Monohydroxy conjugated linoleic acid, preparation method and application thereof

Abstract

The invention discloses monohydroxy conjugated linoleic acid, a preparation method and application thereof, which relate to a novel conjugated linoleic acid derivative, namely the monohydroxy conjugated linoleic acid, the preparation method and the application thereof. The compounds are the monohydroxy conjugated linoleic acid obtained by following steps: stirring linoleic acid and selenium dioxide for 0.5 to 2h at a temperature of between 25 and 60 DEG C; continuing stirring to react for 12 to 48 hour; and adding water to wash the obtained product; collecting an organic solvent layer and recovering a solvent, wherein a molecular formula is C18H32O3, and the morphology is yellowish oily matter. The monohydroxy conjugated linoleic acid is used for preparing medicaments or food for treating obesity or reducing blood fat or reducing blood sugar or improving the immunity or resisting tumor, and preparing antioxidative and whitening skin nursing preparations for external application. L-carnitine can also be added into dihydroxyoleic acid to prepare medicaments or food for treating obesity or reducing blood fat or reducing blood sugar or serve as a feed additive, and the weight ratio ofthe monohydroxy conjugated linoleic acid to the L-carnitine in a product is 4:1-8.

Description

technical field

[0001] The invention relates to the field of chemical medicine, in particular to a novel conjugated linoleic acid derivative which is monohydroxy conjugated linoleic acid, and other preparation methods and applications. Background technique

[0002] Linoleic acid (abbreviated as LA), also known as cis-9, cis-12 octadecadienoic acid. Widely present in vegetable oils and deep-sea fish oils. Linoleic acid is an omega-6 fatty acid, which is one of the important fatty acids necessary for the human body.

[0003] It cannot be synthesized by the body itself and must be ingested from the outside world. In aiding growth, development and pregnancy, especially skin and kidney integrity and childbirth rely only on n-6 fatty acids, of which linoleic acid is effective. In recent years, there have been more and more studies on linoleic acid. With the deepening of research, the physiological and health functions of linoleic acid have been fully understood. Linoleic acid ...

Examples

Embodiment 1

[0124] Into a 50 mL round bottom flask was added 383 mg of SeO 2 , 10mL of dichloromethane, stirred at 25°C for 1 hour, slowly added 1g of linoleic acid with a purity of 98%, and continued to stir for 48 hours. After the reaction, add water to wash, collect the dichloromethane layer, and recover the dichloromethane to obtain 0.90 g of light yellow oil with a yield of 70.2% and a purity of 92% (W / W).

[0125] Analysis of the product: the light yellow oil obtained by the reaction is separated by semi-preparative normal phase high-performance liquid chromatography, and the separation conditions: the mobile phase is n-hexane: Virahol (volume ratio) is 99.4: 0.6; flow rate 8mL / min ; The detector is a differential refractive index detector; the sample is dissolved in n-hexane with a concentration of 100 mg / mL; the sample injection is 150 μL. Under this separation condition, four product peaks ( figure 1 ), the retention times are 15.4min (peak 1), 17.4min (peak 2), 20.1min (peak 3...

Embodiment 2

[0158] Add 200 mg of SeO to a 50 mL round bottom flask 2 , 5mL of dichloromethane, stirred at 60°C for 1 hour, slowly added 2g of linoleic acid with a purity of 90%, and continued to stir for 12 hours. After the reaction, add water to wash, collect the dichloromethane layer, and recycle the dichloromethane to obtain 0.8 g of light yellow oil with a yield of 36.4% and a purity of 88% (W / W). The product is analyzed by normal phase high performance liquid chromatography, analysis conditions: mobile phase is n-hexane: Virahol (volume ratio) is 99.4: 0.6; Flow velocity 2mL / min; Detector is differential refraction detector; Sample concentration is 20mg / min. mL; inject 10 μL. Under this separation condition, four product peaks are obtained, and the retention times are respectively 15.4min (peak 1), 17.4min (peak 2), 20.1min (peak 3), and 21.8min (peak 4). figure 1 , confirmed as compounds: 13-Hydroxy-9Z, 11E-octadecadienoic acid; 13-Hydroxy-9E, 11E-octadecadienoic acid; 9-Hydroxy-1...

