L-Methioninol Chemical Properties

Melting point:

31-33 °C

alpha 

-12.5 º (c=1.4, EtOH)

Boiling point:

120 °C(Press: 3 Torr)

Density 

0.984 (estimate)

refractive index 

n20/D 1.5216(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

pka

12.72±0.10(Predicted)

form 

Crystalline Low Melting Solid

color 

White transparent

optical activity

[α]21/D 12.7°, c = 1.4 in ethanol

BRN 

2231656

CAS DataBase Reference

2899-37-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-37/39-26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29309090

MSDS

• Language:English Provider:L-Methioninol
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
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L-Methioninol Usage And Synthesis

Chemical Properties

white transparent crystalline low melting solid

Uses

L-Methioninol is a methionine derivative that increases bladder excitability by inhibiting stretch-dependent K+ channels.

Synthesis

The general procedure for the synthesis of (S)-2-amino-4-(methylthio)butan-1-ol from L-methionine is as follows (refer to Examples 1-46): 38 mL (300 mmol) of chlorotrimethylsilane was added slowly and dropwise to 200 mL of an anhydrous tetrahydrofuran suspension containing 3.3 g (150 mmol) of lithium borohydride under ice bath cooling conditions. The reaction mixture was stirred for 30 min and then 7.5 g (50 mmol) of L-methionine was added gradually, followed by continued stirring at room temperature overnight. Upon completion of the reaction, methanol was slowly added under ice bath cooling conditions until hydrogen release ceased. Subsequently, the solvent was removed by distillation under reduced pressure. To the residue, 10% sodium hydroxide solution was added and then extracted twice with chloroform. The chloroform extracted layers were combined, dried with anhydrous sodium sulfate and finally the solvent was removed by distillation under reduced pressure to give 5.12 g (75% yield) of the target product (S)-2-amino-4-(methylthio)butan-1-ol (Compound No. 1-46).

References

[1] European Journal of Organic Chemistry, 2008, # 9, p. 1608 - 1614
[2] Angewandte Chemie, 1989, vol. 101, # 2, p. 220 - 222
[3] European Journal of Organic Chemistry, 2004, # 12, p. 2715 - 2722
[4] Journal of Organic Chemistry, 1990, vol. 55, p. 3749 - 3755
[5] Journal of Organic Chemistry, 2008, vol. 73, # 3, p. 1077 - 1087

L-Methioninol(2899-37-8)Related Product Information

• Molasses
• 1-Butanol
• Glycine
• (S)-(+)-2-Amino-1-butanol
• tert-Butanol
• Betaine
• Emamectin
• ALTRENOGEST
• L-GLUCOSE
• L-THREITOL
• methyl methionate
• L-METHIONINE METHYLSULFONIUM IODIDE
• FMOC-L-Methionine
• L-METHIONINE SULFOXIMINE
• Ethyl L-methionate hydrochloride
• L-CYSTATHIONINE
• L-Methionine methyl ester hydrochloride
• N-FORMYL-L-METHIONINE