Domoic acid

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Names

[ CAS No. ]:
14277-97-5

[ Name ]:
Domoic acid

[Synonym ]:
(3S,4S)-4-[(2Z,4E,6R)-6-Carboxyhepta-2,4-dien-2-yl]-3-(carboxymethyl)-L-proline
L-Proline, 3-(carboxymethyl)-4-[(1Z,3E,5R)-5-carboxy-1-methyl-1,3-hexadien-1-yl]-, (3S,4S)-
Domoic acid,(2S,3S,4R,5'R)-2-Carboxy-4-(5'-carboxy-1'-methyl-1Z,3E-hexadienyl)-3-pyrrolidineaceticacid
[2S-[2a,3b,4b(1Z,3E,5S*)]]-2-Carboxy-4-(5-carboxy-1-methyl-1,3-hexadienyl)-3-pyrrolidineacetic Acid
Domoic acid
MFCD00040640
L-Domoic acid
(3S,4S)-4-[(2Z,4E,6R)-6-Carboxy-2,4-heptadien-2-yl]-3-(carboxymethyl)-L-proline

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
607.2±55.0 °C at 760 mmHg

[ Melting Point ]:
228ºC

[ Molecular Formula ]:
C15H21NO6

[ Molecular Weight ]:
311.330

[ Flash Point ]:
321.0±31.5 °C

[ Exact Mass ]:
311.136902

[ PSA ]:
123.93000

[ LogP ]:
0.61

[ Vapour Pressure ]:
0.0±3.7 mmHg at 25°C

[ Index of Refraction ]:
1.545

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UX9665100
CHEMICAL NAME :
3-Pyrrolidineacetic acid, 2-carboxy-4-(5-carboxy-1-methyl-1,3-hexadienyl)-, (2S-(2-alpha,3- beta,4-beta(1Z,3E,5S*)))-
CAS REGISTRY NUMBER :
14277-97-5
LAST UPDATED :
199706
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C15-H21-N-O6
MOLECULAR WEIGHT :
311.37

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
3600 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TOXIA6 Toxicon. (Pergamon Press Ltd., Headington Hill Hall, Oxford OX3 OBW, UK) V.1- 1962- Volume(issue)/page/year: 28,501,1990 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
320 mg/kg/9W-I
TOXIC EFFECTS :
Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol)
REFERENCE :
FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 34,525,1996

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H312-H332

[ Precautionary Statements ]:
P280

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R20/21/22

[ RIDADR ]:
UX9665100

[ RTECS ]:
UX9665100

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

  • tert-butyl (2S,3S,4S)-4-((S)-1-(1,3-dioxolan-2-yl)ethyl)-3-(2-hydroxyethyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate
  • (2S,3S,4S)-1-tert-butyl 2-methyl 3-(2-methoxy-2-oxoethyl)-4-((R)-1-oxopropan-2-yl)pyrrolidine-1,2-dicarboxylate
  • 1-(tert-butyl) 2-methyl (2S,3S,4R)-3-(2-methoxy-2-oxoethyl)-4-(4-methoxybut-3-en-2-yl)pyrrolidine-1,2-dicarboxylate
  • 1-(tert-butyl) 2-methyl (2S,3S,4S)-4-((S)-1-(1,3-dioxolan-2-yl)ethyl)-3-(2-methoxy-2-oxoethyl)pyrrolidine-1,2-dicarboxylate
  • 1-(tert-butyl) 2-methyl (2S,3S,4S)-3-(2-methoxy-2-oxoethyl)-4-(4-oxo-3-(phenylselanyl)butan-2-yl)pyrrolidine-1,2-dicarboxylate
  • 1-(tert-butyl) 2-methyl (2S,3S,4S)-3-(2-methoxy-2-oxoethyl)-4-((Z)-4-oxobut-2-en-2-yl)pyrrolidine-1,2-dicarboxylate
  • tert-butyl (3S,4S,5S)-3-((S)-1-(1,3-dioxolan-2-yl)ethyl)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-(2-methoxy-2-oxoethyl)-2-oxopyrrolidine-1-carboxylate
  • (R,3E,5Z)-6-((3S,4S,5S)-1-(tert-butoxycarbonyl)-4-(2-methoxy-2-oxoethyl)-5-(methoxycarbonyl)pyrrolidin-3-yl)-2-methylhepta-3,5-dienoic acid
  • 1-(tert-butyl) 2-methyl (2S,3S,4S)-4-((R,2Z,4E)-7-hydroxy-6-methylhepta-2,4-dien-2-yl)-3-(2-methoxy-2-oxoethyl)pyrrolidine-1,2-dicarboxylate

DownStream

Articles

Metal-organic framework UiO-66 modified magnetite@silica core-shell magnetic microspheres for magnetic solid-phase extraction of domoic acid from shellfish samples.

J. Chromatogr. A. 1400 , 10-8, (2015)

Fe3O4@SiO2@UiO-66 core-shell magnetic microspheres were synthesized and characterized by transmission electron microscopy, scanning electron microscopy, X-ray diffraction, Fourier transform infrared s...

The prostaglandin EP1 receptor potentiates kainate receptor activation via a protein kinase C pathway and exacerbates status epilepticus.

Neurobiol. Dis. 70 , 74-89, (2014)

Prostaglandin E2 (PGE2) regulates membrane excitability, synaptic transmission, plasticity, and neuronal survival. The consequences of PGE2 release following seizures has been the subject of much stud...

Ursolic acid improves domoic acid-induced cognitive deficits in mice.

Toxicol. Appl. Pharmacol. 271(2) , 127-36, (2013)

Our previous findings suggest that mitochondrial dysfunction is the mechanism underlying cognitive deficits induced by domoic acid (DA). Ursolic acid (UA), a natural triterpenoid compound, possesses m...


More Articles

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