24S-Hydroxycholesterol

24S-Hydroxycholesterol
Names
	IUPAC name (24S)-Cholest-5-ene-3β,24-diol
	Systematic IUPAC name (1R,3aS,3bS,7S,9aR,9bS,11aR)-1-[(2R,5S)-5-Hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-7-ol
	Other names cerebrosterol
Identifiers
CAS Number	474-73-7;
3D model (JSmol)	Interactive image;
Beilstein Reference	3218472
ChEBI	CHEBI:34310;
ChEMBL	ChEMBL171804;
ChemSpider	108790;
KEGG	C13550;
PubChem CID	121948;
UNII	47IMW63S3F;
CompTox Dashboard (EPA)	DTXSID101313419 ;
	InChI InChI=1S/C27H46O2/c1-17(2)25(29)11-6-18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20+,21+,22-,23+,24+,25+,26+,27-/m1/s1 Key: IOWMKBFJCNLRTC-XWXSNNQWSA-N;
	SMILES C[C@H](CC[C@@H](C(C)C)O)[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	C27H46O2
Molar mass	402.663 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

24S-Hydroxycholesterol (24S-HC), also known as cholest-5-ene-3,24-diol or cerebrosterol, is an endogenous oxysterol produced by neurons in the brain to maintain cholesterol homeostasis.^[1] It was discovered in 1953 by Alberto Ercoli, S. Di Frisco, and Pietro de Ruggieri, who first isolated the molecule in the horse brain^[2] and then demonstrated its presence in the human brain.^[3]

^ Mahley RW (2016). "Central Nervous System Lipoproteins: ApoE and Regulation of Cholesterol Metabolism". Arterioscler Thromb Vasc Biol. 36 (7): 1305–15. doi:10.1161/ATVBAHA.116.307023. PMC 4942259. PMID 27174096.
^ Ercoli A, Di Frisco S, De Ruggieri P (1953). "Isolation, constitution and biological significance of cerebrosterol, a companion of cholesterol in the horse brain". Boll Soc Ital Biol Sper. 29 (4): 494–7. PMID 13105923.
^ Di Frisco S, De Ruggieri P, Ercoli A (1953). "Isolation of cerebrosterol from human brain". Boll Soc Ital Biol Sper. 29 (7): 1351–2. PMID 13140512.

[pmid27174096-1] Mahley RW (2016). "Central Nervous System Lipoproteins: ApoE and Regulation of Cholesterol Metabolism". Arterioscler Thromb Vasc Biol. 36 (7): 1305–15. doi:10.1161/ATVBAHA.116.307023. PMC 4942259. PMID 27174096.

[pmid13105923-2] Ercoli A, Di Frisco S, De Ruggieri P (1953). "Isolation, constitution and biological significance of cerebrosterol, a companion of cholesterol in the horse brain". Boll Soc Ital Biol Sper. 29 (4): 494–7. PMID 13105923.

[pmid13140512-3] Di Frisco S, De Ruggieri P, Ercoli A (1953). "Isolation of cerebrosterol from human brain". Boll Soc Ital Biol Sper. 29 (7): 1351–2. PMID 13140512.

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