CAS 14277-97-5

(-)-Domoic acid

Description:

(-)-Domoic acid is a naturally occurring amino acid and a potent neurotoxin, primarily known for its role in marine biotoxins associated with harmful algal blooms, particularly from species like Pseudo-nitzschia. It is classified as a glutamate analog, which allows it to interact with glutamate receptors in the nervous system, potentially leading to excitotoxicity and neurodegenerative effects. The substance has a molecular formula of C15H19N O6 and features multiple functional groups, including carboxylic acids and an amine, contributing to its solubility in water. (-)-Domoic acid is known to cause amnesic shellfish poisoning (ASP) in humans and marine animals, characterized by symptoms such as gastrointestinal distress, neurological impairment, and in severe cases, death. Its structure includes a bicyclic ring system, which is crucial for its biological activity. Due to its toxicity, (-)-Domoic acid is monitored in seafood and marine environments to ensure public health safety.

Formula: C₁₅H₂₁NO₆

InChI: InChI=1S/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

InChI key: InChIKey=VZFRNCSOCOPNDB-AOKDLOFSSA-N

SMILES: C(C(O)=O)[C@H]1[C@@H](\C(=C/C=C/[C@H](C(O)=O)C)\C)CN[C@@H]1C(O)=O

Synonyms:

• (2S,3S,4S)-2-Carboxy-4-[(1Z,3E,5R)-5-carboxy-1-methyl-1,3-hexadien-1-yl]-3-pyrrolidineacetic acid
• (3S,4S)-3-(carboxymethyl)-4-[(1Z,3E,5R)-5-carboxy-1-methylhexa-1,3-dien-1-yl]-L-proline
• 3-Pyrrolidineacetic acid, 2-carboxy-4-(5-carboxy-1-methyl-1,3-hexadienyl)-, [2S-[2α,3β,4β(1Z,3E,5S*)]]-
• 3-Pyrrolidineacetic acid, 2-carboxy-4-[(1Z,3E,5R)-5-carboxy-1-methyl-1,3-hexadien-1-yl]-, (2S,3S,4S)-
• 3-Pyrrolidineacetic acid, 2-carboxy-4-[(1Z,3E,5R)-5-carboxy-1-methyl-1,3-hexadienyl]-, (2S,3S,4S)-
• <span class="text-smallcaps">L</span>-Domoic acid
• Domoic Acid, Mytilus edulis
• Domoic acid = Domoins�ure
• NSC 288031
• Domoic acid

Domoic acid

CAS: 14277-97-5

Formula: C₁₅H₂₁NO₆

Molecular weight: 311.33

Ref: 4Z-D-811

Domoic Acid-d3

Controlled Product

CAS: 14277-97-5

Formula: C₁₅D₃H₁₈NO₆

Color and Shape: Neat

Molecular weight: 314.349

Ref: TR-D531302

Domoic Acid

Controlled Product

CAS: 14277-97-5

Formula: C₁₅H₂₁NO₆

Color and Shape: Beige

Molecular weight: 311.33

Ref: TR-D531300

Domoic acid, with 5% acetonitrile at 50 µg/0.5 ml aqueous solution

CAS: 14277-97-5

Domoic acid, with 5% acetonitrile at 50 µg/0.5 ml aqueous solution, is a neurotoxic compound derived from certain species of marine algae, specifically from the genus Pseudo-nitzschia. It acts as a potent excitotoxin by binding to kainate glutamate receptors in the central nervous system, leading to excessive neuronal excitation and potential neurotoxicity. This overstimulation can cause damage to neurons, leading to a variety of neurological effects.

Formula: C₁₅H₂₁NO₆

Purity: Min. 95%

Molecular weight: 311.33 g/mol

Ref: 3D-XD184364

Domoic acid

CAS: 14277-97-5

Domoic acid is a neurotoxin that has been shown to induce neuronal death in vitro and in vivo. Domoic acid inhibits the activity of ligand-gated ion channels, which increases the cytosolic Ca2+ concentration. This toxin also induces mitochondrial membrane potential loss, causing apoptosis. Domoic acid binds to the NMDA receptor and blocks glutamate binding. It also inhibits ATP synthase by competing with ADP for binding sites on the enzyme's F1 portion. Domoic acid has low potency as a neurotoxin because it does not readily cross the blood-brain barrier or enter cells via passive diffusion.

Formula: C₁₅H₂₁NO₆

Purity: Min. 90 Area-%

Color and Shape: Beige Powder

Molecular weight: 311.33 g/mol

Ref: 3D-FD168217