4-Dehydroepiandrosterone

4-Dehydroepiandrosterone (4-DHEA) is a steroid that is an isomer of 5-dehydroepiandrosterone.

4-Dehydroepiandrosterone
Skeletal formula of 4-dehydroepiandrosterone
Ball-and-stick model of the 4-dehydroepiandrosterone molecule
Names
IUPAC name
3β-Hydroxyandrost-4-en-17-one
Systematic IUPAC name
(3aS,3bR,7S,9aR,9bS,11aS)-7-Hydroxy-9a,11a-dimethyl-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-1-one
Other names
Androst-4-en-3β-ol-17-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,13-16,20H,3-10H2,1-2H3/t13-,14-,15-,16-,18-,19-/m0/s1 checkY
    Key: VMYTXBKVYDESSJ-USOAJAOKSA-N checkY
  • O=C1CC[C@@]2([H])[C@]3([H])CCC4=C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@@]21C
  • O=C4[C@]3(CC[C@@H]2[C@@]1(C(=C/[C@@H](O)CC1)\CC[C@H]2[C@@H]3CC4)C)C
Properties
C19H28O2
Molar mass 288.431 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

4-DHEA has been prepared by laboratory synthesis.[1][2]

Synonyms

Synonyms for 4-dehydroepiandrosterone are:

3β-Hydroxy-4-androsten-17-one, 3β-hydroxyandrost-4-en-17-one, 3β-hydroxy-D4-androsten-17-one, 3β-hydroxyandrost-4-en-17-one, 3β-hydroxy-etioallocholan-4-en-17-one, and 4-androsten-3β-ol-17-one.

References
  1. Klimstra, Paul D.; Colton, F. B. Synthesis of 3β-hydroxyestr-4-en-17-one and 3β-hydroxyandrost-4-en-17-one. Steroids (1967), 10(4), 411-24.
  2. Ward, Margaret G.; Orr, James C.; Engel, Lewis L. A convenient synthesis of 3β-hydroxyandrost-4-en-17-one. Journal of Organic Chemistry (1965), 30(5), 1421-3.



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