(1S,3R,4R,5R)-3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid
Chlorogenic acid
CAS: 327-97-9
Molecular Formula: C16H18O9
(1S,3R,4R,5R)-3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid - Names and Identifiers
| Name | Chlorogenic acid |
| Synonyms | Chlorogenic acid 3-O-Caffeoylquinic acid Honeysuckle Flower Extract 5-O-(3,4-dihydroxycinnamoyl)-L-quinic acid 3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid (1S,3R,4R,5R)-3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid |
| CAS | 327-97-9 |
| EINECS | 206-325-6 |
| InChI | InChI=1/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16+/m1/s1 |
(1S,3R,4R,5R)-3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid - Physico-chemical Properties
| Molecular Formula | C16H18O9 |
| Molar Mass | 354.31 |
| Density | 1.65g/cm3 |
| Melting Point | 205-209℃ |
| Boling Point | 665°C at 760 mmHg |
| Specific Rotation(α) | -35.0°～ -38.0°(C=1, H2O) |
| Flash Point | 245.5°C |
| Water Solubility | SOLUBLE IN HOT WATER |
| Solubility | Soluble in ethanol and acetone, very slightly soluble in ethyl acetate, insoluble in chloroform, ether, benzene and other lipophilic organic solvents. |
| Vapor Presure | 1.38E-18mmHg at 25°C |
| Appearance | White to light yellowish brown powder |
| Storage Condition | 2-8℃ |
| Refractive Index | 1.69 |
| MDL | MFCD00003862 |
| Use | Used as pharmaceutical raw materials and intermediates |
(1S,3R,4R,5R)-3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid - Risk and Safety
| Safety Description | S24/25 - Avoid contact with skin and eyes. |
(1S,3R,4R,5R)-3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid - Introduction
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- chlorogenic acid is one of the main antibacterial and antiviral effective pharmacological components of Flos lonicerae.
- chlorogenic acid has a wide range of antibacterial effects, but can be inactivated by protein in vivo. Similar to caffeic acid, oral or intraperitoneal injection can improve the central excitability of rats. Can increase the small intestine peristalsis of rats and mice and the tension of rat uterus. Beneficial role of bile, can enhance the secretion of bile in rats. People have sensitization, inhalation of plant dust containing this product, asthma, dermatitis and so on.
Last Update：2024-04-09 19:43:38
(1S,3R,4R,5R)-3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid - Uses and methods of synthesis
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pharmacological action
- chlorogenic acid, also known as "chlorogenic acid", "coffee tannic acid" and "coffee tannic acid", is a phenylpropanoid compound produced by shikimic acid pathway in the process of aerobic respiration, for caffeoylquinic acid derivatives, strong antioxidant capacity, but also anti-HIV, anti-tumor cells, antibacterial, improve central excitement, choleretic, anti-teratogenic, anti-allergic and regulation of cytochrome P450 ligase activity and other functions.
- It is widely present in honeysuckle plants with high content. The needle-like crystals were obtained from water as hemihydrate and became anhydrate at 110 °c. Melting point 208 °c,[α]D25-33.5 ° (water, C = 1),K = 2.2 x 10-3(27 °c). There is a weak sour taste and convergence. 25 ° C in water solubility of 4%, soluble in hot water, soluble in ethanol, acetone, ethyl acetate-soluble, insoluble in chloroform, ether and carbon disulfide. Azeotrope with concentrated hydrochloric acid to give the blue dye. Can make bromine water fading, and concentrated hydrogen iodide azeotropic to benzoic acid, and water at 230 ℃ for the thermal decomposition of phenol, and dilute hydrochloric acid for the thermal decomposition of caffeic acid and cinchona acid, etc, room temperature and dilute alkali only caffeic acid and cinchona acid. Chlorogenic acid and its isomers isochlorogenic acid and neochlorogenic acid also exist in the fruit, leaves and other tissues of dicotyledonous plants, which are important factors in plant metabolism. Chlorogenic acid has a good biological activity, with the inhibition of the transparent enzyme and glucose -6-phosphatase, the free radical of the clear anti-lipid peroxidation, anti-mutagenic and cardiovascular crown, lipid-lowering has a special effect, it also has antibacterial, antiviral, liver-protecting and choleretic effects.
