α-aminobutyric acid
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| Structural formula of α-aminobutyric acid without specifying the stereochemistry | ||||||||||||||||||||||
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| Surname | α-aminobutyric acid | |||||||||||||||||||||
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| Molecular formula | C 4 H 9 NO 2 | |||||||||||||||||||||
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| properties | ||||||||||||||||||||||
| Molar mass | 103.12 g mol −1 | |||||||||||||||||||||
| Physical state |
firmly |
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| Melting point |
292–303 ° C (decomposition) |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||||||||||||||
α-aminobutyric acid (also called Aba or AABA for short) is a non-proteinogenic α- amino acid and one of the aminobutyric acids . Structurally, it is derived from butyric acid by substituting the α- hydrogen atom with an amino group (-NH 2 ) . A rather rarely used common name is butyrin .
Isomers
| Stereoisomers of α-aminobutyric acid | ||||
| Surname | L- α-aminobutyric acid | D -α-aminobutyric acid | ||
| other names | (+) - α-aminobutyric acid ( S ) -α-aminobutyric acid |
(-) - α-Aminobutyric acid ( R ) -α-aminobutyric acid |
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| CAS number | 1492-24-6 | 2623-91-8 | ||
| 2835-81-6 (racemate) | ||||
| EC number | 216-083-3 | 220-084-4 | ||
| 220-616-5 (racemate) | ||||
| ECHA info card | 100.014.622 | 100.018.260 | ||
| 100.018.742 (racemate) | ||||
| PubChem | 80283 | - | ||
| 6657 (racemate) | ||||
| DrugBank | DB04454 (racemate) | |||
| Wikidata | Q27104317 | Q76967546 | ||
| Q285687 (racemate) | ||||
A well-known structural isomer is γ-aminobutyric acid (GABA), an inhibitory neurotransmitter .
Extraction
α-aminobutyric acid is u. a. obtained from threonine by hydrolysis with hydrochloric acid. It is also obtained from 2-bromobutanoic acid by reaction with aqueous NH 3 .
meaning
During alcoholic fermentation , α-aminobutyric acid is broken down by microorganisms such as yeast to form 1-propanol , a fusel alcohol .
Occurrence
β-Aminobutyric acid (BABA) is a naturally occurring non-proteinogenic amino acid . In plants it acts against various pathogens.
Web links
- Entry on α-aminobutyric acid in the ChemIDplus database of the United States National Library of Medicine (NLM)
Individual evidence
- ↑ CRC Handbook of Tables for Organic Compound Identification , Third Edition, 1984, ISBN 0-8493-0303-6 .
- ↑ a b L-2-Aminobutyric acid data sheet from Sigma-Aldrich , accessed on December 1, 2019 ( PDF ).
- ↑ Kurt Heyns, Wolfgang Walter: The formation of α-aminobutyric acid from threonine during hydrolysis with hydrochloric acid . In: Die Naturwissenschaften , 1952 , 39 (22) , p. 507.
- ↑ Werner Baltes and Reinhard Matissek: Food chemistry . Jumper; 7., completely revised. 2011 edition; ISBN 978-3-64216538-2 ; P. 473.
- ↑ Ton, J. and Mauch-Mani, B. (2004): Beta-amino-butyric acid-induced resistance against necrotrophic pathogens is based on ABA-dependent priming for callose. In: Plant J. 38 (1); 119-130; PMID 15053765