The Extraction, Separation And Analysis About Natural Aldehyde Compounds

ObjectiveTo discuss the present pattern and coexisting relationship of the natural aldehyde compounds, analyze the polar inversion of the aldehyde compounds by a sodium bisulfite additive reaction, study the extraction, separation and purification methods of the natural aldehyde products by a special reaction of sodium bisulfite, and improve the qualitative and quantitative analysis of cinnamic aldehyde in Cinnamomum cassia Presl.Materials and Methods(1) We searched the general subjects from both domestic and international literature, including Chemical Abstracts, by the method of handicraft and machine searches, and discussed the present pattern and coexisting relationship of the natural aldehyde compounds.(2) We took a series of hydroxyl and methoxy substituted benzaldehyde compounds as the materials, transferred them into water soluble sodiumα-hydroxyalkane sulfonate derivatives by a sodium bisulfite addition reaction in hydrophobic two-phase solvent system. The partition coefficients of these compounds in different ratios of ethyl acetate-sodium bisulfite water solution two-phase system were measured by high performance liquid chromatography. Original aldehyde compounds were recovered from sodiumα-hydroxyalkane sulfonate derivatives by adding hydrochloric acid and the partition extraction.(3) We took the dried peel of Cinnamomum cassia Presl which contain some natural aldehyde compounds, extracted, separated, and purified the chemical constituents by sodium bisulfite addition reaction and silica gel column chromatography, and identify their structures by means of their spectroscopic data and chemical properties.(4) We extracted the dried peel of Cinnamomum cassia Presl with some organic solvents such as ethyl acetate, acetonitrile, and methanol, and determined the extracting conditions in the qualitative and quantitative analysis according to the spot of cinnamic aldehyde dimethyl acetal on thin-layer chromatography. The content determination method of cinnamic aldehyde in cinnamon was approved with high performance liquid chromatography and with a mobile phase of methanol-water.Results(1) The natural aldehyde compounds are present as phenylpropanoid, terpenoid, saponin, alkaloid, coumarin, anthraquinone and so on with their chemical structure's types.(2) The partition coefficients of hydroxyl and methoxy substituted benzaldehyde compounds are grow down quickly along with the increasing ratios of sodium bisulfite in the ethyl acetate-sodium bisulfite water solution two-phase system, and then reach to a balance.(3) Cinnamic aldehyde, 2-methoxy cinnamic aldehyde, and cinnamic aldehyde dimethyl acetal are extracted and identified from the peel of Cinnamomum cassia Presl.(4) When we take acetonitrile as the extraction solvent from cinnamon, the generation of cinnamic aldehyde dimethyl acetal can be inhibited, and the content of cinnamic aldehyde can be improved. By sodium bisulfite addition reaction, we extracted, separated and identified cinnamic aldehyde, 2-methoxy cinnamic aldehyde and cinnamic aldehyde dimethyl acetal from cinnamon. Conclusions(1) In some plants, there are many aldehyde compounds, which have same skeleton linked with aldehyde group but have different other substituting groups. A series of different valence state compounds can be found in some other plants, such as methyl (-CH3), hydroxymethyl (-CH2OH), aldehyde (-CHO), carboxyl (-COOH), and carboxylic ester (-COOR) groups, which have same skeleton. That is to say, a series of compounds coexist with aldehyde compounds in plant.(2) The lipid-soluble natural aldehyde compounds are formed into water soluble sodiumα-hydroxyalkanesulfonate derivatives by a sodium bisulfite addition reaction, and are separated from other lipid-soluble materials. The original aldehyde compounds were recovered from sodiumα-hydroxyalkane sulfonate derivatives by adding hydrochloric acid and the partition extraction.(3) Cinnamic aldehyde dimethyl acetal was firstly obtained as a natural compound. It is a specificity that with sodium bisulfite addition reaction to extract and separate the aldehyde compounds.(4) By the improved method, we can repress the generation of cinnamic aldehyde dimethyl acetal, save some costs, and carry out the qualitative and quantitative analysis of cinnamic aldehyde in C. cassia preferably.