ChemicalBook > CAS DataBase List > DOMOIC ACID

DOMOIC ACID

Product Name
DOMOIC ACID
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
Formula Weight
311.33
MOL File
14277-97-5.mol
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DOMOIC ACID Property

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
optical activity
-109.612 (H2O)
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)
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Safety

Hazard Codes 
Xn
Risk Statements 
20/21/22
Safety Statements 
36/37
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.
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H302Harmful if swallowed

H370Causes damage to organs

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P405Store locked up.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
D6152
Product name
Domoic acid
Purity
≥90% (HPLC)
Packaging
1mg
Price
$234
Updated
2023/01/07
Sigma-Aldrich
Product number
D6152
Product name
Domoic acid
Purity
≥90% (HPLC)
Packaging
5mg
Price
$772
Updated
2023/01/07
Cayman Chemical
Product number
21433
Product name
Domoic Acid
Purity
≥98%
Packaging
500μg
Price
$99
Updated
2021/12/16
Cayman Chemical
Product number
21433
Product name
Domoic Acid
Purity
≥98%
Packaging
1mg
Price
$158
Updated
2021/12/16
Tocris
Product number
0269
Product name
Domoic acid
Purity
≥95%(HPLC)
Packaging
500U
Price
$197
Updated
2021/12/16
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DOMOIC ACID Chemical Properties,Usage,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).

Uses

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 associated with ingestion of certain cultured blue mussels. Domoic acid is a structural analog of Kainic acid (K135000). DA. EU regulated marine toxin.

Uses

Domoic acid has been used:

  • as an excitatory neurotoxin to determine brain transcriptional response
  • to study its cytotoxic, genotoxic and immunotoxic effects on the marine mussel M. edulis
  • to study its neurobehavioral effects on mouse fetuses

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.]

DOMOIC ACID Preparation Products And Raw materials

Raw materials

Preparation Products

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14277-97-5, DOMOIC ACIDRelated Search:

Trifluoroacetic acid Thickening agent Pyrrolidine Benzimidazole Methylene Blue trihydrate MONOCROTALINE PATULIN Acetic acid DEOXYNIVALENOL Zearalenone TOXIN II, ANEMONIA SULCATA KAINIC ACID (2S,3S)-3-METHYLPYRROLIDINE-2-CARBOXYLIC ACID DOMOIC ACID 3-Pyrrolidineacetic acid DOMOIC ACID = DOMOINS?URE DOMOIC ACID PRITY: 90% POTEN MUSSEL TISSUE - DOMOIC ACID(CRM STANDARD)

  • (2S,3S,4S)-4-[(2Z,4E,6R)-6-carboxyhepta-2,4-dien-2-yl]-3-(carboxymethyl)pyrrolidine-2-carboxylic acid
  • Domoic Acid, Mytilus edulis - CAS 14277-97-5 - Calbiochem
  • 3-Pyrrolidineacetic acid, 2-carboxy-4-[(1Z,3E,5R)-5-carboxy-1-methyl-1,3-hexadien-1-yl]-, (2S,3S,4S)-
  • (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
  • Domoic acid, 100ppm
  • Myticus edulis, homogenized (Domoic acid)
  • omoicaci
  • 14277-97-5 DOMOIC ACID
  • Domoic acid in ACN/H2O
  • Myticus edulis, homogenized (Domoic acid) in mussel homogenate
  • 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