Cholesteryl benzoate

Cholesteryl benzoate: Cholesteryl benzoate

Identifiers

CAS number 604-32-0

PubChem 2723613

ChemSpider 2005815^Y

Jmol-3D images Image 1
Image 2

SMILES

C[C@H](CCCC(C)C) [C@H]4CC[C@@]3 ([H])[C@]2([H]) CC=C1C[C@@H] (OC(c5ccccc5)=O) CC[C@@](C)1[C@] ([H])2CC[C@@]34C
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)c5ccccc5

InChI

InChI=1S/C34H50O2/c1-23(2)10-9-11-24(3)29-16-17-30-28-15-14-26-22-27(36-32(35)25-12-7-6-8-13-25)18-20-33(26,4)31(28)19-21-34(29,30)5/h6-8,12-14,23-24,27-31H,9-11,15-22H2,1-5H3/t24-,27+,28+,29-,30+,31+,33+,34-/m1/s1^Y
Key: UVZUFUGNHDDLRQ-LLHZKFLPSA-N^Y
InChI=1/C34H50O2/c1-23(2)10-9-11-24(3)29-16-17-30-28-15-14-26-22-27(36-32(35)25-12-7-6-8-13-25)18-20-33(26,4)31(28)19-21-34(29,30)5/h6-8,12-14,23-24,27-31H,9-11,15-22H2,1-5H3/t24-,27+,28+,29-,30+,31+,33+,34-/m1/s1
Key: UVZUFUGNHDDLRQ-LLHZKFLPBM

Properties

Molecular formula C₃₄H₅₀O₂

Molar mass 490.76 g/mol

Melting point
149-150 °C

Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Cholesteryl benzoate, also called 5-cholesten-3-yl benzoate, is an organic chemical, an ester of cholesterol and benzoic acid. It is a liquid crystal material forming cholesteric liquid crystals with helical structure.

It can be used with cholesteryl nonanoate and cholesteryl oleyl carbonate in some thermochromic liquid crystals.

It is used in some hair colors, make-ups, and some other cosmetic preparations.^[1]

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

Cholesteryl benzoate was the first material in which liquid crystal properties were discovered. In the late 1880s Friedrich Reinitzer, an Austrian botanist, while studying the chemicals in plants, heated cholesteryl benzoate. At 145 °C the material melted, yielding a cloudy fluid, which changed to the originally expected clear liquid at 178.5 °C. In 1888, the German physicist Otto Lehmann concluded the cloudy fluid presents a new phase of matter, and coined the term liquid crystal.

References

^ Record in the Household Products Database of NLM

Categories:
Steroids
Liquid crystals
Benzoates

Cholesteryl benzoate

Identifiers
CAS number	604-32-0
PubChem	2723613
ChemSpider	2005815^Y
Jmol-3D images	Image 1 Image 2
SMILES C[C@H](CCCC(C)C) [C@H]4CC[C@@]3 ([H])[C@]2([H]) CC=C1C[C@@H] (OC(c5ccccc5)=O) CC[C@@](C)1[C@] ([H])2CC[C@@]34C 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)c5ccccc5
InChI InChI=1S/C34H50O2/c1-23(2)10-9-11-24(3)29-16-17-30-28-15-14-26-22-27(36-32(35)25-12-7-6-8-13-25)18-20-33(26,4)31(28)19-21-34(29,30)5/h6-8,12-14,23-24,27-31H,9-11,15-22H2,1-5H3/t24-,27+,28+,29-,30+,31+,33+,34-/m1/s1^Y Key: UVZUFUGNHDDLRQ-LLHZKFLPSA-N^Y InChI=1/C34H50O2/c1-23(2)10-9-11-24(3)29-16-17-30-28-15-14-26-22-27(36-32(35)25-12-7-6-8-13-25)18-20-33(26,4)31(28)19-21-34(29,30)5/h6-8,12-14,23-24,27-31H,9-11,15-22H2,1-5H3/t24-,27+,28+,29-,30+,31+,33+,34-/m1/s1 Key: UVZUFUGNHDDLRQ-LLHZKFLPBM
Properties
Molecular formula	C₃₄H₅₀O₂
Molar mass	490.76 g/mol
Melting point	149-150 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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Cholesteryl nonanoate — IUPAC name [10,13 dimethyl 17 (6 methylheptan 2 yl) 2,3,4,7,8,9,11,12,14,15,16,17 dodecahydro 1H cyclopenta[ … Wikipedia
Cholesteryl chloride — Cholesteryl chloride[1] IUPAC name … Wikipedia
Cholesteryl oleyl carbonate — Identifiers CAS number 17110 51 9 … Wikipedia
Liquid crystal — Schlieren texture of liquid crystal nematic phase Liquid crystals (LCs) are a state of matter that have properties between those of a conventional liquid and those of a solid crystal.[1] For instance, an LC may flow like a liquid, but its… … Wikipedia
Cholesteric liquid crystal — A cholesteric liquid crystal is a type of liquid crystal with a helical structure and which is therefore chiral. Cholesteric liquid crystals are also known as chiral nematic liquid crystals. They organize in layers with no positional ordering… … Wikipedia
Friedrich Reinitzer — Friedrich Richard Reinitzer (February 25, 1857 in Prague February 16, 1927 in Graz) was an Austrian botanist and chemist. In late 1880s, experimenting with cholesteryl benzoate, he discovered properties of liquid crystals (named so later by Otto… … Wikipedia
Blue Phase Mode LCD — History= In Reinitzer s reports from 1888 on the melting behaviour of cholesteryl benzoate there is a note that the substance briefly turned blue as it changed from clear to cloudy upon cooling. This subtle effect however remained unexplored for… … Wikipedia
Friedrich Richard Reinitzer — Friedrich Reinitzer Friedrich Reinitzer. Friedrich Richard Reinitzer (25 février 1857, Prague 16 février 1927, Graz) est un botaniste et chimiste autrichi … Wikipédia en Français
Reinitzer — Friedrich Reinitzer Friedrich Reinitzer. Friedrich Richard Reinitzer (25 février 1857, Prague 16 février 1927, Graz) est un botaniste et chimiste autrichi … Wikipédia en Français

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Cholesteryl benzoate

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Cholesteryl benzoate

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