2185-02-6

Basic information

• Product Name: L-HOMOSERINE LACTONE, HYDROCHLORIDE
• Synonyms: 2(3H)-Furanone,3-aminodihydro-,(3S)-(9CI);L-Homoserine lactone, (S)-2-Amino-4-butyrolactone hydrochloride;(3S)-3-Amino-4,5-dihydrofuran-2(3H)-one;(3S)-3β-Aminooxolane-2-one;(S)-3-Amino-4,5-dihydrofuran-2(3H)-one;(S)-3β-Aminotetrahydrofuran-2-one;3β-Amino-4,5-dihydrofuran-2(3H)-one;L-Homoserine lactone
• CAS NO: 2185-02-6
• Molecular Formula: C₄H₇NO₂
• Molecular Weight: 137.6
• EINECS: 218-571-1
• Product Categories: VARIOUSAMINE;A - H;Amino Acids;Modified Amino Acids
• Mol File: 2185-02-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 221-226℃
• Boiling Point: 316.4°C at 760 mmHg
• Flash Point: 168.8°C
• Appearance: /
• Density: 1.206±0.06 g/cm3(Predicted)
• Vapor Pressure: 0.000411mmHg at 25°C
• Storage Temp.: −20°C
• PKA: 7.89±0.20(Predicted)
• Water Solubility: soluble
• CAS DataBase Reference: L-HOMOSERINE LACTONE, HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: L-HOMOSERINE LACTONE, HYDROCHLORIDE(2185-02-6)
• EPA Substance Registry System: L-HOMOSERINE LACTONE, HYDROCHLORIDE(2185-02-6)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: R36/37/38:
• Safety Statements: S26:; S37/39:
• WGK Germany: 3
• Hazardous Substances Data: 2185-02-6(Hazardous Substances Data)

Usage

General Description

L-Homoserine lactone hydrochloride is a chemical compound that is classified as a lactone and is derived from the amino acid L-homoserine. It is commonly used as a synthetic intermediate in the production of various pharmaceuticals and organic compounds. L-Homoserine lactone hydrochloride has also been studied for its potential role as a signaling molecule in bacteria and for its potential use in biofilm inhibition and as a quorum sensing inhibitor. Additionally, it has been investigated for its antibacterial and antifungal properties. L-HOMOSERINE LACTONE, HYDROCHLORIDE is soluble in water and is typically stored and handled under controlled conditions due to its potentially hazardous nature.

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

Upstream product

• 106827-72-9 Trt-L-Hse(Trt)-Gly-NH₂ 
• 105183-60-6 (S)-benzyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate 
• 106827-71-8 Trt-L-Hse(Trt)-L-Leu-NH₂ 

Downstream Products

• 672-15-1 L-homoserine 
• 1464-42-2 (d)selenomethionine 
• 1464-42-2 (l)selenomethionine 
• 10364-50-8 2-Amino-4-bromo-butyric acid 
• 84245-58-9 2-Benzyloxycarbonylamino-N-((S)-2-oxo-tetrahydro-furan-3-yl)-malonamic acid tert-butyl ester 
• 116857-07-9 (L)-N-Fmoc-homoserine lactone 
• 126049-72-7 (R)-3-Hydroxy-N-((S)-2-oxo-tetrahydro-furan-3-yl)-butyramide 
• 76924-95-3 N-(3-oxohexanoyl)-L-homoserine lactone 
• 168982-69-2 N-(3-oxododecanoyl)-L-homoserine lactone 
• 886755-21-1 3-Oxo-dec-9-enoic acid ((S)-2-oxo-tetrahydro-furan-3-yl)-amide 
• 147795-40-2 N-(3-oxodecanoyl)-L-homoserine lactone 
• 177158-19-9 N-(3-oxotetradecanoyl)-L-homoserine lactone 
• 886755-20-0 3-Oxo-oct-7-enoic acid ((S)-2-oxo-tetrahydro-furan-3-yl)-amide 
• 15159-65-6 (2S)-2-amino-4-bromobutanoic acid hydrobromide 

Relevant articles and documents

De novo synthesis, structural assignment and biological evaluation of pseudopaline, a metallophore produced by Pseudomonas aeruginosa

Pseudopaline is an opine carboxylate metallophore produced by Pseudomonas aeruginosa for harvesting divalent metals. However, the structure of pseudopaline is not fully elucidated. Herein, we report the first de novo total synthesis and isolation of pseudopaline, which allows unambiguous determination and confirmation of both the absolute and the relative configuration of the natural product. The synthesis highlights an efficient and stereocontrolled route using the asymmetric Tsuji-Trost reaction as the key step. The preliminary structure-activity relationship study indicated that one pseudopaline derivative shows comparable activity to pseudopaline. Moreover, a pseudopaline-fluorescein conjugate was prepared and evaluated, which confirmed that pseudopaline could be transported in the bacteria. Since the metal acquisition by P. aeruginosa is crucial for its ability to cause diseases, our extensive structural and functional studies of pseudopaline may pave the way for developing new therapeutic strategies such as the "Trojan horse" antibiotic conjugate against P. aeruginosa.