- chlorogenic acid is a condensation product of caffeic acid and quinic acid, which is blue in case of iron, similar to tannin, but does not precipitate protein, so it has no convergence effect. Caffeic acid and chlorogenic acid have more extensive antibacterial effect, but can be inactivated by protein in vivo. This product is similar to caffeine, oral or intraperitoneal injection, can improve the central excitability of rats. Chlorogenic acid and caffeic acid oral, can increase the secretion of hydrochloric acid in human stomach, and can make the pulse slower, and quinic acid can not. Chlorogenic acid can significantly increase the peristalsis of small intestine of rats or mice, chlorogenic acid, caffeic acid, quinic acid can enhance the tension of rat uterus, this effect can be canceled by papaverine, and atropine can not affect it. Caffeic acid and chlorogenic acid can also enhance the bile secretion of rats. In the rabbit ileum specimens in vitro, this product can enhance the role of epinephrine, but the role of elevated blood glucose epinephrine, etc. are not affected.
Liver protection and choleresis
chlorogenic acid contained in Flos lonicerae has beneficial effect on bile secretion in rats. Hypodermic injection of 200mg/kg of total saponins from Lonicera fulvotomentosa can significantly antagonize the increase of GPT in liver and the content of triglyceride in liver induced by CCl4, paracetamol and galactosamine, and obviously reduce the severity of liver pathological injury, the sum of the number of liver punctate necrosis and the occurrence rate of necrosis were significantly reduced.
Inhibition of hyaluronidase and glucose -6-phosphatase
- plum hyaluronate (HAase) is one of the enzymes that cleave mucopolysaccharides, which can catalyze the decomposition of hyaluronic acid (HA) and is related to the permeability and inflammatory response of the vascular system. HA is a mucopolysaccharide composed of uronic acid and acetyl glucosamine, which has a variety of functions, such as healing wounds, moisturizing the skin, lubricating joints and preventing inflammation. From the ethyl acetate extract of the root of Echinacea angustifolia DC, it was found that 3, 5-dicaffeoylquinic acid (artichoke acid) and chlorogenic acid had a strong inhibitory effect on HAase activation.
- animal in vitro studies have shown that chlorogenic acid can irreversibly inhibit the hydrolysis of glucose -6-phosphatase, reduce the decomposition of liver glycogen and reduce the absorption of exogenous glucose. Studies in animals have demonstrated that the use of chlorogenic acid can reduce the hyperglycemic peak (due to hepatic glycolysis) caused by the use of glucagon. Therefore, chlorogenic acid can reduce the blood glucose level and increase the concentration of glucose -6-phosphate and glycogen in the liver.
Molecular structure characteristics
chlorogenic acid is an ester formed by caffeic acid and quinic acid, and its molecular structure has three unstable parts: ester bond, unsaturated double bond and polyphenol. During extraction from plants, isomerization often occurs through hydrolysis and migration of molecular lactone groups. Due to the special structure of chlorogenic acid, it can be extracted from plants by ethanol, acetone, methanol and other polar solvents, but due to the instability of chlorogenic acid itself, the extraction can not be high temperature, strong light and prolonged heating. The test solution of chlorogenic acid is most stable when it is stored in brown bottle and refrigerator (2 ℃).
Preparation Method
from (1S)-1-ethoxyformyloxy-3-cis-3, 4-dihydroxy-trans-cinnamyloxy]-4 & prime;-Trans -5 & prime;-trans-dihydroxycyclohexane-& gamma;-methyl formate is hydrolyzed with barium hydroxide in methanol, or chlorogenic acid is isolated from green coffee beans.
Last Update：2022-01-01 08:48:43
(1S,3R,4R,5R)-3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid - Nature
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| specific rotation | -36 ° (c=1, H2O) |
| Solubility | Soluble in ethanol and acetone. |
| Merck | 14,2142 |
| EPA chemical information | Chlorogenic acid (327-97-9) |
Last Update：2024-04-09 19:43:38
(1S,3R,4R,5R)-3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid - Determination of content and toxicity by HPLC
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Content determination by HPLC
- chromatographic conditions: using eighteen alkyl silane bonded silica gel as filler; Acetonitrile-0.4% phosphoric acid solution (13:87) as mobile phase; Detection wavelength was 327nm. The number of theoretical plates is greater than 1000 according to the chromatographic peak of chlorogenic acid.
