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Method for preparing all-trans-beta-carotene

A carotene, all-trans technology, which is applied in the directions of organic chemistry methods, chemical instruments and methods, compounds of Group 5/15 elements of the periodic table, etc. problems, to achieve the effect of inhibiting the occurrence of side reactions, reducing solubility, and high yield

Active Publication Date: 2018-11-06
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] The production process of this route C15 phosphine salt is relatively simple, and the by-product triphenylphosphine can be recycled, but the solid strong base used in the reaction is exothermic violently, and the cis-isomer of β-carotene in the reaction needs to go through a special isoform Qualified products can only be obtained through structuralization steps. The processing steps are many and complicated, and the total reaction yield can only reach about 80%.

Method used

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  • Method for preparing all-trans-beta-carotene
  • Method for preparing all-trans-beta-carotene
  • Method for preparing all-trans-beta-carotene

Examples

Experimental program
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Effect test

Embodiment 1

[0070] 55.13g (0.11mol) of 2,4-pentadiene pentadecyl phosphate, 8.21g (0.05mol) of 2,7-dimethyl-2,4,6-octatriene-1,8- Dialdehyde, 12.8g (0.12mol) sodium carbonate, 150g anhydrous methanol are stirred and dissolved under a nitrogen atmosphere;

[0071] Mix 0.11g (0.5mmol) No.1 ionic liquid with 10g methanol, add the methanol solution of the ionic liquid dropwise into the reaction system at 10°C for 20min, and continue the reaction at 10°C for 3h after the dropwise addition;

[0072] After the reaction was completed, it was filtered, washed with water, and dried to obtain 25.46 g of all-trans β-carotene with a yield of 95%, and the content determined by HPLC was 97%.

[0073] figure 1 For trans-β-carotene standard high performance liquid chromatography (purchased from Zhejiang Xinhecheng Pharmaceutical Co., Ltd.), figure 2 It is the high performance liquid phase spectrum of trans-β-carotene synthesized by the present invention.

[0074] According to HPLC-MC identification, ...

Embodiment 2

[0076] 55.13g (0.11mol) of 2,4-pentadiene pentadecyl phosphate, 8.21g (0.05mol) of 2,7-dimethyl-2,4,6-octatriene-1,8- Dialdehyde, 12.8g (0.12mol) sodium carbonate, 150g anhydrous methanol are stirred and dissolved under a nitrogen atmosphere;

[0077] Mix 0.11g (0.5mmol) No.1 ionic liquid with 10g methanol, add the methanol solution of the ionic liquid into the reaction system dropwise at -10°C, dropwise for 20min, and continue the reaction at -10°C for 3h after the dropwise addition ;

[0078] After the reaction was completed, it was filtered, washed with water, and dried to obtain 23.3 g of all-trans β-carotene with a yield of 87%, and the content determined by HPLC was 97%.

Embodiment 3

[0080] 55.13g (0.11mol) of 2,4-pentadiene pentadecyl phosphate, 8.21g (0.05mol) of 2,7-dimethyl-2,4,6-octatriene-1,8- Dialdehyde, 12.8g (0.12mol) sodium carbonate, 150g anhydrous methanol are stirred and dissolved under a nitrogen atmosphere;

[0081] Mix 0.11g (0.5mmol) of No.1 ionic liquid with 10g of methanol, add the methanol solution of the ionic liquid into the reaction system dropwise at 60°C for 20min, and continue the reaction at 60°C for 3h after the addition;

[0082] After the reaction was completed, it was filtered, washed with water, and dried to obtain 21.98 g of all-trans β-carotene with a yield of 82%, and the content determined by HPLC was 97%.

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Abstract

The invention provides a method for preparing all-trans-beta-carotene. According to the method for preparing the all-trans-beta-carotene, an alkaline ionic liquid provides a strong alkaline environment, so that 2,4-pentadiene pentadecarbonate and 2,7-dimethyl-2,4,6-zinc triene-1,8-dialdehyde react under the weak base action to obtain the all-trans-beta-carotene directly. The method for preparing the all-trans-beta-carotene has the advantages that a strong alkaline ionic liquid serves as an alkaline assistant, the selectivity and yield of beta-carotene both reach 94% or above, and the purity oftrans-beta-carotene in a product reaches 96%; the reaction operation is simple, the product is separated quickly, and the method is environmentally friendly and suitable for industrialized production.

Description

technical field [0001] The invention belongs to the field of nutritional chemical synthesis, and in particular relates to a preparation method of all-trans β-carotene. Background technique [0002] β-Carotene (β-Carotene) is the precursor of vitamin A, commonly known as provitamin A, also known as carotenoid, which is the earliest carotenoid that attracted people's attention. missing nutrients. β-carotene has significant functions in anti-cancer, prevention of cardiovascular disease, cataract and anti-oxidation. It can also prevent various degenerative diseases caused by aging and aging, and has a wide range of uses. The structural formula of β-carotene is shown in 0, and its molecular formula is C 40 h 56 , molecular weight 536.88, CAS number 7235-40-70. [0003] [0004] The chemical synthesis of β-carotene has received continuous attention in recent years. The existing chemical synthesis methods of β-carotene mainly include C20+C20 route, C15+C10+C15 (C15 phosphine...

Claims

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Application Information

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IPC IPC(8): C07C403/24C07D233/58C07D233/56
CPCC07B2200/09C07C403/24C07C2601/16C07D233/56C07D233/58C07F9/5442
Inventor 李莉宋明炎潘亚男吕英东刘英瑞林龙王延斌黎源
Owner WANHUA CHEM GRP CO LTD
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