DOMOIC ACID

DOMOIC ACID Structure
CAS No.
14277-97-5
Chemical Name:
DOMOIC ACID
Synonyms
C13732;Domoic;omoicaci;NSC 288031;DOMOIC ACID;L-Domic acid;(-)-Domic acid;DoMoic Acid-d3;(-)-DoMoic Acid-d3;Domoic acid, 100ppm
CBNumber:
CB2359498
Molecular Formula:
C15H21NO6
Molecular Weight:
311.33
MOL File:
14277-97-5.mol
Modify Date:
2023/4/23 13:52:06

DOMOIC ACID 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)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS07,GHS08
Signal word  Danger
Hazard statements  H302-H370
Precautionary statements  P260-P264-P270-P301+P312-P308+P311-P405
Hazard Codes  Xn
Risk Statements  20/21/22
Safety Statements  36/37
WGK Germany  3
RTECS  UX9665100
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 Chemical Properties,Uses,Production

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).

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.

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

Raw materials

Preparation Products

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(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- C13732 (2S,3S,4S)-2-Carboxy-4-[(1Z,3E,5R)-5-carboxy-1-Methyl-1,3-hexadien-1-yl]-3-pyrrolidineacetic Acid NSC 288031 (-)-DoMoic Acid-d3 (2S,3S,4S)-2-Carboxy-4-[(1Z,3E,5R)-5-carboxy-1-Methyl-1,3-hexadien-1-yl]-3-pyrrolidineacetic Acid-d3 DoMoic Acid-d3 2-carboxy-4-(5-carboxy-1-methyl-1,3-hexadienyl)-3-pyrrolidineaceticaci(2s DOMOIC ACID DOMOIC ACID, MYTILUS EDULIS 3-beta,4-beta(1z,3e,5s*)))--(2-alph 2S-[2ALPHA, 3BETA, 4BETA (1Z, 3E, 5R)]-2-CARBOXY-4-(5-CARBOXY-1-METHYL-1,3-HEXADIENYL)-3-PYRROLIDINEACETIC ACID (2S,3S,4R,5'R)-2-CARBOXY-4-(5'-CARBOXY-1'-METHYL-1Z,3E-HEXADIENYL)-3-PYRROLIDINEACETIC ACID Domoic 3-Pyrrolidineacetic acid, 2-carboxy-4-(1Z,3E,5R)-5-carboxy-1-methyl-1,3-hexadienyl-, (2S,3S,4S)- AMNESICSHELLFISHPOISON AMNESICSHELLFISHPOISONING DOMOICACID=DOMOINSRE 14277-97-5 DOMOIC ACID omoicaci Myticus edulis, homogenized (Domoic acid) Domoic acid, 100ppm 3-Pyrrolidineacetic acid, 2-carboxy-4-[(1Z,3E,5R)-5-carboxy-1-methyl-1,3-hexadien-1-yl]-, (2S,3S,4S)- Domoic Acid, Mytilus edulis - CAS 14277-97-5 - Calbiochem (2S,3S,4S)-4-[(2Z,4E,6R)-6-carboxyhepta-2,4-dien-2-yl]-3-(carboxymethyl)pyrrolidine-2-carboxylic acid Buprenorphine Impurity 23 14277-97-5 Biochemicals and Reagents BioChemical Amino Acids and Peptides A - H Cell Signaling and Neuroscience Cell Biology Ligand-Gated Ion Channels Modified Amino Acids Ion Channels Ionotropic Glutamate Receptor Modulators Amino Acids & Derivatives Heterocycles Intermediates & Fine Chemicals Pharmaceuticals Glutamate receptor AlgaeNeurotransmitters AMPA/Kainate AgonistsIon Channels Ionotropic Glutamate Receptor Modulators Cell Signaling and Neuroscience Excitatory Amino Acids Ligand-Gated Ion Channels Toxins and Venoms