N-Methyl-L-proline
- CAS NO.:475-11-6
- Empirical Formula: C6H11NO2
- Molecular Weight: 129.16
- MDL number: MFCD00011565
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-06 18:33:45
What is N-Methyl-L-proline?
The Uses of N-Methyl-L-proline
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.
Properties of N-Methyl-L-proline
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. |
form | Powder |
pka | 2.37±0.20(Predicted) |
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 |
CAS DataBase Reference | 475-11-6 |
Safety information for N-Methyl-L-proline
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H332:Acute toxicity,inhalation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P233:Keep container tightly closed. P260:Do not breathe dust/fume/gas/mist/vapours/spray. P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P304:IF INHALED: P312:Call a POISON CENTER or doctor/physician if you feel unwell. P321:Specific treatment (see … on this label). P330:Rinse mouth. P340:Remove victim to fresh air and keep at rest in a position comfortable for breathing. P362:Take off contaminated clothing and wash before reuse. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P302+P352:IF ON SKIN: wash with plenty of soap and water. P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P332+P313:IF SKIN irritation occurs: Get medical advice/attention. P337+P313:IF eye irritation persists: Get medical advice/attention. P403:Store in a well-ventilated place. P405:Store locked up. P403+P233:Store in a well-ventilated place. Keep container tightly closed. P501:Dispose of contents/container to..… |
Computed Descriptors for N-Methyl-L-proline
InChIKey | CWLQUGTUXBXTLF-YFKPBYRVSA-N |
SMILES | C(O)(=O)[C@@H]1CCCN1C |
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