3-nitropropionic acid
Structural formula | |||||||||||||||||||
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General | |||||||||||||||||||
Surname | 3-nitropropionic acid | ||||||||||||||||||
other names |
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Molecular formula | C 3 H 5 NO 4 | ||||||||||||||||||
Brief description |
beige solid |
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properties | |||||||||||||||||||
Molar mass | 119.08 g mol −1 | ||||||||||||||||||
Physical state |
firmly |
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Melting point |
68-70 ° C |
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safety instructions | |||||||||||||||||||
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Toxicological data | |||||||||||||||||||
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
3-Nitropropionic acid , also called hiptagenic acid , is a compound belonging to the carboxylic acids . Formally, it can be understood as a derivative of propanoic acid and differs from it by a nitro group on the third carbon atom.
In nature it occurs in the form of an ester with glucose in the compound hiptagin , which was first isolated in 1920 from the root bark of Hiptage madablota . The free carboxylic acid can be obtained from this by hydrolysis .
synthesis
3-Nitropropionic acid can be produced from propiolactone and sodium nitrite in an aqueous solution.
The synthesis from 3-iodopropanoic acid and silver nitrite gives better yields .
literature
- Eberhard Teuscher, Ulrike Lindequist: Biogenic poisons. 3. Edition. Wissenschaftliche Verlagsgesellschaft, Stuttgart 2010, ISBN 978-3-8047-2438-9 .
Individual evidence
- ↑ a b c d e data sheet 3-Nitropropionic acid from Sigma-Aldrich , accessed on March 18, 2011 ( PDF ).
- ↑ K. Gorter: L'hiptagine, glucoside nouveau retiré de l'Hiptage Madablota Gaertn. In: Bull Jard Bot Buitenzorg. 2, 1920, p. 187.
- ^ LC Carter, WJ McChesney: Hiptagenic Acid Identified as β-Nitropropionic Acid. In: Nature . 164, 1949, pp. 575-576. doi: 10.1038 / 164575b0 .
- ↑ a b M. T. Bush, O. Touster, JE Brockman: The production of β-Nitropropionic acid by a strain of Aspergillus Flavus. In: J.Biol.Chem. 188, 1951, pp. 685-693. (PDF)