Digitoxigenin

Digitoxigenin, a cardenolide, is the aglycone of digitoxin.

Digitoxigenin[1]

Names
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
CAS Number	143-62-4^Y
3D model (JSmol)	Interactive image
Beilstein Reference	95448
ChEMBL	ChEMBL1453
ChemSpider	3571902
ECHA InfoCard	100.005.095
EC Number	205-603-4
PubChem CID	4369270
RTECS number	FH4975000
UNII	S63WOD4VOL^Y
CompTox Dashboard (EPA)	DTXSID80162276
InChI 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
SMILES 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
Chemical formula	C23H34O4
Molar mass	374.51
Appearance	solid
Melting point	252 to 253 °C (486 to 487 °F; 525 to 526 K)
Hazards
Main hazards	Toxic
R-phrases (outdated)	Toxic if swallowed
S-phrases (outdated)	In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
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.