924-49-2

Usage

Uses

Used in Pharmaceutical Industry:
DL-GAMMA-AMINO-B-HYDROXYBUTYRIC ACIDCRYS TALLINE is used as an antispasmodic agent for its ability to reduce muscle spasms and provide relief from pain and discomfort.
Used in Veterinary Medicine:
DL-GAMMA-AMINO-B-HYDROXYBUTYRIC ACIDCRYS TALLINE is used as a treatment to reduce the uptake of iodine by the thyroid glands in animals, helping to manage and treat thyroid-related conditions.

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

• 91350-64-0 N-(3-cyano-2-hydroxy-propyl)-benzamide 
• 16011-10-2 (Z)-4-phthalimidocrotonic acid 
• 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 

Downstream Products

• 7010-89-1 3-Hydroxy-4-guanidino-buttersaeure 
• 38090-53-8 trans-4-aminocrotonic acid 
• 461-06-3 CARNITINE 
• 157542-04-6 (RS)-<1-(benzyloxycarbonyl)amino>-butan-2,4-diol 
• 77680-79-6 3-Hydroxy-4-(3,4,5-trimethoxy-thiobenzoylamino)-butyric acid 
• 83349-20-6 4-<(Benzyloxycarbonyl)amino>-3-hydroxybutanoic acid 
• 858124-22-8 3-hydroxy-4-{4-methoxy-3-[(E)-2-(4-trifluoromethoxyphenyl)vinyl]benzoylamino}butyric acid 
• 133995-97-8 1-Benzyloxy-4-aminomethylazetidin-2-one 
• 1173983-50-0 methyl 4-[(2,6-dinitrophenyl)amino]-3-hydroxybutanoate 
• 127852-78-2 4-tert-butoxycarbonylamino-3-hydroxy-butyric acid 

Relevant academic research and scientific papers

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.

METHODS OF TREATING FRAGILE X SYNDROME, DOWN?S SYNDROME, AUTISM AND RELATED DISORDERS

Disclosed herein are methods of treating fragile X syndrome, fragile X-associated tremor/ataxia syndrome, Down?s syndrome and other forms of mental retardation, and/or autism comprising administering a GABA B agonist prodlug to a subject suffering therefrom. The GABAB agonist prodrugs can be compounds of Formula (I), (II) or (III) as disclosed herein

Use of GABA and GABAB agonists

The present invention provides methods of stimulating tissue growth, including islet cell growth, by administering GABA or a GABA agonist to act on GABAB receptors and GABAB-like receptors to activate cell replication.

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.

Carboxy- and Cyano-Hydroxylation of Alkenes. - Synthesis of 3-Hydroxy-4-amino Acids and Butyrolactones via the Isoxazoline Route

Dichloro- and dibromoformaldoximes are useful 1,3-dipolar cycloaddition reagents.They are conveniently preparated in situ, in high yields by dihalogenation of glyoxalic acid aldoxime with N-bromo- and N-chlorosuccinimide or tert-butyl hypochlorite.Dehydrohalogenation with potassium hydrogen carbonate in the presence of alkenes gives 3-halo-isoxazolines in a one-pot reaction.Reduction with iron pentacarbonyl gives β-hydroxynitriles.Methoxylation and catalytic reduction give β-hydroxy esters.Allyl alcohols and allylamines are transformed with halonitrile oxides into butyrolactones (DL-angelica lactone) and DL-3-hydroxy-4-amino acids (carnitine, 4-amino-3-hydroxybutyric acid), respectively.The lactonization is best effected by heating the γ-silyloxy ester in acetic acid with potassium hydrogen sulfate as catalyst.A synthesis of N-Boc-dihydromuscimol is described.

Composition containing a penem or carbapenem antibiotic and the use of the same

Administration of an N-acylated amino acid in association with a penem or carbapenem antibiotic relieves or eliminates the renal problems associated with administration of the antibiotic alone. The amino acid derivative and antibiotic may be formulated together as a composition or administered separately, either simultaneously or sequentially.

Delta-hydroxy-beta-lysine derivatives and their production

A compound of the formula wherein R1 and R4 are independently amino or an organic residue bonded through nitrogen, R2 is hydrogen or alkyl which may be substituted, R3 is hydrogen or a protecting group and R5 is hydroxyl which may be substituted or amino which may be substituted or salts thereof; with the proviso that when R1 is amino, sorbylamino or hexanoylamino, R2 is hydrogen or methyl, R4 is amino which may be protected adn R5 is hydroxyl or 2-amidinoethylamino, R3 is a protecting group, and that when R1 is amino, leucylamino, acetylamino or benzyloxycarbonylamino, R3 is hydrogen, methyl or 2--tettrahydropyranyl, R4 is amino, acetylamino or benzyloxycarbonylamino and R5 is hydroxyl which may be substituted or amino which may be substituted, R2 is alkyl which may be substituted, has antibacterial activities against drug-resistant bacteria and therefore can be useful as a chemotherapeutic drug for bacterial infections in mammals.

OXIDATIVE DEGRADATION OF β- AND γ-AMINO ACIDS BY CONTACT GLOW DISCHARGE ELECTROLYSIS

The degradation of β- and γ-amino acids in aqueous solutions by contact glow discharge electrolysis (CGDE) was studied.It was found that the reaction is actually a stepwise oxidative degradation by hydroxyl radical produced by CGDE.

Total Synthesis of (R)-Glycerol Acetonide and the Antiepileptic and Hypotensive Drug (-)-γ-Amino-β-hydroxybutyric Acid (GABOB): Use of Vitamin C as a Chiral Starting Material

Ascorbic acid (Vitamin C) (9) is shown to be a useful, inexpensive chiral starting material for natural products synthesis.It is converted in high yield via two synthetic operations into (R)-glycerol acetonide (7), the more inaccessible enantiomer of glycerol acetonide.Since D-(R)-glyceraldehyde acetonide (4) and the corresponding alcohol 1 have been used in many total syntheses of a wide variety of compounds, the ready availability of the opposite enantiomers L-(S)-glyceraldehyde acetonide (6) and glycerol (7) should be of greate value.As one indication of this potential synthetic utility, the hypotensive, antiepileptic compound (R)-(-)-γ-amino-β-hydroxybutyric acid (GABOB) (8) has been synthesized from ascorbic acid (9) via nine steps in 10percent overall yield.As further evidence of the importance of these synthesis, several useful intermediates for the preparation of the highly active hypotensive agents, the aryloxypropanolamines (5), were prepared from Vitamin C.