42453-21-4

Basic information

• Product Name: (D,L)-4-AMINO-2-METHYL-BUTANOIC ACID
• Synonyms: (D,L)-4-AMINO-2-METHYL-BUTANOIC ACID;4-Amino-2-methylbutanoic acid
• CAS NO: 42453-21-4
• Molecular Formula: C₅H₁₁NO₂
• Molecular Weight: 131.17
• Product Categories: Small molecule
• Mol File: 42453-21-4.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (D,L)-4-AMINO-2-METHYL-BUTANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (D,L)-4-AMINO-2-METHYL-BUTANOIC ACID(42453-21-4)
• EPA Substance Registry System: (D,L)-4-AMINO-2-METHYL-BUTANOIC ACID(42453-21-4)

Safety Data

• Hazardous Substances Data: 42453-21-4(Hazardous Substances Data)

Usage

Uses

Used in Animal Feed Industry:
(D,L)-4-AMINO-2-METHYL-BUTANOIC ACID is used as a dietary supplement in animal feed for improving the nutritional value and promoting animal growth. It is particularly beneficial in providing the essential amino acid that may not be sufficiently synthesized by the animal's body, thus supporting overall health and development.
Used in Medical Treatments:
(D,L)-4-AMINO-2-METHYL-BUTANOIC ACID is used as a source of sulfur in some medical treatments, specifically for its role in detoxification processes and liver health. It aids in preventing liver damage from certain toxins, highlighting its importance in maintaining liver function and overall metabolic health.
Used in Pharmaceutical and Health Supplements:
(D,L)-4-AMINO-2-METHYL-BUTANOIC ACID is utilized in the formulation of pharmaceutical products and health supplements due to its essential role in the body's protein synthesis and its potential benefits in liver detoxification. Its inclusion in these products aims to support optimal health and well-being.

Synthetic route

2-(3'-cyanobutyl)-1H-isoindole-1,3(2H)-dione (120539-96-0) → 4-Amino-2-methylbutyric acid (42453-21-4)

Conditions	Yield
With hydrogenchloride for 14h; Heating;	75%

4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-ethyl-butyronitrile → 4-Amino-2-methylbutyric acid (42453-21-4)

Conditions	Yield
With hydrogenchloride Heating;	75%

ethyl 2-methyl-4-phthalimidobutanoate (732303-86-5) → 4-Amino-2-methylbutyric acid (42453-21-4)

Conditions	Yield
With hydrogenchloride; acetic acid at 140℃; for 18h;	65%

formic acid (64-18-6) + 3-butene-1-amine (2524-49-4) → 4-Amino-2-methylbutyric acid (42453-21-4) + 5-aminopentanoic acid (660-88-8)

Conditions	Yield
With hydrogen; oxygen In water for 3h;	A 38% B 4%

formic acid (64-18-6) + crotylamine (21035-54-1) → 4-Amino-2-methylbutyric acid (42453-21-4) + (±)-2-(aminomethyl)butanoic acid (4385-92-6)

Conditions	Yield
With hydrogen; oxygen In water for 3h;	A 19% B 17%

3-methyl-2-pyrrolidinone (2555-05-7) → 4-Amino-2-methylbutyric acid (42453-21-4)

Conditions	Yield
With hydrogenchloride
With hydrogenchloride Heating;

(2S,4R)-4-methylglutamic acid (31137-74-3) → 4-Amino-2-methylbutyric acid (42453-21-4)

Conditions	Yield
With pyridoxal 5'-phosphate at 32℃; for 46h; pyridine-HCl buffer (pH 4.5), glutamate decarboxylase; Yield given;

(2S,4S)-4-methylglutamic acid (6141-27-1) → 4-Amino-2-methylbutyric acid (42453-21-4)

Conditions	Yield
With pyridoxal 5'-phosphate at 32℃; for 22h; pyridine-HCl buffer (pH 4.5), glutamate decarboxylase; Yield given;

D,L-erythro-γ-methylglutamate (14561-55-8) → 4-Amino-2-methylbutyric acid (42453-21-4)

Conditions	Yield
With pyridoxal 5'-phosphate at 32℃; for 46h; pyridine-HCl buffer (pH 4.5), glutamate decarboxylase; Yield given;
With pyridoxal 5'-phosphate at 32℃; for 22h; pyridine-HCl buffer (pH 4.5), glutamate decarboxylase; Yield given;
Multi-step reaction with 3 steps 1: 1.) Et3N, 2.) CF3CO2H / 1.) H2O, room temperature, 2 h, 2.) CH2Cl2, 2.5 h 2: 91 percent / MgSO4 / 1 h / 37 °C / Tris buffer (pH 9), leucine aminopeptidase 3: pyridoxal phosphate / 46 h / 32 °C / pyridine-HCl buffer (pH 4.5), glutamate decarboxylase View Scheme

