924-49-2

Basic information

• Product Name: DL-GAMMA-AMINO-B-HYDROXYBUTYRIC ACIDCRYS TALLINE
• Synonyms: Aminohydroxybutyric;DL-G-AMINO-B-HYDROXYBUTYRICACID;(+-)-3-Hydroxy-4-aminobutanoic acid;(RS)-3-Hydroxy-γ-aminobutyric acid;(RS)-4-Amino-3-hydroxybutanoic acid;(RS)-γ-Amino-β-hydroxybutyric acid;3-Hydroxy-4-aminobutanoic acid;3-Hydroxy-GABA
• CAS NO: 924-49-2
• Molecular Formula: C₄H₉NO₃
• Molecular Weight: 119.12
• EINECS: 213-106-9
• Product Categories: Pharmaceutical material and intermeidates;GAMIBETAL
• Mol File: 924-49-2.mol
• Article Data: 12

Chemical Properties

• Melting Point: 223 °C (dec.)(lit.)
• Boiling Point: 222.38°C (rough estimate)
• Flash Point: 180.3 °C
• Appearance: White to Yellow/Powder
• Density: 1.3126 (rough estimate)
• Refractive Index: 1.4183 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: pK1: 3.834(+1);pK2: 9.487(0) (25°C,μ=0.1)
• Water Solubility: almost transparency
• Merck: 14,444
• CAS DataBase Reference: DL-GAMMA-AMINO-B-HYDROXYBUTYRIC ACIDCRYS TALLINE(CAS DataBase Reference)
• NIST Chemistry Reference: DL-GAMMA-AMINO-B-HYDROXYBUTYRIC ACIDCRYS TALLINE(924-49-2)
• EPA Substance Registry System: DL-GAMMA-AMINO-B-HYDROXYBUTYRIC ACIDCRYS TALLINE(924-49-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: ES7015000
• TSCA: Yes
• Hazardous Substances Data: 924-49-2(Hazardous Substances Data)

Usage

Chemical Properties

White crystalline powder

Uses

Reduces uptake of iodine by the thyroid glands in animals. Antispasmodic

Purification Methods

Crystallise the acid from H2O or aqueous EtOH. Recrystallise it by dissolving it (CO2H), pK Est( 2) in H2O and adding MeOH or EtOH. It is not very soluble in CHCl3 or EtOAc. [Renaud & Seebach Synthesis 424 1986, Beilstein 4 IV 3187.]

InChI:InChI=1/C4H9NO3/c5-2-3(6)1-4(7)8/h3,6H,1-2,5H2,(H,7,8)

Synthetic route

(DL)-4-amino-3-hydroxybutanenitrile hydrochloride (74889-64-8) → DL-4-amino-3-hydroxybutyric acid (924-49-2)

Conditions	Yield
Stage #1: (DL)-4-amino-3-hydroxybutanenitrile hydrochloride With sulfuric acid for 0.0833333h; Heating; Stage #2: With sulfuric acid In water for 3h; Heating;	75%
With sulfuric acid In water for 3h; Heating;	70%

4-amino-3-oxobutanoic acid hydrochloride → DL-4-amino-3-hydroxybutyric acid (924-49-2)

Conditions	Yield
With hydrogen; dihydrogen hexachloroplatinate; palladium on activated charcoal; iron(III) chloride

(+/-)-4-amino-3-hydroxybutyric acid methyl ester hydrochloride → DL-4-amino-3-hydroxybutyric acid (924-49-2)

Conditions	Yield
With hydrogenchloride for 3h; Heating;	90%

N-(3-cyano-2-hydroxy-propyl)-benzamide (91350-64-0) → DL-4-amino-3-hydroxybutyric acid (924-49-2)

Conditions	Yield
With hydrogen bromide

(Z)-4-phthalimidocrotonic acid (16011-10-2) → DL-4-amino-3-hydroxybutyric acid (924-49-2)

Conditions	Yield
With hydrogenchloride

thalassospiramide D (1417995-87-9) → L-valine (72-18-4) + DL-4-amino-3-hydroxybutyric acid (924-49-2) + (Z)-3-decenamide + 4-amino-5-hydroxy-penta-2-enoic acid + N-methyl-L-tyrosine (537-49-5) + phenethylamine (64-04-0)

