Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

459224

Sigma-Aldrich

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

97%

Synonym(s):

L-Homoserine lactone hydrochloride, HSI

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

Looking for similar products? Visit Product Comparison Guide

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKBC9254V
MKBC9254
18911JR
11903EQ

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 1

1 of 1

5′-Deoxy-5′-(methylthio)adenosine

Sigma-Aldrich

D5011

5′-Deoxy-5′-(methylthio)adenosine

Design, synthesis and antibacterial evaluation of novel AHL analogues
Ren J, et al.
Bioorganic & Medicinal Chemistry Letters, 23(14), 4154-4156 (2013)
Natural products from social amoebae
Barnett R and Stallforth P
Chemistry?A European Journal , 24(17), 4202-4214 (2018)
L R Brunham et al.
The pharmacogenomics journal, 14(6), 555-563 (2014-05-28)
Differences in the frequency of pharmacogenomic variants may influence inter-population variability in drug efficacy and risk of adverse drug reactions (ADRs). We investigated the diversity of ∼ 4500 genetic variants in key drug-biotransformation and -response genes among three South East
Reaction of (S)-homoserine lactone with Grignard reagents: synthesis of amino-keto-alcohols and β-amino acid derivatives
Gundogdu O, et al.
Tetrahedron Asymmetry, 28(9), 1163-1168 (2017)
Amanda L May et al.
Analytical chemistry, 84(3), 1243-1252 (2012-01-13)
A range of acylhomoserine lactones (AHLs) are used as intraspecies quorum sensing signals by Gram-negative bacteria, and the detection and quantitation of these molecules is of interest. This manuscript reports a liquid chromatographic-isotope dilution tandem mass spectrometric method for the
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service