CAS 22348-64-7

(22S)-Hidroxicolesterol

Descrição:

(22S)-Hidroxicolesterol é um composto esteroide que desempenha um papel significativo em vários processos biológicos, particularmente no metabolismo do colesterol e dos hormônios esteroides. É caracterizado pela presença de um grupo hidroxila na posição 22 do carbono da estrutura do colesterol, o que o distingue de outros derivados do colesterol. Este composto é tipicamente encontrado em tecidos animais e está envolvido na regulação da homeostase do colesterol e nas vias de sinalização celular. (22S)-Hidroxicolesterol pode influenciar a expressão gênica e tem sido estudado por suas potenciais implicações na saúde cardiovascular e na neurobiologia. Sua estrutura molecular contribui para sua natureza hidrofóbica, embora o grupo hidroxila confira certo grau de polaridade, permitindo que interaja tanto com ambientes lipídicos quanto aquosos. O composto também é de interesse na pesquisa farmacológica devido aos seus potenciais efeitos na proliferação e diferenciação celular. Assim como muitos esteróis, (22S)-Hidroxicolesterol está sujeito à conversão metabólica, o que pode afetar sua atividade biológica e função dentro do corpo.

Fórmula: 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

Chave InChI: 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]

Sinónimos:

• 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

Fórmula: C₂₇H₄₆O₂

Pureza: 98%

Cor e Forma: Solid

Peso molecular: 402.6529

Ref: IN-DA00BCZK

22-β-Hydroxy Cholesterol

CAS: 22348-64-7

Fórmula: C₂₇H₄₆O₂

Peso molecular: 402.66

Ref: 4Z-C-5336

22(S)-Hydroxycholesterol

CAS: 22348-64-7

Fórmula: C₂₇H₄₆O₂

Pureza: ≥ 95.0%

Cor e Forma: White to off-white powder or solid

Peso molecular: 402.65

Ref: 7W-GL1699

22b-Hydroxy Cholesterol

Produto Controlado

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),

Fórmula: C₂₇H₄₆O₂

Cor e Forma: Off White Solid

Peso molecular: 402.65

Ref: TR-H918020

22β-Hydroxy cholesterol

Produto Controlado

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.

Fórmula: C₂₇H₄₆O₂

Pureza: Min. 95%

Peso molecular: 402.65 g/mol

Ref: 3D-FH23943

22β-Hydroxycholesterol

CAS: 22348-64-7

Fórmula: C₂₇H₄₆O₂

Peso molecular: 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]

Fórmula: C₂₇H₄₆O₂

Cor e Forma: Solid

Peso molecular: 402.65

Ref: TM-T36130