Cubebol

Cubebol is a natural sesquiterpene alcohol first identified in cubeb oil. It is also found in basil. It was patented as a cooling agent in 2001 by Firmenich, an international flavor company. The taste of cubebol is cooling and refreshing.[1] The patent describes application of cubebol as a refreshing agent in various products, ranging from chewing gum to sorbets, drinks, toothpaste, and gelatin-based confectioneries.[2]

Cubebol
Names
Preferred IUPAC name
(3S,3aR,3bR,4S,7R,7aR)-3,7-Dimethyl-4-(propan-2-yl)octahydro-1H-cyclopenta[1,3]cyclopropa[1,2-a]benzen-3-ol
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C15H26O/c1-9(2)11-6-5-10(3)15-8-7-14(4,16)13(15)12(11)15/h9-13,16H,5-8H2,1-4H3/t10-,11+,12-,13+,14+,15-/m1/s1 Y
    Key: KONGRWVLXLWGDV-BYGOPZEFSA-N Y
  • InChI=1/C15H26O/c1-9(2)11-6-5-10(3)15-8-7-14(4,16)13(15)12(11)15/h9-13,16H,5-8H2,1-4H3/t10-,11+,12-,13+,14+,15-/m1/s1
    Key: KONGRWVLXLWGDV-BYGOPZEFBC
  • [H][C@]12[C@H]([C@H](C)C)CC[C@@H](C)[C@]31[C@@]([H])2[C@@](C)(O)CC3
  • O[C@]3(CC[C@@]12[C@@H](CC[C@H]([C@@H]1[C@H]23)C(C)C)C)C
Properties
C15H26O
Molar mass 222.37 g/mol
Melting point 61 to 62 °C (142 to 144 °F; 334 to 335 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

References
  1. Leffingwell, John C., Ph.D. (2001). "Cool without Menthol & Cooler than Menthol and Cooling Compounds as Insect Repellents". Leffingwell & Associates. Retrieved 2006-09-15.
  2. U.S. Patent 6,214,788
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