Method for synthesizing nootkatone, and its application

A synthesis method and technology of nokatone, which is applied in the field of synthesis of unsaturated ketene compounds, can solve the problems of low content, limited dosage, difficulty in isolation, etc., and achieve the effects of good selectivity, rich cigarette flavor, and convenient post-processing

Inactive Publication Date: 2006-09-13
YUNNAN REASCEND TOBACCO TECH GRP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

It has been isolated from natural essential oils for many years, but because of its ...

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  • Method for synthesizing nootkatone, and its application
  • Method for synthesizing nootkatone, and its application

Examples

Experimental program
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Embodiment 1

[0015] (2) Mix 15g of balentene, 300ml of ethyl acetate, 4g of sodium bicarbonate and 60g of tert-butyl hydroperoxide (TBHP), and add the balun 10% aqueous solution of sodium hypochlorite in an equimolar amount of alkene, after the mixture was stirred for 13 hours, 50 g of sodium bisulfite was added, and after standing for 6 hours, the water layer was separated into layers. %NaHCO 3 Wash, wash with water three times, add 10g of anhydrous sodium sulfate to dry for 20h, distill off ethyl acetate to obtain 16.2g of nokadone primary product, carry out vacuum distillation on the primary product, and collect fractions at 185~195°C / 1300Pa. The obtained product was separated by a silica gel column (V (n-hexane) / V (ether) = 3 / 1), and the component with Rf = 0.51 was collected, and 13.1 g of colorless needle crystals were obtained after low-temperature recrystallization. Yield 82%, melting point 34.5~35.5℃, optical rotation [α] D 25 =+189.5°(c 0.50, CH 3 OH), refractive...

Embodiment 2

[0020] (2) Mix 10g of balentene, 200ml of ethyl acetate, 4g of sodium bicarbonate and 60g of tert-butyl hydroperoxide (TBHP), and add the balun 10% aqueous solution of sodium hypochlorite in an equimolar amount of alkene, after the mixture was stirred for 4 hours, 45 g of sodium bisulfite was added, and after standing for 3 hours, the water layer was separated into layers, and the water layer was extracted three times with ethyl acetate, and the organic layers were combined, and the organic layer was washed with 10 %NaHCO 3 Washing, washing with water three times, adding 10g of anhydrous sodium sulfate to dry for 20h, distilling off ethyl acetate to obtain 12.3g of nokadone primary product, the primary product was subjected to vacuum distillation, and the fraction at 185~195°C / 1300Pa was collected. The obtained product was separated by a silica gel column (V (n-hexane) / V (ether)=3 / 1), and the component with Rf=0.51 was collected, and 8.8 g of colorless needle crys...

Embodiment 3

[0025] (2) Mix 20g of balentene, 400ml of ethyl acetate, 8g of sodium bicarbonate and 80g of tert-butyl hydroperoxide (TBHP), and add the balun 10% aqueous solution of sodium hypochlorite in an equimolar amount of alkene. After the mixture was stirred for 15 hours, 55 g of sodium bisulfite was added. After standing for 12 hours, the water layer was separated into layers. The water layer was extracted three times with ethyl acetate, and the organic layers were combined. %NaHCO3 Washing, washing with water three times, adding 15g of anhydrous sodium sulfate to dry for 24h, distilling off ethyl acetate to obtain 24.5g of nokadone primary product, the primary product was subjected to vacuum distillation, and the fraction at 185~195°C / 1300Pa was collected. The obtained product was separated by a silica gel column (V (n-hexane) / V (ether) = 3 / 1), and the component with Rf = 0.51 was collected, and 16.9 g of colorless needle crystals were obtained after low-temperature rec...

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Abstract

A process for preparing the nootkatone used for essence of cigarette includes such steps as extracting valencene from valerian oil by supercritical separation, and converting it to nootkatone in the solution of sodium hypochlorite-tert-butyl hydrogen peroxide (TBHP) mixture.

Description

technical field [0001] The invention relates to a synthesis method and application of an unsaturated enone compound, that is, a synthesis method and application of nokadone. Background technique [0002] Nokadone (5,6-dimethyl-8-isopropylbicyclo[4,4,0]dec-1-en-3-one), also known as narone, belongs to Eremophillane ) is an unsaturated enone of the bicyclic sesquiterpenes. It was discovered in the 1960s from Alaska cork (Chamaecyparis nootkatensis) oil and grapefruit peel oil, and its unique structure was identified. Nokatone has a sharp aroma, but it is an important aroma component in grapefruit peel and grapefruit juice, and it can enhance the aroma and taste of grapefruit in essence. It has been isolated from natural essential oils for many years, but because of its low content in natural essential oils, it is difficult to separate and its usage is limited. Contents of the invention [0003] The purpose of the present invention is to solve the problems in the prior art...

Claims

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Application Information

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IPC IPC(8): C07C45/27C07C49/653C11B9/00
CPCY02P20/54
Inventor 陈永宽谢冰刘维涓王保兴杨伟祖
Owner YUNNAN REASCEND TOBACCO TECH GRP
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