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Method for synthesizing cis-lycopene isomer from full trans lycopene with photochemistry isomerization reaction

A technology of cis-lycopene and photochemical reaction, which is applied in the field of synthetic photochemistry, can solve problems such as difficult implementation, and achieve mild reaction conditions and environment-friendly effects

Inactive Publication Date: 2008-12-03
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

It has been reported recently [C.Y.Wang, B.H.Chen.Tomato pulp as source for the production of lycopene powder containing high proportion of cis-isomers. Eur Food Res Technol, 2006, 222:347~353] using carbon dioxide supercritical extraction technology at high temperature and high pressure (at a pressure of 350 bar and a temperature of 90°C), the cis-isomer accounts for up to 53.8% of the total lycopene, but high temperature and high pressure are difficult to implement in production applications

Method used

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  • Method for synthesizing cis-lycopene isomer from full trans lycopene with photochemistry isomerization reaction
  • Method for synthesizing cis-lycopene isomer from full trans lycopene with photochemistry isomerization reaction
  • Method for synthesizing cis-lycopene isomer from full trans lycopene with photochemistry isomerization reaction

Examples

Experimental program
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Effect test

Embodiment 1

[0021] In a 30 ml glass test tube, 2 mg of all-trans lycopene was dissolved in 20 g of petroleum ether (60-90° C.) at a concentration of 0.01 wt%. Seal the mouth with a rubber stopper, and insert two injection needles on the rubber stopper. One is longer for nitrogen to pass into the photochemical reaction liquid, and the other is shorter for air and nitrogen mixed gas out of the photochemical reaction liquid surface. Adjusting the nitrogen flow rate does not cause the reaction liquid to overflow and make the bubbles uniform, on the one hand to protect the lycopene, on the other hand, it can also stir the photochemical reaction liquid to make the reaction uniform. Place the test tube 3 mm in front of the glass cold trap equipped with a 450-watt high-pressure mercury lamp (product of Beijing Electric Light Source Research Institute), and insert the borosilicate glass with a wavelength shorter than 283 nm between the test tube and the cold trap. Type filter. The reaction device is p...

Embodiment 2

[0023] In a 30 ml glass test tube, 200 mg of all-trans lycopene was dissolved in 20 g of tetrahydrofuran with a concentration of 1 wt%. Seal the mouth with a rubber stopper, insert two injection needles into the rubber stopper, one longer for nitrogen to pass into the photochemical reaction liquid, and the other shorter for gas to be discharged outside the surface of the photochemical reaction liquid. Adjusting the nitrogen flow rate does not cause the reaction liquid to overflow and make the bubbles uniform, on the one hand to protect the lycopene, on the other hand, it can also stir the photochemical reaction liquid to make the reaction uniform. Place the test tube 3 mm in front of the glass cold trap equipped with a 450-watt high-pressure mercury lamp (product of Beijing Electric Light Source Research Institute), and insert the borosilicate glass with a wavelength shorter than 283 nm between the test tube and the cold trap. Type filter. The reaction device was placed in an opaq...

Embodiment 3

[0025] In a 30 ml glass test tube, 3 mg of all-trans lycopene was dissolved in 20 g of n-hexane at a concentration of 0.015 wt%. Seal the mouth with a rubber stopper, insert two injection needles into the rubber stopper, one longer for nitrogen to pass into the photochemical reaction liquid, and the other shorter for gas to be discharged outside the surface of the photochemical reaction liquid. Adjusting the nitrogen flow rate does not cause the reaction liquid to overflow and make the bubbles uniform, on the one hand to protect the lycopene, on the other hand, it can also stir the photochemical reaction liquid to make the reaction uniform. Place the test tube 3 mm in front of the glass cold trap equipped with a 450-watt high-pressure mercury lamp (product of Beijing Electric Light Source Research Institute), insert a cut-off filter with a wavelength shorter than 450 nanometers between the test tube and the cold trap sheet. The reaction device was placed in an opaque fume hood, an...

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Abstract

The invention belongs to the synthetic photochemistry technical field and relates to a photochemical synthetic method for synthesizing cis-lycopene, in particular to a method for synthesizing all-trans-lycopene into cis-lycopene isomer through photochemical isomerization reaction. The method comprises the following steps that: the all-trans-lycopene is dissolved into nonpolar or polar solvent, and a 450 watt high-pressure mercury lamp is used for illumination through a cut-off filter capable of cutting off different wavelengths under the condition of nitrogen protection; the temperature of a photochemical reaction liquid is controlled to between 23 and 30 DEG C, and a photochemical reaction mixture containing high proportion of the cis-lycopene isomer is prepared; the photochemical reaction mixture containing high proportion of the cis-lycopene isomer is evaporated to be dryness, and refined edible oil is added into the photochemical reaction mixture for preparing oil with high percentage of the cis-lycopene isomer; and the oil is limpid and azarin. The method uses the photochemical isomerization reaction to synthesize the cis isomer lycopene which can occupy 73 weight percent of the total amount of isomer, and 73 weight percent is the peak value reported until now. The photochemical isomerization reaction has mild temperature and friendly environment.

Description

Technical field [0001] The invention belongs to the technical field of synthetic photochemistry, and relates to a photochemical synthesis method for synthesizing cis-lycopene, in particular to a method for synthesizing cis-lycopene isomers from all-trans lycopene by photochemical isomerization reaction. Background technique [0002] Lycopene is a natural pigment found in tomatoes, which mammals cannot synthesize by themselves. The structural formula of all-trans lycopene is as follows: [0003] [0004] Lycopene is a long-chain molecule with 11 conjugated double bonds and a non-conjugated double bond at each end. Its special structure gives it special health care functions. Lycopene is closely related to reducing the risk of prostate and other cancers and reducing the incidence of chronic diseases such as myocardial infarction [Isabel Goni, Jose Serrano, and Fulgencio Saura-Calixto, Bioaccessibility of β-carotene, lutein, and lycopene from fruits and vegetables, J. Agric. Food ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C11/00C07C5/22C07B53/00
Inventor 王雪松刘颙颙程学新张宝文
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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