16504-57-7

Basic information

• Product Name: D-BETA-HOMOSERINE
• Synonyms: (-)-4-HYDROXY-3-AMINOBUTYRIC ACID;D-BETA-HOMOSERINE;D-BETA-HOMOSERINE [(S)-3-AMINO-4-HYDROXY-BUTYRIC ACID (-)];H-D-BETA-HOSER-OH;H-D-BETA-HOMOSERINE;H-D-SER-(C*CH2)OH;ASPARTIMOL;(S)-3-AMINO-4-HYDROXY-BUTYRIC ACID
• CAS NO: 16504-57-7
• Molecular Formula: C₄H₉NO₃
• Molecular Weight: 119.12
• Product Categories: β-Homo Amino Acids;Beta amino acids;pharmacetical;amino acids
• Mol File: 16504-57-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 223-225 °C
• Boiling Point: 374.546 °C at 760 mmHg
• Flash Point: 180.319 °C
• Appearance: /
• Density: 1.313 g/cm³
• Vapor Pressure: 3.84E-07mmHg at 25°C
• Refractive Index: 1.51
• Storage Temp.: 2-8°C(protect from light)
• PKA: 3.69±0.10(Predicted)
• CAS DataBase Reference: D-BETA-HOMOSERINE(CAS DataBase Reference)
• NIST Chemistry Reference: D-BETA-HOMOSERINE(16504-57-7)
• EPA Substance Registry System: D-BETA-HOMOSERINE(16504-57-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• Hazardous Substances Data: 16504-57-7(Hazardous Substances Data)

Usage

General Description

D-BETA-HOMOSERINE is a naturally occurring amino acid and a key intermediate in the metabolic pathway for threonine biosynthesis. It is an important building block for the synthesis of various compounds and proteins in living organisms. D-BETA-HOMOSERINE is also used in the production of antibiotics, pharmaceuticals, and other biologically active compounds. Additionally, it has been studied for its potential therapeutic applications in the treatment of metabolic disorders and neurological diseases. Overall, D-BETA-HOMOSERINE plays a crucial role in various biological processes and has potential applications in medicine and biotechnology.

InChI:InChI=1/C4H9NO3/c5-3(2-6)1-4(7)8/h3,6H,1-2,5H2,(H,7,8)/t3-/m0/s1

Upstream product

• 777-33-3 N-trifluoroacetyl-L-aspartic acid anhydride 
• 586952-09-2 benzyl (E)-4-hydroxy-2-butenoate 

Downstream Products

• 1429347-11-4 (S)-3-((4-(N-(2,4-dimethylphenyl)-N-isobutylsulfamoyl)phenyl)amino)-4-hydroxybutanoic acid 
• 1429347-09-0 (R)-3-((4-(N-(2,4-dimethylphenyl)-N-isobutylsulfamoyl)-2-methylphenyl)amino)-4-hydroxybutanoic acid 
• 1455087-67-8 (R)-3-(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxamido)-4-hydroxybutanoic acid 

Relevant articles and documents

An approach to the synthesis of anti-β2,3-amino acids: Application of β-trifluoroacetamidoorganozinc reagents

An approach to the synthesis of anti-β2,3-amino acids is reported. The key steps involve stereoselective lactone alkylation followed by ring opening with iodotrimethylsilane/ethanol to give iodo esters. Formation of the organozinc reagents from

Synthesis and rearrangements of D-glucosyl esters of aspartic acid linked through the 1- or 4-carboxyl group.

Catalytic hydrogenation of 2,3,4,6-tetra-O-benzyl-1-O-[1-benzyl N-(benzyloxycarbonyl)-L-aspart-4-oyl]-alpha-D-glucopyranose (1alpha) in acetic acid-2-methoxyethanol gave 1-O-(L-beta-aspartyl)alpha-D-glucopyranose (2alpha) contaminated with 2-O-(L-alpha-aspartyl)-D-glucopyranose (8). Evidence that 8 was formed from the 1-oyl isomer of 1alpha, namely 2,3,4,6-tetra-O-benzyl-1-O-[4-benzyl N-(benzyloxycarbonyl)-L-aspart-1-oyl]-alpha-D-glucopyranose (7alpha), via 1 leads to 2 acyl migration, was obtained by submitting the deprotected D-glucosyl ester to successive N-acetylation, esterification, and O-acetylation; the final product was identified as a approximately 4:1 mixture of 2,3,4,6-tetra-O-acetyl-1-O-[1-methyl N-(acetyl)-L-aspart-4-oyl]-alpha-D-glucopyranose (4alpha) and 1,3,4,6-tetra-O-acetyl-2-O-[4-methyl N-(acetyl)-L-aspart-1-oyl]-D-glucopyranose (6) which were also prepared by definitive methods. On the other hand, deprotection of 1beta gave isomerically pure 2beta which was converted into the peracetylated ester derivative 4β an explanation for the differences in aglycon isomeric purity of 2alpha and 2beta is given. Hydrogenolysis of 7beta under the above conditions led to intermolecular transesterification with scission of the C-1 ester bond to give 1-(2-methoxyethyl) L-aspartic acid and D-glucose. Catalytic hydrogenation of 7alpha and 7beta, performed in the presence of trifluoroacetic acid, afforded 1-O-(L-alpha-aspartyl)-alpha- and -beta-D-glucopyranoside trifluoroacetate salts (11alpha and 11beta), respectively. The structure of 11beta was established by successive conversion into 2,3,4,6-tetra-O-acetyl-1-O-[4-methyl N-(acetyl)-L-aspart-1-oyl]-beta-D-glucopyranose (5beta) which was also prepared by definitive methods. Analogous treatment of 11alpha gave the N-acetyl derivative 12 which underwent 1 leads to 2 acyl migration during esterification with diazomethane to give the N-acetyl methyl ester derivative 10; acetylation of 10 afforded 6.