10283. δ-Decalactone

Nomenclature

CAS number: 705-86-2
Tetrahydro-6-pentyl-2H-pyran-2-one; 5-decanolide.
C10H18O2; mol wt 170.25.
C 70.55%, H 10.66%, O 18.80%.

Description and references

Naturally occuring aroma constituent of dairy products, coconuts, rum, and fruits including raspberries, peaches, and strawberries. Prepn of R-(+)-form by hydrogenation of Massoi lactone (R-()-2-decen-5-olide): Th. M. Meijer, Recl. Trav. Chim. Pays-Bas 59, 191 (1940); P. H. van der Schaft et al., Appl. Microbiol. Biotechnol. 36, 712 (1992) DOI; of S-()-form by hydrogenation of lactones from jasmine oil: M. Winter et al., Helv. Chim. Acta 45, 1250 (1962) DOI. Synthesis of racemic mixture: K.-W. Rosenmund, H. Bach, Ber. 94, 2401, 2406 (1961) DOI DOI. Synthesis and sensory characteristics of enantiomers: A. Mosandl, M. Gessner, Z. Lebensm.-Unters. Forsch. 187, 40 (1988) DOI. Partition behavior and odor characteristics: C. Guyot et al., J. Agric. Food Chem. 44, 2341 (1996) DOI. Fragrance monograph: D. L. J. Opdyke, Food Cosmet. Toxicol. 14, Suppl. 1, 739 (1976) DOI.

Chemical structure

Properties

Colorless liquid; creamy-coconut and peach-like flavor and odor. bp11 157°. Very sol in alcohol, propylene glycol. Insol in water. Log P (oil/water): 3.4. LD50 orally in rats: >5 g/kg; dermally in rabbits: >5 g/kg (Opdyke).

Derivative

R-Form.

Nomenclature

CAS number: 2825-91-4

Properties

Fruity-sweet, milky odor. Creamy, fruity peach, apricot taste. bp0.02 117-120°. d27.5 0.9540. nD26 1.4537. [α]D +39.68° (neat). [α]D20 +60° (c = 1.0-1.3 in CH3OH).

Derivative

S-Form.

Nomenclature

CAS number: 59285-67-5

Properties

Odor and taste similar to the R(+)-form, but more intense. Odor is fruity-sweet, creamy peach, with a fatty, buttery tonality. bp9 142-144°. d425 0.9690. nD25 1.4544. [α]D20 49.7° (neat). [α]D20 61° (c = 1.0-1.3 in CH3OH).

Use

Ingredient in perfumes, and commercial cream and butter flavorings.