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Method for preparing steviol

A technology of steviol and steviol glycosides, which is applied in the field of synthesis of natural compounds, can solve the problems of difficult recovery, easy inactivation, unavoidable high price of biological enzymes, etc., and achieve the effect of easy separation and high product purity

Inactive Publication Date: 2015-04-01
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Although enzyme catalysis has many advantages, it cannot be avoided that biological enzymes have disadvantages such as expensive, difficult to recycle, and easy to inactivate.

Method used

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  • Method for preparing steviol

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Stevioside St was prepared as a 5 mg / mL aqueous solution, kept at 50°C for 0.5 h, and 0.5 mmol / g St ferric chloride (dissolved in water) was added. After 24 h of reaction, a large amount of white precipitates were formed. After suction filtration, washing with water, and second recrystallization from methanol, steviol can be obtained. The number of moles of glucose generated is three times the number of moles of stevioside St. As determined by HPLC, the conversion rate of St was 98.0%, the yield of steviol was 85%, and the purity was 98.5%. 13 CNMR (400MHz, Pyr), 41.6(C1), 20.4(C2), 39.2(C3), 44.4(C4), 57.5(C5), 23.2(C6), 42.4(C7), 42.4(C8), 54.8(C9 ),40.4(C10),21.3(C11),41.2(C12),80.9(C13),48.0(C14),48.6(C15),158.3(C16),103.4(C17),29.9(C18),180.6(C19 ), 16.2(C20); 1 H NMR (400MHz, Pyr), δ14.70 (s, 1H, H-19), 5.49 (dd, J=3.9, 2.3Hz, 1H, H-17), 5.04 (d, J=1.6Hz, 1H, H-17).

Embodiment 2

[0016] Ferric chloride was replaced by aluminum chloride and cuprous chloride of the same molar number, and all other experimental conditions were the same as in Example 1. After 24 hours of reaction, the conversion rates of St were 84.5 and 65.0%, respectively.

Embodiment 3

[0018] Rebaudioside A was formulated into a 50mg / mL aqueous solution, kept at a constant temperature of 0.5h at 85°C, added 1mmol / g Reb A in an aqueous ferric chloride solution, and reacted for 12h. The conversion rate of Reb A was determined to be 85.0% by HPLC, and that of steviol was Yield 96.5%.

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Abstract

The invention discloses a method for preparing steviol, belonging to the technical field of synthesis of natural compounds. Common Lewis acid is used as a catalyst to directly catalyze the hydrolysis of stevioside to prepare the steviol by a one-step process. The method has the advantages of high selectivity, high conversion rate, simple separation and purification process and the like. The invention provides an efficient, simple and cheap novel method for preparing steviol.

Description

technical field [0001] The invention belongs to the technical field of synthesis of natural compounds, and in particular relates to a method for preparing steviol by using common Lewis acids to directly catalyze the hydrolysis of steviol glycosides. Background technique [0002] Steviol (13-hydroxykaur-16-en-18-oic acid, steviol) is an aglycon of steviol glycosides, a typical tetracyclic diterpenoid, with different numbers of glucosyl groups attached to its C13 and C19 positions , rhamnosyl or xylosyl, thus forming steviol glycosides with different taste and physical and chemical properties. Steviol glycosides are a class of sweeteners with high sweetness and low calorie value extracted from the leaves of Stevia rebaudiana (Stevia rebaudiana) originating in South America, mainly including stevioside (Stevioside, St), rebaudioside A ( rebaudioside A, Reb A), rebaudioside B (rebaudioside B, Reb B), rebaudioside C (rebaudioside C, Reb C), rebaudioside E (rebaudioside E, Reb E)...

Claims

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Application Information

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IPC IPC(8): C07C62/32C07C51/09C07C51/347
Inventor 万会达夏咏梅方云李丹
Owner JIANGNAN UNIV
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