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Chlorogenic Acid CAS 327-97-9

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  • Appearance: White powder
  • Purity: 99. 0%min
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  • Zhishang Chemical: Chlorogenic Acid Supplier & Manufacturer

Basic Info

What is Chlorogenic Acid?

Chlorogenic acid (CGA) is depsilic acid formed by the condensation of caffeic acid and quinic acid, also known as caffeic acid. It is produced by shikimic acid from cinnamic acid and quinic acid in plants during aerobic respiration. A phenylpropanoid substance synthesized via the pathway. The main pharmacological effects of chlorogenic acid are lowering blood pressure, lowering blood lipids, lowering blood sugar, anti-inflammatory, anti-viral, anti-tumor, antioxidant, anti-fatigue, strengthening muscles and bones, anti-aging, etc. CGA is a water-soluble phenolic compound that is widely distributed in the plant kingdom. It is abundant in Eucommia ulmoides and honeysuckle. It is also found in other plants such as coffee, green tea, apples and carrots. It is cheap and easy to obtain and has few side effects.

Chlorogenic acid in plants is derived from shikimic acid synthesized from phosphoenolpyruvate produced by the emp pathway and 4-p-erythrose produced by the PPP cycle. This pathway is also called cinnamic acid. way. Chlorogenic acid is widely distributed, ranging from higher dicotyledonous plants to lower ferns, and is mainly found in plants such as Lonicerae, Eucommiaceae, Asteraceae, and Rosaceae. The highest contents include Eucommia ulmoides (up to 5% in bark), honeysuckle (up to 5% in flowers), sunflower (up to 3% in seeds), coffee (up to 2% in coffee beans), and chrysanthemum (0.2% )wait. In addition, chlorogenic acid can be artificially synthesized through a four-step chemical reaction starting from quinic acid. Reports show that the current total yield of chlorogenic acid synthesis has reached 65%.

The extraction of plant-derived chlorogenic acid is mainly carried out using organic solvents such as ethanol, acetone, methanol, etc., including stone mercaptan method, lead salt precipitation method, alcohol precipitation method and other new methods. Beijing Shengtaier continues to improve its processing technology through ultrasonic and negative pressure low-temperature extraction technology, online ultra-high-speed centrifugation technology, negative pressure low-temperature concentration technology, graded alcohol precipitation and resin technology, membrane filtration technology, vacuum drying technology, low-temperature belt Seven major technologies, including spray drying technology, have greatly improved the extraction rate and product quality of chlorogenic acid.

Chlorogenic Acid Uses

Chlorogenic acid is an important biologically active substance that has antibacterial, antiviral, leukocyte-increasing, liver-protective and choleretic properties, anti-tumor, lowering blood pressure, lowering blood lipids, scavenging free radicals and stimulating the central nervous system.

