CAS 22348-64-7

(22S)-Hydroxycholesterol

Description:

(22S)-Hydroxycholesterol is a sterol compound that plays a significant role in various biological processes, particularly in the metabolism of cholesterol and steroid hormones. It is characterized by the presence of a hydroxyl group at the 22nd carbon position of the cholesterol backbone, which distinguishes it from other cholesterol derivatives. This compound is typically found in animal tissues and is involved in the regulation of cholesterol homeostasis and cellular signaling pathways. (22S)-Hydroxycholesterol can influence gene expression and has been studied for its potential implications in cardiovascular health and neurobiology. Its molecular structure contributes to its hydrophobic nature, although the hydroxyl group imparts some degree of polarity, allowing it to interact with both lipid and aqueous environments. The compound is also of interest in pharmacological research due to its potential effects on cell proliferation and differentiation. As with many sterols, (22S)-Hydroxycholesterol is subject to metabolic conversion, which can affect its biological activity and function within the body.

Formula: C₂₇H₄₆O₂

InChI: InChI=1/C27H46O2/c1-17(2)6-11-25(29)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+/m0/s1

InChI key: InChIKey=RZPAXNJLEKLXNO-QUOSNDFLSA-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:

• Cholest-5-ene-3β,22-diol, (20S,22S)-
• (22S)-22-Hydroxycholesterol
• Cholest-5-ene-3,22-diol, (3β,22S)-
• (22S)-Hydroxycholesterol
• (3β,22S)-Cholest-5-ene-3,22-diol
• (20S,22S)-Cholest-5-ene-3β,22-diol
• Cholest-5-ene-3β,22(S)-diol
• C05502
• 22BF-HYDROXYCHOLESTEROL
• 5-CHOLESTENE-3BETA,22[R]-DIOL
• (3S,8S,9S,10R,13R,14S,17R)-17-[(2S,3R)-3-hydroxy-6-methyl-heptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• 22(S)-HYDROXYCHOLESTEROL
• 5-CHOLESTENE-3BETA,22[S]-DIOL
• 3BETA,22BETA-DIHYDROXY-5-CHOLESTENE
• 22BETA-HYDROXYCHOLESTEROL
• 22-HYDROXYCHOLESTEROL (22R)
• 5-CHOLESTEN-3-BETA, 22(R)-DIOL
• 22[S]-Hydroxycholesterol (not deuterated)
• 22β-Hydroxy Cholesterol
• 22(R)-OH-CH
• CHOLEST-5-ENE-3,22(S)-DIOL;22(S)-HYDROXYCHOLESTEROL
• 22β-Hydroxycholesterol, 5-Cholestene-3β,22(S)-diol
• (5-Cholestene-322(S)-diol)
• CHOLEST-5-ENE-3BETA,22R-DIOL
• (22S)-Cholest-5-ene-3β,22-diol
• 22-ALPHA-HYDROXYCHOLESTEROL
• 5-CHOLESTEN-3-BETA, 22(S)-DIOL

Cholest-5-ene-3,22-diol, (3b,22S)-

CAS: 22348-64-7

Formula: C₂₇H₄₆O₂

Purity: 98%

Color and Shape: Solid

Molecular weight: 402.6529

Ref: IN-DA00BCZK

22-β-Hydroxy Cholesterol

CAS: 22348-64-7

Formula: C₂₇H₄₆O₂

Molecular weight: 402.66

Ref: 4Z-C-5336

22(S)-Hydroxycholesterol

CAS: 22348-64-7

Formula: C₂₇H₄₆O₂

Purity: ≥ 95.0%

Color and Shape: White to off-white powder or solid

Molecular weight: 402.65

Ref: 7W-GL1699

22b-Hydroxy Cholesterol

Controlled Product

CAS: 22348-64-7

Applications The 22S-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: Off White Solid

Molecular weight: 402.65

Ref: TR-H918020

22β-Hydroxy cholesterol

Controlled Product

CAS: 22348-64-7

22-Hydroxycholesterol is a product of cholesterol synthesis, which is formed by the side-chain cleavage of cholesterol. This compound has been shown to inhibit cholesterol acyltransferase and to be cytotoxic in vitro. 22-Hydroxycholesterol has also been shown to have an inhibitory effect on protein synthesis and on the activity of forskolin, an activator of adenylate cyclase that is involved in the regulation of cellular levels of cAMP. The antioxidant properties of 22-hydoxycholesterol may be due to its chemical structure, which includes a hydroxyl group. This compound also shows an insulin-sensitizing effect in mice fed a high fat diet.

Formula: C₂₇H₄₆O₂

Purity: Min. 95%

Molecular weight: 402.65 g/mol

Ref: 3D-FH23943

22β-Hydroxycholesterol

CAS: 22348-64-7

Formula: C₂₇H₄₆O₂

Molecular weight: 402.66

Ref: ST-EA-CP-C71037

22(S)-hydroxy Cholesterol

CAS: 22348-64-7

22(S)-hydroxy Cholesterol is a synthetic oxysterol and a modulator of the liver X receptor (LXR). [1] t prevents monocyte chemoattractant protein 1 (MCP-1) expression induced by the LXR agonist GW 3965 in primary hepatocytes and downregulates mRNA expression of the LXR target genes CD36, ACSL1, and SCD-1 in human myotubes. It decreases triacylglycerol and diacylglycerol synthesis from labeled palmitate and acetate, respectively, in human myoblasts by 50% when used at a concentration of 10 uM. 22(S)-hydroxy Cholesterol also reduces fatty acid synthase (FAS) reporter activity through an LXR response element in the promoter region in COS-1 cells transfected with RXRα and LXRα and decreases the expression of MCP-1 and CCR2 in a mouse model of chronic ethanol consumption.[1] [2] Dietary supplementation of 22(S)-hydroxy cholesterol (30 mg/kg per day) leads to less body weight gain and lower liver triacylglycerol levels in rats when fed either a regular chow or high-fat diet as well as prevents an increase in plasma triacylglycerol levels resulting from a high-fat diet.[3]

Formula: C₂₇H₄₆O₂

Color and Shape: Solid

Molecular weight: 402.65

Ref: TM-T36130