92-100%(HPLC) , 78111-17-8

Synonym(s):
OA;Okadaic Acid, Prorocentrum sp. - CAS 78111-17-8 - Calbiochem

CAS NO.：78111-17-8

Empirical Formula: C44H68O13

Molecular Weight: 805

MDL number: MFCD00083455

EINECS: 616-589-8

PRODUCT Properties

• Melting point: 164-166 °C
• alpha: D20 +21° (c = 0.33 in CHCl3); D25 +25.4° (c = 0.24 in CHCl3)
• Boiling point: 672.95°C (rough estimate)
• Density: 1.0795 (rough estimate)
• refractive index: 1.5940 (estimate)
• storage temp.: -20°C
• solubility: DMSO: ≥1 mg/mL
• form: translucent film
• pka: 3.87±0.16(Predicted)
• color: translucent
• optical activity: +2120 (CHCl3)
• Water Solubility: It is soluble in ethanol (25 mg/ml), DMSO (25 mg/ml), methanol (<1 mg/ml), chloroform, acetone, ethyl acetate, DMF, and dimethylsulfoxide. Insoluble in water, unless first dissolved in organic solvents, such as DMSO or ethanol.
• Merck: 13,6891
• Stability: Stable. Light and heat-sensitive. Combustible. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: 78111-17-8
• EPA Substance Registry System: 1,7-Dioxaspiro[5.5]undec-10-ene-2-propanoic acid, .alpha,5-dihydroxy-.alpha.,10-dimethyl-8-[(1R,2E)-1-methyl-3-[(2R,4'aR,5R,6'S,8'R,8'aS)-octahydro-8'-hydroxy-6'-[(1S,3S)-1-hydroxy-3-[(2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undec-2-yl]butyl]-7'-methylenespiro[furan-2(3H),2'(3'H)-pyrano[3,2-b]pyran]-5-yl]-2-propen-1-yl]-, (.alpha.R,2S,5R,6R,8S)- (78111-17-8)

Description and Uses

Marine algal blooms, natural phenomena produced by the overgrowth of microscopic marine algae, have become a public health concern because of their increasing frequency and severity. About 300 phytoplanktonic species are known to have the ability to cause these blooms, and one-fourth of them are able to produce toxins, also called phycotoxins. Shellfish, mainly bivalve mollusks, and fish may accumulate these phycotoxins by direct filtration of the producer algal cells or by feeding on contaminated organisms. Human intoxications caused by phycotoxins occur worldwide through consumption of marine fishery products containing bioaccumulated toxins.
According to their toxic effects and chemical properties, phycotoxins are classified into different categories. Diarrheic shellfish poisoning (DSP) toxins are one of the most relevant groups of the phytoplanktonic toxins because its presence produces not only severe economic losses, but also health effects in human consumers. The first registered DSP episode after shellfish consumption occurred in 1961 in The Netherlands. However, no relationship with the phycotoxins was established at that time. It was in 1976 when the association between the frequent occurrence of gastroenteritis and the ingestion of phycotoxin-contaminated shellfish was proved the first time. Since then, a large number of DSP episodes have been documented worldwide. However, this number is believed to be much higher because these episodes are not often well documented for the reason that the acute symptoms are sometimes light and intoxicated people do not always require medical assistance. Okadaic acid (OA) and its analogs, the dinophysistoxins (DTX), are lipophilic marine toxins produced by several phytoplanktonic species and responsible for DSP in humans. OA, the main representative toxin of this group, was first isolated in 1981 from the black sponge Halichondria okadai as well as from H. melanodocia. It is usually accumulated by several marine organisms, mainly bivalve mollusks, by eating phytoplankton containing OA. This toxin is highly distributed all over the world, but is especially abundant in Japan in Europe. OA exposure can represent a severe threat to human health beyond its DSP effects, because it was demonstrated to be a specific inhibitor of several types of serine/threonine protein phosphatases and a tumor promoter in animal carcinogenesis experiments.

OA is a natural marine toxin produced by different phytoplanktonic species mainly from the dynoflagellates group. It may pass through the food chain to humans who ingest OAcontaminated organisms. Thus, it does not have any commercial applications in medicine, food, construction, or similar industries. However, because of its well-known ability to selectively inhibit several types of serine/threonine protein phosphatases, it is often used in research as a useful tool for studying cellular processes regulated by reversible phosphorylation of proteins, including control of glycogen metabolism, coordination of the cell cycle and gene expression, and maintenance of cytoskeletal structure.
Furthermore, it was reported that other marine toxins, different from OA, can also act as specific protein phosphatase (mainly PP1 and PP2A) inhibitors. They are called OA class tumor promoters and were proved to be able to cause skin, stomach, and liver tumors in animals. This has led some authors to suggest a new concept of tumor promotion: the okadaic acid pathway. In this regard, studies with OA, as well as with other OA class tumor promoters, could deepen the knowledge of the mechanisms of cancer development in humans.

Safety

• Symbol(GHS): GHS06
• Signal word: Danger
• Hazard statements: H301+H311+H331-H315
• Precautionary statements: P280-P301+P310+P330-P302+P352+P312-P304+P340+P311
• Hazard Codes: T
• Risk Statements: 23/24/25-38
• Safety Statements: 26-36/37-45
• RIDADR: UN 3462 6.1/PG 1
• WGK Germany: 3
• RTECS: AA8227800
• F: 10
• HazardClass: 6.1(a)
• PackingGroup: II
• HS Code: 29321900
• Hazardous Substances Data: 78111-17-8(Hazardous Substances Data)
• Toxicity: LD50 i.p. in mice: 192 mg/kg (Shibata)