chlorogenic acid 5-98%（10% 25% 30% 50% 90%） (HPLC)

 

Molecular formula: C16H18O9

CAS No: 327-97-9

Einecs No:206-325-6

Molecular weight: 354.31

Solubility: chlorogenic acid 98%   Good solubility in water

Melting point:205-209

Appearance: Fine crystal powder

Color: White （chlorogenic acid 98% 99%）

 

 

Chlorogenic acid Usage And Synthesis

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Chlorogenic acid is also called "green" auspicious acid, tannins "coffee", "coffee tannic acid", is a plant produce a styrene acrylic compounds through shikimic acid hitches in aerobic respiration process.It is coffee acyl quinic acid derivatives.The oxidation resistance is strong, and also has the anti HIV, anti tumor cells, antibacterial, improve central excited, cholagogue function.It has teratogenic, allergy and regulate the activity of cytochrome P450 ligase, and other functions.It is widely exist in more content honeysuckle plants. It is obtained by the water needle crystal, and it is the hemihydrate, when 110 ℃ it is to hydrate. Melting point is 208 ℃, [a] D25 33.5 ° (water, C = 1), K = 2.2 x 10-3 (27 ℃).It is weak acidity and convergence. When 25 ℃ , the solubility in water is 4%, easily soluble in hot water, but soluble in ethanol, acetone, slightly soluble in ethyl acetate, insoluble in chloroform, ether and carbon disulfide. It is azeotropic with concentrated hydrochloric acid and come to blue dye. It can make the bromine water fade, It is azeotropic with strong hydrogen iodide and obtain benzoic acid, It is obtained phenol by thermal decomposition together with water at 230 ℃, It decomposite to caffeic acid and quinic acid with dilute hydrochloric acid, and caffeic acid and quinic acid with dilute alkali at room temperature. Chlorogenic acid and its isomer different chlorogenic acid and green chlorogenic acid are in fruits of dicotyledonous plants, leaves, and other organizations,which is an important factor for plant metabolism. Chlorogenic acid has good biological activity, the transparent acid enzyme and inhibition of glucose-6-phosphatase, free radical lipid perxidation qing mutagenesis resistance and cardiovascular crown reinforcement, special efficacy in lipid-lowering, both anti-bacterial anti-virus, protecting liver cholagogic.

Chlorogenic acid as the condensation product of caffeic acid and quinic acid, is blue when meeting with iron, which is similar to tannins , but not precipitated with protein, so no convergence. Caffeic acid and chlorogenic acid has the wide bacteriostasis, but can be inactivated protein in the body. This product is similar to caffeine, oral or intraperitoneal injection, can improve the rat central excitability. Oral the drug of chlorogenic acid and coffee acid can increase the amount of hydrochloric acid secretion in the stomach, and can make slow pulse, and quinic acid is not. Chlorogenic acid could significantly increase small intestine peristalsis on the rat or mouse. Chlorogenic acid, caffeic acid and quinic acid can increase the tension of rat uterus, this function can be cancelled by papaverine, while atropine can't influence. Caffeic acid, chlorogenic acid, also can promote bile secretion in rats. On the specimens of rabbit ileum in vitro, this product can enhance the effect of adrenaline, but has no effect on blood glucose of adrenaline.

 

 

Introduction

Chlorogenic acid is an organic compound with the chemical formula C16H18O9, which is one of the main antibacterial and antiviral active pharmacological components of honeysuckle[1]. The hemihydrate of chlorogenic acid is needle crystal (water). 110 ℃ into anhydrous compound. The solubility in water at 25°C is 4%, and the solubility in hot water is greater. Chlorogenic acid is easily soluble in ethanol and acetone, and very slightly soluble in ethyl acetate. Chlorogenic acid has a broad antibacterial effect, but can be inactivated by protein in vivo. Chlorogenic acid is similar to caffeic acid and can increase the central excitability of rats when administered orally or intraperitoneally. Chlorogenic acid can increase intestinal peristalsis and rat uterine tone in rats and mice. Chlorogenic acid has a choleretic effect and can increase bile secretion in rats. Chlorogenic acid has a sensitizing effect on people. After inhaling the plant dust containing this product, asthma and dermatitis may occur.

 

 

 

Picture 1 The appearance of chlorogenic acid

 

Chlorogenic acid has a wide range of biological activities, and modern scientific research on the biological activity of chlorogenic acid has gone deep into many fields such as food, health care, medicine and daily chemical industry. Chlorogenic acid is an important biologically active substance, which has the functions of antibacterial, antiviral, increasing white blood cells, protecting liver and gallbladder, antitumor, lowering blood pressure, lowering blood lipid, scavenging free radicals and exciting the central nervous system.

