22-Dihydroergocalciferol

22-Dihydroergocalciferol is a form of vitamin D, also known as vitamin D4.[2] It has the systematic name (5Z,7E)-(3S)-9,10-seco-5,7,10(19)-ergostatrien-3-ol.[1]

Not to be confused with octamethylcyclotetrasiloxane.
22-Dihydroergocalciferol
Names
IUPAC name
(3S,5Z,7E)-9,10-Secoergosta-5,7,10(19)-trien-3-ol
Systematic IUPAC name
(1S,3Z)-3-[(2E)-2-{(1R,3aS,7aR)-1-[(2R,5S)-5,6-Dimethylheptan-2-yl]-7a-methyloctahydro-4H-inden-4-ylidene}ethylidene]-4-methylidenecyclohexan-1-ol
Other names
(5Z,7E)-(3S)-9,10-seco-5,7,10(19)-ergostatrien-3-ol
(24S)-Methylcalciol
22,23-Dihydroercalciol[1]
Vitamin D4
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.007.389
UNII
  • InChI=1S/C28H46O/c1-19(2)20(3)9-10-22(5)26-15-16-27-23(8-7-17-28(26,27)6)12-13-24-18-25(29)14-11-21(24)4/h12-13,19-20,22,25-27,29H,4,7-11,14-18H2,1-3,5-6H3/b23-12+,24-13-/t20-,22+,25-,26+,27-,28+/m0/s1 checkY
    Key: DIPPFEXMRDPFBK-JPWDPSJFSA-N checkY
  • InChI=1/C28H46O/c1-19(2)20(3)9-10-22(5)26-15-16-27-23(8-7-17-28(26,27)6)12-13-24-18-25(29)14-11-21(24)4/h12-13,19-20,22,25-27,29H,4,7-11,14-18H2,1-3,5-6H3/b23-12+,24-13-/t20-,22+,25-,26+,27-,28+/m0/s1
    Key: DIPPFEXMRDPFBK-JPWDPSJFBS
  • O[C@@H]1CC(\C(=C)CC1)=C\C=C2/CCC[C@]3([C@H]2CC[C@@H]3[C@H](C)CC[C@H](C)C(C)C)C
Properties
C28H46O
Molar mass 398.675 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Vitamin D4 is found in certain mushrooms, being produced from ergosta-5,7-dienol (22,23-dihydroergosterol) instead of ergosterol.[3]

See also

References
  1. Nomenclature of Vitamin D Archived 2017-08-23 at the Wayback Machine, IUPAC
  2. Definition of dihydroergocalciferol
  3. Phillips KM, Horst RL, Koszewski NJ, Simon RR (2012). "Vitamin d(4) in mushrooms". PLOS ONE. 7 (8): e40702. Bibcode:2012PLoSO...740702P. doi:10.1371/journal.pone.0040702. PMC 3411670. PMID 22870201.
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