- preparation of reference solution: an appropriate amount of chlorogenic acid reference was accurately weighed, placed in a brown measuring flask, and 50% methanol was added to prepare a solution containing 40 μg per ml, which was obtained (stored below 10 ° C.).
- preparation of sample solution: take the sample dry powder about 0.5g, precision weighing, put it in a plug Erlenmeyer flask, precision add 50% methanol 50ml, weigh, ultrasonic treatment for 30min, cool, weigh, make up the lost weight with 50% methanol, shake well, filter, discard the initial filtrate, Take 5ml of continued filtrate accurately, put it in a 25ml brown measuring flask, add 50% methanol to the scale and shake to obtain.
- measurement: 10 μl of each of the reference substance and the sample solution were accurately extracted, respectively, and injected into a liquid chromatograph for measurement.
Toxicity
chlorogenic acid has sensitization effect on human, can cause asthma, dermatitis and other allergic reactions, but oral administration of this reaction, because chlorogenic acid can be converted into small intestinal secretions into a substance without sensitization activity. The toxicity of chlorogenic acid was very small, and the LD50 of the young rats was more than 1 g/kg, and the intraperitoneal injection was more than 0.25g/kg.
Last Update：2022-01-01 08:48:44
(1S,3R,4R,5R)-3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid - Chemical properties and uses
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chemical properties
hemihydrate is a needle-like crystal (water). 110 °c became an anhydrous compound, Melting Point: 208 °c,[α]20D-35.2. (C = 2.8). 25 ° C water solubility of 4%, hot water solubility greater. Soluble in ethanol and acetone, very slightly soluble in ethyl acetate.
Purpose
- has a wide range of antibacterial effect, beneficial to gallbladder, hemostasis, increase white blood cells and antiviral effect, has the effect of shortening blood coagulation and bleeding time. For the treatment of Upper Respiratory Infections, anti-inflammatory antipyretic, cooling blood heat.
- used as pharmaceutical raw materials and intermediates
- qingrejiedu, cool wind heat, with broad-spectrum antibacterial, hemolytic Streptococcus, dysentery stem, typhoid Bacillus and other bacteria have obvious inhibitory effect.
Last Update：2022-01-01 08:48:45
(1S,3R,4R,5R)-3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid - Safety Information
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mark of dangerous goods Xi
Hazard category code 68
Safety instructions 24/25
WGK Germany 3
RTECS# GU8480000
Hazard Note Irritant
Last Update：2022-01-01 08:48:45
(1S,3R,4R,5R)-3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid - Other uses
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category toxic substances
Toxic grade poisoning
Acute toxicity intraperitoneal-rat LDL0: 4000 mg/kg
Flammable hazard characteristics flammable; Spicy and irritating smoke released from fire scene
Storage and Transportation characteristics: low temperature, ventilation and drying in warehouse
Extinguishing agent water, carbon dioxide, dry powder, sand
Last Update：2022-01-01 08:48:45
(1S,3R,4R,5R)-3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid - Plant Origin
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Eucommia ulmoides Oliv. The leaves of Lonicera japonica Thumb. Lonicera hypogluca Miq. Lonicera confusa DC. Or Lonicera dasytyla Rehd. The dried flower bud or band of the first flower, Rosaceae plant Crataegus Crataegus oxyactha Linn. The fruit of the plant Lythrum salicaria L. Flower, absence of plants of nipponaceae, poxgrass, donea viscose (L.) tacp., polypodium vulgare L. Rhizomes, Verbenaceae pseudobuccina cachytarpheta (L.) vahl root, Cruciferae plant, cabbage, Brassica oleracea L.var.capitata L. Stem, leaf, Polygonaceae plants oblate Whole grass of polygolum aviculare L.; Whole grass of Caprifoliaceae plant Galium verum L.; Whole grass of Caprifoliaceae plant Sambucus javanica Reinw. Leaves of sweet potato (ipomea batatas). Seeds of caffeaarabical, medium-and large-fruit coffee (caffealiberkel1.exh1en.).
