Cholesterol

Cholesterol
Names
	IUPAC name Cholest-5-en-3β-ol
	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-ol
	Other names Cholesterin, Cholesteryl alcohol
Identifiers
CAS Number	57-88-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16113 ;
ChEMBL	ChEMBL112570 ;
ChemSpider	5775 ;
ECHA InfoCard	100.000.321
IUPHAR/BPS	2718;
KEGG	D00040 ;
PubChem CID	5997;
UNII	97C5T2UQ7J ;
CompTox Dashboard (EPA)	DTXSID3022401 ;
	InChI InChI=1S/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1 Key: HVYWMOMLDIMFJA-DPAQBDIFSA-N ; InChI=1/C27H46O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1 Key: HVYWMOMLDIMFJA-DPAQBDIFBB;
	SMILES C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C;
Properties
Chemical formula	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)
Solubility in water	0.095 mg/L (30 °C)
Solubility	soluble in acetone, benzene, chloroform, ethanol, ether, hexane, isopropyl myristate, methanol
Magnetic susceptibility (χ)	-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). verify (what is ?) Infobox references

Cholesterol is the principal sterol of all higher animals, distributed in body tissues, especially the brain and spinal cord, and in animal fats and oils.^[3]^[4]

Cholesterol is biosynthesized by all animal cells^{[citation needed]} and is an essential structural and signaling component of animal cell membranes. In vertebrates, hepatic cells typically produce the greatest amounts. In the brain, astrocytes produce cholesterol and transport it to neurons.^[5] It is absent among prokaryotes (bacteria and archaea), although there are some exceptions, such as Mycoplasma, which require cholesterol for growth.^[6] Cholesterol also serves as a precursor for the biosynthesis of steroid hormones, bile acid^[7] and vitamin D.

Elevated levels of cholesterol in the blood, especially when bound to low-density lipoprotein (LDL, often referred to as "bad cholesterol"), may increase the risk of cardiovascular disease.^[8]

François Poulletier de la Salle first identified cholesterol in solid form in gallstones in 1769. In 1815, chemist Michel Eugène Chevreul named the compound "cholesterine".^[9]^[10]

^ ^a ^b "Cholesterol, 57-88-5". PubChem, National Library of Medicine, US National Institutes of Health. 9 November 2019. Retrieved 14 November 2019.
^ ^a ^b "Safety (MSDS) data for cholesterol". Archived from the original on 12 July 2007. Retrieved 20 October 2007.
^ "Cholesterol". MedlinePlus, National Library of Medicine, US National Institutes of Health. 10 December 2020. Retrieved 23 August 2023.
^ Cholesterol at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
^ Wang, Hao; Kulas, Joshua A.; Wang, Chao; Holtzman, David M.; Ferris, Heather A.; Hansen, Scott B. (17 August 2021). "Regulation of beta-amyloid production in neurons by astrocyte-derived cholesterol". Proceedings of the National Academy of Sciences. 118 (33). Bibcode:2021PNAS..11802191W. doi:10.1073/pnas.2102191118. PMC 8379952. PMID 34385305.
^ Razin S, Tully JG (May 1970). "Cholesterol requirement of mycoplasmas". Journal of Bacteriology. 102 (2): 306–110. doi:10.1128/JB.102.2.306-310.1970. PMC 247552. PMID 4911537.
^ Hanukoglu I (December 1992). "Steroidogenic enzymes: structure, function, and role in regulation of steroid hormone biosynthesis". The Journal of Steroid Biochemistry and Molecular Biology. 43 (8): 779–804. doi:10.1016/0960-0760(92)90307-5. PMID 22217824. S2CID 112729.
^ Cite error: The named reference Brunzell_2008 was invoked but never defined (see the help page).
^ Chevreul ME (1816). "Recherches chimiques sur les corps gras, et particulièrement sur leurs combinaisons avec les alcalis. Sixième mémoire. Examen des graisses d'homme, de mouton, de boeuf, de jaguar et d'oie" [Chemical researches on fatty substances, and particularly on their combinations o filippos ine kapios with alkalis. Sixth memoir. Study of human, sheep, beef, jaguar and goose fat]. Annales de Chimie et de Physique (in French). 2: 339–372 [346]. Je nommerai cholesterine, de χολη, bile, et στερεος, solide, la substance cristallisée des calculs biliares humains, ... [I will name cholesterine – from χολη (bile) and στερεος (solid) – the crystalized substance from human gallstones ...]
^ Olson RE (February 1998). "Discovery of the lipoproteins, their role in fat transport and their significance as risk factors". The Journal of Nutrition. 128 (2 Suppl): 439S–443S. doi:10.1093/jn/128.2.439S. PMID 9478044.

[pubchem-1] "Cholesterol, 57-88-5". PubChem, National Library of Medicine, US National Institutes of Health. 9 November 2019. Retrieved 14 November 2019.

[MSDS-2] "Safety (MSDS) data for cholesterol". Archived from the original on 12 July 2007. Retrieved 20 October 2007.

[mlp-3] "Cholesterol". MedlinePlus, National Library of Medicine, US National Institutes of Health. 10 December 2020. Retrieved 23 August 2023.

[4] Cholesterol at the U.S. National Library of Medicine Medical Subject Headings (MeSH)

[5] Wang, Hao; Kulas, Joshua A.; Wang, Chao; Holtzman, David M.; Ferris, Heather A.; Hansen, Scott B. (17 August 2021). "Regulation of beta-amyloid production in neurons by astrocyte-derived cholesterol". Proceedings of the National Academy of Sciences. 118 (33). Bibcode:2021PNAS..11802191W. doi:10.1073/pnas.2102191118. PMC 8379952. PMID 34385305.

[6] Razin S, Tully JG (May 1970). "Cholesterol requirement of mycoplasmas". Journal of Bacteriology. 102 (2): 306–110. doi:10.1128/JB.102.2.306-310.1970. PMC 247552. PMID 4911537.

[Hanukoglu_1992-7] Hanukoglu I (December 1992). "Steroidogenic enzymes: structure, function, and role in regulation of steroid hormone biosynthesis". The Journal of Steroid Biochemistry and Molecular Biology. 43 (8): 779–804. doi:10.1016/0960-0760(92)90307-5. PMID 22217824. S2CID 112729.

[Brunzell_2008-8] Cite error: The named reference Brunzell_2008 was invoked but never defined (see the help page).

[9] Chevreul ME (1816). "Recherches chimiques sur les corps gras, et particulièrement sur leurs combinaisons avec les alcalis. Sixième mémoire. Examen des graisses d'homme, de mouton, de boeuf, de jaguar et d'oie" [Chemical researches on fatty substances, and particularly on their combinations o filippos ine kapios with alkalis. Sixth memoir. Study of human, sheep, beef, jaguar and goose fat]. Annales de Chimie et de Physique (in French). 2: 339–372 [346]. Je nommerai cholesterine, de χολη, bile, et στερεος, solide, la substance cristallisée des calculs biliares humains, ... [I will name cholesterine – from χολη (bile) and στερεος (solid) – the crystalized substance from human gallstones ...]

[Olson_1998-10] Olson RE (February 1998). "Discovery of the lipoproteins, their role in fat transport and their significance as risk factors". The Journal of Nutrition. 128 (2 Suppl): 439S–443S. doi:10.1093/jn/128.2.439S. PMID 9478044.

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