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Trans-N-(4- hydroxyl-3-methoxybenzy)-8-methyl-5-nonenamide and preparation method thereof

A technology of methoxybenzyl and nonenamide, applied in the field of capsaicinoids and preparation thereof, can solve problems such as no synthesis report, and achieve the effects of low cost, readily available raw materials, and mild reaction conditions

Inactive Publication Date: 2010-07-14
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But there is no synthetic report of N-(4-hydroxyl-3-methoxybenzyl)-8-methyl-5-nonenamide in the above-mentioned documents

Method used

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  • Trans-N-(4- hydroxyl-3-methoxybenzy)-8-methyl-5-nonenamide and preparation method thereof
  • Trans-N-(4- hydroxyl-3-methoxybenzy)-8-methyl-5-nonenamide and preparation method thereof
  • Trans-N-(4- hydroxyl-3-methoxybenzy)-8-methyl-5-nonenamide and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] (1) 4.0g NaBH 4 Dubbed 50mL aqueous solution, and added a small amount of NaOH. The solution was slowly added dropwise to 100 g of 25% glutaraldehyde solution in an ice-water bath, and reacted for 4 hours after the dropwise addition was completed. Then 1M dilute HCl was added dropwise until pH = 3-4. Add 2M NaOH aqueous solution dropwise to the product to adjust the pH of the product to 8-9; distill off the water under reduced pressure, then add an appropriate amount of acetone and anhydrous Na 2 SO 4 Drying; filtering; the filtrate is distilled under reduced pressure to remove acetone; and then distilled under reduced pressure to collect 1,5-pentanediol product, and the yield can reach 91%.

[0037] Weigh 5.2g of 1,5-pentanediol, 13.1g of 40% hydrobromic acid, and 300mL of n-heptane into a three-necked flask, add an appropriate amount of concentrated sulfuric acid, and react under reflux for 8h. Separate the n-heptane phase with a separatory funnel, and wash the n-...

Embodiment 2

[0049] (1) Mix 8.0g KBH4 into 100mL aqueous solution, and add a small amount of NaOH. The solution was slowly added dropwise to 150 g of 25% glutaraldehyde solution in an ice-water bath, and reacted for 5 hours after the dropwise addition was completed. Then 1M dilute HCl was added dropwise until pH = 3-4. Add 2M NaOH aqueous solution dropwise to the product to adjust the pH of the product to 8-9; distill off the water under reduced pressure, then add an appropriate amount of acetone and anhydrous Na 2 SO 4 Drying; filtering; the filtrate is distilled under reduced pressure to remove acetone; and then distilled under reduced pressure to collect 1,5-pentanediol product with a yield of 88%.

[0050] Weigh 10.4g of 1,5-pentanediol, 30.5g of 40% hydrobromic acid, and 500mL of n-heptane into a three-necked flask, add an appropriate amount of concentrated sulfuric acid, and react under reflux for 8h. Separate the n-heptane phase with a separatory funnel, and wash the n-heptane ph...

Embodiment 3

[0060] (1) 5.8g KBH 4 Dubbed 70mL aqueous solution, and added a small amount of KOH. The solution was slowly added dropwise to 100 g of 25% glutaraldehyde solution in an ice-water bath, and reacted for 5 hours after the dropwise addition was completed. Then 2M dilute HCl was added dropwise to pH=3-4. Add 2M NaOH aqueous solution dropwise to the product to adjust the pH of the product to 8-9; distill off the water under reduced pressure, then add an appropriate amount of acetone and anhydrous Na 2 SO 4 Drying; filtering; the filtrate is distilled under reduced pressure to remove acetone; and then distilled under reduced pressure to collect 1,5-pentanediol product with a yield of 89%.

[0061] Weigh 15.5g of 1,5-pentanediol, 30.5g of 40% hydrobromic acid, and 800mL of n-heptane into a three-necked flask, add an appropriate amount of concentrated sulfuric acid, and react under reflux for 8 hours, while removing the generated water through an oil-water separator . Separate th...

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Abstract

The invention discloses trans-N-(4-hydroxyl-3-methoxybenzy)-8-methyl-5-nonenamide which has a structural formula as shown in a formula (1). The trans-N-(4-hydroxyl-3-methoxybenzy)-8-methyl-5-nonenamide is prepared by the following steps of: carrying out a single bromination reaction on pentanediol to generate 5-bromo-pentanol; oxidizing the 5-bromo-pentanol to generate 5-bromo-valeric acid; reacting the 5-bromo-valeric acid with triphenylphosphorus to generate (5-carboxyl-amyl)triphenylbromophosphine; reacting the (5-carboxyl-amyl)triphenylbromophosphine with isovaleraldehyde to generate cis-8-methyl-5-nonenoic acid; reacting the cis-8-methyl-5-nonenoic acid with a sodium nitrite / nitric acid solution to obtain trans-8-methyl-5-nonenoic acid; reacting the trans-8-methyl-5-nonenoic acid with an acetylation reagent to obtain trans-8-methyl-5-enoic acid chloride; reacting vanillin with ammonium formate to obtain vanillic amine; acidizing the vanillic amine and neutralizing with alkali liquor; and then reacting the mixture with the trans-8-methyl-5-enoic acid chloride to obtain the trans-N-(4-hydroxyl-3-methoxybenzy)-8-methyl-5-nonenamide. The invention has the advantages of simple and convenient process and mild reaction conditions; and the prepared product provides a new development space for the research on capsaicin substances. The formula (1) is described in specification.

Description

technical field [0001] The invention relates to capsaicin-like substances and a preparation method thereof, especially trans-N-(4-hydroxy-3-methoxybenzyl)-8-methyl-5-nonenamide and a preparation method thereof. Background technique [0002] The fruit of the capsicum plant (capsicum genus) is one of the most consumed condiments worldwide. These pepper fruits contain at least 12 kinds of capsaicinoids that can produce a spicy taste, namely capsaicin (N-(4-hydroxy-3-methoxybenzyl)-8-methyl-6-nonenamide) , Dihydrocapsaicin (N-(4-hydroxy-3-methoxybenzyl)-8-methyl-nonamide), norcapsaicin (N-(4-hydroxy-3-methoxybenzyl) -7-methyl-5-octenamide), nordihydrocapsaicin (N-(4-hydroxy-3-methoxybenzyl)-7-methyl-octylamide), homocapsaicin (I) (N-(4-hydroxy-3-methoxybenzyl)-9-methyl-7-decenamide), homodihydrocapsaicin (I) (N-(4-hydroxy-3-methoxybenzyl base)-9-methyl-decenamide), homocapsaicin (II) (N-(4-hydroxy-3-methoxybenzyl)-8-methyl-6-decenamide), homodihydrocapsaicin Base (II) (N-(4-...

Claims

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Application Information

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IPC IPC(8): C07C233/20C07C231/02
Inventor 王俊莲周圣泽彭必先张孝彬周祥凤
Owner ZHEJIANG UNIV
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