14277-97-5 Usage
Description
Domoic acid, a heterocyclic amino acid neurotoxin, is synthesized by various marine algaes and is a structural analog of kainic acid. It is an L-proline derivative with a carboxymethyl group at position 3 and a 6-carboxyhepta-2,4-dien-2-yl group at position 4. Domoic acid is known to be responsible for amnesic shellfish poisoning associated with the ingestion of certain cultured blue mussels.
Uses
Used in Marine Toxin Research:
Domoic acid is used as an excitatory neurotoxin for studying its cytotoxic, genotoxic, and immunotoxic effects on marine organisms, such as the mussel M. edulis. It helps researchers understand the brain transcriptional response and the potential impact of this toxin on marine ecosystems.
Used in Neurobehavioral Studies:
Domoic acid is employed as a neurotoxin to study its neurobehavioral effects on mouse fetuses, providing insights into the potential neurological impacts of this toxin on developing organisms.
Used in Pharmaceutical Research:
As a structural analog of kainic acid, domoic acid may be used in the development of new pharmaceuticals targeting the central nervous system. Its unique properties could potentially be harnessed for therapeutic applications, although further research is needed to explore this possibility.
Used in Regulatory Compliance:
Domoic acid is regulated as a marine toxin in the European Union, and its presence in shellfish and other seafood products is monitored to ensure public health and safety. This regulatory use helps protect consumers from the potential risks associated with amnesic shellfish poisoning.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 14277-97-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,2,7 and 7 respectively; the second part has 2 digits, 9 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 14277-97:
(7*1)+(6*4)+(5*2)+(4*7)+(3*7)+(2*9)+(1*7)=115
115 % 10 = 5
So 14277-97-5 is a valid CAS Registry Number.
InChI:InChI=1/C15H21NO6/c1-8(4-3-5-9(2)14(19)20)11-7-16-13(15(21)22)10(11)6-12(17)18/h3-5,9-11,13,16H,6-7H2,1-2H3,(H,17,18)(H,19,20)(H,21,22)/b5-3+,8-4-/t9-,10+,11-,13+/m1/s1
14277-97-5Relevant articles and documents
Chemistry of the shellfish toxin domoic acid: characterization of related compounds
Walter, John A.,Falk, Michael,Wright, Jeffrey L. C.
, p. 430 - 436 (2007/10/02)
Five new compounds related to the neurotoxin domoic acid have been characterized by spectroscopic methods.They include a diastereoisomer that occurs naturally with domoic acid in mussels and four hydrogenation products.The stereochemistry of the two epimeric tetrahydro derivatives could not be assigned on the basis of the NMR data alone because of high conformational flexibility.However, a clear-cut assignment was possible by molecular modelling in combination with the NMR data.
Total synthesis of (-)-domoic acid. A revision of the original structure
Ohfune,Tomita
, p. 3511 - 3513 (2007/10/02)
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