Cholesteryl benzoate

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Cholesteryl benzoate
Cholesteryl benzoate.png
Names
IUPAC name
Cholest-5-en-3β-yl benzoate
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 benzoate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.150 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • 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 Yes check.svgY
    Key: UVZUFUGNHDDLRQ-LLHZKFLPSA-N Yes check.svgY
  • 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
  • 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
  • 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
Properties
C34H50O2
Molar mass 490.76 g/mol
Melting point 149 to 150 °C (300 to 302 °F; 422 to 423 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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. [2] In 1888, the German physicist Otto Lehmann concluded the cloudy fluid presents a new phase of matter, and coined the term liquid crystal. [3]

Related Research Articles

<span class="mw-page-title-main">Crystal</span> Solid material with highly ordered microscopic structure

A crystal or crystalline solid is a solid material whose constituents are arranged in a highly ordered microscopic structure, forming a crystal lattice that extends in all directions. In addition, macroscopic single crystals are usually identifiable by their geometrical shape, consisting of flat faces with specific, characteristic orientations. The scientific study of crystals and crystal formation is known as crystallography. The process of crystal formation via mechanisms of crystal growth is called crystallization or solidification.

<span class="mw-page-title-main">Filtration</span> Process that separates solids from fluids

Filtration is a physical separation process that separates solid matter and fluid from a mixture using a filter medium that has a complex structure through which only the fluid can pass. Solid particles that cannot pass through the filter medium are described as oversize and the fluid that passes through is called the filtrate. Oversize particles may form a filter cake on top of the filter and may also block the filter lattice, preventing the fluid phase from crossing the filter, known as blinding. The size of the largest particles that can successfully pass through a filter is called the effective pore size of that filter. The separation of solid and fluid is imperfect; solids will be contaminated with some fluid and filtrate will contain fine particles. Filtration occurs both in nature and in engineered systems; there are biological, geological, and industrial forms.

<span class="mw-page-title-main">Liquid crystal</span> State of matter with properties of both conventional liquids and crystals

Liquid crystal (LC) is a state of matter whose properties are between those of conventional liquids and those of solid crystals. For example, a liquid crystal may flow like a liquid, but its molecules may be oriented in a crystal-like way. There are many types of LC phases, which can be distinguished by their optical properties. The contrasting textures arise due to molecules within one area of material ("domain") being oriented in the same direction but different areas having different orientations. LC materials may not always be in a LC state of matter.

<span class="mw-page-title-main">Melting</span> Material phase change

Melting, or fusion, is a physical process that results in the phase transition of a substance from a solid to a liquid. This occurs when the internal energy of the solid increases, typically by the application of heat or pressure, which increases the substance's temperature to the melting point. At the melting point, the ordering of ions or molecules in the solid breaks down to a less ordered state, and the solid melts to become a liquid.

<span class="mw-page-title-main">Phase (matter)</span> Region of uniform physical properties

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<span class="mw-page-title-main">Crystallization</span> Process by which a solid with a highly organized atomic or molecular structure forms

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<span class="mw-page-title-main">Thermochromism</span> Property of substances to change colour due to a change in temperature

Thermochromism is the property of substances to change color due to a change in temperature. A mood ring is an excellent example of this phenomenon, but thermochromism also has more practical uses, such as baby bottles which change to a different color when cool enough to drink, or kettles which change color when water is at or near boiling point. Thermochromism is one of several types of chromism.

A coolant is a substance, typically liquid, that is used to reduce or regulate the temperature of a system. An ideal coolant has high thermal capacity, low viscosity, is low-cost, non-toxic, chemically inert and neither causes nor promotes corrosion of the cooling system. Some applications also require the coolant to be an electrical insulator.

4-Hydroxybenzoic acid, also known as p-hydroxybenzoic acid (PHBA), is a monohydroxybenzoic acid, a phenolic derivative of benzoic acid. It is a white crystalline solid that is slightly soluble in water and chloroform but more soluble in polar organic solvents such as alcohols and acetone. 4-Hydroxybenzoic acid is primarily known as the basis for the preparation of its esters, known as parabens, which are used as preservatives in cosmetics and some ophthalmic solutions. It is isomeric with 2-hydroxybenzoic acid, known as salicylic acid, a precursor to aspirin, and with 3-hydroxybenzoic acid.

<span class="mw-page-title-main">Cholesteric liquid crystal</span>

A cholesteric liquid-crystal display (ChLCD) is a display containing a 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 within layers, but a director axis which varies with layers. The variation of the director axis tends to be periodic in nature. The period of this variation is known as the pitch, p. This pitch determines the wavelength of light which is reflected.

<span class="mw-page-title-main">Georges Friedel</span> French mineralogist (1865–1933)

Georges Friedel was a French mineralogist and crystallographer.

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.

Cholesteryl oleyl carbonate (COC) is an organic chemical, a carbonate ester of cholesterol and oleyl alcohol with carbonic acid. It is a liquid crystal material forming cholesteric liquid crystals with helical structure. It is a transparent liquid, or a soft crystalline material with melting point around 20 °C. It can be used with cholesteryl nonanoate and cholesteryl benzoate in some thermochromic liquid crystals.

<span class="mw-page-title-main">Cholesteryl chloride</span> Chemical compound

Cholesteryl chloride, also called 3-chlorocholest-5-ene or 3β-chlorocholest-5-ene, is an organic chemical, an organochloride derivate cholesterol. It is a liquid crystal material forming clockwise cholesteric liquid crystals. It is a transparent liquid, or a soft crystalline material with melting point around 94-96 °C.

<span class="mw-page-title-main">Friedrich Reinitzer</span> Austrian botanist and chemist (1857–1927)

Friedrich Richard Reinitzer was an Austrian botanist and chemist. In late 1880s, experimenting with cholesteryl benzoate, he discovered properties of liquid crystals.

A blue phase mode LCD is a liquid crystal display (LCD) technology that uses highly twisted cholesteric phases in a blue phase. It was first proposed in 2007 to obtain a better display of moving images with, for example, frame rates of 100–120 Hz to improve the temporal response of LCDs. This operational mode for LCDs also does not require anisotropic alignment layers and thus theoretically simplifies the LCD manufacturing process.

<span class="mw-page-title-main">Temperature sensitive glass</span>

Temperature sensitive glass is a glass material that reacts to ambient temperatures radiated off of other surfaces, e.g. hands or water. The liquid crystals beneath the glass surface impact color upon temperature. There are three main phases of these crystals: nematic, smectic, and chiral.

References

  1. Cholesteryl benzoate at the National Library of Medicine
  2. "Introduction to Liquid Crystals". CWRU Polymers and Liquid Crystals. Case Western Reserve University. Archived from the original on 5 March 2016. Retrieved 5 February 2016.
  3. "History and Properties of Liquid Crystals". Official Web Site of the Nobel Prize. Retrieved 5 February 2016.