7-Dehydrocholesterol (Provitamin D₃, CAS 434-16-2) is a naturally occurring sterol and the immediate biosynthetic precursor to vitamin D₃ (cholecalciferol). Structurally, 7-Dehydrocholesterol is a cholesterol derivative differing from cholesterol by the presence of an additional double bond at the C7 position of the B-ring of the steroid nucleus, forming a conjugated diene system between C5 and C7.
7-Dehydrocholesterol is a natural sterol and the biological precursor to vitamin D₃, playing an essential role in human vitamin D biosynthesis . The conjugated diene group of 7-Dehydrocholesterol absorbs UV radiation in the wavelength range of 250-310 nm, leading to the opening of the B-ring of the steroid nucleus and the formation of provitamin D₃ . 7-Dehydrocholesterol is synthesized in the skin from cholesterol and transported to the skin surface, where exposure to UVB radiation converts it to an activated form of the vitamin precursor (cholecalciferol) . In addition to its role in vitamin D biosynthesis, 7-Dehydrocholesterol serves as a critical intermediate in the synthesis of various steroid hormones and bile acids, and is used as a reference standard in pharmaceutical analysis for vitamin D-related compounds .
Product Parameters
Parameter
Specification
Product Name
7-Dehydrocholesterol
CAS Number
434-16-2
Molecular Formula
C₂₇H₄₄O
Molecular Weight
384.64 g/mol
Appearance
White to off-white to faint yellow powder or crystals
Melting Point
148-152 °C (lit.)
pKa
14.91 ± 0.70 (predicted)
LogP
9.460 (est)
Stability
Light sensitive
Storage Condition
−20 °C
Bioactivity
7-Dehydrocholesterol (7-DHC) is a 5,7-conjugated diene sterol and a biosynthetic precursor of cholesterol. When exposed to ultraviolet B (UVB) radiation, it contributes to the production of vitamin D3.
Synthetic Route
Isolated and extracted from pig skin, it can also be prepared from cholesterol via esterification, bromination, elimination and hydrolysis.
Application
1. An important intermediate for the synthesis of vitamin D3;
2. Additives in skin care and sun protection cosmetics;
3. Internal standard for sterol determination;
4. Other laboratory reagents.
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From vitamin D synthesis to quality control testing, Cosperpharm provides the high-quality sterol reference materials you need. Contact us today to discuss your 7-Dehydrocholesterol requirements.
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