CAS 22348-64-7

(22S)-Hidroxicolesterol

Descripción:

(22S)-Hidroxicolesterol es un compuesto esteroide que desempeña un papel significativo en varios procesos biológicos, particularmente en el metabolismo del colesterol y las hormonas esteroides. Se caracteriza por la presencia de un grupo hidroxilo en la posición 22 del carbono de la estructura del colesterol, lo que lo distingue de otros derivados del colesterol. Este compuesto se encuentra típicamente en tejidos animales y está involucrado en la regulación de la homeostasis del colesterol y las vías de señalización celular. (22S)-Hidroxicolesterol puede influir en la expresión génica y se ha estudiado por sus posibles implicaciones en la salud cardiovascular y la neurobiología. Su estructura molecular contribuye a su naturaleza hidrofóbica, aunque el grupo hidroxilo le confiere cierto grado de polaridad, permitiéndole interactuar tanto con entornos lipídicos como acuosos. El compuesto también es de interés en la investigación farmacológica debido a sus posibles efectos en la proliferación y diferenciación celular. Al igual que muchos esteroides, (22S)-Hidroxicolesterol está sujeto a conversión metabólica, lo que puede afectar su actividad biológica y función dentro del cuerpo.

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

Clave 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%

Forma y color: 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%

Forma y color: White to off-white powder or solid

Peso molecular: 402.65

Ref: 7W-GL1699

22b-Hydroxy Cholesterol

Producto 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

Forma y color: Off White Solid

Peso molecular: 402.65

Ref: TR-H918020

22β-Hydroxy cholesterol

Producto 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

Forma y color: Solid

Peso molecular: 402.65

Ref: TM-T36130