L-Homoserine lactone hydrochloride Chemical Properties

Melting point:

210-220 °C (dec.)(lit.)

alpha 

-25 º (c=0.5, water)

refractive index 

-26 ° (C=0.2, H2O)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

solubility 

DMSO (Slightly), Methanol (Slightly), Water (Slightly)

form 

Solid

color 

White to Pale Beige

biological source

rabbit

optical activity

[α]20/D 27.8°, c = 1 in H2O

Water Solubility 

soluble

BRN 

3562187

InChI

InChI=1/C4H7NO2.ClH/c5-3-1-2-7-4(3)6;/h3H,1-2,5H2;1H/t3-;/s3

InChIKey

XBKCXPRYTLOQKS-DFWYDOINSA-N

SMILES

[C@H]1(N)CCOC1=O.Cl |&1:0,r|

CAS DataBase Reference

2185-03-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36-37/39

WGK Germany 

3

F 

3-10

HS Code 

29322090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

L-Homoserine lactone hydrochloride Usage And Synthesis

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.

Synthesis

The general procedure for synthesizing L-homoserine lactone hydrochloride from L-homoserine is as follows: mix L-homoserine (0.84 mol) with 600 mL of concentrated hydrochloric acid (6.1 mol). The reaction mixture was stirred for about 15 minutes until all solids were completely dissolved. Subsequently, the water was removed by distillation under reduced pressure over a period of 1.5 hours. Finally, the residue was dried. The yield of this step was 99% to give 2-amino-4-butyrolactone hydrochloride.

References

[1] Patent: US7368600, 2008, B2. Location in patent: Page/Page column 16-17
[2] Tetrahedron Asymmetry, 1995, vol. 6, # 11, p. 2819 - 2828
[3] Patent: US2011/53890, 2011, A1. Location in patent: Page/Page column 3
[4] Journal of Organic Chemistry, 2016, vol. 81, # 11, p. 4516 - 4529
[5] Tetrahedron Letters, 2010, vol. 51, # 50, p. 6500 - 6502

L-Homoserine lactone hydrochloride(2185-03-7)Related Product Information

• ALTRENOGEST
• 6-Aminocaproic acid
• L-ALPHA-PHOSPHATIDYLSERINES, BRAIN, BOVINE
• L-Homoserine
• Glycine
• D-Cycloserine
• TRIOXSALEN
• Topotecan hydrochloride
• DL-Serine
• L-Lactide
• Tris(hydroxymethyl)aminomethane
• Gamma Butyrolactone
• 3-FURANAMINE, TETRAHYDRO-
• (S)-3-AMINOTETRAHYDROFURAN
• (S)-TETRAHYDROFURAN-3-AMINE HYDROCHLORIDE
• 3-AMINODIHYDRO-2(3H)-FURANONE HYDROIODIDE
• D-HOMOSERINE LACTONE HYDROCHLORIDE
• TETRAHYDRO-FURAN-3-YLAMINE HCL