Carotol

Carotol
Names
Preferred IUPAC name
(3R,3aS,8aR)-6,8a-Dimethyl-3-(propan-2-yl)-2,3,4,5,8,8a-hexahydroazulen-3a(1H)-ol
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1/C15H26O/c1-11(2)13-7-9-14(4)8-5-12(3)6-10-15(13,14)16/h5,11,13,16H,6-10H2,1-4H3/t13-,14+,15+/m1/s1
    Key: XZYQCFABZDVOPN-ILXRZTDVBA
  • O[C@@]12CC\C(=C/C[C@]2(CC[C@@H]1C(C)C)C)C
Properties
C15H26O
Molar mass 222.366 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Carotol was first isolated by scientists Asahina and Tsukamoto in 1925.[1] It is one of the primary components found in carrot seed oil comprising approximately 40% of this essential oil.[2] This sesquiterpene alcohol is thought to be formed in carrot seeds (Daucus carota L., Umbelliferae) during the vegetation period. Additionally, studies have shown that carotol may be involved in allelopathic interactions expressing activity as an antifungal, herbicidal and insecticidal agent.[3]

  1. ^ Cross A.D. (1960). "The Chemistry of Naturally Occurring 1,2 Epoxides". Quarterly Reviews, Chemical Society. 14 (4): 317–335. doi:10.1039/qr9601400317.
  2. ^ Sridhar, S; Rajagopal, RV; Rajavel, R; Masilamani, S; Narasimhan, S (2003). "Antifungal Activity of Some Essential Oils". J. Agric. Food Chem. 51 (26): 7596–7599. doi:10.1021/jf0344082. PMID 14664513.
  3. ^ Wieczorek, P (2006). "Structure of natural antibiotic CP-47,444". Chemik. 59 (11): 25–26, 55–59.