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CAS No. : | 406-76-8 | MDL No. : | MFCD00066765 |
Formula : | C7H15NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 161.20 | Pubchem ID : | - |
Synonyms : |
(±)-Carnitin
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide In ethanol at 20℃; for 2h; | A solution of DL-carnitine hydrochloride (1.0 g, 5.05 mmol) and sodium hydroxide (0.303 g, 7.58 mmol) in ethanol (15 mlitre) was stirred at room temperature for 2 h. The formed white precipitate (NaCl) was removed by filtration, and the solvent was evaporated under reduced pressure to give a white solid, carnitine inner salt. A suspension of the carnitine inner salt and 1-iodooctadecane (2.31 g, 6.06 mmol) in DMF-dioxane (3 : 5, 40 mlitre) was heated with an oil-bath at 120 °C under Ar2 for 4 h. The solvent was removed by rotavapor and vacuum, and the residue was chromatographied with silica gel column using CH3OH-CH3Cl as eluant to give 2.22 g (81 %) of stearyl carnitine ester as a white solid:1H NMR (CDCl3) δ 4.79 (m, 1 H), 4.43 (d, J = 5.3, 1 H), 4.09(t, J =6.9, 2 H), 4.03 (d, J = 13.o, 1 H), 3.67 (dd, J = 10.3, 13.3, 1 H), 3.51 (s, 9 H), 2.79 (dd, J =5.7, 17.0, 1 H), 2.66 (dd, J = 7.0, 17.1, 1 H), 1.80-1.60 (m, 4 H), 1.26 (broad s, 28 H), 0.88 (t, J = 6.6, 3 H). LSIMS (NBA): m/e 414.4 for C25H52NO3 (cation). | |
With sodium hydroxide In ethanol at 20℃; for 2h; | B A solution of DL-caraitine hydrochloride (2.164 g, 10.93 mmol) and sodium hydroxide (0.6561 g, 16.41 mmol) in EtOH (32.4 mL) was stirred at RT for 2 h. The resulting white solid (NaCl) was removed by filtration, and the solvent was removed under reduced pressure to give a white solid. That was dried over P2O5 in vaccum (oil pump) for 5 h. A suspension of the DL-carnitine inner salt and benzyl bromide (2.240 g, 13.11 mmol) in DMF (20 mL) was heated at 1250C under nitrogen for 8 h (solid of carnitine gradually dissolved). The solvent was removed by rotary evaporation and the residue was kept in vacuum (oil pump) for 1 h. The solid was washed with ethyl ether (2 x 20 mL). The remaining solid (3.9550 g) was recrystallized from anhydrous acetonitrile to give DL- camitine benzyl ester bromide (3.050 g, 9.182 mmol, 84%), mp 164-1670C. IR (KBr) 3254, 1733, 1453, 1412, 1320, 1184 cm"1.NMR: 1H (200 Mz, D2O) 7.51-7.32 (m, 5H C6H5), 5.19 (d, J= 2.9, 2H, CH2C6H5), 4.75-4.55 (m, IH, CH), 3.45-3.38 (m, 2H, CH2N), 3.16 (s, 9H, N(CH3)3), 2.76-2.64 (m, 2H, CH2COO). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; | Preparation of the organic nutrient salt of carnitine and homotaurine: L-camitine inner salt (10.6 g, 0.066 mole) was dissolved in water (15 ml.) with brief heating. To the solution was added homotaurine (9.16, 0.066 mole) with constant stirring.More water (10 mL) was added to give a clear solution. Solvent was evaporated under reduced pressure. The residual solid was suspended in isobutanol (30 mL); and the mixture was concentrated to dryness under reduced pressure. The isobutanol treatment was repeated with a second portion of 15 mL isobutanol. The residual material (18.0 g) was suspended in acetone (200 mL) and the mixture was stirred overnight at room temperature.The solid material was collected by filtration, dried at 60 C under vacuum, giving a white crystalline powder (17.8 g). 1H-NMR spectrum of the product was recorded in D2O (seeFigure 1). |