Domoic acid

Domoic acid
Names
Preferred IUPAC name
(2S,3S,4S)-4-[(2Z,4E,6R)-6-Carboxyhepta-2,4-dien-2-yl]-3-(carboxymethyl)pyrrolidine-2-carboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.159.099 Edit this at Wikidata
EC Number
  • 630-802-1
UNII
  • 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 checkY
    Key: VZFRNCSOCOPNDB-AOKDLOFSSA-N checkY
  • 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
    Key: VZFRNCSOCOPNDB-AOKDLOFSBM
  • O=C(O)[C@H]1NC[C@H](/C(=C\C=C\[C@H](C(=O)O)C)C)[C@@H]1CC(=O)O
Properties
C15H21NO6
Molar mass 311.334 g·mol−1
Density 1.273 g/cm3
Vapor pressure 2.62×10−16 mmHg (34.9 fPa)
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H302, H312, H332
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Domoic acid (DA) is a kainic acid-type neurotoxin that causes amnesic shellfish poisoning (ASP).[1] It is produced by algae and accumulates in shellfish, sardines, and anchovies. When sea lions, otters, cetaceans, humans, and other predators eat contaminated animals, poisoning may result. Exposure to this compound affects the brain, causing seizures, and possibly death.[2]

  1. ^ Clayden J, Read B, Hebditch KR (2005). "Chemistry of domoic acid, isodomoic acids, and their analogues". Tetrahedron. 24 (61): 5713–24. doi:10.1016/j.tet.2005.04.003.
  2. ^ "Domoic Acid Toxicity". The Marine Mammal Center. Retrieved 2 April 2015.