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Synthetic method and application of MACAmide

A technology of macamide and a synthesis method, which is applied in the synthesis of macamide and the field of macamide, can solve the problems of complex components of maca, low purity of macamide, limited source of raw materials, etc., and achieves the treatment of male sexual dysfunction. , Improve male fertility, the effect of easy control of operating conditions

Active Publication Date: 2015-04-15
INST OF PROCESS ENG CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The growth environment of maca is harsh, the yield is low, the content of macamide in maca is extremely low (<0.2%), and the components in maca are complex, so that the method of preparing macamide with maca as raw material and biochemical separation is because Separation and purification are difficult, raw material sources are limited, and large-scale preparation is not possible.
Therefore, macamide is obtained by chemical synthesis, which solves the problems of lack of raw material resources, waste of solvent in the purification step, and low utilization rate of maca raw materials.
[0005] In the prior art, there are reports to synthesize macamides with benzylamine and palmitoyl chloride, but due to the limitation of fatty acid chloride raw materials, it is impossible to synthesize multiple macamides; Hexylcarbodiimide initiates the synthesis of macamide under the catalysis of pyrrolidinylpyridine, but the purity of macamide in the product is low

Method used

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  • Synthetic method and application of MACAmide
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  • Synthetic method and application of MACAmide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] A kind of one-step synthetic macamide---the method of N-benzyl-hexadecanamide:

[0035]Weigh 0.01mol HOAt, 0.01mol EDC·HCl and 0.01mol DIPEA respectively in 7.3mL DCM (dichloromethane), then add 0.01mol benzylamine, 0.01mol palmitic acid, the ratio of reaction raw materials to DCM is 50% (w / v), stirring overnight at 10°C; adding 50mL of deionized water, stirring at room temperature for 30min, filtering and vacuum drying to obtain the product;

[0036] Performance Testing:

[0037] Infrared: FT / IR-660 infrared meter, the peak value is V max =3303(N-H), 2917, 2849, 1639(C=O), 1549(N-C), 1454(N-C=O), 730 and 696 (benzene ring) cm -1 ;

[0038] Mass Spectrum: Thermo's LCQ DECAXP Ion Hydrazine Mass Spectrum, m / z346.2;

[0039] NMR: Bruker AVANCE III600 NMR instrument 1 H spectrum (600MHz, CDCl 3 ), δ=2.20(t,J=7.65Hz,2H,H=2), δ=1.65(t,J=7.05Hz,2H,H=3), δ=1.26(s,br,24H,H= 4-15), δ=0.88(t,J=6.75Hz,3H,H=16), δ=4.435(d,J=7.65Hz,2H,H=1`), δ=7.29(m,5H, H=3`-7`), δ=5.73(s,1...

Embodiment 2

[0044] A kind of one-step chemical synthesis macamide---the method of N-benzyl-octadecylamide:

[0045] Weigh 0.1mol HOAt, 0.1mol EDC·HCl and 0.1mol DIPEA respectively in 2730mL DCM, then add 0.1mol benzylamine, 0.01mol stearic acid, the ratio of reaction materials to DCM is 0.5% (w / v) at 40°C Stir overnight under the same conditions, and evaporate the solvent to dryness; add 200 mL of deionized water, stir at room temperature for 30 min, filter and dry in vacuo to obtain the product;

[0046] Performance Testing:

[0047] Infrared: FT / IR-660 infrared meter, the peak value is V max =3306 (N-H), 2918, 2849, 1639 (C=O), 1552 (N-C), 1455 (N-C=O), 1428, 743, 730 and 699 (benzene ring) cm -1 ;

[0048] Mass Spectrum: Thermo's LCQ DECAXP Ion Hydrazine Mass Spectrum, m / z374.3;

[0049] NMR: Bruker AVANCE III600 NMR instrument 1 H spectrum (600MHz, CDCl 3 ), δ=2.20(t,J=7.65Hz,2H,H=2), δ=1.65(t,J=7.05Hz,2H,H=3), δ=1.29(s,br,24H,H= 4-17), δ=0.88(t,J=6.75Hz,3H,H=18), δ=4.44(d,J=7....

Embodiment 3

[0054] A method for chemically synthesizing macamide in one step——N-benzyl-9 cis-oleic acid amide:

[0055] Weigh 0.015mol HOAt, 0.02mol EDC·HCl and 0.03mol DIPEA into 30mL DCM, then add 0.01mol benzylamine and 0.01mol oleic acid, stir at 30°C for 12h; add 50mL of deionized water, stir at room temperature for 30min , filtered and dried in vacuo to obtain the product;

[0056] Performance Testing:

[0057] Infrared: FT / IR-660 infrared instrument, V max =3299 (N-H), 3002 (C=C-H), 2919, 2849, 1640 (C=O), 1554 (N-C), 1463.98 (N-C=O), 725 and 696 (benzene ring);

[0058] Mass Spectrum: Thermo's LCQ DECAXP Ion Hydrazine Mass Spectrum, m / z372.3;

[0059] NMR: Bruker AVANCE III600 NMR instrument 1 H spectrum (600MHz, CDCl 3 ), δ=2.21(t,J=7,65Hz,2H,H=2), δ=1.66(m,J=6,45Hz,2H,H=3), δ=1.28(s,br,8H, H=4-7), δ=2.047(m,J=3,90Hz,4H,H=8,11), δ=5.34(m,J=2,00Hz,2H,H=9,10), δ =1.30(s,br,12H,H=12-17), δ=0.879(t,J=6,60Hz,3H,H=18), δ=4,13(q,J=7,10Hz,2H ,H=1`), δ=7,319(m,5H,H=3`-7`), δ=5,65(...

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Abstract

The invention relates to a synthetic method of MACAmide. The method includes following steps: with a fatty acid and benzylamine or m-methoxybenzylamine as reaction raw materials, mixing the raw materials in a dichloromethane solution in which HOAt, EDC.HCl and DIPEA are dissolved; performing a reaction with stirring; washing a reaction product with water; and drying a substance being undissolved in water to obtain the MACAmide. The method is simple in processes and the raw materials are easy to obtain. Operation conditions of the method are easy to control. The reaction product can reach a purity of 95% without purification. The invention provides basis for industrialized synthesis of the MACAmide. In addition, the MACAmide has effects of enhancing male reproductive ability and treating male sexual dysfunction. The invention provides market prospects to application of the MACAmide.

Description

technical field [0001] The invention belongs to the field of biopharmaceuticals, and relates to a method for synthesizing macamide and its application, in particular to a method for synthesizing macamide without a purification step and the application of the macamide prepared by the method. Background technique [0002] Maca (Lepidium meyenii Walp.) is an annual herbaceous plant belonging to the genus Brassicaceae. It is native to the Andes Mountains in South America at an altitude of 3500-4500m. my country began to introduce and plant maca in Lijiang, Yunnan in 2002, and it has become the world's largest maca planting base. Maca has rich nutritional value and medicinal value. Studies have shown that Maca has the functions of improving the fertility of humans and animals, improving sexual function, inhibiting prostate enlargement, anti-fatigue, anti-depression, improving osteoporosis, and improving memory. [0003] Macamides are a series of compounds that are combined with...

Claims

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Application Information

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IPC IPC(8): C07C231/02C07C233/05C07C233/09C07C235/76C07C233/20A61P15/08A61P15/00
Inventor 赵兵陈金金赵庆生
Owner INST OF PROCESS ENG CHINESE ACAD OF SCI
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