  1. Antibacterial effect
    Chlorogenic acid has strong antibacterial and anti-inflammatory effects. It can bind to the outer membrane of bacteria and destroy the membrane structure, depleting the intracellular potential and releasing cytoplasmic macromolecules, ultimately leading to bacterial death. Wei Yuchao et al. (2020) used the Oxford cup method to study the in vitro antibacterial effect of chlorogenic acid. The results showed that chlorogenic acid had good antibacterial effects on Staphylococcus aureus, Escherichia coli, Salmonella and Proteus mirabilis. Wang Hongyi et al. (2020) also showed that chlorogenic acid can affect the normal growth and reproduction of bacteria and enhance the antibacterial effect by enhancing the cell membrane permeability of Escherichia coli and Salmonella Enteritidis.
  2. Antioxidant effect
    Chlorogenic acid is an effective phenolic antioxidant, and its antioxidant capacity is stronger than caffeic acid, tocopherol (vitamin E) and ascorbic acid. Chlorogenic acid contains a certain amount of R-OH groups, which can form hydrogen free radicals with antioxidant effects to eliminate the activity of free radicals such as DPPH free radicals, hydroxyl free radicals and superoxide anions, and can also inhibit the formation of low-density lipoproteins. Oxidation, thereby protecting tissues from oxidative damage. Wang Xiang (2020) et al. explored the possible mechanism by which chlorogenic acid reduces lung tissue damage in sepsis model rats and found that chlorogenic acid can improve oxidative stress response and reduce the generation of inflammatory factors and free radicals by activating the Nrf2 signaling pathway. Reduce inflammatory response in septic rats. Chang Xiaocui (2020) used chlorogenic acid to repair chicken liver damage caused by cadmium. Research shows that chlorogenic acid can alleviate the oxidative damage of chicken liver caused by cadmium and effectively improve the antioxidant capacity of chickens. Chlorogenic acid plays an important role in effectively scavenging free radicals in the body and maintaining the normal structure and function of body cells.
  3. Other biological activities
    Because chlorogenic acid has special inhibitory effects on hyaluronic acid (HAase) and glucose-6-phosphatase (Gl-6-Pase), chlorogenic acid is useful for healing wounds, preventing inflammation, and regulating blood sugar balance in the body. It has a certain therapeutic effect. Chlorogenic acid also has strong inhibitory and killing effects on a variety of diseases and viruses. Chlorogenic acid has pharmacological effects such as lowering blood pressure, increasing white blood cells, significantly increasing gastrointestinal motility, and promoting gastric juice secretion.

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Application of Chlorogenic Acid

Oxygen free radicals are one of the important factors causing endothelial damage, and a large number of experiments have proven that chlorogenic acid is a free radical scavenger and antioxidant [23, 24]. It scavenges oxygen free radicals and resists lipid peroxidation. It can protect vascular endothelial cells and thus have an effective protective effect on the cardiovascular system. Studies have found that chlorogenic acid can protect cardiomyocytes.

The active hydroxyl groups in the chlorogenic acid molecules can form hydrogen free radicals with antioxidant effects, thereby eliminating the activity of hydroxyl free radicals and protecting tissues from oxidative damage. It may be related to the fact that chlorogenic acid can inhibit the formation of 8-OH-dG when DNA is attacked by reactive oxygen species.

Research shows that chlorogenic acid has the effect of scavenging free radicals, and the scavenging effect is dose-related with its concentration. Other studies have also proven that chlorogenic acid extracted from green tea, coffee and artemisia can play a good antioxidant role.

Research has found that natural polyphenols represented by chlorogenic acid can protect collagen from free radicals such as reactive oxygen species, and effectively prevent ultraviolet rays from damaging human skin. There are currently a number of European patents for adding chlorogenic acid to skin sunscreens and shampoos. These products all have a certain effect on anti-radiation.

A large number of experiments have proven that chlorogenic acid has anti-mutagenic and anti-cancer effects. For example: chlorogenic acid in vegetables and fruits can inhibit the mutagenicity of carcinogens aflatoxin B1 and benzo[a]pyrene by inhibiting activating enzymes; chlorogenic acid can cause tumor cells to produce larger amounts in an alkaline environment. DNA fragments and cause nuclear agglutination; chlorogenic acid can inhibit the increase in 8-hydroxydeoxyguanosine (8-OH-dG) induced by 4-nitroquinoline-1-oxide (4NQO), which is a carcinogen. and important substances in the process of cellular oxidative stress response. Chlorogenic acid can also achieve anti-cancer and anti-cancer effects by reducing the utilization rate of carcinogens and their transportation in the liver.

In terms of antibacterial properties, current research generally believes that chlorogenic acid has a very good effect against Staphylococcus aureus, Escherichia coli, Bacillus subtilis, Legionella and other bacteria. For example, antibacterial experiments on chlorogenic acid extracted from honeysuckle found that , chlorogenic acid has good activity against Staphylococcus aureus and Escherichia coli.

