4- Hydroxydecanoic Acid Lactone

Decalactone FEMA No. 2360 4-Hydroxydecanoic Acid Lactone 170.25/C10Hi8O2/ CH3(CH2)5CHCH2CH2C=0 1 o colorless to pale yel liq/ fruity, peach s—prop glycol veg oils ins—water/ 281° 1 mL in 1 mL 95% ale... 

Synonyms y-N-Decalactone Decanolide-1,4 y-N-Hexyl-y-butyrolactone 5-Hexyldihydro-2(3H)-furanone 4-Hydroxydecanoic acid lactone... 

Hydroxydecanoic acid lactone 4-Hydroxydecanoic acid, y-lactone Hydroxydecanoic acid-y-lactone. Seey-Decalactone... 

Hydroxy-1,4-cineole, H-80139 6-Hydroxydecanoic acid Lactone, in H-80147 4-Isopropenyl-1 -methyl-1,2-cyclohexanediol,... 

Guajen 4145 l-Hexyl-l,3-butadiene 2740 5-Hydroxydecanoic acid lactone 9879... 

Tetrahydro-6-pentyl-2W- Pvran-2-one 5-Hydroxydecanoic acid lactone 705-86-2 170.249 liq -27 121 ... 

The nature of the product strongly depends on the length of the hydroxy acid generally when the hydroxyl group is remote the yield of lactone drops significantly. For example, 10-hydroxydecanoic acid [1679-53-4] does not produce any decanoUde instead, the reaction proceeds by intermolecular oligomerization, and a complex mixture of di-, tri-, tetra-, and pentalactones results (90). However, when Pseudomonas sp. or Candida iylindracea]i 2Lses are incubated with 16-hydroxyhexadecanoic acid [506-13-8] hexadecanoUde is the predorninant product (91). 

Decanolide (y-decalactone) Ricinoleic acid Yarrowia lipolytica llgL, 55 h, several tons per year Final acidification and temperature increase effect cyclisation of all 4-hydroxydecanoic acid to the corresponding lactone [222, 224, 228]... 

Macrolides. Nine- and ten-membered lactones cannot be obtained from treatment with Cs2C03 in DMF because of preferred inlcrmolecular cyclization (9, 100).2 However, the mesylate of 9-hydroxydecanoic acid is cyclized by Cs2C03 in DMF to phoracantholid 1 (1) in 45% yield together with I lie diolide (25% yield). Similar treatment of the mesylate of 10-hydroxydecanoic acid results in the lactone and the diolide in the ratio 7 3. Cyclization proceeds in very low yield when an a,/5-double bond is introduced.3... 

Candida strains convert ricinoleic acid into If-decalactone, which displays the fatty, fruity aroma typical of peaches. Ricinoleic acid (12-hydroxy octadec-9-enoic acid) is the major fatty acid in castor oil (approx. 80 %). The yeast can lipolyze castor oil glycerides and the liberated ricinoleic acid is subsequently metabolized via d-oxidation and eventually converted to 4-hydroxy-decanoic acid (Figure 5). Recently a European patent has been filed (20) essentially covering the same procedure. Shake culture fermentations were carried out on 100 ml scale for one week. The 4-hydroxydecanoic acid formed was converted to )f-decalactone by boiling the crude, acidified (pH 1.5) fermentation broth for a period of 10 minutes. The lactone was isolated via solvent extraction and a yield of some 5 g/1 was obtained. The same lactone was detected as the major volatile component formed when the yeast, Sporobolomyces odorus was grown in standard culture medium (21). Although the culture medium displayed an intense fruity, typical peach-like odor, the concentration of y-decalactone amounted to no more than 0.5 mg/1. 

Natural y-decalactone is produced biotechnologically starting from ricinoleic acid, which is degraded by P-oxidation to 4-hydroxydecanoic acid, which lactonizes at lower pH to yield y-decalactone [197a], [197b],... 

One of the earliest and most commercially successful examples of producing flavoring materials by fermentation is the production of 4-decalactone from castor oil (Figure 9.11, [83]). Castor oil is unique in that it is made up of nearly 80% ricinoleic acid (12-hydroxy-9-octadecenoic acid). Yarrowia lipolytica initially hydrolyses the ricinoleic acid from the triglyceride and then through P-oxidation, converts this acid to 4-hydroxydecanoic acid. This acid forms a lactone at low pHs to yield the y-decalactone. The yield on this process is generally considered to be ca. 6 g/L which is very attractive. 

In addition, the ethyl esters of 5-hydroxyoctanoic acid and 5-hydroxydecanoic acid should contribute to the aroma. A part of the esters hydrolyzes during cooking and the hydroxy acids released cyclize to the corresponding lactones. 

Lipase CA also polymerized hydrophobic oxyacids efficiently [88]. The DP value was beyond 100 in the polymerization of l6-hydroxyhexadecanoic acid, 12-hydroxydodecanoic acid, or 10-hydroxydecanoic acid under vacuum at high temperature (90 °C) for 24 h, whereas a polyester with a lower molecular weight was formed from 6-hydroxyhexanoic acid under similar reaction conditions. This difference may be due to the lipase-substrate interaction. Similar behaviors were reported in the lipase-catalyzed ring-opening polymerization of lactones in different ring sizes [24,25]. 

Hydroxydecanoic acid y-lactone 5-Hexyldihydro-2(3/y)-furanone CigHigOg 706-14-9 170.249 llq 301(8) ... 

A linear polymer of 10-hydroxydecanoic acid was synthesized with PEG-lipase in benzene [87] and a lactone with a 17-membered ring was also synthesized from 16-hydroxyhex-adecanoic acid ethyl ester [88]. These are inter- and intramolecular esterifications of each substrate, respectively. Among them, bioactive lactones, which are chiral and widely utilized in the fields of foods, perfumes, and pharmaceuticals, are synthesized by the enzymic method rather than by organic reaction. 

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