Skip to Content
MilliporeSigma
All Photos(1)

Documents

O7760

Sigma-Aldrich

Okadaic acid sodium salt from Prorocentrum concavum

≥90% (HPLC), film

Synonym(s):

OA

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C44H67NaO13
CAS Number:
209266-80-8
Molecular Weight:
826.98
MDL number:
MFCD00210208
UNSPSC Code:
12352106
PubChem Substance ID:
329818921
NACRES:
NA.77

biological source

plant (Prorocentrum concavum)

Quality Level

200

Assay

≥90% (HPLC)

form

film

color

translucent

solubility

0.1% acetic acid in CH3CN: H2O (1:1): 250 μg/mL, clear, colorless

storage temp.

−20°C

SMILES string

[Na+].C[C@@H]1CC[C@]2(CCCCO2)O[C@@H]1[C@@H](C)C[C@H](O)[C@H]3O[C@@H]4CC[C@@]5(CC[C@@H](O5)\C=C\[C@@H](C)[C@@H]6CC(C)=C[C@@]7(O[C@@H](CC[C@H]7O)C[C@@](C)(O)C([O-])=O)O6)O[C@H]4[C@H](O)C3=C

InChI

1S/C44H68O13.Na/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);/q;+1/p-1/b10-9+;/t26-,27-,28+,30+,31+,32+,33-,34+,35-,36-,37+,38+,39-,41-,42+,43-,44-;/m1./s1

InChI key

BYHIFOCTDVNQQT-GHIYGBLASA-M

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.

Features and Benefits

This compound is featured on the Phosphoprotein Phosphatases (Serine/Threonine) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Diego Figueroa et al.
Journal of toxicology and environmental health. Part A, 83(15-16), 573-588 (2020-07-21)
Okadaic acid-group (OA-group) is a set of lipophilic toxins produced only in seawater by species of the Dinophysis and Prorocentrum genera, and characterized globally by being associated with harmful algal blooms (HABs). The diarrhetic shellfish poisoning toxins okadaic acid (OA)
Zhiyuan Fang et al.
Autophagy, 19(8), 2240-2256 (2023-02-14)
Acetaminophen (APAP) overdose is the predominant cause of drug-induced liver injury worldwide. The macroautophagy/autophagy-lysosomal pathway (ALP) is involved in the APAP hepatotoxicity. TFEB (transcription factor EB) promotes the expression of genes related to autophagy and lysosomal biogenesis, thus, pharmacological activation
Ning Zhang et al.
Autophagy, 6(8), 1157-1167 (2010-10-12)
FTY720, a sphingosine analog, is a novel immunosuppressant currently undergoing multiple clinical trials for the prevention of organ transplant rejection and treatment of various autoimmune diseases. Recent studies indicate an additional cytotoxic effect of FTY720 and its preclinical efficacy in
Abira Rajah et al.
Scientific reports, 9(1), 11430-11430 (2019-08-09)
Cell migration is an important biological phenomenon involved in many homeostatic and aberrant physiological processes. Phosphorylation of the focal adhesion adaptor protein, paxillin, on serine 273 (S273) has been implicated as a key regulator of cell migration. Here, it is
Dan Li et al.
Autophagy, 17(4), 872-887 (2020-03-07)
Oxidative stress underlies a number of pathological conditions, including cancer, neurodegeneration, and aging. Antioxidant-rich foods help maintain cellular redox homeostasis and mitigate oxidative stress, but the underlying mechanisms are not clear. For example, sulforaphane (SFN), an electrophilic compound that is
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service