Arctium lappa L.Last Update：2022-01-01 08:48:46
(1S,3R,4R,5R)-3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid - Physical properties and chemical structure
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physical properties
hemihydrate is a needle-like crystal (water). 110 ° c. Became an anhydrous compound, melting point 208 ° c., [α ]24D-35.2 ° c. (c = 2.8).
25 ° C water solubility of 4%, hot water solubility greater; Soluble in ethanol and acetone, very slightly soluble in ethyl acetate, insoluble in chloroform, ether, benzene and other lipophilic organic solvents. 13C NMR(H2O)A:126.6(C-1), 114.1(C-2), 144.2(C-3), 147.0(C-4), 116.0(C-5), 122.6(C-6), 145.9(C-7), 115.2(C-8), 168.9(C-9); B: 76.6(C-1), 38.3(C-2), 70.6(C-3), 72.8(C-4), 71.0(C-5), 37.3(C-6), 180.1(C-7)[1]. Chlorogenic acid is an ester formed by caffeic acid and quinic acid. Its molecular structure has three unstable parts: ester bond, unsaturated double bond and polyphenol. Microherb studies have shown that isomerization often occurs through hydrolysis and migration of molecular lactone groups during extraction from plants. Due to the special structure of chlorogenic acid, it can be extracted from plants by ethanol, acetone, methanol and other polar solvents, but due to the instability of chlorogenic acid itself, the extraction can not be high temperature, strong light and prolonged heating. It is recommended to keep it sealed in the dark at low temperature.
chemical structure
- Chlorogenic acid (hereinafter referred to as CA) is a condensed phenolic acid produced from Caffeic acid and quinic acid (1-hydroxyhexahydrogallic acid), it is a kind of phenylpropanoid compound produced by shikimic acid pathway in the process of aerobic respiration.
- According to the different binding sites and numbers of caffeoyls on quinic acid, theoretically, there are 10 kinds of chlorogenic acid isomers composed of mono-caffeoylquinic acid and di-caffeoylquinic acid, which are 1-caffeoylquinic acid, 3-caffeoylquinic acid, 4-caffeoylquinic acid, 5-caffeoylquinic acid, 1, 3-dicaffeoylquinic acid, 1, 4-dicaffeoylquinic acid, 1, 5-dicaffeoylquinic acid, 3, 4-dicaffeoylquinic acid, 3, 5-dicaffeoylquinic acid, 4, 5-dicaffeoylquinic acid. However, so far, the isomers of chlorogenic acid found in plants are as follows: chlorogenic acid (3-caffeoylquinic acid), cryptochlorogenic acid (Band510)(4-caffeoylquinic acid), neochlorogenic acid (5-caffeoylquinic acid), isochlorogenic acid A(3, 5-dicaffeoylquinic acid), isochlorogenic acid B(3, 4-dicaffeoylquinic acid) isochlorogenic acid C(4, 5-dicaffeoylquinic acid), lythistin (1, 3-dicaffeoylquinic acid).
Last Update：2022-01-01 08:48:47
(1S,3R,4R,5R)-3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid - Test method
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determined by HPLC
- chromatographic conditions and system suitability test, using eighteen alkyl silane bonded silica gel as filler; Acetonitrile-0.4% phosphoric acid solution (13:87) as mobile phase; The detection wavelength was 327nm. The number of theoretical plates shall not be less than 1000 calculated from the peak of chlorogenic acid. Preparation of reference solution an appropriate amount of chlorogenic acid reference was accurately weighed, placed in a brown measuring flask, and 50% methanol was added to prepare a solution containing 4 μg per 1ml, that is, a solution (stored below 10 ° C.).
- Yu Huazhong et al. The content of chlorogenic acid in eucommia ulmoides leaves was determined by UV-Vis spectrophotometry. The results showed that the method had good stability and repeatability, and the recovery rate was 104. 2%. Chlorogenic acid in 5. 05~40. 4 Lg/ ml, the absorbance $A = A325- A345 showed A good linear relationship with the concentration. This method is simple, rapid, accurate and stable, and can be used for the determination of chlorogenic acid in eucommia ulmoides leaves.
