25-Hydroxycholesterol

{{Use dmy dates|date=December 2023}}{{cs1 config|name-list-style=vanc}}{{chembox

|ImageFile=25-Hydroxycholesterol.svg

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|IUPACName=

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|Section1={{Chembox Identifiers

| CASNo=2140-46-7

| PubChem=65094

| ChEBI=42977

| ChemSpiderID=58604

| EC_number=635-752-4

| KEGG=C15519

| UNII=767JTD2N31

| DrugBank=04705

| InChI=1S/C27H46O2/c1-18(7-6-14-25(2,3)29)22-10-11-23-21-9-8-19-17-20(28)12-15-26(19,4)24(21)13-16-27(22,23)5/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t18-,20+,21+,22-,23+,24+,26+,27-/m1/s1

| InChIKey=INBGSXNNRGWLJU-ZHHJOTBYSA-N

| SMILES=CC(CCCC(C)(C)O)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C

}}

|Section2={{Chembox Properties

| Formula=C₂₇H₄₆O₂

| MolarMass=402.7

| Appearance=

| Density=

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|Section3={{Chembox Hazards

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}}25-Hydroxycholesterol is a derivative of cholesterol, which plays a role in various biological processes in humans and other species. It is involved in cholesterol metabolism, antivirus process, inflammatory and immune response, and survival signaling pathway. 25-hydroxycholesterol is biosynthesized from cholesterol by adding a hydroxyl group at the position 25-carbon of a steroid nucleus. This reaction is catalyzed by cholesterol 25-hydroxylase, a family of enzymes that use oxygen and a di-iron cofactor to catalyze hydroxylation reaction.{{cite journal |vauthors=Zhang J, Zhu Y, Wang X, Wang J |title=25-hydroxycholesterol: an integrator of antiviral ability and signaling |journal=Front Immunol |volume=14 |issue= |pages=1268104 |date=2023 |pmid=37781400 |pmc=10533924 |doi=10.3389/fimmu.2023.1268104 |url= |doi-access=free }}{{cite journal |vauthors=Cao Q, Liu Z, Xiong Y, Zhong Z, Ye Q |title=Multiple Roles of 25-Hydroxycholesterol in Lipid Metabolism, Antivirus Process, Inflammatory Response, and Cell Survival |journal=Oxid Med Cell Longev |volume=2020 |issue= |pages=8893305 |date=2020 |pmid=33274010 |pmc=7695496 |doi=10.1155/2020/8893305 |url= |doi-access=free }}

The CYP3A4 enzyme, a member of the cytochrome P450 family, can catalyze the oxidation of 25-hydroxycholesterol to 7α,25-dihydroxycholesterol, whereas 25-hydroxycholesterol can inhibit CYP4F2 mRNA expression, so that members of the cytochrome P450 family are also involved in the metabolism of 25-hydroxycholesterol besides cholesterol 25-hydroxylase.{{cite journal |vauthors=Hsu MH, Savas U, Griffin KJ, Johnson EF |title=Regulation of human cytochrome P450 4F2 expression by sterol regulatory element-binding protein and lovastatin |journal=J Biol Chem |volume=282 |issue=8 |pages=5225–36 |date=February 2007 |pmid=17142457 |doi=10.1074/jbc.M608176200 |url= |doi-access=free }}

25-hydroxycholesterol has been found in various organisms such as mice, rats, rabbits, and cows. {{As of|2023|post=,}} its presence in other species has not been extensively studied.