Retronecin
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| General | ||||||||||
| Surname | Retronecin | |||||||||
| other names |
(1 R , 7a R ) -7- (hydroxymethyl) -2,3,5,7a-tetrahydro-1 H -pyrrolizin-1-ol |
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| Molecular formula | C 8 H 13 NO 2 | |||||||||
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| properties | ||||||||||
| Molar mass | 155.19 g mol −1 | |||||||||
| Physical state |
firmly |
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| Melting point |
120 ° C |
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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 . | ||||||||||
Retronecin is the basic body from which most pyrrolizidine alkaloids are derived through esterification of the two hydroxyl groups .
Occurrence
Retronecin occurs in a variety of plants of the genera ragweeds and Crotalaria as well as the Boraginaceae family .
use
Retronecin is a strong poison and is consumed by many insects to protect themselves against predators. In the insect metabolism, it also serves as a precursor for the production of male sex pheromones .
The use of grain contaminated with alkaloid-containing herbs or the use of these herbs for medical or dietary purposes repeatedly leads to poisoning by retronecin in humans, sometimes of an epidemic nature. The toxic effect is based on damage to liver and lung cells. A cyclic diester of retronecin is monocrotaline .
Individual evidence
- ↑ a b Retronecine, Merck Index , 12th Edition, 8334
- ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
- ↑ Gadi VP Reddy, Angel Guerrero: Interactions of insect pheromones and plant semiochemicals. In: Trends in Plant Science. 9, 2004, pp. 253-261, doi : 10.1016 / j.tplants.2004.03.009 .
- ^ E. Roeder, H. Wiedenfeld: Plants containing pyrrolizidine alkaloids used in the Traditional Indian Medicine – including Ayurveda. In: Die Pharmazie , 68.2 (2013): pp. 83–92.
- ^ Entry on retronecin in the Hazardous Substances Data Bank , accessed on November 2, 2014.