N-Methyl-L-proline Chemical Properties

Melting point:

114-116 °C(lit.)

Boiling point:

227℃

Density 

1.153

Flash point:

91.1℃

refractive index 

1.5000

storage temp. 

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

solubility 

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

pka

2.37±0.20(Predicted)

form 

Powder

color 

White to off-white

Water Solubility 

Soluble in water and methanol(both 50 mg/ml-clear-colorless solution)

InChI

InChI=1S/C6H11NO2/c1-7-4-2-3-5(7)6(8)9/h5H,2-4H2,1H3,(H,8,9)/t5-/m0/s1

InChIKey

CWLQUGTUXBXTLF-YFKPBYRVSA-N

SMILES

C(O)(=O)[C@@H]1CCCN1C

CAS DataBase Reference

475-11-6

Safety Information

WGK Germany 

3

HazardClass 

IRRITANT

MSDS

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N-Methyl-L-proline Usage And Synthesis

Uses

N-Methyl-L-proline, is an aminoacid which is widely used in pharmaceuticals and food industry.

Definition

ChEBI: N-methylproline is an L-proline derivative obtained by replacement of the amino hydrogen by a methyl group. It has a role as a plant metabolite and a human metabolite. It is a L-proline derivative and a tertiary amino compound. It is a tautomer of a N-methylproline zwitterion.

Synthesis

L-Proline 86 (2.0 g, 17.4 mmol) was dissolved in methanol (20 mL) and to this solution was added 40% aqueous formaldehyde solution (1.4 mL, 19.1 mmol). This was followed by the addition of 10% palladiumon-charcoal catalyst (500 mg) and the resulting slurry was stirred in a hydrogen atmosphere overnight. The slurry was then filtered through a Celite pad to remove the catalyst. The pad was washed with methanol and the combined filtrates were concentrated under reduced pressure. The residue was taken up in ethanol-benzene (1:1, 100 mL) and concentrated a second time to provide a solid, which was recrystallized from methanol-diethyl ether. In this way N-Methyl-L-proline was isolated as fine needles (2.2 g, 98%). Mp 142-145 °C. [α]23 D -78.0° (c 2.0, MeOH). 1H NMR (300 MHz, D2O) δ 3.71-3.65 and 3.55-3.51 (2m, 1H), 3.00-2.91 (m, 1H), 2.74 (s, 3H), 2.34-2.28 (m, 1H), 1.99-1.78 (m, 3H). 13C NMR (75 MHz, CDCl3) δ 173.06, 70.18, 55.83, 40.26, 28.34, 22.37. IR (KBr disk) ν 3000-2800 (CH, saturated), 2675 and 2605 (ammonium ion), 1669 (CO2H), 1612 (CO2 -), 1468, 1401, 1354, 1327, 1234, 1183, 1112, 1056, 1025, 808, 775 cm-1. HRMS calcd for C6H11NO2 (M+) 129.0790, found 129.0784.

N-Methyl-L-proline(475-11-6)Related Product Information

• N-METHYL-L-PROLINE MONOHYDRATE 98
• N-Methyl-L-proline
• N-Cbz-Hydroxy-L-proline
• L-Alanyl-L-proline
• BOC-HYP(BZL)-OH
• BOC-L-Proline
• N-(2,4-DINITROPHENYL)-L-PROLINE
• Fmoc-Pro-OH
• GLYCYL-L-PROLINE
• 4-METHOXY-2-METHYLBENZOIC ACID
• (S)-4-METHYLENE-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER
• L-Proline
• H-ALA-PRO-OME HCL
• Z-ALA-PRO-OH
• PHE-PRO
• H-PRO-PRO-OH HCL
• H-MET-PRO-OH
• H-VAL-PRO-OTBU HCL