CAS 17954-98-2

22(R)-hydroxycholesterol

Description:

22(R)-hydroxycholesterol is a sterol compound that plays a significant role in various biological processes, particularly in the regulation of cholesterol metabolism and signaling pathways. It is an oxysterol, which means it is a derivative of cholesterol that has undergone oxidation. This compound is characterized by the presence of a hydroxyl group at the 22nd carbon position, which distinguishes it from other cholesterol derivatives. 22(R)-hydroxycholesterol is known to act as a ligand for liver X receptors (LXRs), influencing gene expression related to lipid metabolism and inflammation. Additionally, it can modulate the synthesis of steroid hormones and bile acids. The compound is typically found in various tissues and is involved in cellular signaling mechanisms. Its CAS number, 17954-98-2, is a unique identifier that facilitates the identification and study of this specific chemical substance in scientific literature and databases. Overall, 22(R)-hydroxycholesterol is an important molecule in the context of cholesterol homeostasis and cellular function.

Formula: C₂₇H₄₆O₂

InChI: InChI=1/C27H46O2/c1-17(2)7-6-8-18(3)22-11-12-23-21-10-9-19-15-20(28)16-25(29)27(19,5)24(21)13-14-26(22,23)4/h9,17-18,20-25,28-29H,6-8,10-16H2,1-5H3/t18-,20-,21+,22-,23+,24+,25?,26-,27+/m1/s1

InChI key: InChIKey=RZPAXNJLEKLXNO-GFKLAVDKSA-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@@H]([C@@H](CCC(C)C)O)C)[H])[H]

Synonyms:

• (3β,22R)-Cholest-5-ene-3,22-diol
• (22R)-Hydroxycholesterol
• Cholest-5-ene-3β,22-diol, (20S,22R)-
• (22R)-22-Hydroxycholesterol
• Cholest-5-ene-3,22-diol, (3β,22R)-
• CHOLEST-5-ENE-3BETA,22R-DIOL
• 5-CHOLESTEN-3-BETA, 22(R)-DIOL
• 22α-Hydroxycholesterol, 5-Cholestene-3β,22(R)-diol, 5-Cholestene-3β,22[R]-diol
• 22(R)-OH-CH
• 22[R]-Hydroxycholesterol (not deuterated)
• Cholest-5-ene-3,22-diol, (3beta,22R)-
• 22BF-HYDROXYCHOLESTEROL
• 22BETA-HYDROXYCHOLESTEROL
• 22R-OHC
• 22(R)-HYDROXYCHOLESTEROL
• Cholesterol 22α-Hydroxy
• 22α-Hydroxy Cholesterol
• Cholest-5-ene-3β,22(R)-diol
• (22a-Hydroxycholesterol, 5-Cholestene-322(R)-diol)
• 22α-hydroxycholesterol
• 5-CHOLESTENE-3BETA,22[R]-DIOL
• 22-ALPHA-HYDROXYCHOLESTEROL
• (20S,22R)-Cholest-5-ene-3β,22-diol
• 3BETA,22BETA-DIHYDROXY-5-CHOLESTENE
• (3beta,22R)-Cholest-5-ene-3,22-diol
• 22-HYDROXYCHOLESTEROL (22R)
• 5-Cholestene-3β,22(R)-diol
• Narthesterol
• 5-Cholestene-3β,22[R]-diol

(8S,9S,10R,13S,14S,17R)-17-((2S,3R)-3-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: 17954-98-2

Formula: C₂₇H₄₆O₂

Purity: 98%

Color and Shape: Solid

Molecular weight: 402.6529

Ref: IN-DA002734

22(R)-Hydroxycholesterol

CAS: 17954-98-2

Formula: C₂₇H₄₆O₂

Molecular weight: 402.65

Ref: 7W-GK8616

22(R)-Hydroxycholesterol

CAS: 17954-98-2

22(R)-Hydroxycholesterol

Purity: 98%

Ref: 54-OR1039802

22-α-Hydroxy Cholesterol

CAS: 17954-98-2

Formula: C₂₇H₄₆O₂

Molecular weight: 402.66

Ref: 4Z-C-5314

22α-Hydroxy Cholesterol

Controlled Product

CAS: 17954-98-2

Applications The 22R-metabolite of Cholesterol (C432501). 22-Hydroxycholesterol inhibits chemokine receptor activity.
References Samson, M., et al.: J. Biol. Chem., 272, 24934 (1997), Mackay, C., et al.: Nature Immunol., 2, 95 (2001), Navenot, J., et al.: J. Mol. Biol., 313, 1181 (2001),

Formula: C₂₇H₄₆O₂

Color and Shape: Neat

Molecular weight: 402.65

Ref: TR-H918015

22α-Hydroxy cholesterol

Controlled Product

CAS: 17954-98-2

22a-Hydroxycholesterol is a naturally occurring, oxygenated cholesterol metabolite. It binds to the transcriptional coactivator retinoid X receptor (RXR) and inhibits the activity of certain liver enzymes. 22a-Hydroxycholesterol has been shown to have toxic effects on mouse tumors and to inhibit the production of ATP in vitro. 22a-Hydoxycholesterol also inhibits the function of ATP binding cassette (ABC) transporter proteins, which are involved in cholesterol transport from cells. The long-term toxicity of 22a-hydroxycholesterol is not well understood, although it has been shown that this metabolite can induce autoimmune diseases in rats.

Formula: C₂₇H₄₆O₂

Purity: Min. 95%

Molecular weight: 402.65 g/mol

Ref: 3D-FH23942

22α-Hydroxy Cholesterol

CAS: 17954-98-2

Formula: C₂₇H₄₆O₂

Molecular weight: 402.66

Ref: ST-EA-CP-C71056