CAS 70741-38-7

8-Dehydrocholesterol

Description:

8-Dehydrocholesterol is a sterol compound that serves as a precursor in the biosynthesis of cholesterol and vitamin D3 in the human body. It is characterized by its molecular structure, which includes a steroid nucleus with a double bond at the 8th position, distinguishing it from cholesterol. This compound is typically found in the skin and is involved in the photoconversion process when exposed to ultraviolet light, leading to the formation of vitamin D3. 8-Dehydrocholesterol is a white to off-white crystalline solid, and it is soluble in organic solvents such as ethanol and chloroform but has limited solubility in water. Its chemical formula reflects its complex structure, which includes multiple rings and functional groups typical of sterols. In terms of biological significance, it plays a crucial role in maintaining cellular functions and is also studied for its potential implications in various health conditions, including skin disorders and metabolic diseases. Proper handling and storage are essential due to its sensitivity to light and heat.

Formula: C₂₇H₄₄O

InChI: InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9,18-19,21,23-24,28H,6-8,10-17H2,1-5H3/t19-,21+,23-,24+,26+,27-/m1/s1

InChI key: InChIKey=VUKORTMHZDZZFR-BXAZICILSA-N

SMILES: C[C@@]12[C@](C3=C([C@]4(C)C(=CC3)C[C@@H](O)CC4)CC1)(CC[C@@]2([C@@H](CCCC(C)C)C)[H])[H]

Synonyms:

• (3β)-Cholesta-5,8-dien-3-ol
• 70741-38-7
• 8,9-Dehydrocholesterol
• 8-Dehydrocholesterol
• Cholesta-5,8-dien-3-ol, (3β)-
• Cholesta-5,8-dien-3β-ol

8-Dehydro Cholesterol

CAS: 70741-38-7

Formula: C₂₇H₄₄O

Molecular weight: 384.65

Ref: 4Z-C-5381

8-Dehydrocholesterol

CAS: 70741-38-7

Applications 8-Dehydrocholesterol is an intermediate in the synthesis of Zymostenol, which is the derivative of Zymosterol (Z701520), an sterol intermediate in the biosynthesis of cholesterol (C432501).
References Roland, E.D., et al.: J. Am. Chem. Soc., 111, 278 (1989); Echevarria, F., et al.: J. Biol. Chem., 265, 8484 (1990); Baranovskii, A.V., et al.: Russian. J. Bioorg. Chem., 28, 250 (2002); Schoenheimer, et al.: J. Biol. Chem., 105, 355 (1934);

Formula: C₂₇H₄₄O

Color and Shape: Neat

Molecular weight: 384.64

Ref: TR-D230295

8(9)-dehydrocholesterol

Controlled Product

CAS: 70741-38-7

8(9)-dehydrocholesterol is a cholesterol precursor that can be synthesized by the liver. It is an intermediate in the synthesis of cholesterol and bile acids. 8(9)-Dehydrocholesterol has been found to have high levels of activity against cerebrotendinous xanthomatosis, which is a rare genetic disorder that causes neurological problems and skin lesions. 8(9)-Dehydrocholesterol is also used as a diagnostic marker for this disease. This molecule has been shown to have some biochemical abnormalities, such as high values of creatine kinase, which are associated with fatty acid oxidation disorders.

Formula: C₂₇H₄₄O

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 384.64 g/mol

Ref: 3D-VCA74138

8-Dehydrocholesterol

CAS: 70741-38-7

8-Dehydrocholesterol is a compound whose elevated concentration is a diagnostic biochemical hallmark of classical Smith-Lemli-Opitz syndrome.

Formula: C₂₇H₄₄O

Color and Shape: Solid

Molecular weight: 384.648

Ref: TM-T19164