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Merck
CN

B0912

Brevetoxin 2

Synonym(s):

Brevetoxin B, PbTx-2

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About This Item

Empirical Formula (Hill Notation):
C50H70O14
CAS Number:
79580-28-2
Molecular Weight:
895.08
UNSPSC Code:
12352200
PubChem Substance ID:
24891538
MDL number:
MFCD00214092

Key Documents

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SMILES string

[H]C(=O)C(=C)C[C@@H]1C[C@H](O)[C@]2(C)O[C@]3([H])C[C@]4([H])O[C@]5([H])C[C@]6(C)O[C@]7(C)CC[C@]8([H])O[C@]9([H])C[C@]%10(C)O[C@]%11([H])C(C)=CC(=O)O[C@@]%11([H])C[C@@]%10([H])O[C@@]9([H])C[C@@H](C)[C@@]8([H])O[C@@]7([H])C[C@@]6([H])O[C@@]5(C)CC=C[C@@]4([H])O[C@@]3([H])C[C@@]2([H])O1

storage temp.

−20°C

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General description

Polycyclic polyethers from the marine dinoflagellate Ptychodiscus brevis (Gymnodinium breve).
Red tide toxin; acts by opening Na+ channels.

Biochem/physiol Actions

Potent toxins responsible for "red tide" fish kills, these compounds disrupt neurotransmission by opening sodium channels.
Red tide toxin; acts by opening Na+ channels.

Other Notes

This form has an unusual acrolein side-chain on one of the terminal rings.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

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

Storage Class

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

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
098K1065
087K1927
115K1441
035K0828
109H1269

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Satoru Ujihara et al.
Bioorganic & medicinal chemistry letters, 18(23), 6115-6118 (2008-10-25)
Ladder-shaped polyether (LSP) compounds are thought to interact with transmembrane alpha-helices, but direct evidence has scarcely obtained for these interactions. We adopted a transmembrane alpha-helix of glycophorin A, and quantitatively evaluated its interaction with LSPs such as yessotoxin (YTX), desulfated
Tadashi Nakata
Chemical record (New York, N.Y.), 10(3), 159-172 (2010-05-27)
Since the isolation of brevetoxin-B, a red tide toxin, many bioactive marine natural products featuring synthetically challenging trans-fused polycyclic ether ring systems have been reported. We have developed SmI(2)-induced cyclization of beta-alkoxyacrylate with aldehyde, affording 2,6-syn-2,3-trans-tetrahydropyran (THP) or 2,7-syn-2,3-trans-oxepane with
S Sudarsanam et al.
Journal of computer-aided molecular design, 6(3), 223-233 (1992-06-01)
We have developed an approach to search for molecules that can be used as lead compounds in designing an inhibitor for a given proteolytic enzyme when the 3D structure of a homologous protein is known. This approach is based on
Christopher J Morten et al.
Journal of the American Chemical Society, 131(19), 6678-6679 (2009-05-01)
Water is an effective promoter of the endo-selective opening of trisubstituted epoxides, enabling related cascades leading to a variety of substituted ladder polyether structures. When used in conjunction with a tetrahydropyran-templated nucleophile, water can overcome the powerful electronic directing effect
Juan Tang et al.
Biosensors & bioelectronics, 38(1), 86-93 (2012-06-12)
A facile and feasible magneto-controlled immunosensing platform was designed for sensitive electrochemical immunoassay of brevetoxin B (BTX-2) in seafood by using guanine-assembled graphene nanoribbons (GGNRs) as molecular tags on a home-made magnetic carbon paste electrode. Initially, monoclonal mouse anti-BTX-2 antibodies
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