Squalane

Structural formula
General
Surname	Squalane
other names	2,6,10,15,19,23-hexamethyltetracosane ( IUPAC ) Cosbiol Vitabiosol Roban
Molecular formula	C 30 H 62
Brief description	colorless, oily liquid
External identifiers / databases
CAS number 111-01-3 EC number 203-825-6 ECHA InfoCard 100.003.478 PubChem 8089 Wikidata Q380055
properties
Molar mass	422.82 g mol −1
Physical state	liquid
density	0.81 g cm −3  (25)
Melting point	−38 ° C
boiling point	176 ° C / 0.05 mmHg
Vapor pressure	15 ± 5.4 · 10 7 Pa
solubility	almost insoluble in water slightly soluble in acetone and ethanol soluble in diethyl ether and benzene
Refractive index	1.4530 (15 ° C)
safety instructions
GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Squalane , a colorless oil, is an acyclic triterpene - hydrocarbon and together with the squalene base compound of most triterpenes. In general, it follows the properties of the alkanes . Squalane is made up of two farnesane tail-tail units (see terpenes for explanation). Botrycoccan is an isomer of squalane.

Occurrence

Squalane occurs (alongside squalene) in fish liver oil and many vegetable oils (e.g. wheat germ oil, rice germ oil, avocado oil, olive oil, ...).

Extraction

Among other things, squalane is obtained from sharks to a not inconsiderable extent in the USA. Today, however, it is also possible to obtain the compound by hydrogenating squalene or isolating it from vegetable oils. In order to clarify the origin, it is called phytosqualane in this case.

properties

Squalane is a clear, colorless and odorless, oily liquid. Its flash point is 217 ° C.

use

As phytosqualane, squalane is used in cosmetic products as a lipid component that softens and smoothes the skin. It is used as a conditioner in hair care products . In gas chromatography , squalane is used as a particularly apolar stationary phase.

It is also used as a lubricant and transformer oil .

Web links

• Entry on squalane . In: P. J. Linstrom, W. G. Mallard (Eds.): NIST Chemistry WebBook, NIST Standard Reference Database Number 69 . National Institute of Standards and Technology , Gaithersburg MD

Individual evidence

1. ↑ ^{a b c d} Hans G. Hirschberg: Handbook of process engineering and plant construction. Springer-Verlag, 2013, ISBN 978-3-642-58357-5 , p. 489 ( limited preview in Google book search).
2. ↑ ^{a b c d e} Squalane data sheet at Sigma-Aldrich , accessed on May 15, 2017 ( PDF ).
3. ↑ A. Zafar, J. Chickos, "The vapor pressure and vaporization enthalpy of squalene and squalane by correlation gas chromatography" J. Chem. Thermodynamics 135 (2019) 192-197.
4. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-282.
5. ↑ ^{a b c d} Brigitte Bridegroom; Lexicon of Cosmetic Raw Materials; ISBN 978-3-8391-3136-7 .
6. ↑ Vazhiyil Venugopal: Marine Products for Healthcare: Functional and Bioactive Nutraceutical Compounds from the Ocean . CRC Press, 2008, ISBN 978-1-4200-5263-3 , p. 177 ( limited preview in Google book search).
7. ↑ EC Smith Collective: Animal Ingredients A to Z . AK Press, 2004, ISBN 978-1-902593-81-4 , p. 47 ( limited preview in Google book search).
8. ↑ Squalene . In: Wissenschaft-Online Lexikon der Biologie.