Dihydroxyoleic acid, preparation method and application thereof

A technology of bishydroxyoleic acid and bishydroxyl, applied in the preparation of carboxylates, preparation of organic compounds, preparations for skin care, etc., can solve problems such as differences, achieve high yield, mild reaction conditions, and improve immunity. Effect

Inactive Publication Date: 2009-12-30
ZHONGSHAN UNICARE NATURAL MEDICINE +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, after years of research, people have a better understanding of the functional properties of oleic acid, but there are still some differences

Method used

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  • Dihydroxyoleic acid, preparation method and application thereof
  • Dihydroxyoleic acid, preparation method and application thereof
  • Dihydroxyoleic acid, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0093] Into a 50 mL round bottom flask was added 383 mg of SeO 2 , 10 mL of dichloromethane, stirred at 25°C for 1 hour, slowly added 1 g of conjugated linoleic acid (conjugated linoleic acid contains cis 9, trans 11-conjugated linoleic acid and trans 10, cis 12-conjugated Two isomers of linoleic acid, with a purity of 95%) were stirred and reacted for 48 hours. After the reaction, add water to wash, collect the dichloromethane layer, and recycle the dichloromethane to obtain 0.98 g of light yellow oil with a yield of 70.8% and a purity of 90% (W / W).

[0094] 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 98: 2; 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 ...

Embodiment 2

[0132] 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 conjugated linoleic acid with a purity of 95%, and continued to stir for 12 hours. After the reaction, add water to wash, collect the dichloromethane layer, and recover the dichloromethane to obtain 0.8 g of light yellow oil with a yield of 40% and a purity of 88% (W / W). The product was analyzed by normal phase high performance liquid chromatography.

[0133] Analysis conditions: the mobile phase is n-hexane / isopropanol (volume ratio) 98 / 2; the flow rate is 2 mL / min; the detector is a differential refractive index detector; the sample concentration is 20 mg / mL; the sample injection is 10 μL. Under this separation condition, obtain four product peaks, retention time is respectively 20.4min (peak 1), 21.3min (peak 2), 22.9min (peak 3), 24.9min (peak 4). figure 1 , confirmed as compounds: 12,13-dihydroxy-10E-octadecenoic acid, 11,12-dihydroxy-9E-octa...

Embodiment 3

[0135] Into a 50 mL round bottom flask was added 3.83 g of SeO 2, 200mL of toluene, stirred at 25°C for 2 hours, slowly added 10g of conjugated linoleic acid with a purity of 90%, and continued to stir for 48 hours. After the reaction, add water to wash, collect the toluene layer, and recover the toluene to obtain 9 g of light yellow oil, with a yield of 65.1% and a purity of 84% (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 20.4min (peak 1), 21.3min (peak 2), 22.9min (peak 3), 24.9min min (peak 4), compared with the standard of four isomers, confirmed to be compounds: 12,13-dihydroxy-10E-octadecenoic acid, 11,12-dihydroxy-9E-octadecenoic acid , 10,11-dihydroxy-12E-octadecenoic acid, 9,10-dihydroxy-11E-octadecenoic acid.

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Abstract

The invention discloses dihydroxyoleic acid, a preparation method and application thereof, which relate to a novel octadecenoic acid derivative, namely the dihydroxyoleic acid, the preparation method and the application thereof. The compound is the dihydroxyoleic acid obtained by the following steps: stirring conjugated 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; adding water to wash the obtained product; and collecting an organic solvent layer and recovering a solvent, wherein a molecular formula is C18H34O4, and the morphology is yellowish oily matter. The dihydroxyoleic acid can be used for preparing medicaments or food for treating obesity, reducing blood fat, reducing blood sugar and improving the immunity, and preparing antioxidative and whitening skin nursing preparations for external application. L-carnitine can also be added into the dihydroxyoleic acid to prepare medicaments or food for treating obesity, reducing blood fat and reducing blood sugar or serve as a feed additive, and the weight ratio of the dihydroxyoleic acid to the L-carnitine in a product is 4:1-8.

Description

technical field [0001] The invention relates to the field of chemical medicines, in particular to new octadecenoic acid derivatives, dihydroxy oleic acid and its preparation method and application. Background technique [0002] Oleic acid, also known as octadecenoic acid, is an unsaturated fatty acid with double bonds, and its molecular formula is C 18 h 34 o 2 . The content of oleic acid in fatty acids accounts for about 40% to 50%. The content of oleic acid in vegetable oil varies depending on the variety of vegetable oil. The content of oleic acid in tea oil can be as high as 83%, that in peanut oil is about 54%, and that in coconut oil is only 5%. %~6%. Oleic acid is an important chemical reagent, which can be widely used in chemical analysis, organic synthesis and pharmaceutical preparation, etc. It is mainly used as ointment base in pharmaceuticals. According to research reports (Chinese Food and Nutrition, 2005, 4:44-46), oleic acid has some important physiologic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C59/58C07C51/367A61K31/191A61P3/04A61P3/06A61P3/10A61K8/365A61Q19/00
Inventor 杨得坡李珍冀军锋杜若吉马伟杜柯霖王冬梅王创鲁冰山朱龙平
Owner ZHONGSHAN UNICARE NATURAL MEDICINE
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