30800

7-Dehydrocholesterol

≥95.0% (HPLC)

• Synonym(s): (−)-7-Dehydrocholesterol, 3β-Hydroxy-5,7-cholestadiene, 5,7-Cholestadien-3β-ol, Provitamin D₃
• Empirical Formula (Hill Notation): C₂₇H₄₄O
• CAS Number: 434-16-2
• Molecular Weight: 384.64
• NACRES: NA.79
• PubChem Substance ID: 57648485
• eCl@ss: 39023139
• UNSPSC Code: 12352211
• EC Number: 207-100-5
• MDL number: MFCD00003624
• Beilstein/REAXYS Number: 2224615

Properties

• biological source: synthetic
• Quality Segment: 100
• assay: ≥95.0% (HPLC)
• form: powder or crystals
• optical activity: [α]20/D -115±8°, c = 1% in chloroform
• color: white to faint yellow
• mp: 148-152 °C (lit.)
• storage temp.: −20°C
• SMILES string: [H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C
• 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/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25+,26+,27-/m1/s1
• InChI key: UCTLRSWJYQTBFZ-DDPQNLDTSA-N

Description

General description

7-Dehydrocholesterol (7-DHC), a 5,7-conjugated diene sterol is a biosynthetic precursor of cholesterol. It helps in the production of vitamin D₃ when exposed to ultraviolet B (UVB) radiation.

Application

7-Dehydrocholesterol has been used as an internal standard to determine sterols.

Biochem/physiol Actions

Down-regulates cholesterol biosynthesis in cultured Smith-Lemi-Opitz syndrome skin fibroblasts.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)