| Identification | More | [Name]
L-Methioninol | [CAS]
2899-37-8 | [Synonyms]
(2S)-2-AMINO-4-METHYLSULFANYL-BUTAN-1-OL
4-METHYLMERCAPTO-2-AMINO-1-BUTANOL
H-L-MET-OL
H-METHIONINOL
H-MET-OL
L-(-)-2-AMINO-4-METHYLTHIO-1-BUTANOL
L-2-AMINO-4-METHYLTHIO-1-BUTANOL
L-(-)-METHIONINOL
L-METHIONINOL
(S)-2-AMINO-4-METHYLMERCAPTO-1-BUTANOL
(S)-2-AMINO-4-METHYLSULFANYL-BUTAN-1-OL
(S)-(-)-2-AMINO-4-METHYLTHIO-1-BUTANOL
(S)-2-AMINO-4-METHYLTHIO-1-BUTANOL
(S)-(-)-METHIONANOL
(S)-(-)-METHIONINOL
L-Methionionl
L-2-amino-4-methylthiobutan-1-ol
D-(S)-(-)-Methionanol
L-(R)-(+)-Methionanol
L-Met-ol | [EINECS(EC#)]
220-788-1 | [Molecular Formula]
C5H13NOS | [MDL Number]
MFCD00004735 | [Molecular Weight]
135.23 | [MOL File]
2899-37-8.mol |
| Chemical Properties | Back Directory | [Appearance]
white transparent crystalline low melting solid | [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.)
| [Fp ]
>230 °F
| [storage temp. ]
2-8°C | [solubility ]
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | [form ]
Crystalline Low Melting Solid | [pka]
12.72±0.10(Predicted) | [color ]
White transparent | [Optical Rotation]
[α]21/D 12.7°, c = 1.4 in ethanol | [BRN ]
2231656 | [CAS DataBase Reference]
2899-37-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes .
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29309090 |
| Hazard Information | Back Directory | [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 |
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