Overview
Rutin is widely found in the plant kingdom and it has been found that rutin-containing plants are contained in at least 70 species, such as tobacco, sassafras, buckwheat and dandelion. In particular, glutinous rice (which is the unopened flower bud of the plant Sophorajaponica) and buckwheat are the most abundant, and can be used as a raw material for extracting rutin in large quantities. Rutin is a glycoside synthesized by dehydration of a hydroxyl group at the 3 position of Quercetin with Rutinose [a disaccharide composed of glucose (Glucose) and rhamnose].
Rutin is a light yellow powder or very fine needle crystal, containing three molecules of water of crystallization, melting point of 174 ~ 178 ° C, anhydrate of 188 ~ 190 ° C. Solubility: 1:10000 in cold water; 1:200 in hot water; 1:650 in cold ethanol; 1:60 in hot ethanol; 1:12 in cold pyridine. Slightly soluble in acetone, ethyl acetate, insoluble in benzene, ether, chloroform, petroleum ether, soluble in alkali and yellow.
Rutin has a vitamin P-like effect. It helps to maintain and restore the normal elasticity of capillaries. It is mainly used as an auxiliary therapeutic agent for the prevention and treatment of hypertension, and can also be used to prevent other hemorrhagic diseases caused by lack of rutin.
Experimental purpose and requirements
1. Purpose
1 Master the principle and operation of extracting flavonoids by alkali-acid method through extraction and purification of rutin.
2 Through the detection of rutin structure, the general procedures and methods for the study of glycosyl structure are known.
3 understand the application of UV and NMR in the structural identification of flavonoids.
2. Claim
1 to get the following three compounds: rutin, quercetin, rutin all-acetyl compounds.
2 It is possible to preliminarily infer the structure of rutin based on chemical tests and UV and NMR data. A general understanding of the structure of flavonoids is known.
experiment method
1. Extraction and separation of rutin (see figure below)
2. Identification of rutin
1) Qualitative reaction of rutin
Take 3~4mg of rutin, add 5~6ml of ethanol to dissolve it, and divide it into three parts for the following test:
A. Take 1~2ml of the above solution, add 2 drops of concentrated hydrochloric acid, and add a little magnesium powder, pay attention to observe the color change.
B. Take 1~2ml of the above solution, then add 2% citric acid in methanol solution, pay attention to observe the color change, continue to add 2% ZrOCl2 methanol solution to the test tube, and record the color change in detail.
C. Take 1~2ml of the above solution, then add 10%α-equal volume of naphthol ethanol solution, shake well, add concentrated sulfuric acid along the tube wall, pay attention to observe the color change produced by the two liquid surfaces.
2) UV spectrum analysis of rutin
The rutin was dissolved in pure methanol, and the specified reagent was added to determine the UV spectrum. The spectrum was analyzed and the structure was initially determined.
3) Analysis of NMR spectrum of rutin
A. Analysis of NMR spectrum of trimethylsilyl ether of rutin
B. NMR Spectral Analysis of Decaacetyl Rutin
4) Identification of sugars and aglycones after hydrolysis of rutin
A. Hydrolysis method: Weigh accurately 1g (±0.01g) of rutin, add 100ml of 1% sulfuric acid, heat for 40min, put it cool, and filter. The resulting precipitate was washed with a little water to remove the acid, dried and weighed to calculate the weight ratio of aglycone to sugar. It is then recrystallized from ethanol (95% to about 10 ml) to give the aglycon.
B. Identification of aglycones: Controlled by paper chromatography against the control.
The main points and precautions of this experiment
1 rutin extraction method, focusing on the principle and precautions of the alkali-acid method.
2 The purpose, significance and precautions of the qualitative experiment.
The application of 3UV and NMR spectroscopy in the detection of rutin structure.
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