3-nitropropionic acid

Structural formula
General
Surname	3-nitropropionic acid
other names	Hiptagenic acid; 3-nitropropanoic acid; β-nitropropionic acid; β-nitropropanoic acid;
Molecular formula	C 3 H 5 NO 4
Brief description	beige solid
External identifiers / databases
EC number	208-003-0
ECHA InfoCard	100.007.276
PubChem	1678
ChemSpider	1615
Wikidata	Q223104
properties
Molar mass	119.08 g mol −1
Physical state	firmly
Melting point	68-70 ° C
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 301-315-319-335
	P: 261-301 + 310-305 + 351 + 338
Toxicological data	68.1 mg kg −1 ( LD 50 , mouse , oral )
	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)

[Sigma-1] ↑ ^a ^b ^c ^d ^e data sheet 3-Nitropropionic acid from Sigma-Aldrich , accessed on March 18, 2011 ( PDF ).

[2] K. Gorter: L'hiptagine, glucoside nouveau retiré de l'Hiptage Madablota Gaertn. In: Bull Jard Bot Buitenzorg. 2, 1920, p. 187.

[3] LC Carter, WJ McChesney: Hiptagenic Acid Identified as β-Nitropropionic Acid. In: Nature . 164, 1949, pp. 575-576. doi: 10.1038 / 164575b0 .

[Bush-4] 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)