2185-03-7

Basic information

• Product Name: L-Homoserine lactone hydrochloride
• Synonyms: HSL;HOMOSERINE LACTONE HYDROCHLORIDE;HOMOSERINE(L-) LACTONE HCL;L-(-)-HOMOSERINE LACTONE HYDROCHLORIDE;L-HOMOSERINE LACTONE HYDROCHLORIDE;L-(-)-A-AMINO-G-BUTYROLACTONE HYDROCHLORIDE;(S)-(-)-ALPHA-AMINO-GAMMA-BUTYROLACTONE HYDROCHLORIDE;(S)-2-AMINO-4-BUTYROLACTONE HYDROCHLORIDE
• CAS NO: 2185-03-7
• Molecular Formula: C₄H₇NO₂*ClH
• Molecular Weight: 137.56
• EINECS: 218-571-1
• Product Categories: Amino Acid Derivatives;Amino Acids 13C, 2H, 15N;Amino Acids & Derivatives
• Mol File: 2185-03-7.mol
• Article Data: 31

Chemical Properties

• Melting Point: 210-220 °C (dec.)(lit.)
• Boiling Point: 257.1 °C at 760 mmHg
• Flash Point: 120.1 °C
• Appearance: white solid
• Vapor Pressure: 0.000411mmHg at 25°C
• Refractive Index: -26 ° (C=0.2, H2O)
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• Water Solubility: soluble
• BRN: 3562187
• CAS DataBase Reference: L-Homoserine lactone hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: L-Homoserine lactone hydrochloride(2185-03-7)
• EPA Substance Registry System: L-Homoserine lactone hydrochloride(2185-03-7)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 2185-03-7(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

(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.

InChI:InChI=1/C4H5NO2.ClH/c5-3-1-2-7-4(3)6;/h1-3H,5H2;1H

Upstream product

• 498-19-1 L-(-)-homoserine 
• 63-68-3 L-methionine 
• 79-11-8 chloroacetic acid 
• 96-34-4 methyl chloroacetate 
• 7540-67-2 O-acetyl-L-homoserine 
• 1492-23-5 O-succinyl-L-homoserine 
• 55154-48-8 (S)-N-(2-oxo-tetrahydrofuran-3-yl)-2-phenylacetamide 
• 42417-39-0 (RS)-α-amino-γ-butyrolactone hydrochloride 
• 33693-66-2 α-Azido-γ-butyrolacton 
• 104347-03-7 2-Amino-4-(2-methoxy-ethoxymethoxy)-butyric acid methyl ester 
• 83427-81-0 (S)-N-tritylhomoserine lactone 
• 128669-50-1 (S)-2-hydroxyimino-3-(N-tritylamino)oxolane 
• 56-84-8 L-Aspartic acid 
• 672-15-1 L-homoserine 

Downstream Products

• 89959-29-5 N-(benzyloxycarbonyl)glycyl-L-homoserine lactone 
• 35677-89-5 benzyl (3S)-2-oxotetrahydro-3-furanylcarbamate 
• 160141-24-2 N-(tert-butoxycarbonyl)-2(S)-[2(S)-amino-3(S)-methyl]-pentyloxy-3-phenyl-propionyl-homoserine lactone 
• 96-48-0 4-butanolide 
• 3211-76-5 Seleno-L-methionine 
• 216596-71-3 N-undecanoyl-L-homoserine lactone 
• 40856-59-5 tert-butyl (3S)-2-oxotetrahydrofuran-3-ylcarbamate 
• 158530-68-8 (S)-2-amino-1,1-diphenylbutane-1,4-diol 
• 15159-65-6 (2S)-2-amino-4-bromobutanoic acid hydrobromide 
• 116857-07-9 (L)-N-Fmoc-homoserine lactone 
• 1195-16-0 N-acetyl-DL-homocysteinethiolactone 

Relevant articles and documents

Regioselective Reductions of Diacids: Aspartic Acid to Homoserine

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A Unified Approach to Phytosiderophore Natural Products

This work reports on the concise total synthesis of eight natural products of the mugineic acid and avenic acid families (phytosiderophores). An innovative ?east-to-west“ assembly of the trimeric products resulted in a high degree of divergence enabling the formation of the final products in just 10 or 11 steps each with a minimum of overall synthetic effort. Chiral pool starting materials (l-malic acid, threonines) were employed for the outer building blocks while the middle building blocks were accessed by diastereo- and enantioselective methods. A highlight of this work consists in the straightforward preparation of epimeric hydroxyazetidine amino acids, useful building blocks on their own, enabling the first synthesis of 3’’-hydroxymugineic acid and 3’’-hydroxy-2’-deoxymugineic acid.

Synthesis of new chalcone-based homoserine lactones and their antiproliferative activity evaluation

Three series of new homoserine lactone analogs were efficiently synthesized starting from methionine and further evaluated for their antiproliferative activity against different cancer cell lines. Among these compounds, some of the chalcone containing compounds 6a-n showed acceptable antiproliferative activity against prostate cancer cells DU145 and PC-3 with the IC50 values less than 10 μM. Compounds 6c, 6e and 6h inhibited growth of DU145 and PC-3 cells at low micromolar levels with the IC50 values ranging from 3.0 to 5.0 μM, much more potent than natural OdDHL. Compound 6e concentration-dependently inhibited colony formation and cell migration of DU145 cells. A synergistic effect on the growth inhibition and the apoptosis of DU145 cells was observed when compound 6e was used in combination with TRAIL. OdDHL or 6e treatment concentration-dependently activated TRAIL death receptor DR5 which may account for the observed synergistic effect of 6e or OdDHL with TRAIL on the growth inhibition and cell apoptosis. Compound 6e also inhibited migration of DU145 cells in a time- and concentration-dependent manner. The data suggest that quorum sensing molecules OdDHL and 6e may improve the sensitivity of DU145 cells toward TRAIL via activating DR5, compound 6e may be used as a potential lead compound for developing new TRAIL receptor agonists.