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Cholesteryl benzoate

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.

Cholesteryl benzoate
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
  • 604-32-0 Y
3D model (JSmol)
  • Interactive image
  • Interactive image
ChemSpider
  • 2005815 Y
ECHA InfoCard 100.009.150
  • 2723613
UNII
  • N09H13SHLB Y
  • DTXSID10897509
  • 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
  • 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).
Y verify (what is YN ?)

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]

References edit

  1. ^ Cholesteryl benzoate at the National Library of Medicine
  2. ^ . 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.

cholesteryl, benzoate, also, called, cholesten, benzoate, organic, chemical, ester, cholesterol, benzoic, acid, liquid, crystal, material, forming, cholesteric, liquid, crystals, with, helical, structure, namesiupac, name, cholest, benzoatesystematic, iupac, n. 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 Cholesteryl benzoate NamesIUPAC name Cholest 5 en 3b yl benzoateSystematic 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 benzoateIdentifiersCAS Number 604 32 0 Y3D model JSmol Interactive imageInteractive imageChemSpider 2005815 YECHA InfoCard 100 009 150PubChem CID 2723613UNII N09H13SHLB YCompTox Dashboard EPA DTXSID10897509InChI 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 YKey UVZUFUGNHDDLRQ LLHZKFLPSA N YInChI 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 s1Key UVZUFUGNHDDLRQ LLHZKFLPBMSMILES 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 c5ccccc5C 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 34CPropertiesChemical formula C34H50O2Molar mass 490 76 g molMelting 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 Y verify what is Y N Infobox references 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 References edit Cholesteryl benzoate at the National Library of Medicine 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 History and Properties of Liquid Crystals Official Web Site of the Nobel Prize Retrieved 5 February 2016 Retrieved from https en wikipedia org w index php title Cholesteryl benzoate amp oldid 1153185236, wikipedia, wiki, book, books, library,

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