| Identification | Back Directory | [Name]
DIGITONIN | [CAS]
11024-24-1 | [Synonyms]
DIGITIN
DIGITONIN
DigitoninGr
5% Digitonin
Digitonin USP
Digitonin, AR
DIGITONIN(RG)
DIGITONIN TECH
Digitonin ,50%
yl-(1.fwdarw.4)-
Digitonin,Digitin
galactopyranoside]
DIGITONIN CRYSTALLINE
Digitonin, High Purity
DIGITONIN WATER SOLUBLE
DIGITONIN,CRYSTAL,REAGENT
DIGITONINANALYTICAL GRADE
DIGITONIN, ALCOHOL-SOLUBLE
Digitonin, approx. 50% (TLC)
Digitonin, approx. 50% (TLC) 5GR
Digitonin, approx. 50% (TLC) 500MG
DIGITONIN, USED AS NON-IONIC DETERGE
Digitonin, approx. 50%, water soluble
DIGITONIN WATER SOLUBLERESEARCH GRADE
(1→3)]-O-β-D-glucopyranosyl-(1→4)- β-D-
DIGITONIN (DIGITIN) HIGH PURITY RECEPTOR SOLUBILIZING
beta-d-galactopyranoside,(2alpha,3beta,5alpha,15beta,25theta)-2,15-dihyd
roxyspirostan-3-ylo-beta-d-glucopyranosyl-(1.fwdarw.3)-o-beta-d-galactopyran
osyl-(1.fwdarw.2)-o-[beta-d-xylopyranosyl-(1.fwdarw.3)]-o-beta-d-glucopyranos
2α,3β,5α,15β,25R)-2,15-dihydroxyspirostan-3-yl-O-β-D-glucopyranosyl-1β-D-Galactopyranoside
Digitogenin,3-[O-β-D-glucopyranosyl-(1→3)-O-β-D-galactopyranosyl-(1→2)-O-[β-D-xylopyranosyl-
(2.alpha.,3.beta.,5.alpha.,15.beta.,25R)-2,15-dihydroxyspirostan-3-ylO-.beta.-D-glucopyranosyl-(1.beta.-D-Galactopyranoside
(2.alpha.,3.beta.,5.alpha.,15.beta.,25R)-2,15-dihydroxyspirostan-3-yl O-.beta.-D-glucopyranosyl-(1 .beta.-D-Galactopyranoside
[(25R)-2α,15β-Dihydroxy-5α-spirostan-3β-yl]4-O-[2-O-[3-O-(β-D-glucopyranosyl)-β-D-galactopyranosyl]-3-O-(β-D-xylopyranosyl)-β-D-glucopyranosyl]-β-D-galactopyranoside
25R,5ALPHA-SPIROSTAN-2ALPHA,3BETA,15BETA-TRIOL 3BETA-O-BETA-D-GALACTOPYRANOSYL-(1->3)-O-BETA-D-GALACTYOPYRANOSYL-(1->2)-O-BETA-D-[3-O-BETA-D-XYLOPYRANOSYL]-(1->4)-O-BETA-D-GALACTOPYRANOSIDE
beta.-D-Galactopyranoside, (2.alpha.,3.beta.,5.alpha.,15.beta.,25R)-2,15-dihydroxyspirostan-3-yl O-.beta.-D-glucopyranosyl-(1?3)-O-.beta.-D-galactopyranosyl-(1?2)-O-.beta.-D-xylopyranosyl-(1?3)-O-.beta.-D-glucopyranosyl-(1?4)- | [EINECS(EC#)]
234-255-6 | [Molecular Formula]
C56H92O29 | [MDL Number]
MFCD00077729 | [MOL File]
11024-24-1.mol | [Molecular Weight]
1229.31 |
| Chemical Properties | Back Directory | [Appearance]
white crystalline powder | [Melting point ]
230-240 °C (dec.)(lit.)
| [alpha ]
D20 -54° (0.45 g in 15.8 ml methanol) | [Boiling point ]
788.4°C (rough estimate) | [density ]
1.1421 (rough estimate) | [refractive index ]
-52 ° (C=1, EtOH) | [storage temp. ]
Store at RT. | [solubility ]
H2O: 10 mg/mL at 95 °C hot, clear, colorless
| [form ]
White powder | [pka]
12.68±0.70(Predicted) | [color ]
white
| [biological source]
plant seeds (Digitalis purpurea) | [optical activity]
[α]20/D 54°, c = 2.8 in methanol(lit.) | [Water Solubility ]
H2O: ~5% (w/v) (solubilized by heating to 95 °C - 98 °C and then cooling to room temp.) | [Merck ]
14,3161 | [BRN ]
78654 | [Stability:]
Hygroscopic | [InChIKey]
FAAZZWIYYDUONB-JYIJKGCVSA-N | [EPA Substance Registry System]
Digitonin (11024-24-1) |
| Hazard Information | Back Directory | [Chemical Properties]
white crystalline powder | [Uses]
enhances membrane permeability | [Uses]
Natural surfactant useful for receptor solubilization and cell permeabilization, e.g., blood platelets, hepatocytes, yeast or tumor cells | [Uses]
Clinical reagent (cholesterol determination). | [General Description]
Crystals or white powder. | [Air & Water Reactions]
Forms soapy aqueous suspension . | [Reactivity Profile]
DIGITONIN is incompatible with strong oxidizing agents and strong acids. (NTP, 1992 | [Fire Hazard]
Flash point data for DIGITONIN are not available; however, DIGITONIN is probably combustible. | [Biological Activity]
Digitonin plays a key role in permeabilizing cell membranes. It is capable of lysing eukaryotic cells but not bacterial membranes. It is also used to solubilize membrane components. It helps to create pores by interacting specifically with cholesterol in the membrane. It is preferred in biotechnology due to its mild detergency. This membrane-active compound act with doxorubicin against multi-drug resistant cancer cells. | [Purification Methods]
This digitoxin hexa-glycoside can be recrystallised from aqueous 85% EtOH or MeOH/diethyl ether. It is purified by preparative paper chromatography and developed with the upper phase of a mixture of nBuOH/H2O/AcOH (4:5:1), and the spot (RF 0.36) is eluted with 25% CCl3CO2H in CHCl3. It has also been purified by countercurrent distribution. It forms an ethanolate, and complexes with cholesterol and other sterols. [Ruhenstroth-Bauer & Breitenfeld Hoppe Seyler's Z Physiol Chem 302 111 1955, Grisvold J Am Pharm Assoc 23 664 1934, Beilstein 19 IV 1243.] |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
23/24/25 | [Safety Statements ]
22-28-36/37-45 | [RIDADR ]
UN 3462 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
IH2050050
| [F ]
3-10 | [HazardClass ]
6.1(a) | [PackingGroup ]
II | [HS Code ]
29389090 | [Safety Profile]
Poison by ingestion,
intravenous, intraperitoneal, and
subcutaneous routes. Mutation data
reported. See also DIGITALIS. When
heated to decomposition it emits acrid
smoke and irritating fumes. |
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