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78111-17-8

Basic Information
CAS No.: 78111-17-8
Name: OKADAIC ACID
Article Data: 6
Molecular Structure:
Molecular Structure of 78111-17-8 (OKADAIC ACID)
Formula: C44H68 O13
Molecular Weight: 805.016
Synonyms: 1,7-Dioxaspiro[5.5]undec-10-ene-2-propanoicacid, a,5-dihydroxy-a,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-propenyl]-,(aR,2S,5R,6R,8S)- (9CI);Acanthifolicin, 9,10-deepithio-9,10-didehydro-; 1,7-Dioxaspiro[5.5]undecane,acanthifolicin deriv.; Spiro[furan-2(3H),2'(3'H)-pyrano[3,2-b]pyran],acanthifolicin deriv.; 1,7-Dioxaspiro[5.5]undec-10-ene-2-propanoic acid, a,5-dihydroxy-a,10-dimethyl-8-[1-methyl-3-[octahydro-8'-hydroxy-6'-[1-hydroxy-3-(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-propenyl]-,[2'R-[2'a[R*[1R*[2S*(R*),5R*,6R*,8S*],2E]],4'ab,6'b[1S*,3S*(2S*,3R*,6S*)],8'a,8'aa]]-; NSC 677083; Okadaic acid
EINECS: 616-589-8
Density: 1.28 g/cm3
Melting Point: 164-166 °C
Boiling Point: 921.6 °C at 760 mmHg
Flash Point: 269.4 °C
Solubility: DMSO: ≥1 mg/mL
Appearance: white crystals or powder
Hazard Symbols: ToxicT
Risk Codes: 23/24/25-38
Safety: A poison by intraperitoneal route. Questionable carcinogen. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating vapors.
Transport Information: UN 3462 6
PSA: 182.83000
LogP: 5.21360
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Chemistry

MF: C44H68O13
Density: 1.28 g/cm3
MW: 805.002920 g/mol
Flash Point: 269.4 °C
Storage temp: −20°C
Solubility: DMSO: ≥1 mg/mL
Appearance: translucent film
Index of Refraction: 1.584 
Melting Point: 164-166 °C
Vapour Pressure: 0 mmHg at 25°C   
Enthalpy of Vaporization: 152.12 kJ/mol 
Boiling Point: 921.6 °C at 760 mmHg
Appearance: white crystals or powder
Stability: Stable. Light and heat-sensitive. Combustible. Incompatible with strong oxidizing agents.  
IUPAC Name: (2R)-3-[(2S,6R,8S,11R)-2-[(E,2R)-4-[(2S,2'R,4R,6R,8aR)-4-hydroxy-2-[(1S,3S)-1-hydroxy-3-[(3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]butyl]-3-methylidenespiro[4a,7,8,8a-tetrahydro-4H-pyrano[3,2-b]pyran-6,5'-oxolane]-2'-yl]but-3-en-2-yl]-11-hydroxy-4-methyl-1,7-dioxaspiro[5.5]undec-4-en-8-yl]-2-hydroxy-2-methylpropanoic acid
Synonyms: OA ; Okadaic acid, prorocentrum concavum ; Okadaic acid ; 9,10-Deepithio-9,10-didehydroacanthifolicin ; 9,10-Deepithio-9,10-didehydroacanthiofolicin ; Halochondrine a ; 9,10-Deepithio-9,10-didehydro-acanthifolici ; Okadaic acid >95% protein phosphatase i
Following is the molecular structure of Okadaic acid (78111-17-8):

Toxicity Data With Reference

1.    

sce-hmn-lym 3800 µmol/L

    MUREAV    Mutation Research. 289 (1993),275.
2.    

sce-hmn-ovr 2500 µmol/L

    MUREAV    Mutation Research. 289 (1993),275.
3.    

msc-ham-lng 10 µg/L

    MUREAV    Mutation Research. 250 (1991),375.
4.    

ipr-mus LD50:192 µg/kg

    JACSAT    Journal of the American Chemical Society. 103 (1981),2469.

Safety Profile

A poison by intraperitoneal route. Questionable carcinogen. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating vapors.
Safety Information
Hazard Codes: T
T: Toxic
Risk Statements: 23/24/25-38
23/24/25: Toxic by inhalation, in contact with skin and if swallowed 
38: Irritating to the skin  
Safety Statements: 26-36/37-45
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36/37: Wear suitable protective clothing and gloves 
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)  
RIDADR: UN 3462 6.1/PG 1
WGK Germany: 3
RTECS: AA8227800
F10: Keep under argon.
HazardClass: 6.1(a)
PackingGroup: II

Specification

 Okadaic acid (78111-17-8) is a toxin that accumulates in bivalves and causes diarrhetic shellfish poisoning. It was named from the marine sponge Halichondria okadai, from which okadaic acid was isolated for the first time. It has also been isolated from another marine sponge, H. malanodocia, as a cytotoxin. The real producer of okadaic acid is a marine dinoflagellate.
Administration of okadaic acid has been shown to profoundly increase the secretion of nerve growth factor, and to also promote nerve growth factor gene transcription and the stability of mRNA in primary cultures of cortical astrocytes.
The cytotoxicities of okadaic acid as EC50 against the P388 and L1210 cell lines are 1.7 nanomolar and 17 nanomolar, respectively. Additionally, okadaic acid strongly inhibits protein serine / threonine phosphatase 1, 2A, and 2B. The inhibitory effect of okadaic acid is strongest for 2A, followed by 1, and then 2B. The dissociation constant of the inhibition on protein serine / threonine phosphatase 2A is 30 pico-molar.