The antibacterial test of chlorogenic acid in tobacco also found that in addition to its activity against Staphylococcus aureus and Escherichia coli, chlorogenic acid also has an inhibitory effect on Bacillus subtilis. Its antibacterial mechanism may be related to non-competitive inhibition of arylamine acetyltransferase in bacteria. In terms of anti-virus, research has found that the chlorogenic acid obtained from the extract of Soul-Returning Grass has an inhibitory effect on influenza virus, respiratory syncytial virus and adenovirus.

Studies have shown that oral administration of chlorogenic acid has a tendency to reduce visceral fat accumulation and body fat mass in rats. Intravenous administration of chlorogenic acid at 5 mg/mL for 3 weeks can reduce plasma cholesterol and triglycerides in rats by 44% respectively. Studies have found that honeysuckle extract can reduce serum and liver tissue.

The inhibitory effect of chlorogenic acid on leukemia cells was studied and it was found that sodium chlorogenic acid stored in the dark at -20 ℃ can selectively inhibit the proliferation of bcr-abl positive leukemia cell line K562 cells. Sodium chlororthonate stored at 4°C has an enhanced inhibitory effect on the proliferation of the bcr-abl-positive leukemia cell line K562, and also has an inhibitory effect on the proliferation of bcr-abl-negative Jurkat cells. In their anti-tumor activity screening of phenolic compounds in Blood Vinegar, they found that chlorogenic acid has an inhibitory effect on human chronic myeloid leukemia K562 cells.

Studies have found that chlorogenic acid has a greater impact on the levels of NF-γ and TNF-α in the supernatant of intraepithelial lymphocytes (IEL) and intestinal lamina propria lymphocytes (LPL). In vitro studies have shown that chlorogenic acid can significantly enhance T cell proliferation induced by influenza virus antigens and induce the production of IFN-γ and IFN-α by human lymphocytes and human peripheral blood leukocytes.

In addition, chlorogenic acid can also increase the levels of IgE, IgG1 and IL-4 in rats. Chlorogenic acid can enhance the function of macrophages. Therefore, chlorogenic acid has certain immune-modulating abilities.

The hypoglycemic pharmacodynamics of chlorogenic acid was studied, and it was found that the crude extract of chlorogenic acid can effectively reduce the blood sugar of mice with alloxan type diabetes, and there was no significant difference in blood sugar values between high, medium and low dose groups after administration. The difference indicates that the drug is not dose-dependent. However, it had no significant effect on blood sugar in normal mice. Honeysuckle extract can reduce blood sugar in sucrose hyperglycemic mice and alloxan diabetic model mice.

In addition, research also shows that the hypoglycemic effect of chlorogenic acid within 3 hours is not statistically different from that of glibenclamide. The mechanism may be related to the inhibition of glucose-6-phosphate translocase and glucose absorption.

In addition to the above many pharmacological activities, chlorogenic acid also has anti-inflammatory activity. It is reported that chlorogenic acids can play an anti-inflammatory role by inhibiting the activity of hyaluronidase (HAase). In addition, chlorogenic acid also has hepatoprotective, choleretic, and antispasmodic effects.

Extraction of Chlorogenic Acid from Plant-derived Natural Products

There are many extraction methods for chlorogenic acid, including some traditional methods and emerging methods, such as water extraction, reflux extraction, ultrasonic extraction, microwave-assisted extraction, enzymatic method, enzymatic hydrolysis-ultrasonic combination method, supercritical extraction method, etc.

The water extraction method, also known as the decoction method, is a method in which the sample is immersed in water, heated and boiled for a certain period of time, the leachate is separated, the sample is heated and boiled multiple times, and finally the leachate is combined. This is a very traditional and ancient method that continues to this day. When this method is used for extraction, the leachate obtained has complex components, is relatively viscous, is difficult to filter, and is not conducive to refining. And the extracted target substances are required to be soluble in water and stable and adaptable to temperature and humidity. Although the extraction rate of this method is indeed not high compared with the subsequent new extraction methods that have appeared successively, such as microwave-assisted extraction, reflux extraction, ultrasonic extraction, etc., this method can avoid the pollution of organic solvents and protect the ecology. environment.

