7-Dehydrocholesterol

File:Skinlayers.png

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.<ref>Template:Cite book</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> 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.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> 7-DHC was discovered by Nobel-laureate organic chemist Adolf Windaus.

Biosynthesis

It is synthesized from lathosterol by the enzyme lathosterol oxidase (lathosterol 5-desaturase). This is the next-to-last step of cholesterol biosynthesis.<ref name="pmid12812989">Template:Cite journal</ref> Defective synthesis results in the human inherited disorder lathosterolosis resembling Smith–Lemli–Opitz syndrome.<ref name="pmid12812989"/> Mice where this gene has been deleted lose the ability to increase vitamin D₃ in the blood following UV exposure of the skin.<ref name="pmid28330720">Template:Cite journal</ref>

Location

The skin consists of two primary layers: an inner layer, the dermis, comprising largely connective tissue, and an outer, thinner epidermis. The thickness of the epidermis ranges from 0.04 mm to greater than 0.6 mm.<ref>Template:Cite journal</ref> The epidermis comprises five strata; from outer to inner, they are the stratum corneum, stratum lucidum, stratum granulosum, stratum spinosum, and stratum basale. The highest concentrations of 7-dehydrocholesterol are found in the epidermal layer of skin—specifically in the stratum basale and stratum spinosum.<ref name="Norman_1998">Template:Cite journal</ref> The production of pre-vitamin D₃ is, therefore, greatest in these two layers.

Radiation

Synthesis of pre-vitamin D₃ in the skin involves UVB radiation, which effectively penetrates only the epidermal layers of skin. 7-Dehydrocholesterol absorbs UV light most effectively at wavelengths between 295 and 300 nm and, thus, the production of vitamin D₃ will occur primarily at those wavelengths.<ref name="pmid6281884">Template:Cite journal</ref> 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.<ref name = "Norman_1998" /> Light-emitting diodes (LEDs) can be used to produce the radiation.<ref name="pmid28904394">Template:Cite journal</ref>

Another important consideration is the quantity of 7-dehydrocholesterol present in the skin. Under normal circumstances, ample quantities of 7-dehydrocholesterol (about 25–50 μg/cm² of skin) are available in the stratum spinosum and stratum basale of human skin to meet the body's vitamin D requirements. 7-DHC insufficiency has been proposed as an alternate cause for Vitamin D deficiency.<ref name=whackjob>Template:Cite journal</ref>

Sources

7-DHC can be produced by animals and plants via different pathways. It is not produced by fungi in significant amounts. It is made by some algae, but the pathway is poorly understood.<ref>Template:Cite journal</ref>

Industrially, 7-DHC generally comes from lanolin, and is used to produce vitamin D3 by UV exposure.<ref name="Holick05">Template:Cite journal</ref> Lichen (Cladonia rangiferina) is used to produce vegan D3.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>Template:Cite journal</ref>

7-DHC is used for vitamin D3 synthesis via lanosterol in land animals, via cycloartenol in plants, and in algae together with another provitamin D ergosterol for D2. In fungi solely ergosterol is used for synthesis of D2 via lanosterol.<ref>Template:Cite journal</ref>

See also

• Vitamin D
• Smith–Lemli–Opitz syndrome
• 7-Dehydrocholesterol reductase