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Previtamin D₃

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Previtamin D₃
Names

IUPAC name (3S,6Z)-9,10-Secocholesta-5(10),6,8-trien-3-ol
Systematic IUPAC name (1S)-4-Methyl-3-[(Z)-2-{(1R,3aR,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl}ethen-1-yl]cyclohex-3-en-1-ol
Other names Previtamin D₃
Identifiers
CAS Number	1173-13-3^Y 17592-07-3^Y
3D model (JSmol)	Interactive image
ChemSpider	78098^Y 4832524 (E)-en^Y 9660762 (1S)-1-ol, (E)-en, (1R,7aR)-7a-meth,-1-hept, (2R)-2-yl^Y 9375051 (1S)-1-ol, (Z)-en, (1R,7aR)-7a-meth,-1-hept, (2R)-2-yl^Y
ECHA InfoCard	100.013.304
EC Number	241-561-3
MeSH	Previtamin+D(3)
PubChem CID	86590 6178113 (E)-en 25245851 (1S)-1-ol, (Z)-en, (2R)-2-yl 11485943 (1S)-1-ol, (E)-en, (1R,7aR)-7a-meth,-1-hept, (2R)-2-yl 11199982 (1S)-1-ol, (Z)-en, (1R,7aR)-7a-meth,-1-hept, (2R)-2-yl
UNII	HDA46400N5^Y 6RR0I9PK8W^Y
InChI InChI=1S/C27H44O/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-27(25,26)5)12-13-23-18-24(28)14-11-20(23)3/h10,12-13,19,21,24-26,28H,6-9,11,14-18H2,1-5H3^Y Key: YUGCAAVRZWBXEQ-UHFFFAOYSA-N^Y
SMILES CC(C)CCCC(C)C1CCC2C(C=CC3=C(C)CCC(O)C3)=CCCC12C
Properties
Chemical formula	C₂₇H₄₄O
Molar mass	384.648 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Previtamin D₃ is an intermediate in the production of cholecalciferol (vitamin D₃).

It is formed by the action of UV light, most specifically UVB light of wavelengths between 295 and 300 nm, acting on 7-dehydrocholesterol in the epidermal layers of the skin.^[1]^[2]^[3]

The B ring of the steroid nucleus structure is broken open, making a secosteroid. This then undergoes spontaneous isomerization into cholecalciferol, the prohormone of the active form of vitamin D, calcitriol.

The synthesis of previtamin D₃ is blocked effectively by sunscreens.^[4]

Interactive pathway map

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Click on genes, proteins and metabolites below to link to respective articles. ^{[§ 1]}

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|alt=Vitamin D Synthesis Pathway (view / edit)]]

Vitamin D Synthesis Pathway (view / edit)

^ The interactive pathway map can be edited at WikiPathways: "VitaminDSynthesis_WP1531".

References

[edit]

^ MacLaughlin JA, Anderson RR, Holick MF (May 1982). "Spectral character of sunlight modulates photosynthesis of previtamin D3 and its photoisomers in human skin". Science. 216 (4549): 1001–3. Bibcode:1982Sci...216.1001M. doi:10.1126/science.6281884. PMID 6281884.

^ Webb AR (September 2006). "Who, what, where and when-influences on cutaneous vitamin D synthesis". Progress in Biophysics and Molecular Biology. 92 (1): 17–25. doi:10.1016/j.pbiomolbio.2006.02.004. PMID 16766240.

^ Pope SJ, Holick MF, Mackin S, Godar DE (2008). "Action spectrum conversion factors that change erythemally weighted to previtamin D3-weighted UV doses". Photochemistry and Photobiology. 84 (5): 1277–83. doi:10.1111/j.1751-1097.2008.00373.x. PMID 18513232. S2CID 23246616.

^ Sayre RM, Dowdy JC (2007). "Darkness at noon: sunscreens and vitamin D3". Photochemistry and Photobiology. 83 (2): 459–63. doi:10.1562/2006-06-29-RC-956. PMID 17115796. S2CID 23767593.

Vitamins (A11)

Fat
soluble

A	α-Carotene β-Carotene Retinol^# Tretinoin^#
D	D₂ Ergosterol Ergocalciferol^# D₃ 7-Dehydrocholesterol Previtamin D₃ Cholecalciferol^# 25-hydroxycholecalciferol Calcitriol (1,25-dihydroxycholecalciferol) Calcitroic acid D₄ Dihydroergocalciferol D₅ D analogues Alfacalcidol Dihydrotachysterol Calcipotriol Tacalcitol Paricalcitol
E	Tocopherol Alpha Beta Gamma Delta Tocotrienol Alpha Beta Gamma Delta Tocofersolan
K	Naphthoquinone Phylloquinone (K₁)^# Menaquinones (K₂) Menadione (K₃)^‡ Various (K₄) 4-Amino-2-methyl-1-naphthol (K₅)^‡ 2-Methylnaphthalene-1,4-diamine (K₆) 4-Amino-3-methyl-1-naphthol (K₇)

Water
soluble

Combinations

Multivitamins

^#WHO-EM

^‡Withdrawn from market

Clinical trials:

^†Phase III
^§Never to phase III

This organic chemistry article is a stub. You can help Wikipedia by expanding it.

Retrieved from "https://en.wikipedia.org/w/index.php?title=Previtamin_D3&oldid=1234921930" Categories: ●Vitamin D ●Secosteroids ●Indanes ●Secondary alcohols ●Cyclohexenols ●Organic chemistry stubs Hidden categories: ●Chemical articles with multiple compound IDs ●Multiple chemicals in an infobox that need indexing ●Chemical articles with multiple CAS registry numbers ●Chemical articles with multiple PubChem CIDs ●Articles without InChI source ●Articles without EBI source ●Articles without KEGG source ●ECHA InfoCard ID from Wikidata ●Articles containing unverified chemical infoboxes ●Articles with short description ●Short description matches Wikidata ●All stub articles ●This page was last edited on 16 July 2024, at 20:36 (UTC). ●Text is available under the Creative Commons Attribution-ShareAlike License 4.0; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization. ●Privacy policy ●About Wikipedia ●Disclaimers ●Contact Wikipedia ●Code of Conduct ●Developers ●Statistics ●Cookie statement ●Mobile view