(S)-4-Amino-3-hydroxybutanoic acid

Base Information

• Chemical Name: (S)-4-Amino-3-hydroxybutanoic acid
• CAS No.: 7013-05-0
• Molecular Formula: C4H9NO3
• Molecular Weight: 119.12
• UNII: CM46XGM78M
• DSSTox Substance ID: DTXSID401342720
• Nikkaji Number: J21.884G
• Wikidata: Q27275534
• ChEMBL ID: CHEMBL296263
• Mol file: 7013-05-0.mol

Synonyms:7013-05-0;(S)-4-AMINO-3-HYDROXYBUTANOIC ACID;(3S)-4-amino-3-hydroxybutanoic acid;GABOB (beta-hydroxy-GABA);Butanoic acid, 4-amino-3-hydroxy-, (3S)-;(S)-(+)-3-Hydroxy-GABA;(S)-4-Amino-3-hydroxy-butyric acid;UNII-CM46XGM78M;CM46XGM78M;CHEMBL296263;(+)-gamma-amino-beta-hydroxybutyric acid;gamma-Amino-beta-hydroxybutyric acid, (+)-;(S)-(+)-4-AMINO-3-HYDROXYBUTANOIC ACID;(S)-(+)-4-Amino-3-hydroxybutyric acid;beta-Hydroxy-GABA;aminohydroxybutyric acid;b-hydroxy-GABA;aminohydroxybutyric-acid;(S)-GABOB;S-(+)-GABOB;SCHEMBL1555143;YQGDEPYYFWUPGO-VKHMYHEASA-N;DTXSID401342720;BDBM50021186;MFCD00672884;AKOS016844198;S(+)-4-amino-3-hydroxybutanoic acid;CS-W023137;(S)-(+)-.BETA.-HYDROXY-GABA;(s)-beta-hydroxyl-gamma-aminobutyric acid;AC-13943;AS-35997;PD118693;(S)-4-AMINO-3-HYDROXYBUTANOICACID;A15949;EN300-268153;(S)-(+)-4-Amino-3-hydroxybutyric acid, 97%;A836784;(3S)-(+)-4-AMINO-3-HYDROXYBUTANOIC ACID;(+)-.GAMMA.-AMINO-.BETA.-HYDROXYBUTYRIC ACID;(S)-.GAMMA.-AMINO-.BETA.-HYDROXYBUTYRIC ACID;Q27275534;.GAMMA.-AMINO-.BETA.-HYDROXYBUTYRIC ACID, (+)-;Z1203578293;.GAMMA.-AMINO-.BETA.-HYDROXYBUTYRIC ACIDD(+)-FORM [MI]

Chemical Property of (S)-4-Amino-3-hydroxybutanoic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 3.84E-07mmHg at 25°C
• Melting Point: 207-212 °C
• Refractive Index: 1.51
• Boiling Point: 374.5 °C at 760 mmHg
• PKA: 4.04±0.10(Predicted)
• Flash Point: 180.3 °C
• PSA: 83.55000
• Density: 1.312 g/cm³
• LogP: -0.51900
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: -4.1
• 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:

98%,99%, ^*data from raw suppliers

(S)-(+)-4-Amino-3-hydroxybutyric acid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C(CN)O)C(=O)O
• Isomeric SMILES: C([C@@H](CN)O)C(=O)O
• Uses: S-(+)-GABOB anticonvulsant and is used in the treatment of epilepsy as it binds to the GABAB receptor.

Technology Process of (S)-4-Amino-3-hydroxybutanoic acid

There total 21 articles about (S)-4-Amino-3-hydroxybutanoic 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: 100.0%

(-)-ethyl 3-cyano-3-hydroxypropionate (132882-98-5) → (S)-4-amino-3-hydroxybutanoic acid (7013-05-0,352-21-6)

Guidance literature:

With borane-THF; nickel dichloride; In isopropyl alcohol; for 2h; Ambient temperature;

DOI:10.1016/S0957-4166(00)82379-4

Reference yield: 100.0%

(S)-4-Amino-3-hydroxy-butyric acid ethyl ester → (S)-4-amino-3-hydroxybutanoic acid (7013-05-0,352-21-6)

Guidance literature:

With hydrogenchloride; for 1h;

DOI:10.1016/S0957-4166(00)80128-7

Reference yield: 95.0%

(S)-3-tert-Butoxy-4-tert-butoxycarbonylamino-butyric acid (99475-69-1) → (S)-4-amino-3-hydroxybutanoic acid (7013-05-0,352-21-6)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; for 16h; Ambient temperature;

DOI:10.1021/jo00350a007

upstream raw materials:

(-)-ethyl 3-cyano-3-hydroxypropionate

4-<(Benzyloxycarbonyl)amino>-3-hydroxybutanoic acid

3,4 epoxybutyric acid

[(5S)-2-oxo-1,3-oxazolidin-5-yl]acetic acid

Downstream raw materials:

(S)-hydroxy-4 phenylacetyl-1 pyrrolidinone-2

(S)-4-Dimethylamino-3-hydroxy-butyric acid

4-Aminobutan-1,3-diol

Refernces

• 1、 Ivsic, Trpimir,Dokli, Irena,Rimac, Ana,Hamersak, Zdenko. "Synthesis of GABOB and GABOB-based chiral units possessing distinct protecting groups". . p. 631 - 638. Retrieved 2014/02/14.
• 2、 Sanyal, Ishita,Shukla, Brajesh,Barman, Piyali Deb,Banerjee, Asish Kumar. "Stereoselective synthesis of (S)-oxiracetam and (S)-GABOB from (R)-glyceraldehyde acetonide". supporting information. p. 2637 - 2640. Retrieved 2013/06/26.