2,3-Diaminopropionic Acid
Structural Formula Vector Image
Title: 2,3-Diaminopropionic Acid
CAS Registry Number: 515-94-6
CAS Name: 3-Aminoalanine
Additional Names: 2,3-diaminopropanoic acid; a,b-diaminopropionic acid
Molecular Formula: C3H8N2O2
Molecular Weight: 104.11
Percent Composition: C 34.61%, H 7.75%, N 26.91%, O 30.74%
Literature References: Prepd by treating 2,3-dibromopropionic acid with ammonia: Klebs, Z. Physiol. Chem. 19, 314 (1894); Winterstein, Küng, ibid. 59, 146 (1909); Neuberg, Silbermann, Ber. 37, 341 (1904); Frankland, J. Chem. Soc. 97, 1318 (1910); by treating 2-amino-3-chloropropionic acid with ammonia under pressure: Fisher et al., Ber. 40, 3717 (1907); by the reduction of cyanooximoacetic acid esters: Godefroi, US 2738363 (1956 to Parke, Davis). Configuration: Karrer et al., Helv. Chim. Acta 9, 314 (1926). See also Bergmann, Grafe, Z. Physiol. Chem. 187, 187 (1930).
 
Derivative Type: DL-Form
Properties: Radially arranged cryst masses. Hygroscopic, also absorbs CO2 from air. Begins to melt at 97°, completely liq at 110-120°. Sol in water, yielding alkaline solns. Practically insol in alcohol, ether.
 
Derivative Type: Hydrochloride
Molecular Formula: C3H8N2O2.HCl
Molecular Weight: 140.57
Percent Composition: C 25.63%, H 6.45%, N 19.93%, O 22.76%, Cl 25.22%
Properties: Needles or leaflets, mp 236-237°. One gram dissolves in 12 ml water, practically insol in alcohol.
Melting point: mp 236-237°
 
Derivative Type: Sulfate hemihydrate
Molecular Formula: (C3H8N2O2)2.H2SO4.½H2O
Molecular Weight: 315.30
Percent Composition: C 22.86%, H 6.07%, N 17.77%, O 43.13%, S 10.17%
Properties: Six-sided leaflets from water, dec 233-234°. One gram dissolves in 31 ml water at 20°.
 
Derivative Type: Methyl ester dihydrochloride
Molecular Formula: C4H10N2O2.2HCl
Molecular Weight: 191.06
Percent Composition: C 25.15%, H 6.33%, N 14.66%, O 16.75%, Cl 37.11%
Properties: Crystals, dec 170°. Freely sol in water.
 
Derivative Type: Ethyl ester dihydrochloride
Molecular Formula: C5H12N2O2.2HCl
Molecular Weight: 205.08
Percent Composition: C 29.28%, H 6.88%, N 13.66%, O 15.60%, Cl 34.57%
Properties: Crystals, mp 164.5-165° (some decompn). Freely sol in water.
Melting point: mp 164.5-165° (some decompn)
 
Derivative Type: L-Form hydrochloride
Molecular Formula: C3H8N2O2.HCl
Molecular Weight: 140.57
Percent Composition: C 25.63%, H 6.45%, N 19.93%, O 22.76%, Cl 25.22%
Properties: Needles from water, [a]D20 +25.0° (c = 5 in 1.0N HCl).
Optical Rotation: [a]D20 +25.0° (c = 5 in 1.0N HCl)
 
Derivative Type: D-Form hydrochloride
Molecular Formula: C3H8N2O2.HCl
Molecular Weight: 140.57
Percent Composition: C 25.63%, H 6.45%, N 19.93%, O 22.76%, Cl 25.22%
Properties: Needles from water, [a]D20 -25.3° (c = 5 in 1.0N HCl).
Optical Rotation: [a]D20 -25.3° (c = 5 in 1.0N HCl)
 
Use: The salts as growth inhibitors for microorganisms.

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