Cholesteryl benzoate

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Cholesteryl benzoate
Cholesteryl benzoate.png
Cholesteryl benzoat.jpg
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
  • c1ccccc1C(=O)O[C@@H]2C/C3=C/C[C@@H]4[C@@H]([C@@]3(C)CC2)CC[C@@]5(C)[C@H]4CC[C@@H]5[C@H](C)CCCC(C)C
  • C(C)CCCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](OC(=O)c5ccccc5)CC[C@]4C)[C@H]3CC[C@]12C
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

In physics, a fluid is a liquid, gas, or other material that may continuously move and deform (flow) under an applied shear stress, or external force. They have zero shear modulus, or, in simpler terms, are substances which cannot resist any shear force applied to them.

<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 can flow like a liquid, but its molecules may be oriented in a common direction as in a solid. 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. An LC material may not always be in an 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

In the physical sciences, a phase is a region of material that is chemically uniform, physically distinct, and (often) mechanically separable. In a system consisting of ice and water in a glass jar, the ice cubes are one phase, the water is a second phase, and the humid air is a third phase over the ice and water. The glass of the jar is another separate phase.

<span class="mw-page-title-main">State of matter</span> Forms, such as solid, liquid and gas, which matter can take

In physics, a state of matter is one of the distinct forms in which matter can exist. Four states of matter are observable in everyday life: solid, liquid, gas, and plasma. Many intermediate states are known to exist, such as liquid crystal, and some states only exist under extreme conditions, such as Bose–Einstein condensates and Fermionic condensates, neutron-degenerate matter, and quark–gluon plasma.

A viscometer is an instrument used to measure the viscosity of a fluid. For liquids with viscosities which vary with flow conditions, an instrument called a rheometer is used. Thus, a rheometer can be considered as a special type of viscometer. Viscometers can measure only constant viscosity, that is, viscosity that does not change with flow conditions.

<span class="mw-page-title-main">Soft matter</span> Subfield of condensed matter physics

Soft matter or soft condensed matter is a type of matter that can be deformed or structurally altered by thermal or mechanical stress of the magnitude of thermal fluctuations. The science of soft matter is a subfield of condensed matter physics. Soft materials include liquids, colloids, polymers, foams, gels, granular materials, liquid crystals, flesh, and a number of biomaterials. These materials share an important common feature in that predominant physical behaviors occur at an energy scale comparable with room temperature thermal energy, and that entropy is considered the dominant factor. At these temperatures, quantum aspects are generally unimportant. When soft materials interact favorably with surfaces, they become squashed without an external compressive force. Pierre-Gilles de Gennes, who has been called the "founding father of soft matter," received the Nobel Prize in Physics in 1991 for discovering that methods developed for studying order phenomena in simple systems can be generalized to the more complex cases found in soft matter, in particular, to the behaviors of liquid crystals and polymers.

A supercritical fluid (SCF) is any substance at a temperature and pressure above its critical point, where distinct liquid and gas phases do not exist, but below the pressure required to compress it into a solid. It can effuse through porous solids like a gas, overcoming the mass transfer limitations that slow liquid transport through such materials. SCFs are superior to gases in their ability to dissolve materials like liquids or solids. Also, near the critical point, small changes in pressure or temperature result in large changes in density, allowing many properties of a supercritical fluid to be "fine-tuned".

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

Crystallization is the process by which solids form, where the atoms or molecules are highly organized into a structure known as a crystal. Some ways by which crystals form are precipitating from a solution, freezing, or more rarely deposition directly from a gas. Attributes of the resulting crystal depend largely on factors such as temperature, air pressure, cooling rate, and in the case of liquid crystals, time of fluid evaporation.

<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.

<span class="mw-page-title-main">4-Hydroxybenzoic acid</span> Chemical compound

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.

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

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.

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

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.