CAS 22348-64-7

(22S)-Idrossicolesterolo

Descrizione:

(22S)-Idrossicolesterolo è un composto steroideo che gioca un ruolo significativo in vari processi biologici, in particolare nel metabolismo del colesterolo e degli ormoni steroidei. È caratterizzato dalla presenza di un gruppo idrossile nella posizione 22 del carbonio della struttura del colesterolo, che lo distingue da altri derivati del colesterolo. Questo composto si trova tipicamente nei tessuti animali ed è coinvolto nella regolazione dell'omeostasi del colesterolo e nelle vie di segnalazione cellulare. (22S)-Idrossicolesterolo può influenzare l'espressione genica ed è stato studiato per le sue potenziali implicazioni nella salute cardiovascolare e nella neurobiologia. La sua struttura molecolare contribuisce alla sua natura idrofobica, sebbene il gruppo idrossile conferisca un certo grado di polarità, permettendo di interagire sia con ambienti lipidici che acquosi. Il composto è anche di interesse nella ricerca farmacologica a causa dei suoi potenziali effetti sulla proliferazione e differenziazione cellulare. Come molti steroli, (22S)-Idrossicolesterolo è soggetto a conversione metabolica, il che può influenzare la sua attività biologica e funzione all'interno del corpo.

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]

Sinonimi:

• 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

Purezza: 98%

Colore e forma: Solid

Peso molecolare: 402.6529

Ref: IN-DA00BCZK

22-β-Hydroxy Cholesterol

CAS: 22348-64-7

Formula: C₂₇H₄₆O₂

Peso molecolare: 402.66

Ref: 4Z-C-5336

22(S)-Hydroxycholesterol

CAS: 22348-64-7

Formula: C₂₇H₄₆O₂

Purezza: ≥ 95.0%

Colore e forma: White to off-white powder or solid

Peso molecolare: 402.65

Ref: 7W-GL1699

22b-Hydroxy Cholesterol

Prodotto controllato

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

Colore e forma: Off White Solid

Peso molecolare: 402.65

Ref: TR-H918020

22β-Hydroxy cholesterol

Prodotto controllato

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

Purezza: Min. 95%

Peso molecolare: 402.65 g/mol

Ref: 3D-FH23943

22β-Hydroxycholesterol

CAS: 22348-64-7

Formula: C₂₇H₄₆O₂

Peso molecolare: 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

Colore e forma: Solid

Peso molecolare: 402.65

Ref: TM-T36130