Conditions	Yield
With hydrogenchloride; N-(2,4-dinitro-5-fluorophenyl)-L-alaninamide at 115℃; for 1h;

4-amino-n-butyric acid (56-12-2) → 4-amino-2-hydroxybutyric acid (13477-53-7) + DL-4-amino-3-hydroxybutyric acid (924-49-2) + glycine (56-40-6) + 3-amino propanoic acid (107-95-9)

Conditions	Yield
In water at 20℃; for 0.666667h; contact glow discharge electrolysis;	A 4.4 % Chromat. B 3.6 % Chromat. C 8.5 % Chromat. D 6.8 % Chromat.

dl-γ-benzamino-β-oxy-butyric acid ethyl ester → DL-4-amino-3-hydroxybutyric acid (924-49-2)

Conditions	Yield
With sulfuric acid
With hydrogen bromide

N-<β-oxy-γ-cyano-propyl>-phthalimide → DL-4-amino-3-hydroxybutyric acid (924-49-2)

Conditions	Yield
With sulfuric acid und nachfolgendes Kochen der mit Wasser verd.Loesung;

methyl 4-(acetylamino)-3-hydroxybutanoate (121596-88-1) → DL-4-amino-3-hydroxybutyric acid (924-49-2)

Conditions	Yield
With hydrogenchloride for 1h; Heating; Yield given;

Upstream product

• 1417995-87-9 thalassospiramide D 
• 56-12-2 4-amino-n-butyric acid 
• 121596-88-1 methyl 4-(acetylamino)-3-hydroxybutanoate 
• 74889-64-8 (DL)-4-amino-3-hydroxybutanenitrile hydrochloride 
• 16011-10-2 (Z)-4-phthalimidocrotonic acid 
• 91350-64-0 N-(3-cyano-2-hydroxy-propyl)-benzamide 

Downstream Products

• 22677-21-0 4-hydroxy-2-oxopyrrolidine 
• 461-06-3 CARNITINE 
• 77680-79-6 3-Hydroxy-4-(3,4,5-trimethoxy-thiobenzoylamino)-butyric acid 
• 157542-04-6 (RS)-<1-(benzyloxycarbonyl)amino>-butan-2,4-diol 
• 542-06-3 (+/-)-4-Dimethylamino-3-hydroxy-buttersaeure 
• 38090-53-8 trans-4-aminocrotonic acid 
• 7010-89-1 3-Hydroxy-4-guanidino-buttersaeure 
• 409341-03-3 tert-butyl 4-hydroxy-2-oxopyrrolidine-1-carboxylate 
• 68252-20-0 4-Trimethylsilyloxy-1H-pyrrolidin-2one 
• 127852-78-2 4-tert-butoxycarbonylamino-3-hydroxy-butyric acid 

Relevant articles and documents

Thalassospiramide G, a new γ-amino-acid-bearing peptide from the marine bacterium Thalassospira sp

In the chemical investigation of marine unicellular bacteria, a new peptide, thalassospiramide G (1), along with thalassospiramides A and D (2-3), was discovered from a large culture of Thalassospira sp. The structure of thalassospiramide G, bearing γ-amino acids, such as 4-amino-5-hydroxy- penta-2-enoic acid (AHPEA), 4-amino-3,5-dihydroxy-pentanoic acid (ADPA), and unique 2-amino-1-(1H-indol-3-yl) ethanone (AIEN), was determined via extensive spectroscopic analysis. The absolute configuration of thalassospiramide D (3), including 4-amino-3-hydroxy-5-phenylpentanoic acid (AHPPA), was rigorously determined by 1H-1H coupling constant analysis and chemical derivatization. Thalassospiramides A and D (2-3) inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated mouse macrophage RAW 264.7 cells, with IC50 values of 16.4 and 4.8 μM, respectively.

An efficient synthesis of (R)-GABOB and of (±)-GABOB

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A short synthesis of 4-amino-3-hydroxybutyric acid (GABOB) via allyl cyanide

4-Amino-3-hydroxybutyric acid was synthesized from allyl cyanide in four steps in an overall yield of 38%. Ultrasonically promoted epoxidation of allyl cyanide with m-chloroperoxybenzoic acid giving oxiranylacetonitrile was used as a key step.