| Identification | Back Directory | [Name]
CONVALLATOXIN | [CAS]
508-75-8 | [Synonyms]
Convapur
orglycon
CORGLYKON
Convalpur
corglycon
korglykon
corglycone
NSC 407808
Convallopan
convallaton
0(22)-enolide
convallotoxin
CONVALLATOXIN
Convallatoxine
convallaotoxin
convallatoxoside
CONVALLATOXIN(P)
(3beta,5beta)-oxo
CONVALLATOXIN(RG)
CONVALLATOXIN USP/EP/BP
Convallatoxin (=Corglycon)
strophanthidinalpha-l-rhamnoside
STROPHANTHIN 3ALPHA-1-RHAMNOSIDE
strophanthidin-3,alpha-l-rhamnosid
Strophanthidin α-L-rhamnopyranoside
STROPHANTHIDIN A-L-RHAMNOPYRANOSIDE
STROPHANTHIDIN ALPHA-L-RHAMNOPYRANOSIDE
6-deoxy-strophanthidin-alpha-l-mannopyranosid
strophanthidin,3-(6-deoxy-alpha-l-mannopyranoside)
3-((6-deoxy-alpha-l-mannopyranosyl)oxy)-5,14-dihydroxy-19-card-20(22)-enolid
3β-(α-L-Rhamnopyranosyloxy)-5,14-dihydroxy-19-oxo-5β,14β-carda-20(22)-enolide
3β5α14-Trihydroxy-19-oxo-5β20(22)-cardenolide 3-(6-deoxy-α-L-mannopyranoside)
3beta-[(6-deoxy-alpha-l-mannopyranosyl)oxy]-5,14-dihydroxy-19-oxo-5beta-card-2
3β-[(6-Deoxy-α-L-mannopyranosyl)oxy]-5,14-dihydroxy-19-oxo-5β,14β-card-20(22)-enolide
20(22),5BETA-CARDENOLID-19-AL-3BETA,5BETA,14BETA-TRIOL-3BETA-D-[A-1-RHAMNOPYRANOSIDE]
5BETA,20[22]-CARDENOLIDE-19-ONE-3BETA,5ALPHA,14-TRIOL-3-[6-DEOXY-ALPHA-L-MANNOPYRANOSYL]
Card-20(22)-enolide, 3-[(6-deoxy-α-L-mannopyranosyl)oxy]-5,14-dihydroxy-19-oxo-, (3β,5β)-
3BETA,5ALPHA,14-TRIHYDROXY-19-OXO-5BETA,20[22]-CARDENOLIDE-3-[6-DEOXY-ALPHA-L-MANNOPYRANOSYL]
Strophanthidin α-L-rhamnopyranoside, 3β,5α,14-Trihydroxy-19-oxo-5β,20(22)-cardenolide 3-(6-deoxy-α-L-mannopyranoside)
(5S,10S,13R,14S)-5,14-dihydroxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-3-[(3,4,5-trihydroxy-6-methyl-2-oxanyl)oxy]-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carboxaldehyde | [EINECS(EC#)]
208-086-3 | [Molecular Formula]
C29H42O10 | [MDL Number]
MFCD00069477 | [MOL File]
508-75-8.mol | [Molecular Weight]
550.64 |
| Chemical Properties | Back Directory | [Melting point ]
238-239℃ (water ) | [alpha ]
D22 -1.7 ± 3° (c = 0.65 in methanol); D25 -9.4 ± 3° (c = 0.72 in dioxane) | [Boiling point ]
542°C (rough estimate) | [density ]
1.41±0.1 g/cm3 (20 ºC 760 Torr) | [refractive index ]
1.5376 (estimate) | [storage temp. ]
Store at -20°C | [solubility ]
Soluble in DMSO | [form ]
Solid | [pka]
13.04±0.70(Predicted) | [color ]
White to Off-White | [Merck ]
13,2538 | [Stability:]
Hygroscopic |
| Hazard Information | Back Directory | [Originator]
Convallatoxin,C-Strong Co., Ltd. | [Uses]
Convallatoxin is a cardenolide that is used in the treatment of congestive heart failure. It may also be used in the treatment of tumor cells at nanomolar concentrations due to its anti-proliferative effects | [Definition]
ChEBI: A cardenolide glycoside that consists of strophanthidin having a 6-deoxy-alpha-L-mannopyranosyl (L-rhamnosyl) group attached at position 3. | [Manufacturing Process]
1 part of grinded flowers Convallaria majalis and 12 parts of water was stirred
for 15 hours at ambient temperature. After a filtration and washing with
water, a clear brown filtrate was mixed with a concentrate solution of lead
acetate. A lead consisted precipitate was filtered off and sodium phosphate
was added to filtrate for removing the remaining lead. The solution was
filtered again and 0.5 - 0.6 parts of a coal was added and the mixture was
stirred for 3 hours at ambient temperature. The coal was filtered off, washed
with a little water and dried at 30°-40°C. A hot CHCl3 was added to dry coal
adsorbent. CHCl3 was distilled off to dryness in vacuum. The residue was
dissolved in a little methanol and the obtained solution was shook 3 times
with 2 volumes of petrol ether and then distilled to dryness in vacuum. This
product was dissolved in minimum absolute ethanol and added to 10 volumes
of dry ether. The formed precipitate was filtered and washed with ether to
give the glycoside as a gray powder. It was crystallized from diluted ethanol
as colorless needles. | [Therapeutic Function]
Cardiotonic | [Purification Methods]
Crystallise convallatoxin from EtOAc, CHCl3/EtOH (9:1) or MeOH/Et2O. The tetraacetate has m 238-242o (from MeOH/Et2O), [] D 25 -5o (CHCl3). [Reyle et al. Helv Chim Acta 33 1541 1950, Fieser & Jacobson J Am Chem Soc 59 2335 1937 Beilstein 1 8 III/IV 3142.] |
|
|