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Capsicine chemical synthesis and purification method

A technology of capsaicin and compounds, which is applied in the field of chemical synthesis and purification of capsaicin and its analogues, can solve the problems of harsh synthetic conditions of capsaicin and unsuitability for industrial production, and achieve easy industrial production, low cost, and easy-to-obtain raw materials Effect

Inactive Publication Date: 2006-11-22
BIOLOGY INST OF SHANDONG ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But in the above-mentioned literature, capsaicin synthetic conditions are all harsher, are not suitable for suitability for suitability for suitability for industrialized production

Method used

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  • Capsicine chemical synthesis and purification method
  • Capsicine chemical synthesis and purification method
  • Capsicine chemical synthesis and purification method

Examples

Experimental program
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Effect test

Embodiment 1

[0034] Embodiment 1: the synthesis of vanillylamine:

[0035] In a 250ml three-neck flask equipped with a reflux condenser and a stirring device, add vanillin (7.6g, 50mmol) and ammonium formate (10g, 160mmol), heat to 150°C for 5h, and after cooling, add concentrated Hydrochloric acid (6ml), reflux for 1 hour, add 70ml of ethanol to crystallize the hydrochloride of vanillylamine to obtain the hydrochloride of vanillylamine, recrystallize once with 95% ethanol to obtain pure hydrochloride of vanillylamine, m.p.216-218℃ , the yield was 49.8%. Dissolve 1.8g of vanillylamine hydrochloride in 30ml of water, add 2M NaOH (10.0ml) dropwise under vigorous stirring, a white precipitate appears in the solution, after suction filtration, water washing and drying, white vanillylamine is obtained, m.p.134-136°C, yield The rate is 56%.

[0036] EI-MS: 153 (M +, 100), 136(70), 122(54), 110(23), 93(20), 65(16), 30(19)

Embodiment 2

[0037] Embodiment 2: the synthesis of vanillylamine:

[0038] In a 250ml three-neck flask equipped with a reflux condenser and a stirring device, add vanillin (15.2g, 0.1mol) and ammonium formate (20g, 0.32mol), heat to 150°C for 5 hours, and after cooling, add Add concentrated hydrochloric acid (12ml), reflux for 1h, then add 70ml of ethanol to crystallize the hydrochloride of vanillylamine, and recrystallize the obtained light brown crystals with 95% ethanol once to obtain pure vanillylamine hydrochloride, which is light Pink needle crystal, m.p.216-218°C, yield 50%. Dissolve 3.5g of vanillyl amine hydrochloride in 50ml of water, add dropwise 2M NaOH (16.4ml) under vigorous stirring, a white precipitate appears in the solution, after suction filtration, water washing and drying, white vanillyl amine is obtained, m.p.134-136°C, harvested The rate is 44.5%. The characterization data are the same as in Example 1.

Embodiment 3

[0039] Embodiment 3: (6-carboxyhexyl) triphenylphosphine bromide is synthesized

[0040] In a 250ml three-necked flask equipped with a stirring and reflux condenser, add 6-bromo-hexanoic acid (5.16g, 24mmol), triphenylphosphine (6.94g, 24mmol), toluene (20ml), heat to reflux for 10h, and after cooling, After filtration, the resulting precipitate was recrystallized with chloroform to obtain white crystals, m.p. 201-203°C, yield 94.2%.

[0041] 1 H NMR (600MHz): δ1.47-1.55 (6H, m, C 2，4，6 -H); 2.16(2H,t,C 2 -H); 3.58(2H, m, C 6 -H); 7.75-7.92 (15H, m, Ar-H); 12.02 (1H, brs, COOH).

[0042] ESI-MS: pos(377); neg(535, 537, 455, 457)

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Abstract

The invention relates to a capsicine or the like, as well as its chemosynthesis and purification method. The capsicine has a general formula disclosed in the specification, wherein R is -CH=CH-, -CH2-CH2-, -CH2- or -CH2CH2CH2. The invention also discloses the process for preparing the compound through reacting vanilla amine with corresponding acyl chloride.

Description

(1) Technical field [0001] The invention belongs to the technical field of vanillyl amide alkaloids, and relates to chemical synthesis and purification methods of capsaicin and its analogues. (2) Background technology [0002] Capsaicin is an extremely pungent vanilla amide alkaloid, which is the main source of the peppery taste and medicinal function. Its chemical structure name is N-[(4-hydroxy-3-methoxy)-methyl]-8-methyl-6-nonenamide, which was first analyzed by modern instruments such as chromatography and nuclear magnetic resonance spectroscopy by Bennett et al. After analyzing its chemical composition, it was found that [Bennet et al., Carotenoid content and vitamin activity in common jalapeño by high pressure liquid chromatography, Journal of the Chemical Society, volume c 442-446, 1968 (D.J.Bennet, G, W, Kirby . Carotenoid Content and Vitamin Activity of Some Common Cultivars of Mexican Pepper (Capsicum annuum) as Determiner by HPLC. J. Chem. Soc. 1968, (c): 442-446...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/17C07C231/02
Inventor 孔学王加宁陈贯虹高永超邱维忠迟建国
Owner BIOLOGY INST OF SHANDONG ACAD OF SCI
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