 

Chlorogenic acid   Uses

Chlorogenic acid is used as a food additive in coffee products, chewing gum and mint. It acts as an intermediate in the biosynthesis of lignin, which is an antioxidant.

 

A major component of green coffee the extracts of which promote weight loss in overweight and obese people. Chlorogenic Acid is an important intermediate in lignin biosynthesis. Chlorogenic Acid is an antioxidant and an inhibitor of the tumor promoting activity of phorbol ester. It has protective effect against streptozotocin-nicotinamide generated oxidative stress induced diabetes and may also pr otect against cardiovascular disease.

 

The structure of chlorogenic acid

Chlorogenic acid (hereinafter referred to as CA) is a depsidic acid generated by caffeic acid (Caffeic acid) and quinic acid (Quinic acid, 1-hydroxyhexahydrogallic acid). A phenylpropanoid compound produced via the shikimate pathway[2]. According to the different binding sites and numbers of caffeoyl on quinic acid, theoretically, there are 10 chlorogenic acid isomers composed of monocaffeoylquinic acid and dicaffeoylquinic acid, which are: 1 -Caffeoylquinic acid, 3-caffeoylquinic acid, 4-caffeoylquinic acid, 5-caffeoylquinic acid, 1,3-dicaffeoylquinic acid, 1,4-dicaffeoylquinic acid Niacinic acid, 1,5-dicaffeoylquinic acid, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid. The chlorogenic acid isomers found in plants are as follows: chlorogenic acid (3-caffeoylquinic acid), cryptochlorogenic acid (Band510) (4-caffeoylquinic acid), neochlorogenic acid (5-caffeoylquinic acid) Caffeoylquinic acid), isochlorogenic acid A (3,5-dicaffeoylquinic acid), isochlorogenic acid B (3,4-dicaffeoylquinic acid), isochlorogenic acid C (4 ,5-dicaffeoylquinic acid), lytherin (1,3-dicaffeoylquinic acid).

 

Antibacterial and antiviral effects

Eucommia chlorogenic acid has strong antibacterial and anti-inflammatory effects, aucubin and its polymers have obvious antibacterial effects, and aucubin has inhibitory effects on Gram-negative and positive bacteria[3]. Acupuncture has antibacterial and diuretic effects, and can promote wound healing; acupuncture and glucoside can also have obvious antiviral effects after pre-culture, but it does not have antiviral functions by itself. Research by the Institute of Advanced Medicine, Aichi Medical University, Japan has confirmed that the alkaline substances extracted from Eucommia ulmoides have the function of resisting viruses that destroy the human immune system. This substance may be used to prevent and treat AIDS.

 

Anti-oxidize effect

Chlorogenic acid is an effective phenolic antioxidant with stronger antioxidant capacity than caffeic acid, p-hydroxybenzoic acid, ferulic acid, syringic acid, butylated hydroxyanisole (BHA) and tocopherol. The reason why chlorogenic acid has antioxidant effect is because it contains a certain amount of R-OH groups, which can form hydrogen free radicals with antioxidant effect to eliminate the activity of free radicals such as hydroxyl free radicals and superoxide anions, thereby protecting Tissue is protected from oxidative damage.

 

Free radical scavenging, anti-aging, anti-musculoskeletal aging

Chlorogenic acid and its derivatives have stronger free radical scavenging effects than ascorbic acid, caffeic acid and tocopherol (vitamin E), can effectively scavenge DPPH free radicals, hydroxyl free radicals and superoxide anion free radicals, and can also inhibit low density Oxidation of lipoproteins. Chlorogenic acid plays an important role in effectively scavenging free radicals in the body, maintaining the normal structure and function of body cells, preventing and delaying the occurrence of tumor mutation and aging. Eucommia chlorogenic acid contains a special ingredient that can promote the synthesis and decomposition of collagen in human skin, bones and muscles. It has the functions of promoting metabolism and preventing decline. It can be used to prevent astronauts from space weightlessness caused by bones and muscles. At the same time, it was found that Eucommia chlorogenic acid has obvious anti-free radical effect both in vivo and in vitro.

 

Mutation suppression and anti-tumor

Modern pharmacological experiments have proved that chlorogenic acid of Eucommia ulmoides has anti-cancer and anti-tumor effects. Japanese scholars have studied the antimutagenicity of chlorogenic acid of Eucommia ulmoides, and found that this effect is related to antimutagenicity components such as chlorogenic acid. The significance of chlorogenic acid for tumor prevention was revealed.

