Title: Squalane
CAS Registry Number: 111-01-3
CAS Name: 2,6,10,15,19,23-Hexamethyltetracosane
Additional Names: perhydrosqualene; dodecahydrosqualene; spinacane
Trademarks: Cosbiol (Laserson & Sabetay); Robane (Robeco); Wax-O-Sol (Life Sci.)
Molecular Formula: C30H62
Molecular Weight: 422.81
Percent Composition: C 85.22%, H 14.78%
Line Formula: [(CH3)2CHCH2CH2CH2CH(CH3)CH2CH2CH2CH(CH3)CH2CH2-]2
Literature References: Prepn by complete hydrogenation of squalene, q.v.: Chapman, J. Chem. Soc. 123, 770 (1923); Heilbron et al., ibid. 1926, 3135. Commercial grades are obtained by direct hydrogenation of shark liver oil and may contain some batyl alcohol: Tsujimoto, Chem. Umschau Fette 34, 256 (1927), C.A. 21, 4081 (1927). Synthesis: J. W. Scott, D. Valentine, Org. Prep. Proced. Int. 12, 7 (1980); T. Mandai et al., Tetrahedron Lett. 22, 763 (1981).
Properties: Oil. Stable to air and oxygen. d415 0.8115. mp ~-38°. bp760 ~350°; bp10 263°; bp5 248°. Flash pt 425°F (218°C). nD15 1.4530. Specific heat at 20° ~0.62. Viscosity (Engler) at 20° ~6.08. Readily sol in ether, gasoline, petr ether, benzene, chloroform, oils. Slightly sol in methanol, ethanol, acetone, glacial acetic acid. Concd H2SO4 at 70° is discolored, but the squalane remains unchanged.
Melting point: mp ~-38°
Boiling point: bp760 ~350°; bp10 263°; bp5 248°
Flash point: Flash pt 425°F (218°C)
Index of refraction: nD15 1.4530
Density: d415 0.8115
Use: Lubricant, transformer oil. Ingredient of watch and chronometer oils. Perfume fixative. In pharmacy and cosmetics as skin lubricant, ingredient of suppositories, carrier of lipid-soluble drugs.
Therap-Cat-Vet: Cerumenolytic. |