10284. δ-Dodecalactone

Nomenclature

CAS number: 713-95-1
6-Heptyltetrahydro-2H-pyran-2-one; 5-dodecanolide.
C12H22O2; mol wt 198.30.
C 72.68%, H 11.18%, O 16.14%.

Description and references

Naturally occuring aroma constituent of dairy products, pork fat, rum, and fruits including peaches, berries, plums, and mangoes. Prepn: K.-W. Rosenmund, H. Bach, Ber. 94, 2401 (1961) DOI; B. M. Dashunin et al., Zh. Prikl. Khim. 42, 1909 (1969). Synthesis of enantiomers: A. Mosandl, M. Gessner, Z. Lebensm.-Unters. Forsch. 187, 40 (1988) DOI; H. Nemoto et al., Synlett 2007, 2343 DOI. Fragrance monograph: D. L. J. Opdyke, Food Cosmet. Toxicol. 17, Suppl. 1, 773 (1979) DOI.

Chemical structure

Properties

Colorless to yellow liquid; powerful fruity, peach-like and oily odor. On dilution the odor is butter-like. bp12 177°. bp1.5 124-125°. d420 0.9555. nD20 1.4620. Flash pt (closed cup): 113°C (235°F). Very sol in alcohol, propylene glycol, vegetable oil. Insol in water. LD50 orally in rats: >5 g/kg; dermally in rabbits: >5 g/kg (Opdyke).

Derivative

R-Form.

Nomenclature

CAS number: 29587-89-1

Properties

Fruity-sweet, apricot odor with fatty-green aspects. Fruity-sweet apricot taste. [α]D20 +46° (c = 1.0-1.3 in CH3OH). [α]D20 +32.3° (c = 2.65 in CHCl3). [α]D20 +48.9° (c = 2.00 in THF).

Derivative

S-Form.

Nomenclature

CAS number: 108943-47-1

Properties

Similar in odor and taste to the R(+)-form, but more intense, with a distinct aldehyde and sweat odor, and fruity, creamy taste. [α]D20 46° (c = 1.0-1.3 in CH3OH). [α]D20 33.2° (c = 1.43 in CHCl3). [α]D20 48.7° (c = 2.00 in THF).

Use

Ingredient in commercial butter and cream flavors.