2-hydroxynonanoic acid

C4 = 3-hydroxybutyric acid, C5 = 3-hydroxyvaleric acid, C6 = 3-hydroxyhexanoic acid, C7 = 3-hydroxyheptanoic acid, C8 = 3-hydroxyoctanoic acid, C9 = 3-hydroxynonanoic acid CIO = 3-hydroxydecanoic acid. 

Lactones that are not energetically favored may be synthesized by driving the equilibrium toward the products. For example, the ten-membered 9-hydroxynonanoic acid lactone is formed in a dilute benzene solution containing a trace of p-tolucncsul Ionic acid. The reaction is driven to completion by distilling the benzene/water azeotrope to remove water and shift the equilibrium to the right. 

Propose a mechanism for the formation of 9-hydroxynonanoic acid lactone, as shown in the preceding figure. 

SYNS ALDEHYDE C-18 >N-AMYLBUTYROLACTONE FEMA No. 2781 4-HYDROXYNONANOIC ACID, y-LACTONE y-NONALACTONE (FCC) 1,4-NONALOLIDE PRUNOUDE... 

Mupirodn, USP, Mupirocin (pseudomonic acid A.Bac-troban) is the major component of a family of. stnictuiullv related antibiotics, pseudomonic acids A to D, produced In the submerged fermentation of Pseudomonas fluoresceia. Although the antimicrobial properties of P.fUiorescemvttK recorded as early as 1887, it was not until 1971 that Fuller et al. identified the metabolites responsible for this activity. The. structure of the major and most potent metaboliK. pseudomonic acid A (which represents 90 to 95% of the active fraction from P. fhtore. cem). was later confirmed b) chemical sy nthesis to be the 9-hydroxynonanoic acid ester of monic acid. 

M.B. Andrus and T.-L. Shi achieved the total synthesis of the 10-membered lactone (-)-tuckolide (decarestrictine D), which potentially inhibits cholesterol biosynthesis. The lactonization was only successful under the Corey-Nicoiaou conditions. Interestingly, the unsubstituted 9-hydroxynonanoic acid did not lactonize under these conditions. 

G.5) 2(3//)-Furanone, dihydro-5-pentyl-, nonano-4-lactone, tetrahydro-5-pentylfuran-2-one, 1,4-nonanolide, -y-nonalactone, 4-hydroxynonanoic acid lactone, amylbutyrolactone 104-61-0] FEMA 2781, 182373-92-0] ( )- [57084-16-9] (/ )- [63357-96-0] (5)- [63357-97-1]... 

Mupirocin calcium cream 2% contains the dihydrate crystalline calcium hemisalt of the antibiotic mupirocin. Chemically, it is ((alpha) E,2 5,3 R,4 R,5 5)-5-[(2 5,3 5,4 5,5 5) -2,3 -epoxy-5-hydroxy-4-methylhexyl]tetra-hydro-3, 4-dihydroxy-(beta)-methyl-2//-pyran-2-crotonic acid, ester with 9-hydroxynonanoic acid, calcium salt (2 1),... 

E)-(2S,3R,4R,5S)-5-([(2S,3S,4S,5S)-2,3-Epoxy-5-hydroxy-4-methylhexyl]tetrahydro-3,4-dihydroxy-p-methyl-2H-pyran-2-crotonic acid ester with 9-hydroxynonanoic acid. 

Dihydro-6-pentyi-2(3//l-1uranone 4-Hydroxynonanoic acid iactone C9H16O2 104-61-0 166.222 oil 134" ... 

With respect to polymer synthesis and to the development of biologically active compounds in recent years, the ozonolysis/reductive cleavage of OA or MO or the fragmentation of the intermediary carbonyl oxide to 9-oxononanoic acid and its respective methyl ester gained attention again [33-39]. 9-Oxononanoic acid can be easily converted to 9-amino- or 9-hydroxynonanoic acid as sources for polyamides and polyesters [40]. A French patent claimed the synthesis of oxo-nonanoic acid via homometathesis of OA, followed by reductive ozonolysis of the unsaturated C18 diacid obtained [41]. 

Hydroxynonanoic acid lactone 4-Hydroxynonanoic acid, y-lactone. See y-Nonalactone... 

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