 

Polyphenols such as chlorogenic acid and caffeic acid in vegetables and fruits can inhibit the mutagenicity of carcinogens aflatoxin B1 and benzo[a]-pyrene by inhibiting activating enzymes; chlorogenic acid can also reduce carcinogenicity by reducing carcinogenicity. The utilization rate of the substance and its transportation in the liver can achieve the effect of anti-cancer and anti-cancer. Chlorogenic acid has a significant inhibitory effect on colorectal cancer, liver cancer and laryngeal cancer, and is considered to be an effective chemoprotective agent for cancer.

 

Cardiovascular protection

As a free radical scavenger and antioxidant, chlorogenic acid has been proved by a large number of experiments that this biological activity of chlorogenic acid can produce a protective effect on the cardiovascular system. Isochlorogenic acid B has strong promotion in rats Pre-isochlorogenic acid B has strong promotion of prostaglandin (PGI2) release and antiplatelet aggregation in rats; antibodies induced to guinea pig lung fragments induce SRS-A The release inhibition rate was 62.3%. Isochlorogenic acid C also promotes the release of PGI2. In addition, isochlorogenic acid B has a strong inhibitory effect on platelet thromboxane biosynthesis and hydroperoxidation-induced endothelin damage.

 

Other biological activities

Because chlorogenic acid has a special inhibitory effect on hyaluronic acid (HAase) and glucose-6-phosphatase (Gl-6-Pase), chlorogenic acid is used for wound healing, healthy and moist skin, lubricating joints, preventing inflammation and The balance control of blood sugar in the body has certain curative effects. Chlorogenic acid also has strong inhibitory and killing effects on various diseases and viruses. Chlorogenic acid has pharmacological effects such as lowering blood pressure, antibacterial, antiviral, anti-inflammatory, increasing white blood cells, preventing diabetes, significantly increasing gastrointestinal motility and promoting gastric secretion, and has obvious curative effect on acute throat inflammation. Studies have shown that oral chlorogenic acid can significantly stimulate the secretion of bile, and has the effect of choleretic and liver protection; it can also effectively inhibit the hemolysis of rat erythrocytes caused by H2O2.

 

 

HPLC method for determination the content

 

(1)Chromatographic conditions: octadecyl silane bonded silica gel as the filling agent; Acetonitrile-0.4% phosphoric acid solution (13:87) as mobile phase; Detection wavelength of 327 nm. Theoretical plate number according to the chromatographic peak of chlorogenic acid is greater than 1000.

 

(2)the preparation of the reference substance solution: precisely weigh the right amount of chlorogenic acid reference substance, placed in brown volumetric flask, adding 50% methanol solution containing 40 μg /mL (saving below 10 ℃).

 

(3)the preparation of sample solution: taking samples of dry powder is about 0.5 g, precision said, with a plug in the conical flask, adding 50 ml 50% methanol , 30 min ultrasonic processing , cooling, weighing, make up the weight loss reduction with 50% methanol, shake well, filtration, abandoned the early filtrate, precision measuring duration of filtrate 5 ml, 25 ml volumetric brown flask , add 50% methanol to the scale, shake well.

 

(4)assimilate precision respectively from each 10 μL reference substance and the sample solution, injection liquid chromatograph, determination,obtained.

 

The character of molecular structure

Chlorogenic acid is formed by caffeic acid and quinic acid, and the molecular structure has ester bond, unsaturated double bond and polyphenol unstable part of the three. In the process of extracted from plants, chlorogenic acid often happen by hydrolysis and intramolecular ester base migration isomerization . Due to the special structure of chlorogenic acid, it can extract from plants by the polarity solvent such as ethanol, acetone, methanol. But due to the instability of chlorogenic acid itself, extraction can not be in high temperature, strong light and heat for a long time. Chlorogenic acid liquid were placed in brown bottle, refrigerator (2 ℃) to save to be the most stable.

 

Reference:

 

1 Zhang Anling, Ma Qiong. Chlorogenic acid and its analogs and biological activity, 2001

 

2 Wu Weihua, Kang Zhen, Ouyang Dongsheng, etc. Progress in Pharmacological Research of Chlorogenic Acid, 2006

 

3 Hu Zongfu, Yu Wenli, Zhao Yaping. Chlorogenic acid scavenging reactive oxygen species and anti-lipid peroxidation research, 2006