2/8/2017 CholesterolWikipedia

Cholesterol
FromWikipedia,thefreeencyclopedia

Cholesterol,fromtheAncientGreekchole(bile)andstereos Cholesterol
(solid)followedbythechemicalsuffixolforanalcohol,is
anorganicmolecule.Itisasterol(ormodifiedsteroid),[4]a
typeoflipidmolecule,andisbiosynthesizedbyallanimal
cells,becauseitisanessentialstructuralcomponentofall
animalcellmembranesessentialtomaintainbothmembrane
structuralintegrityandfluidity.Cholesterolenablesanimal
cellstodispensewithacellwall(toprotectmembrane
integrityandcellviability),therebyallowinganimalcellsto
changeshapeandanimalstomove(unlikebacteriaandplant
cells,whicharerestrictedbytheircellwalls).

Inadditiontoitsimportanceforanimalcellstructure,
cholesterolalsoservesasaprecursorforthebiosynthesisof
steroidhormonesandbileacids.[5]Cholesterolistheprincipal
sterolsynthesizedbyallanimals.Invertebrates,hepaticcells
typicallyproducethegreatestamounts.Itisabsentamong
prokaryotes(bacteriaandarchaea),althoughtherearesome
exceptions,suchasMycoplasma,whichrequirecholesterol
forgrowth.[6]

FranoisPoulletierdelaSallefirstidentifiedcholesterolin
solidformingallstonesin1769.However,itwasnotuntil
1815thatchemistMichelEugneChevreulnamedthe
compound"cholesterine".[7][8]

Contents
1 Physiology
1.1 Function
1.2 Dietarysources
1.3 Biosynthesis Names
1.4 Regulationofcholesterolsynthesis IUPACname
1.5 Plasmatransportandregulationof
absorption (3)cholest5en3ol
1.6 Metabolism,recyclingandexcretion SystematicIUPACname
1.7 Research 2,15dimethyl14(1,5
2 Clinicalsignificance dimethylhexyl)tetracyclo[8.7.0.02,7.011,15]heptadec
2.1 Hypercholesterolemia 7en5ol
2.2 Hypocholesterolemia Othernames
2.3 Cholesteroltesting
(10R,13R)10,13dimethyl17(6methylheptan2
3 Interactivepathwaymap
4 Cholestericliquidcrystals yl)2,3,4,7,8,9,11,12,14,15,16,17dodecahydro1H
5 Stereoisomers cyclopenta[a]phenanthren3ol,Cholesterin,
6 Seealso Cholesterylalcohol[1]
7 Additionalimages
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8 References Identifiers
9 Externallinks CASNumber 57885(http://www.commonche
mistry.org/ChemicalDetail.aspx?r
ef=57885)
Physiology 3Dmodel(Jmol) Interactiveimage(http://chemapp
s.stolaf.edu/jmol/jmol.php?model
Sincecholesterolisessentialforallanimallife,eachcell
=C%5BC%40H%5D%28CCC
synthesizesitbywayofacomplex37stepprocess,
beginningwiththemevalonatepathwayandendingwitha C%28C%29C%29%5BC%40H%
19stepconversionoflanosteroltocholesterol. 5D1CC%5BC%40%40H%5D2%
5BC%40%40%5D1%28CC%5B
Ahumanmaleweighing68kg(150lb)normallysynthesizes C%40H%5D3%5BC%40H%5D2
about1gram(1,000mg)perday,andhisbodycontainsabout CC%3DC4%5BC%40%40%5D
35g,mostlycontainedwithinthecellmembranes.Typical 3%28CC%5BC%40%40H%5D%
dailycholesteroldietaryintakeforamanintheUnitedStates
28C4%29O%29C%29C)
is307mg(abovetheupperlimitrecommendedbythe
ChEBI CHEBI:16113(https://www.ebi.a
DietaryGuidelinesAdvisoryCommittee[9]).
c.uk/chebi/searchId.do?chebiId=1
Mostingestedcholesterolisesterified,andesterified 6113)
cholesterolispoorlyabsorbed.Thebodyalsocompensates ChEMBL ChEMBL112570(https://www.eb
foranyabsorptionofadditionalcholesterolbyreducing
i.ac.uk/chembldb/index.php/comp
cholesterolsynthesis.[10]Forthesereasons,cholesterolin
ound/inspect/ChEMBL112570)
food,seventotenhoursafteringestion,haslittle,ifanyeffect
onconcentrationsofcholesterolintheblood.However, ChemSpider 5775(http://www.chemspider.co
duringthefirstsevenhoursafteringestionofcholesterol,as m/Chemical
absorbedfatsarebeingdistributedaroundthebodywithin Structure.5775.html)
extracellularwaterbythevariouslipoproteins(which
ECHAInfoCard 100.000.321(https://echa.europa.
transportallfatsinthewateroutsidecells),theconcentrations
eu/substanceinformation//substa
increase.[11]Itisalsoimportanttorecognize,however,that
nceinfo/100.000.321)
theconcentrationsmeasuredinthesamplesofbloodplasma
varywiththemeasurementmethodsused.Traditional, IUPHAR/BPS 2718(http://www.guidetopharma
cheapermethodsdonotreflect(a)whichlipoproteinsare cology.org/GRAC/LigandDisplay
transportingthevariousfatmolecules,nor(b)whichcellsare Forward?tab=summary&ligandId
ingesting,burningorexportingthefatmoleculesbeing =2718)
measuredastotalsfromsamplesofbloodplasma. KEGG D00040(http://www.kegg.jp/entr
Cholesterolisrecycledinthebody.Theliverexcretesitina y/D00040)
nonesterifiedform(viabile)intothedigestivetract. PubChem 5997(https://pubchem.ncbi.nlm.n
Typically,about50%oftheexcretedcholesterolisreabsorbed ih.gov/compound/5997)
bythesmallintestinebackintothebloodstream.
UNII 97C5T2UQ7J(http://fdasis.nlm.n
ih.gov/srs/srsdirect.jsp?regno=97
Plantsmakecholesterolinverysmallamounts.[12]Plants
manufacturephytosterols(substanceschemicallysimilarto C5T2UQ7J)
cholesterol),whichcancompetewithcholesterolfor InChI
reabsorptionintheintestinaltract,thuspotentiallyreducing
SMILES
cholesterolreabsorption.[13]Whenintestinalliningcells
Properties
absorbphytosterols,inplaceofcholesterol,theyusually
excretethephytosterolmoleculesbackintotheGItract,an Chemicalformula C27H46O
importantprotectivemechanism. Molarmass 386.65g/mol

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