Domoic Acid

Title: Domoic Acid
CAS Registry Number: 14277-97-5
CAS Name: (2S,3S,4S)-2-Carboxy-4-[(1Z,3E,5R)-5-carboxy-1-methyl-1,3-hexadienyl]-3-pyrrolidineacetic acid
Molecular Formula: C15H21NO6
Molecular Weight: 311.33
Percent Composition: C 57.87%, H 6.80%, N 4.50%, O 30.83%
Literature References: Excitatory amino acid isolated from the red alga Chondria armata Okamura, Rhodomelaceae, known in Japanese as "domoi". Structural analog of kainic acid, q.v. Shown to be responsible for amnesic shellfish poisoning associated with ingestion of certain cultured blue mussels. Isoln: T. Takemoto, K. Daigo, Chem. Pharm. Bull. 6, 578 (1958); eidem, Arch. Pharm. 293, 627 (1960). Series of articles on isoln, structure, and anthelminthic activity: K. Daigo, Yakugaku Zasshi 79, 350-364 (1959), C.A. 53, 14218 (1959). Structural studies: T. Takemoto et al., ibid. 86, 874 (1966), C.A. 66, 28604m (1967). Total synthesis and revised structure: Y. Ohfune, M. Tomita, J. Am. Chem. Soc. 104, 3511 (1982). Neuroexcitatory activity: T. J. Biscoe et al., Nature 255, 166 (1975); R. Zaczek, J. T. Coyle, Neuropharmacology 21, 15 (1982). Effect on kainate receptor activation: G. Debonnel et al., Can. J. Physiol. Pharmacol. 67, 29, 904 (1989). Identification in toxic mussel extracts: J. L. C. Wright et al., Can. J. Chem. 67, 481 (1989). LC determn in shellfish products: J. F. Lawrence et al., J. Chromatogr. 462, 349, 419 (1989). Reviews: M. A. Quilliam, J. L. C. Wright, Anal. Chem. 61, 1053A-1059A (1989); J. Clayden et al., Tetrahedron 61, 5713-5724 (2005).
Derivative Type: Dihydrate
Properties: mp 217° (dec). [a]D12 -109.6° (c = 1.314 in water). uv max: 242 nm (log e 4.24). pKa in water: 2.10, 3.72, 4.93, 9.82. Sol in water, acetic acid. Insol in methanol, ethanol, chloroform, acetone, benzene.
Melting point: mp 217° (dec)
pKa: pKa in water: 2.10, 3.72, 4.93, 9.82
Optical Rotation: [a]D12 -109.6° (c = 1.314 in water)
Absorption maximum: uv max: 242 nm (log e 4.24)
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