(+-)-2-methyl-4-phthalimido-butyric acid anilide → 4-Amino-2-methylbutyric acid (42453-21-4)

Conditions	Yield
With hydrogen iodide; acetic acid

Tiglic acid (80-59-1) → 4-Amino-2-methylbutyric acid (42453-21-4)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 94 percent / p-toluenesulfonic acid / benzene / Heating 2.1: N-bromosuccinimide; dibenzoylperoxide / CCl4 / 18 h / Heating 2.2: dimethylformamide / 18 h / 140 °C 3.1: 98 percent / hydrogen / Pd on C / ethanol / 20 h / 3040 Torr 4.1: 65 percent / hydrochloric acid; acetic acid / 18 h / 140 °C View Scheme

Ethyl tiglate (5837-78-5) → 4-Amino-2-methylbutyric acid (42453-21-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N-bromosuccinimide; dibenzoylperoxide / CCl4 / 18 h / Heating 1.2: dimethylformamide / 18 h / 140 °C 2.1: 98 percent / hydrogen / Pd on C / ethanol / 20 h / 3040 Torr 3.1: 65 percent / hydrochloric acid; acetic acid / 18 h / 140 °C View Scheme

ethyl 2-methyl-4-phthalimidobut-2-enoate (732303-84-3) → 4-Amino-2-methylbutyric acid (42453-21-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 98 percent / hydrogen / Pd on C / ethanol / 20 h / 3040 Torr 2: 65 percent / hydrochloric acid; acetic acid / 18 h / 140 °C View Scheme

L-leucyl-L-erythro-γ-methylglutamate (91307-53-8) → 4-Amino-2-methylbutyric acid (42453-21-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 91 percent / MgSO4 / 1 h / 37 °C / Tris buffer (pH 9), leucine aminopeptidase 2: pyridoxal phosphate / 46 h / 32 °C / pyridine-HCl buffer (pH 4.5), glutamate decarboxylase View Scheme

4-Amino-2-methylbutyric acid (42453-21-4) → 3-methyl-2-pyrrolidinone (2555-05-7)

Conditions	Yield
With titanium(IV) isopropylate In 1,2-dichloro-ethane for 21h; Heating;	81%
With 2,2'-dipyridyldisulphide; triphenylphosphine In acetonitrile for 4.5h; Heating;	62%

phthalic anhydride (85-44-9) + 4-Amino-2-methylbutyric acid (42453-21-4) → rac-2-methyl-4-phthalimidobutanoic acid (63987-58-6, 80640-62-6, 80640-63-7)

Conditions	Yield
at 140℃;

4-Amino-2-methylbutyric acid (42453-21-4) → 4-amino-2-methyl-1-butanol (44565-27-7, 44565-28-8, 64070-19-5, 88390-32-3)

Conditions	Yield
With tetrahydrofuran; lithium aluminium tetrahydride

4-Amino-2-methylbutyric acid (42453-21-4) → (R)-4-amino-2-methyl-1-butanol (44565-27-7, 44565-28-8, 64070-19-5, 88390-32-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 140 °C 2: quinine 3: N2H4+H2O; ethanol 4: lithium alanate; THF View Scheme

4-Amino-2-methylbutyric acid (42453-21-4) → (R)-2MeGABA (96192-37-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 140 °C 2: quinine 3: N2H4+H2O; ethanol View Scheme

4-Amino-2-methylbutyric acid (42453-21-4) → (S)-2-methyl-4-phthalimido-butyric acid (63987-58-6, 80640-62-6, 80640-63-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 140 °C 2: quinine View Scheme

4-Amino-2-methylbutyric acid (42453-21-4) → (R)-2-methyl-4-phthalimido-butyric acid (63987-58-6, 80640-62-6, 80640-63-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 140 °C 2: quinine View Scheme

4-Amino-2-methylbutyric acid (42453-21-4) → (S)-2-methyl-4-phthalimido-butyryl chloride (108758-87-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 140 °C 2: quinine 3: thionyl chloride View Scheme

4-Amino-2-methylbutyric acid (42453-21-4) → N-((S)-5-diazo-3-methyl-4-oxo-pentyl)-phthalimide

Conditions	Yield
Multi-step reaction with 4 steps 1: 140 °C 2: quinine 3: thionyl chloride 4: diethyl ether View Scheme

