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Merck
CN

O4511

Sigma-Aldrich

Okadaic acid from Prorocentrum concavum

≥90% (HPLC), translucent film

Synonym(s):

OA

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About This Item

Empirical Formula (Hill Notation):
C44H68O13
CAS Number:
78111-17-8
Molecular Weight:
805.00
MDL number:
MFCD00083455
UNSPSC Code:
12352202
PubChem Substance ID:
24897998

Key Documents

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biological source

plant (Prorocentrum concavum)

Assay

≥90% (HPLC)

form

translucent film

solubility

DMSO: ≥1 mg/mL
ethanol: ≥1 mg/mL
methanol: ≥1 mg/mL
H2O: insoluble

storage temp.

−20°C

SMILES string

O[C@@H](C[C@@H]([C@@]1([H])O[C@@]2(CCCCO2)CC[C@H]1C)C)[C@]3([H])C([C@@H](O)[C@]4([H])O[C@]5(CC[C@@](/C=C/[C@@H](C)[C@@]6([H])O[C@]7(O[C@H](C[C@@](C)(O)C(O)=O)CC[C@H]7O)C=C(C)C6)([H])O5)CC[C@@]4([H])O3)=C

InChI

1S/C44H68O13/c1-25-21-34(55-44(23-25)35(46)12-11-31(54-44)24-41(6,50)40(48)49)26(2)9-10-30-14-18-43(53-30)19-15-33-39(57-43)36(47)29(5)38(52-33)32(45)22-28(4)37-27(3)13-17-42(56-37)16-7-8-20-51-42/h9-10,23,26-28,30-39,45-47,50H,5,7-8,11-22,24H2,1-4,6H3,(H,48,49)/b10-9+/t26-,27-,28+,30+,31+,32+,33-,34+,35-,36-,37+,38+,39-,41-,42+,43-,44-/m1/s1

InChI key

QNDVLZJODHBUFM-WFXQOWMNSA-N

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Biochem/physiol Actions

Dinoflagellate toxin and an ionophore-like polyether derivative of a 38 carbon, fatty acid. Readily enters cells. Inhibitor of type 1 and type 2A protein phosphatases. Does not inhibit tyrosine phosphatases, alkaline phosphatases or acid phosphatase. Known tumor promotor. Used to study various cellular processes including cell cycle, apoptosis, nitric oxide metabolism and calcium signaling.
Okadaic acid is a dinoflagellate toxin and an ionophore-like polyether derivative of a 38 carbon, fatty acid.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301 + H311 + H331,H315

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Skin Irrit. 2

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SLBK5786V
SLBK4954V
SLBK6729V
MKBR2410V
MKBQ8271V

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M Mourtada-Maarabouni et al.
Oncogene, 28(2), 195-208 (2008-10-07)
Effective control of both cell survival and cell proliferation is critical to the prevention of oncogenesis and to successful cancer therapy. Using functional expression cloning, we have identified GAS5 (growth arrest-specific transcript 5) as critical to the control of mammalian
Keiichi Konoki et al.
Bioorganic & medicinal chemistry, 18(21), 7607-7610 (2010-09-25)
Okadaic acid (OA) and dinophysistoxin-1 (DTX1) cause diarrheic shellfish poisoning. This article examines the biochemical interactions of the two toxins with novel okadaic acid binding proteins (OABPs) 2.1 and 2.3, originally isolated from the marine sponge Halichondria okadai. First, recombinant
Rodrigo González-Romero et al.
Comparative biochemistry and physiology. Toxicology & pharmacology : CBP, 155(2), 175-181 (2011-09-29)
Marine biotoxins synthesized by Harmful Algal Blooms (HABs) represent one of the most important sources of contamination in marine environments as well as a serious threat to fisheries and aquaculture-based industries in coastal areas. Among these biotoxins Okadaic Acid (OA)
J J Fernández et al.
Current medicinal chemistry, 9(2), 229-262 (2002-02-28)
One of the most interesting groups of substances of marine origin, from structural and pharmacological points of view are polyether toxins, which generally present a great diversity in size and potent biological activities. The subject of this review is limited
M A Battistone et al.
Molecular human reproduction, 19(9), 570-580 (2013-05-01)
In all mammalian species studied so far, sperm capacitation correlates with an increase in protein tyrosine (Tyr) phosphorylation mediated by a bicarbonate-dependent cAMP/protein kinase A (PKA) pathway. Recent studies in mice revealed, however, that a Src family kinase (SFK)-induced inactivation
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