The reflux extraction method refers to the use of a heated reflux device to extract sample components with volatile organic solvents (such as ethanol). The solvent is heated and distilled, condensed through the condenser tube, and then flows back into the container to extract the raw materials. This goes back and forth until the extraction is complete. method. The reflux method is a more traditional extraction method. The disadvantages of this method are that the extracted chlorogenic acid has excessive loss, impure quality, and takes a long time. It is not suitable for extracting substances that are easily decomposed by heat. However, the operation is simple and the extraction efficiency is higher than the cold soaking method.

The ultrasonic extraction method uses the cavitation, mechanical and thermal effects of ultrasonic waves to destroy the cell structure, accelerate the release and dissolution of intracellular substances, and effectively improve the extraction efficiency. In general, the ultrasonic extraction method takes shorter extraction time than the reflux method, has less solvent loss, and has higher extraction efficiency.

Microwave-assisted extraction is a method that uses electromagnetic waves to separate components from the matrix and effectively maintain the original state of the extract. This method has a short extraction time, is simple to operate, fast and effective.

Enzymatic method refers to a method that uses biocatalyst enzymes to decompose the components of plant cell walls to improve the extraction rate of active ingredients. This method is simple to operate, has mild conditions, and is environmentally friendly and harmless. However, it should be noted that some phenolic compounds may be destroyed when adjusting the pH.

Compared with other methods, because the enzyme’s action conditions are mild, the extraction temperature is not high, and the enzyme needs to be selected in advance according to the type of extract to improve the purity of chlorogenic acid.

The enzymatic hydrolysis-ultrasonic combined method is a relatively new method. It mainly combines the two methods with complementary advantages. Compared with a single method, the extraction efficiency is higher and the extraction quality is better. The enzyme-assisted ultrasonic extraction (EAUE) method based on polyethylene glycol (PEG-200) was used to extract chlorogenic acid (CGA) from honeysuckle leaves. The extraction process was optimized and verified, and was compared with other conventional extraction processes. Compare. Under the extraction process conditions, the results show that when the polyethylene glycol concentration is 42%, the extraction temperature is 49°C, and the pH value is 4.2, the experimental extraction rate is 6.955%. Compared with thermal reflux extraction, PEG-based EAUE has a better effect on honeysuckle. The extraction efficiency of CGA is higher.

Supercritical extraction is a method that extracts sample components with different solubilities successively to achieve extraction and separation by adjusting the temperature and pressure of the extraction fluid. The chlorogenic acid extracted by this method has less loss, excellent quality and high extraction efficiency, but it is difficult to carry out mass production due to expensive equipment.

References

  1. Chlorogenic Acid – PubChem
  2. Deng Liang, Yuan Hua, & Yu Zongyuan. (2005). Research progress on chlorogenic acid. Chemical and Biological Engineering, 22(7), 4-6.
  3. Clifford, M. N. (1999). “Chlorogenic acids and other cinnamates – nature, occurrence and dietary burden”. Journal of the Science of Food and Agriculture

Chlorogenic Acid Supplier and Manufacturer

As a chlorogenic acid supplier and manufacturer with a strict standard product quality system certificate, Zhishang Chemical has long been providing the best chlorogenic acid raw materials to customers all over the world.

Over the years, relying on professional team experience and customer-centric team concept to meet customer needs in a timely manner, our company enjoys a high reputation in the world. At present, our company has served more than 6,000 customers and has established long-term cooperative relations with customers from many countries.

If you have a demand for chlorogenic acid and related products, please contact our service staff Zhishang Chemical – White directly, and we will provide you with high-quality products at the best price.

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