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Dietary cholesterol

Cholesterol
Chemical structure of cholesterol
Ball-and-stick model of cholesterol
Sample of Cholesterol
Names
IUPAC name
(3β)-cholest-5-en-3-ol
Systematic IUPAC name
2,15-dimethyl-14-(1,5-dimethylhexyl)tetracyclo[8.7.0.02,7.011,15]heptadec-7-en-5-ol
Other names
(10R,13R)-10,13-dimethyl-17-(6-methylheptan-2-yl)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol, Cholesterin, Cholesteryl alcohol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.000.321
KEGG
PubChem CID
UNII
Properties
C27H46O
Molar mass 386.65 g/mol
Appearance white crystalline powder
Density 1.052 g/cm3
Melting point 148 to 150 °C (298 to 302 °F; 421 to 423 K)
Boiling point 360 °C (680 °F; 633 K) (decomposes)
1.8 mg/L (30 °C)
Solubility soluble in acetone, benzene, chloroform, ethanol, ether, hexane, isopropyl myristate, methanol
-284.2·10−6 cm3/mol
Hazards
Flash point 209.3 ±12.4 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Cholesterol, from the Ancient Greek chole- (bile) and stereos (solid) followed by the chemical suffix -ol for an alcohol, is an organic molecule. It is a sterol (or modified steroid), a type of lipid molecule, and is biosynthesized by all animal cells, because it is an essential structural component of all animal cell membranes; essential to maintain both membrane structural integrity and fluidity. Cholesterol enables animal cells to dispense with a cell wall (to protect membrane integrity and cell viability), thereby allowing animal cells to change shape rapidly and animals to move (unlike bacteria and plant cells, which are restricted by their cell walls).

In addition to its importance for animal cell structure, cholesterol also serves as a precursor for the biosynthesis of steroid hormones, bile acid, and vitamin D. Cholesterol is the principal sterol synthesized by all animals. In vertebrates, hepatic cells typically produce the greatest amounts. It is absent among prokaryotes (bacteria and archaea), although there are some exceptions, such as Mycoplasma, which require cholesterol for growth.


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