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| DOMOIC ACID Basic information |
| Product Name: | DOMOIC ACID | | Synonyms: | (2S,3S,4S)-4-[(2Z,4E,6R)-6-carboxyhepta-2,4-dien-2-yl]-3-(carboxymethyl)pyrrolidine-2-carboxylic acid;Domoic Acid, Mytilus edulis - CAS 14277-97-5 - Calbiochem;3-Pyrrolidineacetic acid, 2-carboxy-4-[(1Z,3E,5R)-5-carboxy-1-methyl-1,3-hexadien-1-yl]-, (2S,3S,4S)-;(2S-(2-alpha,3-beta,4-beta(1Z,3E,5S*)))-2-Carboxy-4-(5-carboxy-1-methyl-1,3-hexadienyl)-3-pyrrolidineacetic acid;(-)-Domic acid;(2S)-2α-Carboxy-4β-[(1Z,3E,5R)-5-carboxy-1-methyl-1,3-hexadienyl]-3β-pyrrolidineacetic acid;L-Domic acid;3-Pyrrolidineacetic acid, 2-carboxy-4-(1Z,3E,5R)-5-carboxy-1-methyl-1,3-hexadienyl- | | CAS: | 14277-97-5 | | MF: | C15H21NO6 | | MW: | 311.33 | | EINECS: | | Product Categories: | Amino Acids & Derivatives;Heterocycles;AlgaeNeurotransmitters;Glutamate receptor;Intermediates & Fine Chemicals;Pharmaceuticals;AMPA/Kainate AgonistsIon Channels;Ionotropic Glutamate Receptor Modulators;Cell Signaling and Neuroscience;Excitatory Amino Acids;Ligand-Gated Ion Channels;Toxins and Venoms | | Mol File: | 14277-97-5.mol |
| DOMOIC ACID Chemical Properties |
| Melting point | 213-217℃ | | Boiling point | 451.38°C (rough estimate) | | density | 1.1800 (rough estimate) | | refractive index | 1.5130 (estimate) | | storage temp. | -20°C | | solubility | methanol: 0.6 mg/mL | | form | solid | | pKa | 2.08±0.60(Predicted) | | color | white | | Water Solubility | Soluble in water at 8mg/ml. Soluble in methanol at 0.6mg/ml. | | Merck | 13,3451 | | BRN | 46376 | | Stability: | Light Sensitive | | EPA Substance Registry System | Domoic acid (14277-97-5) |
| Hazard Codes | Xn | | Risk Statements | 20/21/22 | | Safety Statements | 36/37 | | WGK Germany | 3 | | RTECS | UX9665100 | | Hazardous Substances Data | 14277-97-5(Hazardous Substances Data) | | Toxicity | An excitory
amino acid isolated from the red alga Chondria armata. A structural
analog of kainic acid and domoic acid has been shown to be
responsible for the shellfish poisoning associated with eating certain
cultured blue mussels. |
| DOMOIC ACID Usage And Synthesis |
| Chemical Properties | Off-White Solid | | Uses | Labelled Domoic Acid. Domoic Acid is an excitatory amino acid isolated from the red alga Chondria armata Okamura, Rhodomelaceae. Domoic acid shown to be responsible for amnesic shellfish poisoning ass
ociated with ingestion of certain cultured blue mussels. Domoic Acid is a structural analog of Kainic acid (K135000). | | Uses | Domoic Acid is an excitatory amino acid isolated from the red alga Chondria armata Okamura, Rhodomelaceae. Domoic acid shown to be responsible for amnesic shellfish poisoning associated with ingestion of certain cultured blue mussels. Domoic acid is a structural analog of Kainic acid (K135000). DA. EU regulated marine toxin. | | Uses | Domoic acid has been used: - as an excitatory neurotoxin to determine brain transcriptional response
- to study its cytotoxic, genotoxic and immunotoxic effects on the marine mussel M. edulis
- to study its neurobehavioral effects on mouse fetuses
| | Definition | ChEBI: A L-proline derivative that is L-proline substituted by a carboxymethyl group at position 3 and a 6-carboxyhepta-2,4-dien-2-yl group at position 4. It is an analog of kainic acid and is the neurotoxin associated with the a
nesic shellfish poisoning (ASP). | | General Description | Domoic acid, a heterocyclic amino acid neurotoxin is synthesized by various marine algaes. It possess some structural similarity to kainic acid. | | Biological Activity | More potent and possibly more selective than kainate at kainate receptors, as demonstrated in electrophysiological studies. | | Biochem/physiol Actions | Domoic acid is a potent agonist at receptors for excitatory amino acids glutamate and kainate. It has highest affinity for AMPA/kainate receptor of any kainate agonist. It can causes excessive excitation of neurons leading to depletion of energy stores. | | Purification Methods | Domoic acid (~300 mg) is purifed on a Dowex1 column (3.5 x 40 mm, 200-400 mesh, acetate form), washed with H2O until neutral, then eluted with increasing concentrations of AcOH (8L) from 0 to 0.25M. The fraction containing domoic acid (in 50mL) is collected, evaporated to dryness under reduced pressure and recrystallised from aqueous EtOH. It is a glutamate and a Kainate receptor agonist. [Impellizzeri et al. Phytochemistry 14 1549 1975, Takemoto & Diago Arch Pharm 293 627 1960, Beilstein 22/4 V 371.] |
| DOMOIC ACID Preparation Products And Raw materials |
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