Showing metabocard for 7-Dehydrocholesterol (MMDBc0049997)
| Record Information | |
|---|---|
| Version | 1.0 |
| Status | Detected and Quantified |
| Creation Date | 2022-04-29 23:10:04 UTC |
| Update Date | 2024-10-17 07:33:11 UTC |
| Metabolite ID | MMDBc0049997 |
| Metabolite Identification | |
| Common Name | 7-Dehydrocholesterol |
| Description | 7-Dehydrocholesterol (7-DHC), also known as provitamin D3 or 5,7-cholestadien-3-b-ol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 7-dehydrocholesterol is also classified as a sterol. 7-Dehydrocholesterol is known as a zoosterol, meaning that it is a sterol isolated from animals (to distinguish those sterols isolated from plants which are called phytosterols). 7-DHC functions in the serum as a cholesterol precursor and is photochemically converted to vitamin D3 in the skin. Therefore 7-DHC functions as provitamin-D3. The presence of 7-DHC in human skin enables humans and other mammals to manufacture vitamin D3 (cholecalciferol) from ultraviolet rays in the sun light, via an intermediate isomer pre-vitamin D3. 7-DHC absorbs UV light most effectively at wavelengths between 290 and 320 nm and, thus, the production of vitamin D3 will occur primarily at those wavelengths (PMID: 9625080 ). The two most important factors that govern the generation of pre-vitamin D3 are the quantity (intensity) and quality (appropriate wavelength) of the UVB irradiation reaching the 7-dehydrocholesterol deep in the stratum basale and stratum spinosum (PMID: 9625080 ). 7-DHC is also found in the milk of several mammalian species, including cows (PMID: 10999630 ; PMID: 225459 ). It was discovered by Nobel-laureate organic chemist Adolf Windaus. 7-DHC can be produced by animals and plants via different pathways (PMID: 23717318 ). It is not produced by fungi in significant amounts. 7-DHC is made by some algae and can also be produced by some bacteria. |
| Structure |  |
| Synonyms | Not Available |
| Molecular Formula | C27H44O |
| Average Mass | 384.6377 |
| Monoisotopic Mass | 384.33921603 |
| IUPAC Name | Not Available |
| Traditional Name | Not Available |
| CAS Registry Number | 434-16-2 |
| SMILES | Not Available |
| InChI Identifier | 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 |
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