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Menthol derivative containing fatty acid and preparation containing said derivative

A technology of menthol derivatives and fatty acids, applied in the field of medicine

Inactive Publication Date: 2005-08-10
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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  • Menthol derivative containing fatty acid and preparation containing said derivative
  • Menthol derivative containing fatty acid and preparation containing said derivative
  • Menthol derivative containing fatty acid and preparation containing said derivative

Examples

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Embodiment 1

[0013] Embodiment 1: Menthyl laurate (ML)

[0014] Take 5g of menthol and add 50mL of dichloromethane to dissolve, add lauroyl chloride in an equimolar amount, mix well, add 0.5ml of pyridine, react at 30°C for 5 hours, distill off the dichloromethane, add 10ml of water to the resultant, React at 30°C for 0.5 hours to eliminate unreacted lauroyl chloride, add 100ml of water, mix well, extract with dichloromethane three times in total, 30ml each time, combine dichloromethane, use anhydrous sodium sulfate to remove residual water, reduce Dichloromethane was removed by pressure steaming to obtain the product.

[0015] IR (KBr tablet) v / cm -1 : Characteristic peaks 1735.1 (ester, C=O), 1162.5 (C-O), 1112.8 (C-O). 13 C NMR (DMSO-d 6 ), δ: 172 (ester, C=O). ESI-MS m / z: 339.6[M] + .

Embodiment 2

[0016] Embodiment 2: Menthyl myristate (MM)

[0017] Take 5 g of menthol and add 50 mL of toluene to dissolve it, add myristoyl chloride in an equimolar amount, mix well, add 0.3 g of lutidine (DMAP), reflux at 60°C for 3 hours, distill off the toluene, and Add 5ml of water, react at 60°C for 0.5 hours, eliminate unreacted myristoyl chloride, add 100ml of water, mix well, extract with ethyl acetate, a total of three times, 30ml each time, combine the ethyl acetate extracts, wash with anhydrous sulfuric acid Sodium was removed to remove residual moisture, and ethyl acetate was evaporated under reduced pressure to obtain the product.

[0018] IR (KBr tablet) v / cm -1 : Characteristic peaks 1735.0 (ester, C=O), 1160.2 (C-O), 1113.5 (C-O). 13 C NMR (DMSO-d 6 ), δ: 172 (ester, C=O). ESI-MS m / z: 367.6[M] + . proved to be the target compound.

Embodiment 3

[0019] Embodiment 3: menthol oleate (MO)

[0020] Take 5 g of menthol and add 50 mL of isopropyl ether to dissolve, add oleic acid chloride at a molar ratio of 1:1.1, mix well, add 1 ml of triethylamine, reflux at 40°C for 7 hours, distill off the isopropyl ether, and obtain Add 5ml of water, react at 60°C for 0.5 hours, eliminate unreacted oleic acid chloride, add 100ml of water, mix well, extract with dichloromethane, a total of three times, 30ml each time, combine the dichloromethane extracts, and use anhydrous Sodium sulfate was used to remove the residual moisture, and dichloromethane was distilled off under reduced pressure to obtain the product.

[0021] IR (KBr tablet) v / cm -1 : Characteristic peaks 1735.41 (ester, C=O), 1160.8 (C-O), 1112.5 (C-O). 13 C NMR (DMSO-d 6 ), δ: 172 (ester, C=O). ESI-MS m / z: 421.7[M] + . proved to be the target compound.

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Abstract

A menthol derivative containing fatting acid is prepared through catalytic esterifying reaction between menthol and straight-chain or branch-chain C5-C30 fatty acid. A medicine containing said derivative is also disclosed, which has high cerebral target performance.

Description

Technical field: [0001] The invention relates to the technical field of medicine, in particular to a menthol derivative containing fatty acid (menthol fatty acid ester derivative) and a preparation containing the derivative. Background technique: [0002] Menthol is colorless acicular or prismatic crystals or white crystalline powder; it has mint aroma and can selectively stimulate the cold receptors of human skin or mucous membranes, produce cold reflex and cold sensation, and cause skin and mucous membrane vasoconstriction (actually The skin remains normal), and it can also cause contraction of blood vessels in deep tissues to produce therapeutic effects. External use can reduce inflammation, relieve pain, relieve itching, promote blood circulation, reduce edema, etc.; internal use in compound preparations can relieve local inflammation (pharyngitis) and treat colds, and has the effect of strengthening the stomach and dispelling wind. External use is used for local pain r...

Claims

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Application Information

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IPC IPC(8): C07C67/14C07C69/24
Inventor 邓意辉吴红兵
Owner SHENYANG PHARMA UNIVERSITY
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