Digitoxigenin

Title: Digitoxigenin
CAS Registry Number: 143-62-4
CAS Name: (3b,5b)-3,14-Dihydroxycard-20(22)-enolide
Additional Names: D20:22-3,14,21-trihydroxynorcholenic acid lactone; cerberigenin; echujetin; evonogenin
Trademarks: Thevetigenin
Molecular Formula: C23H34O4
Molecular Weight: 374.51
Percent Composition: C 73.76%, H 9.15%, O 17.09%
Literature References: The aglycon of digitoxin, thevetin, cerberin, echujin, evomonosid. Prepn by refluxing digitoxin in a mixture of water + alcohol + HCl: Cloetta, Arch. Exp. Pathol. Pharmakol. 88, 113 (1920); Stoll, Kreiss, Helv. Chim. Acta 17, 592 (1934). Structure: Jacobs, Hoffmann, J. Biol. Chem. 67, 333 (1926); Jacobs, Gustus, ibid. 78, 573; 79, 533 (1928); 82, 402 (1929); Jacobs, Elderfield, ibid. 108, 497 (1935); Elderfield, Chem. Rev. 17, 187 (1935). Stereochemistry: Meyer, Helv. Chim. Acta 30, 1976 (1947). Synthesis: Danieli et al., Tetrahedron 22, 3189 (1966); W. Fritsch et al., Ann. 1974, 621; S. F. Donovan et al., Tetrahedron Lett. 1979, 3287; R. Marinibettolo et al., Can. J. Chem. 59, 1403 (1981); T. Milkova et al., Tetrahedron Lett. 23, 413 (1982). Biosynthesis from neriifolin, q.v.: A. Cruz et al., J. Org. Chem. 42, 3580 (1977).
Properties: Stout prisms from 40% alc, mp 253°. [a]D17 +19.1° (c = 1.36 in methanol). Sol in alc, chloroform, acetone; slightly sol in ethyl acetate; very sparingly sol in ether, water.
Melting point: mp 253°
Optical Rotation: [a]D17 +19.1° (c = 1.36 in methanol)
Derivative Type: 3-Acetyldigitoxigenin
Molecular Formula: C25H36O5
Molecular Weight: 416.55
Percent Composition: C 72.08%, H 8.71%, O 19.20%
Properties: Hexagonal plates from acetone + ether, mp 222-227°. [a]D17 +21.4° (c = 1.02 in chloroform).
Melting point: mp 222-227°
Optical Rotation: [a]D17 +21.4° (c = 1.02 in chloroform)
Digitoxin Digitoxose Diglyme Digoxigenin Dihexyverine

Digitoxigenin[1]
Digitoxigenin.png
Identifiers
CAS number 143-62-4
PubChem 4369270
ChemSpider 3571902
EC-number 205-603-4
ChEMBL CHEMBL1453
RTECS number FH4975000
Beilstein Reference 95448
Jmol-3D images Image 1
Properties
Molecular formula C23H34O4
Molar mass 374.51
Appearance solid[2]
Melting point 252-253 C[2]
Hazards
R-phrases Toxic if swallowed
S-phrases In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
Main hazards Toxic
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Digitoxigenin is cardenolide, obtained especially by hydrolysis of digitoxin[3] (refluxing digitoxin in a mixture of water, alcohol, and hydrochloric acid[4]), which is the aglycon of digitoxin.[5]