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459224

Sigma-Aldrich

(S)-α-Amino-γ-butyrolactone hydrochloride

97%

Synonym(s):

L-Homoserine lactone hydrochloride, HSI

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About This Item

Empirical Formula (Hill Notation):
C4H7NO2 · HCl
CAS Number:
2185-03-7
Molecular Weight:
137.56
Beilstein:
3562187
EC Number:
218-571-1
MDL number:
MFCD00058172
UNSPSC Code:
12352202
PubChem Substance ID:
24869524
NACRES:
NA.22

Quality Level

100

Assay

97%

form

powder or crystals

optical activity

[α]20/D −27.8°, c = 1 in H2O

mp

210-220 °C (dec.) (lit.)

application(s)

peptide synthesis

SMILES string

Cl.N[C@H]1CCOC1=O

InChI

1S/C4H7NO2.ClH/c5-3-1-2-7-4(3)6;/h3H,1-2,5H2;1H/t3-;/m0./s1

InChI key

XBKCXPRYTLOQKS-DFWYDOINSA-N

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Application

(S)-α-Amino-γ-butyrolactone hydrochloride can be used:
  • As a precursor for the preparation of amino-keto-alcohols and β-amino acids.
  • To prepare N-acylhomoserine lactone (AHL) analogs by reacting with substituted 2-chloro-N-phenylacetamide and different halides.
  • As a starting material for the synthesis of L-discadenine.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Bioorganic & Medicinal Chemistry Letters, 23(14), 4154-4156 (2013)
Reaction of (S)-homoserine lactone with Grignard reagents: synthesis of amino-keto-alcohols and β-amino acid derivatives
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Tetrahedron Asymmetry, 28(9), 1163-1168 (2017)
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