Domoic acid
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| General | ||||||||||||||||
| Surname | Domoic acid | |||||||||||||||
| Molecular formula | C 15 H 21 NO 6 | |||||||||||||||
| Brief description |
White dust |
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| properties | ||||||||||||||||
| Molar mass | 311.33 g mol −1 | |||||||||||||||
| Physical state |
firmly |
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| Melting point |
217 ° C (decomposition) |
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| solubility |
Soluble in water: 8 g l −1 (20 ° C) and methanol : 0.6 g l −1 |
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| safety instructions | ||||||||||||||||
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||||||||
Domoic acid is a structural analogue of glutamic acid , but binds to glutamate receptors with a hundred times higher affinity than L- glutamic acid .
Presentation and extraction
Domoic acid was synthesized from ( S ) - pyroglutamic acid in a multistep synthesis .
Biological importance
It is the cause of a human disease known as Amnesic Shellfish Poisoning (ASP), which can occur after eating seafood (especially mussels ) or fish if they came from areas where algal blooms have occurred. Domoic acid primarily attacks regions in and around the hippocampus and in this way damages - but mostly reversibly - the ability to remember by impairing short-term memory . Poisoning by domoic acid can also u. a. Cause nausea , cramps , diarrhea , headache and difficulty breathing . In constitutionally weak patients, the damage can lead to death.
In Germany, the Animal Food Hygiene Regulation (Tier-LMHV, in Appendix 1) allows a maximum amount of 20 mg domoic acid per kg of mussel meat.
The symptoms of poisoning caused by domoic acid are often caused by diatoms of the genus Pseudo-nitzschia (also: Nitzschia pungens ).
See also
Individual evidence
- ↑ a b c d data sheet Domoic acid from Sigma-Aldrich , accessed on March 28, 2011 ( PDF ).
- ↑ Entry on domoic acid. In: Römpp Online . Georg Thieme Verlag, accessed on September 30, 2014.
- ↑ Y. Ohfune and M. Tomita, Journal of the American Chemical Society 104 (1982) 3511th
- ↑ Health consequences of toxic algal blooms. ( Memento of February 9, 2007 in the Internet Archive ).
- ↑ Matthias Kania: Development of polyclonal and monoclonal antibodies for the detection of domoic acid. Weihenstephan Science Center for Nutrition, Land Use and Environment at the Technical University of Munich, 2002 ( PDF ).
- ↑ Animal Food Hygiene Ordinance (PDF; 166 kB) .