4-Amino-2-methylbutyric acid (42453-21-4) → N-(5-diazo-3-methyl-4-oxo-pentyl)-phthalimide

Conditions	Yield
Multi-step reaction with 2 steps 1: 140 °C 2: thionyl chloride / und Behandeln des Reaktionsprodukts mit Diazomethan in Aether View Scheme

Upstream product

• 2555-05-7 3-methyl-2-pyrrolidinone 
• 64-18-6 formic acid 
• 21035-54-1 crotylamine 
• 2524-49-4 3-butene-1-amine 
• 120539-96-0 2-(3'-cyanobutyl)-1H-isoindole-1,3(2H)-dione 
• 31137-74-3 (2S,4R)-4-methylglutamic acid 
• 6141-27-1 (2S,4S)-4-methylglutamic acid 
• 14561-55-8 D,L-erythro-γ-methylglutamate 
• 732303-86-5 ethyl 2-methyl-4-phthalimidobutanoate 
• 80-59-1 Tiglic acid 
• 5837-78-5 Ethyl tiglate 
• 732303-84-3 ethyl 2-methyl-4-phthalimidobut-2-enoate 
• 91307-53-8 L-leucyl-L-erythro-γ-methylglutamate 

Downstream Products

• 63987-58-6 rac-2-methyl-4-phthalimidobutanoic acid 
• 44565-27-7 4-amino-2-methyl-1-butanol 
• 2555-05-7 3-methyl-2-pyrrolidinone 
• 44565-27-7 (R)-4-amino-2-methyl-1-butanol 

Relevant articles and documents

Synthesis and resolution of 2-methyl analogues of GABA

E-4-Amino-2-methylbut-2-enoic acid, (±)-4-amino-2-methylbutanoic acid, (+)-(S)- and (-)-(R)-4-amino-2-methylbutanoic acid, which are analogues of the inhibitory neurotransmitter GABA (γ-aminobutyric acid, 4-aminobutanoic acid), were synthesised from ethyl 2-methyl-4-phthalimidobut-2- enoate, ethyl 2-methyl-4-phthalimidobutanoate, (+)-[(2R-(3,3-dimethylbutyro-1,4- lactonyl)]-(2S)-methyl-4-phthalimidobutanoate and (-)-[(2R-(3,3-dimethylbutyro- 1,4-lactonyl)]-(2R)-methyl-4-phthalimidobutanoate, respectively. The assignment of the absolute configuration of (+)-(S)- and (-)-(R)-4-amino-2-methylbutanoic acid was based on the X-ray crystallographic structure of the (+)-(R,S)-diastereoisomer, and direct comparison of specific rotations with the published data for (-)-(R)-4-amino-2-methylbutanoic acid.

THE HYDROCYANATION ROUTE TO β- AND γ-AMINO ACIDS. A SYNTHESIS OF α-METHYLENE-β-ALANINE

Hydrocyanation of several phthalimidoalkynes proceeds with good regioselection yielding products which were easily converted into unsaturated β- and γ-amino acids.

The Stereochemistry of Organometallic Compounds. XXXII. Hydrocyanation of Derivatives of Amino Alkynes

The hydrocyanation of a range of amino alkyne derivatives has been studied by using nickel-based catalyst systems.The phthalimido derivatives have been shown to give good yields of unsaturated cyano amine derivatives, and some of these have been converted into both saturated and unsaturated amino acids.

FLAME-INDUCED CARBOXYLATION OF UNSATURATED AMINES IN AN AQUEOUS FORMIC ACID SOLUTION

When a hydrogen-oxygen flame was kept in contact with an aqueous formic acid solution of unsaturated amines, carboxylation onto a double bond took place.This reaction revealed to be initiated by addition of a hydrogen atom to the double bond followed by coupling of the resulted substrate radical with a carboxyl radical.

Resolution of γ-Methyl and γ-Fluoroglutamic Acids. Lack of Stereospecificity of Leucine Aminopeptidase with L-Leucyl-L-erythro-γ-substituted Glutamates

The hydrolysis of L-leucyl-γ-substituted D,L-glutamates by leucine aminopeptidase, from porcine kidney, is stereospecific with threo-γ-methyl and threo-γ-fluoroglutamate containing dipeptides whereas there is a lack of stereospecificity with erythro-isomers.The optical purities of L-threo- and L-erythro-glutamate isomers thus obtained have been monitored by gas chromatography, high pressure liquid chromatography, or nuclear magnetic resonance.The optical rotations of optically pure L-isomers have been measured and the discrepancies with former publications are discussed.