CAS 77058-74-3

(24S,25)-Epoxycholesterol

Description:

(24S,25)-Epoxycholesterol is a sterol derivative characterized by its epoxide functional group, which is formed by the oxidation of cholesterol. This compound is notable for its role in cellular processes, particularly in the regulation of cholesterol metabolism and signaling pathways. It is a stereoisomer of epoxycholesterol, specifically with the 24S and 25 positions being crucial for its biological activity. The presence of the epoxide group contributes to its reactivity, allowing it to participate in various biochemical reactions. (24S,25)-Epoxycholesterol is often studied for its implications in cardiovascular health and its potential effects on lipid metabolism. Additionally, it may influence the synthesis of other bioactive lipids and has been implicated in the modulation of cellular functions such as proliferation and apoptosis. As a compound with a specific stereochemistry, its interactions with biological systems can be highly selective, making it a subject of interest in pharmacological and biochemical research.

Formula: C₂₇H₄₄O₂

InChI: InChI=1S/C27H44O2/c1-17(6-11-24-25(2,3)29-24)21-9-10-22-20-8-7-18-16-19(28)12-14-26(18,4)23(20)13-15-27(21,22)5/h7,17,19-24,28H,6,8-16H2,1-5H3/t17-,19+,20+,21-,22+,23+,24+,26+,27-/m1/s1

InChI key: InChIKey=OSENKJZWYQXHBN-XVYZBDJZSA-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](CC[C@H]5C(C)(C)O5)C)[H])[H]

Synonyms:

• (24S)-24,25-Epoxycholesterol
• (24S,25)-Epoxycholesterol
• (3β,24S)-24,25-Epoxycholest-5-en-3-ol
• Cholest-5-en-3-ol, 24,25-epoxy-, (3β,24S)-
• (-)-(24S,25)-Epoxycholesterol

(8S,9S,10R,13R,14S,17R)-17-((R)-4-((S)-3,3-Dimethyloxiran-2-yl)butan-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: 77058-74-3

Formula: C₂₇H₄₄O₂

Purity: 98%

Color and Shape: Solid

Molecular weight: 400.6371

Ref: IN-DA00G2QO

24,25-Epoxy-Cholesterol

CAS: 77058-74-3

Formula: C27H44O2

Purity: >95%

Color and Shape: Solid

Molecular weight: 400.64

Ref: 48-64-0057

(24S)-24,25-Epoxycholesterol

CAS: 77058-74-3

Formula: C₂₇H₄₄O₂

Molecular weight: 400.65

Ref: 4Z-C-5335

(24S)-24,25-Epoxycholesterol

Controlled Product

CAS: 77058-74-3

Applications (24S)-24,25-Epoxycholesterol is a derivative of 4β-Hydroxy Cholesterol (H917980), a metabolite of Cholesterol. It is formed from Cholesterol by the drug-metabolizing enzyme cytochrome P 450 3A4. A potential ligand for the nuclear receptor LXR and also a new endogenous CYP3A marker.
References Breuer, O., et al.: J. Lipid Res., 36, 2275 (1995), Pikuleva, I., et al.: J. Biol. Chem., 273, 18153 (1998), Chawla, A., et al.: Science, 294, 1866 (2001), Bodin, K., et al.: J. Biol. Chem., 276, 38685 (2001),

Formula: C₂₇H₄₄O₂

Color and Shape: Neat

Molecular weight: 400.637

Ref: TR-E589370

(24S)-24,25-Epoxycholesterol

Controlled Product

CAS: 77058-74-3

(24S)-24,25-Epoxycholesterol is a cholesterol derivative that inhibits the ATP-binding cassette transporter. It has been shown to be effective in inhibiting the replication of HIV and other viruses in human macrophages. (24S)-24,25-Epoxycholesterol also has a high affinity for fatty acids and is metabolized to a reactive intermediate by cytochrome P450 enzymes. The reactive intermediate can then interact with hydrogen bonds in proteins and inhibit their function. This drug is an inhibitor of cyclase enzymes, which are found in fatty acid biosynthesis pathways. The drug may also be used as a treatment for hyperlipidemia.

Formula: C₂₇H₄₄O₂

Purity: Min. 95%

Molecular weight: 400.64 g/mol

Ref: 3D-CDA05874

24(S),25-Epoxycholesterol

CAS: 77058-74-3

24(S),25-Epoxycholesterol is an oxysterol agonist of the liver X receptor.

Formula: C₂₇H₄₄O₂

Color and Shape: Solid

Molecular weight: 400.64

Ref: TM-T71756