 27012990.
9: Zhao Y, Xu Y, Jiang C. Efficient biosynthesis of γ-decalactone in ionic liquids by immobilized whole cells of Yarrowia lipolytica G3-3.21 on attapulgite. Bioprocess Biosyst Eng. 2015 Oct;38(10):2045-52. doi: 10.1007/s00449-015-1431-6. Epub 2015 Jun 20. PubMed PMID: 26091898.
10: Sánchez-Sevilla JF, Cruz-Rus E, Valpuesta V, Botella MA, Amaya I. Deciphering gamma-decalactone biosynthesis in strawberry fruit using a combination of genetic mapping, RNA-Seq and eQTL analyses. BMC Genomics. 2014 Apr 17;15:218. doi: 10.1186/1471-2164-15-218. PubMed PMID: 24742100; PubMed Central PMCID: PMC4023230.
11: Chambers AH, Pillet J, Plotto A, Bai J, Whitaker VM, Folta KM. Identification of a strawberry flavor gene candidate using an integrated genetic-genomic-analytical chemistry approach. BMC Genomics. 2014 Apr 17;15:217. doi: 10.1186/1471-2164-15-217. PubMed PMID: 24742080; PubMed Central PMCID: PMC4023330.
12: Kopjar M, Hribar J, Simcic M, Zlatić E, Pozrl T, Pilizota V. Effect of trehalose addition on volatiles responsible for strawberry aroma. Nat Prod Commun. 2013 Dec;8(12):1767-70. PubMed PMID: 24555295.
13: Chambers AH, Evans SA, Folta KM. Methyl anthranilate and γ-decalactone inhibit strawberry pathogen growth and achene Germination. J Agric Food Chem. 2013 Dec 26;61(51):12625-33. doi: 10.1021/jf404255a. Epub 2013 Dec 12. PubMed PMID: 24328200.
14: Braga A, Belo I. Immobilization of Yarrowia lipolytica for aroma production from castor oil. Appl Biochem Biotechnol. 2013 Apr;169(7):2202-11. doi: 10.1007/s12010-013-0131-4. Epub 2013 Feb 19. PubMed PMID: 23420487.
15: Gomes N, Teixeira JA, Belo I. Fed-batch versus batch cultures of Yarrowia lipolytica for γ-decalactone production from methyl ricinoleate. Biotechnol Lett. 2012 Apr;34(4):649-54. doi: 10.1007/s10529-011-0824-0. Epub 2011 Dec 11. PubMed PMID: 22160330.
16: Guo Y, Song H, Wang Z, Ding Y. Expression of POX2 gene and disruption of POX3 genes in the industrial Yarrowia lipolytica on the γ-decalactone production. Microbiol Res. 2012 Apr 20;167(4):246-52. doi: 10.1016/j.micres.2011.10.003. Epub 2011 Nov 23. PubMed PMID: 22115771.
17: Gomes N, Waché Y, Teixeira JA, Belo I. Oil-in-water emulsions characterization by laser granulometry and impact on γ-decalactone production in Yarrowia lipolytica. Biotechnol Lett. 2011 Aug;33(8):1601-6. doi: 10.1007/s10529-011-0593-9. Epub 2011 Mar 24. PubMed PMID: 21431848.
18: Alchihab M, Aldric JM, Aguedo M, Destain J, Wathelet JP, Thonart P. The use of Macronet resins to recover gamma-decalactone produced by Rhodotorula aurantiaca from the culture broth. J Ind Microbiol Biotechnol. 2010 Feb;37(2):167-72. doi: 10.1007/s10295-009-0659-z. Epub 2009 Nov 10. PubMed PMID: 19902280.
19: Alchihab M, Destain J, Aguedo M, Wathelet JP, Thonart P. The utilization of gum tragacanth to improve the growth of Rhodotorula aurantiaca and the production of gamma-decalactone in large scale. Appl Biochem Biotechnol. 2010 Sep;162(1):233-41. doi: 10.1007/s12010-009-8739-0. Epub 2009 Aug 13. PubMed PMID: 19680818.
20: Alchihab M, Destain J, Aguedo M, Majad L, Ghalfi H, Wathelet JP, Thonart P. Production of gamma-decalactone by a psychrophilic and a mesophilic strain of the yeast Rhodotorula aurantiaca. Appl Biochem Biotechnol. 2009 Jul;158(1):41-50. doi: 10.1007/s12010-008-8297-x. Epub 2008 Jul 19. PubMed PMID: 18642100.