7-dehydrocholesterol
Also known as (3beta)-cholesta-5,7-dien-3-ol, 5,7-cholestadien-3beta-ol, 5,7-cholestadien-3-beta-ol, (1S,2R,5S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol, 7DHC, (-)-7-dehydrocholesterol, (3β)-7-dehydrocholesterol, (3β)-cholesta-5,7-dien-3-ol
thumb|250px|right|The epidermal strata of the skin
Chemical data
- Formula
- C27H44O
- Molecular weight
- 384.6 g/mol
- IUPAC name
- (3S,9S,10R,13R,14R,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
- SMILES
- C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3C2=CC=C4[C@@]3(CC[C@@H](C4)O)C)C
- InChIKey
- UCTLRSWJYQTBFZ-DDPQNLDTSA-N
- XLogP
- 8
- Polar surface area
- 20.2 Ų
- H-bond donors
- 1
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Research
1,474 papers~4 min read
Article
7 sectionsContents
- Biosynthesis
- Location
- Radiation
- Sources
- Interactive pathway map
- See also
- References
thumb|250px|right|The epidermal strata of the skin
7-Dehydrocholesterol (7-DHC) is a zoosterol that functions in the serum as a cholesterol precursor, and is photochemically converted to vitamin D3 in the skin, therefore functioning as provitamin-D3. The presence of this compound in human skin enables humans to manufacture vitamin D3 (cholecalciferol). Upon exposure to ultraviolet UV-B rays in the sun light, 7-DHC is converted into vitamin D3 via previtamin D3 as an intermediate isomer. It is also found in the milk of several mammalian species. Lanolin, a waxy substance that is naturally secreted by wool-bearing mammals, contains 7-DHC which is converted into vitamin D by sunlight and then ingested during grooming as a nutrient. In insects 7-dehydrocholesterol is a precursor for the hormone ecdysone, required for reaching adulthood. 7-DHC was discovered by Nobel-laureate organic chemist Adolf Windaus.