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N-Methyl-L-proline

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CAS:475-11-6
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CAS:475-11-6
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N-Methyl-L-proline Basic information
Product Name:N-Methyl-L-proline
Synonyms:N-ME-L-PROLINE HYDROCHLORIDE;N-ME-PROLINE;N-ME-PRO-OH HCL;N-METHYL-L-PROLINE MONOHYDRATE;PYRD(2)-OH H2O;N-ALPHA-METHYL-L-PROLINE;N-ALPHA-METHYL-L-PROLINE HYDRATE;N-ALPHA-METHYL-L-PYRROLIDINE-2-CARBOXYLIC ACID HYDRATE
CAS:475-11-6
MF:C6H11NO2
MW:129.16
EINECS:
Product Categories:amino acids;Amino Acids;I - Z;Modified Amino Acids
Mol File:475-11-6.mol
N-Methyl-L-proline Structure
N-Methyl-L-proline Chemical Properties
Melting point 114-116 °C(lit.)
Boiling point 227℃
density 1.153
Fp 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.
pka2.37±0.20(Predicted)
form Powder
color White to off-white
Water Solubility Soluble in water and methanol(both 50 mg/ml-clear-colorless solution)
InChIInChI=1S/C6H11NO2/c1-7-4-2-3-5(7)6(8)9/h5H,2-4H2,1H3,(H,8,9)/t5-/m0/s1
InChIKeyCWLQUGTUXBXTLF-YFKPBYRVSA-N
SMILESC(O)(=O)[C@@H]1CCCN1C
CAS DataBase Reference475-11-6
Safety Information
WGK Germany 3
HazardClass IRRITANT
MSDS Information
ProviderLanguage
SigmaAldrich English
N-Methyl-L-proline Usage And Synthesis
UsesN-Methyl-L-proline, is an aminoacid which is widely used in pharmaceuticals and food industry.
DefinitionChEBI: 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.
Biological ActivityN-Methyl-L-proline is a proline analogue present in citrus fruits.
SynthesisL-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 synthesis
N-Methyl-L-proline Preparation Products And Raw materials
Tag: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

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