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Merck
CN

O9640

Sigma-Aldrich

Oleandrin

≥98% (HPLC)

Synonym(s):

5β,20(22)-Cardenolide-3β,14,16β-triol-3-([2,6-dideoxy-3-O-methyl-α-L-arabinohexopyranosyl]oxy) 16-acetate, Corrigen, Foliandrin, Folinerin, Neriol, Neriolin, Neriostene

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About This Item

Empirical Formula (Hill Notation):
C32H48O9
CAS Number:
465-16-7
Molecular Weight:
576.72
EC Number:
207-361-5
UNSPSC Code:
12352200
PubChem Substance ID:
329818943

Key Documents

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Assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: >20 mg/mL

storage temp.

room temp

SMILES string

CO[C@H]1C[C@@H](O[C@@H](C)[C@@H]1O)O[C@H]2CC[C@@]3(C)C(CCC4C3CC[C@]5(C)[C@H]([C@H](C[C@]45O)OC(C)=O)C6=CC(=O)OC6)C2

InChI

1S/C32H48O9/c1-17-29(35)24(37-5)14-27(39-17)41-21-8-10-30(3)20(13-21)6-7-23-22(30)9-11-31(4)28(19-12-26(34)38-16-19)25(40-18(2)33)15-32(23,31)36/h12,17,20-25,27-29,35-36H,6-11,13-16H2,1-5H3/t17-,20+,21-,22-,23+,24-,25-,27-,28-,29-,30-,31+,32-/m0/s1

InChI key

JLPDBLFIVFSOCC-XYXFTTADSA-N

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Biochem/physiol Actions

Cardiac glycoside, inhibits Na(+)/K(+) ATPase; potent carcinostatic cardiac glycoside.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H300 + H330,H373

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - STOT RE 2

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
010M47021
010M4702

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Amitava Dasgupta et al.
Annals of clinical biochemistry, 44(Pt 5), 485-487 (2007-09-01)
Oleander poisoning is common in the southern parts of the United States as well as part of Europe and South East Asia. The fluorescence polarization immunoassay (FPIA) for digoxin cross-reacts with oleandrin, the major poison of oleander extract and can
Steffen Frese et al.
Cancer research, 66(11), 5867-5874 (2006-06-03)
Tumor necrosis factor (TNF)-related apoptosis-inducing ligand (Apo2L/TRAIL) belongs to the TNF family known to transduce their death signals via cell membrane receptors. Because it has been shown that Apo2L/TRAIL induces apoptosis in tumor cells without or little toxicity to normal
J Pietsch et al.
International journal of legal medicine, 119(4), 236-240 (2005-05-21)
The study presents a case of non-fatal poisoning with oleander blooms in a 47-year-old female, with emphasis on the importance of toxicological service in a clinical emergency. After repeated vomiting at home, the patient was admitted at the hospital with
Robert A Newman et al.
Integrative cancer therapies, 6(4), 354-364 (2007-12-01)
Lipid-soluble cardiac glycosides such as bufalin, oleandrin, and digitoxin have been suggested as potent agents that might be useful as anticancer agents. Past research with oleandrin, a principle cardiac glycoside in Nerium oleander L. (Apocynaceae), has been shown to induce
Brian J Poindexter et al.
Journal of toxicology and environmental health. Part A, 70(6), 568-574 (2007-03-17)
Oleanders are common, hardy shrubs that grow throughout the southern United States. They contain cardiotonic steroids formed from cardenolides and bufadienolides, making the plant poisonous to both animals and humans. Aliquots of both commercially available oleander and fresh oleander extracts
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