Previtamin D3

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

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
3D model (JSmol)
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)
  • 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 Y
    Key: YUGCAAVRZWBXEQ-UHFFFAOYSA-N Y
  • CC(C)CCCC(C)C1CCC2C(C=CC3=C(C)CCC(O)C3)=CCCC12C
Properties
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

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.

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.

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