Embodiment 3

[0160] Add 700mg of SeO to a 50mL round bottom flask 2 , 30mL of n-hexane, stirred at 40°C for 2 hours, slowly added 1g of linoleic acid with a purity of 75%, and continued to stir for 24 hours. After the reaction was finished, add water to wash, collect the n-hexane layer, and recover the n-hexane to obtain 0.9 g of light yellow oil with a yield of 52.9% and a purity of 70% (W / W). Product adopts normal phase high performance liquid chromatography to analyze, and analysis condition is with embodiment 2, obtains four product peaks, retention time is respectively 15.4min (peak 1), 17.4min (peak 2), 20.1min (peak 3), 21.8 min (peak 4), compared with the standard of the four isomers, confirmed to be the compound: 13-hydroxy-9Z, 11E-octadecadienoic acid; 13-hydroxy-9E, 11E-octadecadienoic acid ; 9-Hydroxy-10E, 12Z-octadecadienoic acid, 9-Hydroxy-10E, 12E-octadecadienoic acid.

technical field

[0001] The invention relates to the field of chemical medicine, in particular to a novel conjugated linoleic acid derivative which is monohydroxy conjugated linoleic acid, and other preparation methods and applications. Background technique

[0002] Linoleic acid (abbreviated as LA), also known as cis-9, cis-12 octadecadienoic acid. Widely present in vegetable oils and deep-sea fish oils. Linoleic acid is an omega-6 fatty acid, which is one of the important fatty acids necessary for the human body.

[0003] It cannot be synthesized by the body itself and must be ingested from the outside world. In aiding growth, development and pregnancy, especially skin and kidney integrity and childbirth rely only on n-6 fatty acids, of which linoleic acid is effective. In recent years, there have been more and more studies on linoleic acid. With the deepening of research, the physiological and health functions of linoleic acid have been fully understood. Linoleic acid ...

Examples

Embodiment 1

[0124] Into a 50 mL round bottom flask was added 383 mg of SeO 2 , 10mL of dichloromethane, stirred at 25°C for 1 hour, slowly added 1g of linoleic acid with a purity of 98%, and continued to stir for 48 hours. After the reaction, add water to wash, collect the dichloromethane layer, and recover the dichloromethane to obtain 0.90 g of light yellow oil with a yield of 70.2% and a purity of 92% (W / W).

[0125] Analysis of the product: the light yellow oil obtained by the reaction is separated by semi-preparative normal phase high-performance liquid chromatography, and the separation conditions: the mobile phase is n-hexane: Virahol (volume ratio) is 99.4: 0.6; flow rate 8mL / min ; The detector is a differential refractive index detector; the sample is dissolved in n-hexane with a concentration of 100 mg / mL; the sample injection is 150 μL. Under this separation condition, four product peaks ( figure 1 ), the retention times are 15.4min (peak 1), 17.4min (peak 2), 20.1min (peak 3...

Embodiment 2

[0158] Add 200 mg of SeO to a 50 mL round bottom flask 2 , 5mL of dichloromethane, stirred at 60°C for 1 hour, slowly added 2g of linoleic acid with a purity of 90%, and continued to stir for 12 hours. After the reaction, add water to wash, collect the dichloromethane layer, and recycle the dichloromethane to obtain 0.8 g of light yellow oil with a yield of 36.4% and a purity of 88% (W / W). The product is analyzed by normal phase high performance liquid chromatography, analysis conditions: mobile phase is n-hexane: Virahol (volume ratio) is 99.4: 0.6; Flow velocity 2mL / min; Detector is differential refraction detector; Sample concentration is 20mg / min. mL; inject 10 μL. Under this separation condition, four product peaks are obtained, and the retention times are respectively 15.4min (peak 1), 17.4min (peak 2), 20.1min (peak 3), and 21.8min (peak 4). figure 1 , confirmed as compounds: 13-Hydroxy-9Z, 11E-octadecadienoic acid; 13-Hydroxy-9E, 11E-octadecadienoic acid; 9-Hydroxy-1...

Embodiment 3

[0160] Add 700mg of SeO to a 50mL round bottom flask 2 , 30mL of n-hexane, stirred at 40°C for 2 hours, slowly added 1g of linoleic acid with a purity of 75%, and continued to stir for 24 hours. After the reaction was finished, add water to wash, collect the n-hexane layer, and recover the n-hexane to obtain 0.9 g of light yellow oil with a yield of 52.9% and a purity of 70% (W / W). Product adopts normal phase high performance liquid chromatography to analyze, and analysis condition is with embodiment 2, obtains four product peaks, retention time is respectively 15.4min (peak 1), 17.4min (peak 2), 20.1min (peak 3), 21.8 min (peak 4), compared with the standard of the four isomers, confirmed to be the compound: 13-hydroxy-9Z, 11E-octadecadienoic acid; 13-hydroxy-9E, 11E-octadecadienoic acid ; 9-Hydroxy-10E, 12Z-octadecadienoic acid, 9-Hydroxy-10E, 12E-octadecadienoic acid.

Images