Translations:7-Dehydrocholesterol/1/en

7-Dehydrocholesterol/1/en

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
CAS Number	434-16-2 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17759 Y
ChemSpider	388534 Y
MeSH	7-dehydrocholesterol
PubChem CID	172
UNII	BK1IU07GKF Y
InChI 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 Y 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
SMILES 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
Chemical formula	C27H44O
Molar mass	384.638

Tracking categories (test):

• SizeSet

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. 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. It was discovered by Nobel-laureate organic chemist Adolf Windaus.