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A1304

Sigma-Aldrich

β-Amanitin

from Amanita phalloides, ≥85% (HPLC), powder, RNA polymerase inhibitor

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About This Item

Empirical Formula (Hill Notation):
C39H53N9O15S
CAS Number:
21150-22-1
Molecular Weight:
919.95
EC Number:
244-244-8
MDL number:
MFCD00151212
UNSPSC Code:
12352200
PubChem Substance ID:
24890528
NACRES:
NA.77
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Product Name

β-Amanitin from Amanita phalloides, ≥85% (HPLC)

Quality Level

200

Assay

≥85% (HPLC)

form

powder

storage temp.

−20°C

SMILES string

CCC(C)C1NC(=O)CNC(=O)C2Cc3c([nH]c4cc(O)ccc34)S(=O)CC(NC(=O)CNC1=O)C(=O)NC(CC(O)=O)C(=O)N5CC(O)CC5C(=O)NC(C(C)C(O)CO)C(=O)N2

InChI

1S/C39H53N9O15S/c1-4-16(2)31-36(60)41-11-28(53)42-25-15-64(63)38-21(20-6-5-18(50)7-22(20)45-38)9-23(33(57)40-12-29(54)46-31)43-37(61)32(17(3)27(52)14-49)47-35(59)26-8-19(51)13-48(26)39(62)24(10-30(55)56)44-34(25)58/h5-7,16-17,19,23-27,31-32,45,49-52H,4,8-15H2,1-3H3,(H,40,57)(H,41,60)(H,42,53)(H,43,61)(H,44,58)(H,46,54)(H,47,59)(H,55,56)

InChI key

IEQCUEXVAPAFMQ-UHFFFAOYSA-N

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General description

β-Amanitin belongs to the family of amatoxins.[1] Amanitins are made of bicyclic octapeptides.[2] β-Amanitin is composed of a carboxyl group and is acidic in nature.[3]

Application

β-Amanitin from Amanita phalloides has been used:
  • as a calibration standard for the quantification of β-Amanitin using liquid chromatography-high resolution-mass spectrometry/mass spectrometry (LC-HR-MS/MS) method.[4]
  • to determine its concentration in urine samples by capillary zone electrophoresis (CZE).[5]
  • in the analysis of β-amanitin in toxic mushrooms by liquid chromatography coupled to time-of-flight mass spectrometry.[2]

Biochem/physiol Actions

Inhibits eukaryotic RNA polymerase II and III; does not inhibit RNA polymerase I or bacterial RNA polymerase; inhibits mammalian protein synthesis.
Toxic constituent of the mushroom, Amanita phalloides, inhibits eukaryotic RNA polymerase II and III, but not RNA polymerase I or bacterial RNA polymerase. Inhibits mammalian protein synthesis.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H300 + H310 + H330

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral

Storage Class Code

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

WGK

WGK 3

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Certificates of Analysis (COA)

Lot/Batch Number
0000390194
0000390194
SLCR3628
SLCN2396
SLCF3317

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H H Maurer et al.
Journal of chromatography. B, Biomedical sciences and applications, 689(1), 81-89 (1997-02-07)
GC-MS is the method of choice for toxicological analysis of toxicants volatile in GC while non-volatile and/or thermally labile toxicants need LC-MS for their determination. Studies are presented on the toxicological detection of the amphetamine-like anorectic clobenzorex in urine by
U Bermbach et al.
Biochemistry, 29(29), 6839-6845 (1990-07-24)
Poly-L-ornithine with an average molecular weight of 32K was reacted with beta-amanitin hydroxysuccinimide ester to form an amide-linked toxin conjugate. Loading of the polymeric chain with amanitin was high, corresponding to up to 35% of the total weight. To this
V Raghavan
Journal of plant physiology, 140(4), 434-440 (1992-01-01)
Poly(A)-RNA fractions of dormant, dark-imbibed (non-germinating) and photoinduced (germinating) spores of Onoclea sensibilis were poor templates in the rabbit reticulocyte lysate protein synthesizing system, but the translational efficiency of poly(A)+RNA was considerably higher than that of unfractionated RNA. Poly(A)+RNA isolated
Ertuğrul Kaya et al.
Turkish journal of medical sciences, 44(5), 728-732 (2014-12-30)
Alpha- and beta-amanitins are the main toxins of the poisonous Amanita phalloides mushroom. Although there are many studies available concerning alpha-amanitin, there are limited data about beta-amanitin in the literature. Therefore, this study is aimed at comparing the toxic effects
Natural Antimicrobials for the Minimal Processing of Foods (2012)
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