Cholesteryl nonanoate

Cholesteryl nonanoate, also called cholesteryl pelargonate, 3β-cholest-5-en-3-ol nonaoate or cholest-5-ene-3-β-yl nonanoate, is an ester of cholesterol and nonanoic acid. It is a liquid crystal material forming cholesteric liquid crystals with helical structure. It forms spherulite crystals.[1]

Cholesteryl nonanoate
Names
IUPAC name
Cholest-5-en-3β-yl nonanoate
Systematic IUPAC name
(1R,3aS,3bS,7S,9aR,9bS,11aR)-9a,11a-Dimethyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-7-yl nonanoate
Other names
Cholesteryl nonanoate, cholesteryl pelargonate, 3β-cholest-5-en-3-ol nonaoate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.013.326
EC Number
  • 214-658-3
UNII
  • InChI=1S/C36H62O2/c1-7-8-9-10-11-12-16-34(37)38-29-21-23-35(5)28(25-29)17-18-30-32-20-19-31(27(4)15-13-14-26(2)3)36(32,6)24-22-33(30)35/h17,26-27,29-33H,7-16,18-25H2,1-6H3/t27-,29+,30+,31-,32+,33+,35+,36-/m1/s1 checkY
    Key: WCLNGBQPTVENHV-MKQVXYPISA-N checkY
  • InChI=1/C36H62O2/c1-7-8-9-10-11-12-16-34(37)38-29-21-23-35(5)28(25-29)17-18-30-32-20-19-31(27(4)15-13-14-26(2)3)36(32,6)24-22-33(30)35/h17,26-27,29-33H,7-16,18-25H2,1-6H3/t27-,29+,30+,31-,32+,33+,35+,36-/m1/s1
    Key: WCLNGBQPTVENHV-MKQVXYPIBA
  • O=C(O[C@@H]4C/C3=C/C[C@@H]1[C@H](CC[C@]2([C@H]1CC[C@@H]2[C@H](C)CCCC(C)C)C)[C@@]3(C)CC4)CCCCCCCC
Properties
C36H62O2
Appearance White crystals
Melting point 77 to 82 °C (171 to 180 °F; 350 to 355 K)
Insoluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Uses

It is used in some hair colors,[2] make-ups, and some other cosmetic preparations; e.g. the ISP ColorFlow line is based on mixtures with e.g. cholesteryl chloride, cholesteryl oleyl carbonate and BHT. The mixture provides an opalescent, iridescent appearance.[3]

It is also used in some pleochroic dyes and together with e.g. cholesteryl oleyl carbonate and cholesteryl benzoate in some thermochromic applications.[4]

It can be also used as a component of the liquid crystals used for liquid crystal displays.

References
  1. Molecular Expressions: Science, Optics and You - Intel Play QX3 Computer Microscope - Movie Gallery: Cholesteryl Nonanoate
  2. Cholesteryl nonanoate in the Consumer Product Information Database
  3. ISP Colorflow
  4. Cholesteryl Ester Liquid Crystals
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