Carotol

Title: Carotol
CAS Registry Number: 465-28-1
CAS Name: [3R-(3a,3aa,8aa)]-2,3,4,5,8,8a-Hexahydro-6,8a-dimethyl-3-(1-methylethyl)-3a(1H)-azulenol
Additional Names: 2,3,4,5,8,8a-hexahydro-3-isopropyl-6,8a-dimethyl-3a(1H)-azulenol
Molecular Formula: C15H26O
Molecular Weight: 222.37
Percent Composition: C 81.02%, H 11.79%, O 7.19%
Literature References: From oil of carrot seeds, Daucus carota L., Umbelliferae: Asahina, Tsukamoto, J. Pharm. Soc. Jpn. 525, 961 (1925), C.A. 20, 2845 (1926); Sorm et al., Collect. Czech. Chem. Commun. 16, 47 (1951); Pigulevskii, Kovaleva, Zh. Prikl. Khim. 32, 2703 (1959). Structure: Sykora et al., Collect. Czech. Chem. Commun. 26, 788 (1961); Zalkow et al., J. Org. Chem. 26, 981 (1961). Stereochemistry: Levisalles, Rudler, Bull. Soc. Chim. Fr. 1964, 2020; 1967, 2059. Synthesis of (+)-form: DeBroissia et al., ibid. 1972, 4314; eidem, Chem. Commun. 1972, 855.
Properties: Liquid. bp2.5 126°. [a]D20 +30.4°. nD20 1.4964. d20 0.9624.
Boiling point: bp2.5 126°
Optical Rotation: [a]D20 +30.4°
Index of refraction: nD20 1.4964
Density: d20 0.9624
Caroverine Caroxazone Carpaine Carpetimycins Carphenazine

Carotol
Carotol.svg
Identifiers
CAS number 465-28-1
PubChem 442347
ChemSpider 390799
Jmol-3D images Image 1
Properties
Molecular formula C15H26O
Molar mass 222.366 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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]