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Previtamin D3

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Previtamin D3
Stereo skeletal formula of previtamin D3 ((1R)-1-ol, (Z)-en, (1R,3aR,7aR)-7a-meth,-1-hept,-3a-hydro, (2R)-2-yl)
Stereo skeletal formula of previtamin D3 ((1R)-1-ol, (Z)-en, (1R,3aR,7aR)-7a-meth,-1-hept,-3a-hydro, (2R)-2-yl)
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
3D model (JSmol)
ChemSpider
  • 78098 checkY
  • 4832524 (E)-en checkY
  • 9660762 (1S)-1-ol, (E)-en, (1R,7aR)-7a-meth,-1-hept, (2R)-2-yl checkY
  • 9375051 (1S)-1-ol, (Z)-en, (1R,7aR)-7a-meth,-1-hept, (2R)-2-yl checkY
ECHA InfoCard100.013.304Edit this at Wikidata
EC Number
  • 241-561-3
MeSHPrevitamin+D(3)
  • 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
  • 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 checkY
    Key: YUGCAAVRZWBXEQ-UHFFFAOYSA-N checkY
  • CC(C)CCCC(C)C1CCC2C(C=CC3=C(C)CCC(O)C3)=CCCC12C
Properties
C27H44O
Molar mass384.648 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

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

It is formed by the action ofUV light, most specifically UVB light of wavelengths between 295 and 300 nm, acting on7-dehydrocholesterol in theepidermal layers of the skin.[1][2][3]

The B ring of thesteroid nucleus structure is broken open, making asecosteroid. This then undergoes spontaneousisomerization into cholecalciferol, theprohormone of the active form of vitamin D,calcitriol.

The synthesis of previtamin D3 is blocked effectively bysunscreens.[4]

Interactive pathway map

[edit]

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

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

References

[edit]
  1. ^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.
  2. ^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.
  3. ^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.
  4. ^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.
Fat
soluble
A
D
E
K (B02B)
Water
soluble
B
C
Combinations
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