Digitoxigenin

Digitoxigenin, a cardenolide, is the aglycone of digitoxin.

Digitoxigenin[1]
Names
IUPAC name
3β,14-Dihydroxy-5β-card-20(22)-enolide
Systematic IUPAC name
4-[(1R,3aS,3bR,5aR,7S,9aS,9bS,11aR)-5a,7-Dihydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]furan-2(5H)-one
Other names
3-β,14-dihydroxy-5-β,14-β-card-20(22)-enolide
5β-Card-20(22)-enolide, 3β,14-dihydroxy-
Card-20(22)-enolide, 3,14-dihydroxy-, (3β,5β)-
NSC 407806
Δ20:22-3,14,21-Trihydroxynorcholenic acid lactone
cerberigenin
echujetin
evonogenin
thevetigenin
Identifiers
3D model (JSmol)
95448
ChEMBL
ChemSpider
ECHA InfoCard 100.005.095
EC Number
  • 205-603-4
RTECS number
  • FH4975000
UNII
  • InChI=1S/C23H34O4/c1-21-8-5-16(24)12-15(21)3-4-19-18(21)6-9-22(2)17(7-10-23(19,22)26)14-11-20(25)27-13-14/h11,15-19,24,26H,3-10,12-13H2,1-2H3/t15-,16+,17-,18+,19-,21+,22-,23+/m1/s1
    Key: XZTUSOXSLKTKJQ-CESUGQOBSA-N
  • InChI=1/C23H34O4/c1-21-8-5-16(24)12-15(21)3-4-19-18(21)6-9-22(2)17(7-10-23(19,22)26)14-11-20(25)27-13-14/h11,15-19,24,26H,3-10,12-13H2,1-2H3/t15-,16+,17-,18+,19-,21+,22-,23+/m1/s1
    Key: XZTUSOXSLKTKJQ-CESUGQOBBG
  • O=C/1OCC(=C\1)\[C@@H]2[C@@]4([C@](O)(CC2)[C@@H]5CC[C@@H]3C[C@@H](O)CC[C@]3(C)[C@H]5CC4)C
Properties
C23H34O4
Molar mass 374.51
Appearance solid
Melting point 252 to 253 °C (486 to 487 °F; 525 to 526 K)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Digitoxigenin can be used to prepare actodigin.[2]

In Lednicer's book on steroids, it is made from deoxycholic acid.

References
  1. http://www.sigmaaldrich.com/catalog/ProductDetail.do?N4=D9404%7CSIGMA&N5=SEARCH_CONCAT_PNO%7CBRAND_KEY&F=SPEC
  2. Ferland, J. M. (1974). "Synthetic Cardenolides and Related Products. III. Isocardenolides". Canadian Journal of Chemistry. 52 (9): 1652–1661. doi:10.1139/v74-239. ISSN 0008-4042.


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