(S)-(-)-4-Amino-2-hydroxybutyric acid

Base Information

• Chemical Name: (S)-(-)-4-Amino-2-hydroxybutyric acid
• CAS No.: 40371-51-5
• Molecular Formula: C₄H₉NO₃
• Molecular Weight: 119.12
• Hs Code.: 29225090
• European Community (EC) Number: 670-305-7
• UNII: 2Z3NQ8MG2T
• Nikkaji Number: J21.882K
• Mol file: 40371-51-5.mol

Synonyms:40371-51-5;(S)-4-amino-2-hydroxybutanoic acid;(S)-(-)-4-AMINO-2-HYDROXYBUTYRIC ACID;(S)-4-Amino-2-hydroxybutyric acid;(2S)-4-amino-2-hydroxybutanoic acid;Butanoic acid, 4-amino-2-hydroxy-, (2S)-;MFCD00674110;Amikacin impurity I;4-amino-(2s)-hydroxybutyric acid;2Z3NQ8MG2T;Butanoic acid, 4-amino-2-hydroxy-, (S)-;L-4-amino-2-hydroxybutyric acid;L-(-)-4-Amino-2-hydroxybutyric acid;4-Amino-2-hydroxybutyric acid, (S)-(-)-;UNII-2Z3NQ8MG2T;SCHEMBL571055;4-amino-2-hydroxy butyric acid;l-2-hydroxy-4-aminobutyric acid;IVUOMFWNDGNLBJ-VKHMYHEASA-N;(S)-4-amino-2-hydroxybutanoicacid;(S)-2-Hydroxy-4-aminobutyric acid;2(S)-hydroxy-4-amino-butyric acid;(2S)-4-amino-2-hydroxybutyric acid;4-amino-2-(S)-hydroxy-butyric acid;AKOS005258875;AKOS006238604;AC-1318;CS-M-55295;CS-W002667;L-gamma-Amino-alpha-hydroxybutyric acid;AS-10799;A6761;AM20100077;L-(-)-gamma-Amino-alpha-hydroxybutyric acid;EN300-86223;(S)-(-)-4-Amino-2-hydroxybutyric acid, 96%;J-509628;L-.GAMMA.-AMINO-.ALPHA.-HYDROXYBUTYRIC ACID;Q-103171;L-(-)-.GAMMA.-AMINO-.ALPHA.-HYDROXYBUTYRIC ACID;Z1203578154;Amikacin impurity I, European Pharmacopoeia (EP) Reference Standard

Chemical Property of (S)-(-)-4-Amino-2-hydroxybutyric acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 1.08E-06mmHg at 25°C
• Melting Point: 207-212 °C
• Refractive Index: -30 ° (C=1, H2O)
• Boiling Point: 361.8 °C at 760 mmHg
• PKA: 3.47±0.10(Predicted)
• Flash Point: 172.6 °C
• PSA: 83.55000
• Density: 1.312 g/cm³
• LogP: -0.51900
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Sensitive.: Hygroscopic
• Solubility.: Methanol (Very Slightly, Heated), Water
• Water Solubility.: almost transparency
• XLogP3: -3.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 119.058243149
• Heavy Atom Count: 8
• Complexity: 83.4

Purity/Quality:

99.5% ^*data from raw suppliers

(S)-(-)-4-Amino-2-hydroxybutyric Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(CN)C(C(=O)O)O
• Isomeric SMILES: C(CN)[C@@H](C(=O)O)O
• Uses: (S)-(-)-4-Amino-2-hydroxybutyric Acid is an analogue of γ-aminobutyric acid (GABA) with potential inhibitory activity on GABA binding and uptake by brain. Injection of (S)-(-)-4-Amino-2-hydroxybutyric Acid showed no significant changes in plasma growth hormone (GH) in healthy patients but increased plasma GH, prolactin, and cortisol levels in cerebrovascular patients. (S)-(-)-4-Amino-2-hydroxybutyric acid may be used in the preparation of 6′-amino-1-N-[(S)-4-amino-2-hydroxybutyryl]-6′-deoxylividomycin A.

Technology Process of (S)-(-)-4-Amino-2-hydroxybutyric acid

There total 6 articles about (S)-(-)-4-Amino-2-hydroxybutyric acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

S-4-benzyloxycarbonylamino-2-hydroxybutyric acid (40371-50-4) → (S)-4-amino-2-hydroxybutanoic acid (3938-83-8,13477-53-7,31771-40-1,40371-51-5)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 48h; under 760 Torr;

Reference yield:

L-2,4-diaminobutyrate (1758-80-1) → (S)-4-amino-2-hydroxybutanoic acid (3938-83-8,13477-53-7,31771-40-1,40371-51-5)

Guidance literature:

With sodium nitrite;

DOI:10.1016/S0040-4039(01)96933-3

Reference yield:

(S)-2-hydroxysuccinamic acid (57229-74-0) → (S)-4-amino-2-hydroxybutanoic acid (3938-83-8,13477-53-7,31771-40-1,40371-51-5)

Guidance literature:

Multistep reaction; (i) Ac2O, Py, (ii) H2, aq. HCl, EtOH, PtO2, (iii) ion-exchange resin + form>;

DOI:10.1246/bcsj.51.3296

upstream raw materials:

L-2,4-diaminobutyrate

(S)-2-hydroxysuccinamic acid

γ-phthalimidoimino-α-hydroxybutyric acid

S-4-benzyloxycarbonylamino-2-hydroxybutyric acid

Downstream raw materials:

S-4-benzyloxycarbonylamino-2-hydroxybutyric acid

4-Benzyloxycarbonylamino-2S-hydroxy butyric acid ethyl ester

(+)-(2S)-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-hydroxybutanoic acid

(S)-4-(1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxamido)-2-hydroxybutanoic acid

Refernces

• 1、 Bentley, Jonathan M.,Wadsworth, Harry J.,Willis, Christine L.. "Enantioselective Syntheses of (S)- and (R)-3-Hydroxypyrrolidin-2-ones via Lactate Dehydrogenase Catalysed Reductions of 4-Benzyloxycarbonylamino-2-oxobutanoic Acid". . p. 231 - 232. Retrieved 2007/10/02.
• 2、 Yoneta,Shibahara,Fukatsu,Seki. "A new synthesis of L-4-amino-2-hydroxybutyric acid. Carboxyl-assisted nitrile synthesis from primary amides". . p. 3296 - 3297. Retrieved 2007/10/05.