459224
(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:
Molecular Weight:
137.56
Beilstein:
3562187
EC Number:
MDL number:
UNSPSC Code:
12352202
PubChem Substance ID:
NACRES:
NA.22
Quality Level
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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
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
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Natural products from social amoebae
Barnett R and Stallforth P
Chemistry?A European Journal , 24(17), 4202-4214 (2018)
Design, synthesis and antibacterial evaluation of novel AHL analogues
Ren J, et al.
Bioorganic & Medicinal Chemistry Letters, 23(14), 4154-4156 (2013)
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)
Cheng-Siang Wong et al.
World journal of microbiology & biotechnology, 28(2), 453-461 (2012-07-19)
A chemically defined medium called KGm medium was used to isolate from a sample of sea water a bacterial strain, MW3A, capable of using N-3-oxohexanoyl-L: -homoserine lactone as the sole carbon source. MW3A was clustered closely to Pseudomonas aeruginosa by
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