ChemicalBook CAS DataBase List 14277-97-5

14277-97-5

Name	DOMOIC ACID
CAS	14277-97-5
Molecular Formula	C15H21NO6
MDL Number	MFCD06795841
Molecular Weight	311.33
MOL File	14277-97-5.mol

Synonyms

C13732 Domoic omoicaci NSC 288031 DOMOIC ACID L-Domic acid (-)-Domic acid DoMoic Acid-d3 (-)-DoMoic Acid-d3 Domoic acid, 100ppm DOMOICACID=DOMOINSRE 14277-97-5 DOMOIC ACID AMNESICSHELLFISHPOISON AMNESICSHELLFISHPOISONING DOMOIC ACID, MYTILUS EDULIS 3-beta,4-beta(1z,3e,5s*)))--(2-alph Myticus edulis, homogenized (Domoic acid) Domoic Acid, Mytilus edulis - CAS 14277-97-5 - Calbiochem 2-carboxy-4-(5-carboxy-1-methyl-1,3-hexadienyl)-3-pyrrolidineaceticaci(2s 3-Pyrrolidineacetic acid, 2-carboxy-4-(1Z,3E,5R)-5-carboxy-1-methyl-1,3-hexadienyl- (2S)-2α-Carboxy-4β-[(1Z,3E,5R)-5-carboxy-1-methyl-1,3-hexadienyl]-3β-pyrrolidineacetic acid (2S,3S,4R,5'R)-2-CARBOXY-4-(5'-CARBOXY-1'-METHYL-1Z,3E-HEXADIENYL)-3-PYRROLIDINEACETIC ACID 3-Pyrrolidineacetic acid, 2-carboxy-4-(1Z,3E,5R)-5-carboxy-1-methyl-1,3-hexadienyl-, (2S,3S,4S)- (2S,3S,4S)-2-Carboxy-4-[(1Z,3E,5R)-5-carboxy-1-Methyl-1,3-hexadien-1-yl]-3-pyrrolidineacetic Acid (2S,3S,4S)-2-Carboxy-4-[(1Z,3E,5R)-5-carboxy-1-Methyl-1,3-hexadien-1-yl]-3-pyrrolidineacetic Acid-d3 3-Pyrrolidineacetic acid, 2-carboxy-4-[(1Z,3E,5R)-5-carboxy-1-methyl-1,3-hexadien-1-yl]-, (2S,3S,4S)- (2S,3S,4S)-4-[(2Z,4E,6R)-6-carboxyhepta-2,4-dien-2-yl]-3-(carboxymethyl)pyrrolidine-2-carboxylic acid 2S-[2ALPHA, 3BETA, 4BETA (1Z, 3E, 5R)]-2-CARBOXY-4-(5-CARBOXY-1-METHYL-1,3-HEXADIENYL)-3-PYRROLIDINEACETIC ACID (2S-(2-alpha,3-beta,4-beta(1Z,3E,5S*)))-2-Carboxy-4-(5-carboxy-1-methyl-1,3-hexadienyl)-3-pyrrolidineacetic 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)

Safety Data

Hazard Codes	Xn
Risk Statements	20/21/22 less more
Safety Statements	36/37 less more
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. less more

Hazard Information

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.

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.]

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