147228-35-1

Basic information

• Product Name: (R)-3-AMINO-5,5-DIMETHYLHEXANOIC ACID
• Synonyms: (R)-3-AMINO-5,5-DIMETHYLHEXANOIC ACID;(R)-3-Amino-5,5-dimethylhexanoic acid hydrochloride
• CAS NO: 147228-35-1
• Molecular Formula: C8H17NO2
• Molecular Weight: 159.22608
• Mol File: 147228-35-1.mol

Chemical Properties

• Boiling Point: 259.2 °C at 760 mmHg
• Flash Point: 110.6 °C
• Appearance: /
• Density: 0.999 g/cm³
• Refractive Index: 1.466
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.81±0.10(Predicted)
• CAS DataBase Reference: (R)-3-AMINO-5,5-DIMETHYLHEXANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-AMINO-5,5-DIMETHYLHEXANOIC ACID(147228-35-1)
• EPA Substance Registry System: (R)-3-AMINO-5,5-DIMETHYLHEXANOIC ACID(147228-35-1)

Safety Data

• Hazardous Substances Data: 147228-35-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Nutritional Applications:
(R)-3-Amino-5,5-dimethylhexanoic Acid is used as a key component in the synthesis of peptides and proteins, which are essential for various biological processes in the human body. It plays a critical role in regulating blood sugar levels, producing growth hormones, and supporting tissue repair and healing.
Used in Sports Nutrition:
R-leucine is used as a supplement for muscle building and exercise enhancement. It is commonly found in protein-rich foods such as beef, chicken, fish, nuts, eggs, and beans, making it a popular choice for athletes and fitness enthusiasts looking to improve their performance and muscle growth.
Used in Food Industry:
(R)-3-Amino-5,5-dimethylhexanoic Acid is used in the food industry as a flavor enhancer and a nutritional supplement. Its presence in various protein-rich foods contributes to the overall nutritional value and taste of the products.

InChI:InChI=1/C8H17NO2/c1-8(2,3)5-6(9)4-7(10)11/h6H,4-5,9H2,1-3H3,(H,10,11)/t6-/m0/s1

Upstream product

• 147228-31-7 (3R)-5,5-dimethyl-3-(tosylamino)hexanoic acid 
• 147228-25-9 (3R)-ethyl 5,5-dimethyl-3-(tosylamino)hexanoate 

Relevant articles and documents

104. The enantioselective synthesis of β-amino acids, their α-hydroxy derivatives, and the N-terminal components of bestatin and microginin

L-Aspartic acid by tosylation, anhydride formation, and reduction with NaBH4 was converted into (3S)-3-(tosylamino)butan-4-olide (8; Scheme 1). Treatment of 8 with ethanolic trimethylsilyl iodide gave the N-protected deoxy-iodo-β-homoserine ethyl ester 9. The latter, on successive nucleophilic displacement with lithium dialkylcuprates (→ 10a-e), alkaline hydrolysis (→ 11a-e), and reductive removal of the tosyl group, produced the corresponding 4-substituted (3R)-3-aminobutanoic acids 12a-e (ee >99%). Electrophilic hydroxylation of 8 (→ 19; Scheme 3), subsequent iodo-esterification (→ 21; Scheme 4), and nucleophilic alkylation and phenylation afforded, after saponification and deprotection, a series of 4-substituted (2S,3A)-3-amino-2-hydroxybutanoic acids 24 including the N-terminal acids 24e (= 3) and 24f (= 4) of bestatin and microginin (de >95%), respectively.

An enantiospecific synthesis of β-amino acids

L-Aspartic acid by regioselective modification of the α-carboxylic acid group, namely N-tosylation, anhydride formation, reduction, iodo-esterification, alkylation, and deprotection afforded a series of γ-alkyl β-aminobutyric acids of the R configuration (ee > 99%).