CAS 516-72-3

20α-Hydroxycholesterol

Description:

20α-Hydroxycholesterol is a steroid compound that plays a significant role in various biological processes, particularly in the context of cholesterol metabolism and steroidogenesis. It is a derivative of cholesterol, characterized by the presence of a hydroxyl group at the 20α position, which influences its biological activity and interactions with cellular receptors. This compound is involved in the regulation of gene expression and can act as a precursor for the synthesis of other steroid hormones. In terms of physical properties, 20α-Hydroxycholesterol is typically a white to off-white solid, soluble in organic solvents, and exhibits a relatively low solubility in water. Its chemical structure allows it to participate in various biochemical pathways, including those related to inflammation and immune response. Additionally, it has been studied for its potential implications in cardiovascular health and neurobiology. As with many steroid compounds, its activity can be influenced by the presence of other biomolecules and environmental factors.

Formula: C₂₇H₄₆O₂

InChI: InChI=1/C27H46O2/c1-18(2)7-6-14-27(5,29)24-11-10-22-21-9-8-19-17-20(28)12-15-25(19,3)23(21)13-16-26(22,24)4/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t20-,21-,22-,23-,24-,25-,26-,27+/m0/s1

InChI key: InChIKey=MCKLJFJEQRYRQT-APGJSSKUSA-N

SMILES: C[C@@]12[C@]([C@]3([C@@]([C@]4(C)C(=CC3)C[C@@H](O)CC4)(CC1)[H])[H])(CC[C@@]2([C@@](CCCC(C)C)(C)O)[H])[H]

Synonyms:

• (20S)-20-Hydroxycholesterol
• (20S)-Cholest-5-ene-3beta,20-diol
• (20S)-Hydroxycholesterol
• (3Beta)-Cholest-5-Ene-3,20-Diol
• (3beta,20R)-cholest-5-ene-3,20-diol
• (3β)-Cholest-5-ene-3,20-diol
• 20-Hydroxycholesterol
• 20S-Cholest-5-ene-3β,20-diol
• 20alpha-Hydroxycholesterol
• Cholest-5-ene-3,20-diol, (3beta)-
• Cholest-5-ene-3,20-diol, (3β)-
• Cholest-5-ene-3beta,20-diol, (20S)-
• Cholest-5-ene-3beta,20alpha-diol
• Cholest-5-ene-3β,20-diol, (20S)-
• Cholest-5-ene-3β,20α-diol
• 20α-Hydroxycholesterol
• Cholest-5-ene-3,20a-diol
• 20(S)-hydroxyCholesterol (20α-Hydroxycholesterol)
• 20α-Hydroxycholesterol (not deuterated)
• 5-CHOLESTEN-3-BETA, 20-ALPHA-DIOL
• 5-cholestene-3β,20α-diol
• 3BETA,20ALPHA-DIHYDROXY-5-CHOLESTENE
• 20S-Cholest-5-ene-3,20-diol
• (3S,8S,9S,10R,13S,14S,17S)-17-[(2R)-2-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• (3)-Cholest-5-ene-3,20-diol
• (20S)-Cholest-5-ene-3,20-diol
• 20α-Hydroxy Cholesterol
• 5-Cholestene-3B,20a-diol
• 5-CHOLESTENE-3B,20ALPHA-DIOL
• Cholest-5-ene-3,20-diol, (3.beta.)-
• C05500
• Cholest-5-ene-3β,20-diol
• 20alpha-Hydroxycholesterol (not deuterated)
• (3S,8S,9S,10R,13S,14S,17S)-17-((S)-2-hydroxy-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
• 20[S]-HYDROXYCHOLESTEROL

20α-HYDROXYCHOLESTEROL

CAS: 516-72-3

Formula: C₂₇H₄₆O₂

Purity: 98%

Color and Shape: Solid

Molecular weight: 402.6529

Ref: IN-DA00DDEL

20(S)-Hydroxycholesterol

CAS: 516-72-3

20(S)-Hydroxycholesterol

Purity: ≥98%

Molecular weight: 402.65g/mol

Ref: 54-BUP03740

(8S,9S,10R,13S,14S,17S)-17-((R)-2-Hydroxy-6-Methylheptan-2-Yl)-10,13-Dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-Tetradecahydro-1H-Cyclopenta[A]Phenanthren-3-Ol

CAS: 516-72-3

(8S,9S,10R,13S,14S,17S)-17-((R)-2-Hydroxy-6-Methylheptan-2-Yl)-10,13-Dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-Tetradecahydro-1H-Cyclopenta[A]Phenanthren-3-Ol

Purity: 98%

Molecular weight: 402.65g/mol

Ref: 54-OR1023243

(20S)-Hydroxy Cholesterol

CAS: 516-72-3

Formula: C₂₇H₄₆O₂

Molecular weight: 402.66

Ref: 4Z-C-5390

20α-Hydroxy Cholesterol-d7

Controlled Product

CAS: 516-72-3

Applications A metabolite of Cholesterol. Cholesterol oxidation product having cytotoxicity effects.
References Higley, N., et al.: Food Chem. Toxicol., 22, 983 (1984), Emanuel, H., et al.: J. Food Sci., 56, 843 (1991), Kilsdonk, E., et al.: J. Lipid Res., 36, 505 (1995), Cantwell, H., et al.: Cell Biol. Toxicol., 14, 401 (1998),

Formula: C₂₇H₃₉D₇O₂

Color and Shape: Neat

Molecular weight: 409.7

Ref: TR-H918002

20α-Hydroxy Cholesterol

CAS: 516-72-3

Applications A metabolite of Cholesterol (C432501). Cholesterol oxidation product having cytotoxicity effects.
References Higley, N., et al.: Food Chem. Toxicol., 22, 983 (1984), Emanuel, H., et al.: J. Food Sci., 56, 843 (1991), Kilsdonk, E., et al.: J. Lipid Res., 36, 505 (1995), Cantwell, H., et al.: Cell Biol. Toxicol., 14, 401 (1998),

Formula: C₂₇H₄₆O₂

Color and Shape: Neat

Molecular weight: 402.65

Ref: TR-H918000

20a-Hydroxy cholesterol

Controlled Product

CAS: 516-72-3

20a-Hydroxy cholesterol is a model system for studying the effects of hydroxylation on fatty acid metabolism. The addition of one hydroxyl group to the 20 carbon position in cholesterol leads to an analog, 20a-hydroxycholesterol. This compound has been shown to inhibit the enzyme activities of 3-hydroxyacyl coenzyme A dehydrogenase and acyl coenzyme A:cholesterol acyltransferase. The inhibition of these enzymes leads to decreased production of both prostaglandin E2 and leukotriene B4, which are pro-inflammatory mediators. 20a-Hydroxycholesterol has also been found to be effective in treating skin cancer and adrenocortical carcinoma by inhibiting lipid synthesis, thereby reducing cell proliferation rates.

Formula: C₂₇H₄₆O₂

Purity: Min. 95%

Molecular weight: 402.65 g/mol

Ref: 3D-FH23941

20(S)-Hydroxycholesterol

CAS: 516-72-3

20(S)-Hydroxycholesterol (20α-Hydroxycholesterol) is an allosteric activator of the oncoprotein smoothened (Smo).

Formula: C₂₇H₄₆O₂

Purity: 99.25% - 99.79%

Color and Shape: Solid

Molecular weight: 402.65

Ref: TM-T10085

(20S)-Hydroxycholesterol

CAS: 516-72-3

Formula: C₂₇H₄₆O₂

Molecular weight: 402.66

Ref: ST-EA-CP-C71036