软骨藻酸

Description

domoic acid · CAS 14277-97-5 · C15H21NO6. UNII M02525818H.

Identification

CAS Registry Number	14277-97-5
PubChem CID	5282253
Molecular formula	C15H21NO6
IUPAC name	(2S,3S,4S)-4-[(2Z,4E,6R)-6-carboxyhepta-2,4-dien-2-yl]-3-(carboxymethyl)pyrrolidine-2-carboxylic acid
UNII (FDA)	M02525818H

Computed Descriptors

Molecular Weight	311.33
XLogP3	-1.3
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	7
Exact Mass	311.13688739
Monoisotopic Mass	311.13688739
Topological Polar Surface Area	124
Heavy Atom Count	22
Formal Charge	0

Physical description & handling notes

• Colorless solid; [HSDB] White powder; [MSDSonline]
• Colorless crystal needles
• White solid
• Soluble in water (8 mg/mL)
• Soluble in water
• Soluble in dilute mineral acids and alkali hydroxide solutions. It is slightly soluble in methanol and ethanol and insoluble in petroleum ether and benzene.

GHS Hazard Classification

Reported hazard statements	H302, H312, H332 (41.8%)

Documented Uses

• Toxic amino acid isolated from a specific red alga (Chondria armata, Okamura, Rhodomelaceae); Causes amnesic shellfish poisoning; [Merck Index] Domoic acid and brevitoxin are toxins found in shellfish (mussels, oysters, and scallops) from the Florida coast and Gulf of Mexico. [MMWR. Vol. 53/RR]
• Seaweed Chondria armata may contain domoic acid and extracts of the plant have been used in Japan as an ascaricidal medication at a dose of 20 mg/person without adverse effects. Its insecticidal properties were also known since flies die soon after landing on the seaweeds.
• Domoic acid has been used to treat GI parasites in humans.
• Isodomoic acid F is found in mollusks. Isodomoic acid F is isolated from mussels.
• Excitatory amino acid isolated from the red alga Chondria armata Okamura, Rhodomelaceae, known in Japanese as "domoi".
• Domoic acid is an excitatory amino acid containing the structure of glutamic acid and resembling kainic acid. Three geometric isomers of domoic acid have been described; they are isodomoic acids D, E, and F. They have little biological activity compared to domoic acid.

Synonyms

domoic acid; 14277-97-5; L-Domoic acid; NSC 288031; (-)-domoic acid; CHEBI:34727; DTXSID20274180; M02525818H; NSC-288031; (3S,4S)-4-[(2Z,4E,6R)-6-carboxyhepta-2,4-dien-2-yl]-3-(carboxymethyl)-L-proline; (2S,3S,4S)-3-(carboxymethyl)-4-[(1Z,3E,5R)-5-carboxy-1-methyl-hexa-1,3-dienyl]pyrrolidine-2-carboxylic acid; (2S,3S,4S)-4-[(2Z,4E,6R)-6-carboxy-6-methylhexa-2,4-dien-2-yl]-3-(carboxymethyl)pyrrolidine-2-carboxylic acid; (2S,3S,4S)-4-[(2Z,4E,6R)-6-carboxyhepta-2,4-dien-2-yl]-3-(carboxymethyl)pyrrolidine-2-carboxylic acid; 3-Pyrrolidineacetic acid, 2-carboxy-4-((1Z,3E,5R)-5-carboxy-1-methyl-1,3-hexadienyl)-, (2S,3S,4S)-; (3S,4S)-4-((2Z,4E,6R)-6-carboxyhepta-2,4-dien-2-yl)-3-(carboxymethyl)-L-proline; (2S,3S,4S)-3-(carboxymethyl)-4-((1Z,3E,5R)-5-carboxy-1-methyl-hexa-1,3-dienyl)pyrrolidine-2-carboxylic acid

Frequently Asked Questions

What are the CAS number and molecular formula of domoic acid?

CAS 14277-97-5; molecular formula C15H21NO6; molecular weight — g/mol.

What other names is domoic acid known by?

domoic acid, 14277-97-5, L-Domoic acid, NSC 288031, (-)-domoic acid, CHEBI:34727.

Is domoic acid classified as hazardous?

Hazard statements reported: H302, H312, H332.

Facts on this page are taken from PubChem (US National Library of Medicine) and Wikidata. Grade-specific data — assay, moisture, particle size, packaging, shelf life — is issued per batch on the COA and is not published here.