(Z)-6-Dodecen-4-olide explained

(Z)-6-Dodecen-4-olide is a volatile, unsaturated lipid and γ-lactone found in dairy products, and secreted as a pheromone by some even-toed ungulates. It has a creamy, cheesy, fatty flavour with slight floral undertones in small concentrations,^[1] ^[2] but contributes towards the strong, musky smell of a few species of antelope and deer in higher concentrations.

Function

(Z)-6-Dodecen-4-olide is believed to play a part in olfactory communication between individuals of the Columbian black-tailed deer (Odocoileus hemionus columbianus), and is secreted into urine during a rut.^[3] (Z)-6-Dodecen-4-olide is then deposited onto the tuft of hair making up the tarsal gland of the deer, as the urine runs down the gland, during a behavior called rub-urination. Similarly, it has also been identified in secretions of the interdigital and pedal glands of the bontebok (Damaliscus pygargus) and the blesbok (Damaliscus pygargus phillipsi)^[4] ^[5] where it is believed to play a role in carrying information about the dominance status, sex, health condition and possibly other characteristics of the animal it came from. The (Z)-6-dodecen-4-olide is replenished daily to maintain the pungent smell. It has also been isolated from Polianthes tuberosa,^[6] a perennial plant used in the perfume industry since the 17th century for its powerful floral scent.

Notes and References

Sarrazin. Elise. Frerot. Eric. Bagnoud. Alain. Aeberhardt. Kasia. Rubin. Mark. 2011-06-22. Discovery of New Lactones in Sweet Cream Butter Oil. Journal of Agricultural and Food Chemistry. 59. 12. 6657–6666. 10.1021/jf201380u. 21599018. 0021-8561. subscription.
Web site: Smell of cis-6-Dodecen-4-olide (Dairy Lactone). Soda Sales.
BROWNLEE. ROBERT G.. SILVERSTEIN. ROBERT M.. MÜLLER-SCHWARZE. DIETLAND. SINGER. ALAN G.. January 1969. Isolation, Identification and Function of the Chief Component of the Male Tarsal Scent in Black-tailed Deer. Nature. 221. 5177. 284–285. 10.1038/221284a0. 1969Natur.221..284B. 4272659. 0028-0836.
Burger. B. V.. Roux. Maritha le. Garbers. C. F.. Bigalke. R.C.. Pachler. K.G.R.. Wessels. P.L.. Christ. V.. Maurer. K. H.. 1977-02-01. Studies on Mammalian Pheromones, II. Further Compounds from the Pedal Gland of the Bontebok (Damaliscus dorcas dorcas). Zeitschrift für Naturforschung C. 32. 1–2. 49–56. 10.1515/znc-1977-1-207. 139777. 1865-7125. free.
Burger. B. V.. Roux. Maritha le. Garbers. C. F.. Spies. H. S. C.. Bigalke. R. G.. Pachler. K. G. R.. Wessels. P. L.. Christ. V.. Maurer. K. H.. 1976-02-01. Studies on Mammalian Pheromones, I. Ketones from the Pedal Gland of the Bontebok (Damaliscus dorcas dorcas). Zeitschrift für Naturforschung C. 31. 1–2. 21–28. 10.1515/znc-1976-1-208. 1865-7125. free.
Maurer. Bruno. Hauser. Arnold. 1982. Identification and Synthesis of New γ-Lactones from Tuberose Absolute (Polianthes tuberosa). Helvetica Chimica Acta. en. 65. 2. 462–476. 10.1002/hlca.19820650204. 1522-2675.