7-Dehydrocholesterol

"Provitamin D3" redirects here. For the inactive form of vitamin D3 synthesized from 7-dehydrocholesterol, see Cholecalciferol.
7-Dehydrocholesterol
Ball-and-stick model of 7-dehydrocholesterol
Names
IUPAC name
Cholesta-5,7-dien-3β-ol
Systematic IUPAC name
(1R,3aR,7S,9aR,9bS,11aR)-9a,11a-Dimethyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,6,7,8,9,9a,9b,10,11,11a-dodecahydro-1H-cyclopenta[a]phenanthren-7-ol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.456 Edit this at Wikidata
MeSH 7-dehydrocholesterol
UNII
  • InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25+,26+,27-/m1/s1-dehydrocholesterol ☒N
    Key: UCTLRSWJYQTBFZ-DDPQNLDTSA-N checkY
  • InChI=1/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25+,26+,27-/m1/s1
    Key: UCTLRSWJYQTBFZ-DDPQNLDTBZ
  • O[C@@H]4C/C3=C/C=C1\[C@H](CC[C@]2([C@H]1CC[C@@H]2[C@H](C)CCCC(C)C)C)[C@@]3(C)CC4
Properties
C27H44O
Molar mass 384.638
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[1][2] 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.[3] 7-DHC was discovered by Nobel-laureate organic chemist Adolf Windaus.

  1. ^ "7-dehydrocholesterol". The American Heritage Stedman's Medical Dictionary. Houghton Mifflin Company. 21 January 2007.
  2. ^ "7-dehydrocholesterol". Answers.com. Archived from the original on 25 October 2012.
  3. ^ Young E (2012). "Thanks to one gene, this fly needs a cactus to escape Neverland". Not Exactly Rocket Science. Archived from the original on 2012-09-30. Retrieved 2012-09-28.