(Z)-6-Dodecen-4-olide
Skeletal structure of (Z)-6-dodecen-4-olide
Skeletal structure of (Z)-6-dodecen-4-olide
Space-filling model of (Z)-6-dodecen-4-olide
Space-filling model of (Z)-6-dodecen-4-olide
Names
Preferred IUPAC name
5-[(2Z)-Oct-2-en-1-yl]oxolan-2-one
Other names
Cis-6-Dodecen-4-olide

2(3H)-furanone dihydro-5-(2-octenyl)

(6Z)-4-hydroxy-6-dodecenoic acid lactone
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.038.619
EC Number
  • 242-497-9
UNII
  • InChI=1S/C12H20O2/c1-2-3-4-5-6-7-8-11-9-10-12(13)14-11/h6-7,11H,2-5,8-10H2,1H3/b7-6- checkY
    Key: QFXOXDSHNXAFEY-SREVYHEPSA-N
  • InChI=1/C18H37NO2
    Key: WWUZIQQURGPMPG-KRWOKUGFBW
  • CCCCC/C=C\CC1CCC(=O)O1
Properties
C12H20O2
Molar mass 196.286
Odor Cheesy, soapy, fatty with a fruity nuance
Density 1.0±0.1 g/cm3
Melting point estimated 17.6 °C
Boiling point estimated 311.2±11.0 °C
estimated 15.6 - 64.9 mg/L
Vapor pressure 0.0±0.7 mmHg
Hazards
Flash point 127.5±16.7 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

(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.

References

  1. ↑ 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. doi:10.1021/jf201380u. ISSN 0021-8561. PMID 21599018.
  2. ↑ "Smell of cis-6-Dodecen-4-olide (Dairy Lactone)". Soda Sales.
  3. ↑ 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. Bibcode:1969Natur.221..284B. doi:10.1038/221284a0. ISSN 0028-0836. S2CID 4272659.
  4. ↑ 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. doi:10.1515/znc-1977-1-207. ISSN 1865-7125. PMID 139777.
  5. ↑ 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. doi:10.1515/znc-1976-1-208. ISSN 1865-7125.
  6. ↑ Maurer, Bruno; Hauser, Arnold (1982). "Identification and Synthesis of New γ-Lactones from Tuberose Absolute (Polianthes tuberosa)". Helvetica Chimica Acta. 65 (2): 462–476. doi:10.1002/hlca.19820650204. ISSN 1522-2675.
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