- method name: Yinqiao Shuangjie suppository-determination of chlorogenic acid-HPLC
Last Update：2022-01-01 08:48:47
(1S,3R,4R,5R)-3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid - Scope of Application
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- the content of chlorogenic acid in Yinqiao Shuangjie suppository was determined by HPLC.
- this method is suitable for treating Yinqiao double suppository.
method principle
This product is dissolved in heated water, shake, filter, continue the filtrate into high performance liquid chromatography for chromatographic separation, with ultraviolet absorption detector, at the wavelength of 324nm detection of chlorogenic acid absorption value, its content was calculated.
Reagents: 1. Methanol, 2. Glacial acetic acid;
Equipment
instrument;
- high performance liquid chromatograph
- column: Eighteen alkyl silane bonded silica gel as filler, the theoretical plate number should be calculated according to the chlorogenic acid peak should not be less than 2000.
- UV detector
chromatographic conditions:
- mobile phase: methanol: Water: glacial acetic acid = 15:85:1
- detection wavelength: 324nm
- column temperature: Room temperature
Sample preparation
- weighing sample
take the product under the weight difference item, cut, mix, take about 0.5g, precision weighing, for the test article.
- preparation of reference solution
the appropriate amount of chlorogenic acid control was accurately weighed, placed in a brown measuring flask, and water was added to prepare a solution containing 10mg per 1ml.
- preparation of test solution
take the product under the weight difference item, cut, mix, take about 0.5g, accurately weigh, put it in an Erlenmeyer flask, heat 40ml water to dissolve, cool, filter, the filtrate was placed in a 100ml measuring flask, the container and the filter were washed twice with hot water (30ml, 20ml), and the washing solution was incorporated into the same measuring flask. Add water to the scale, shake, filter, and take the filtrate as a test solution.
Procedure
The reference solution and the test solution were accurately absorbed 20 & micro;L respectively, injected into the high performance liquid chromatograph, and the chlorogenic acid (C16H18O9) was determined at the wavelength of 324nm with the ultraviolet absorption detector. The peak area, calculate its content. [7]
Last Update：2022-01-01 08:48:48
(1S,3R,4R,5R)-3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid - Main function
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biological activity
chlorogenic acid has a wide range of biological activities. Modern scientific research on the biological activity of chlorogenic acid has been deeply into food, health care, medicine and daily chemical industry and other fields. Chlorogenic acid is an important bioactive substance, which has antibacterial, antiviral, increasing white blood cells, protecting liver and gallbladder, anti-tumor, lowering blood pressure, lowering blood lipid, scavenging free radicals and exciting the central nervous system.
antibacterial, antiviral
chlorogenic acid from eucommia ulmoides has strong antibacterial and anti-inflammatory effect, aucubin and its polymers have obvious antibacterial effect, and aucubin can inhibit Gram-negative and positive bacteria. Aucubin has antibacterial, diuretic effect, and can promote wound healing; Aucubin and glucoside together after pre-culture will produce obvious antiviral effect, but it does not have antiviral function. Japan's Aichi Medical University Institute of Medical Science research confirmed that the alkaline substances extracted from eucommia ulmoides have the function of anti-destruction of the human immune system Virus, this substance may be used for the prevention and treatment of AIDS.
Antioxidant effect
chlorogenic acid is an effective phenolic antioxidant, and its antioxidant capacity is stronger than caffeic acid, p-Hydroxybenzoic acid, ferulic acid, syringic acid, Butylated hydroxyanisole (BHA) and tocopherol. The reason why chlorogenic acid has an antioxidant effect is that it contains a certain amount of R-OH groups, which can form hydrogen radicals with antioxidant effect to eliminate the activity of hydroxyl radicals and superoxide anions and other free radicals, thereby protecting the tissue from damage by oxidation.
scavenging free radicals, 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), and can effectively scavenge DPPH radical, hydroxyl radical and superoxide anion radical, it can also inhibit the oxidation of low density lipoprotein. Chlorogenic acid plays an important role in effectively removing free radicals in the body, maintaining the normal structure and function of the body cells, preventing and delaying the occurrence of tumor mutation and aging. Eucommia ulmoides chlorogenic acid contains a special ingredient that can promote the synthesis and decomposition of collagen protein in human skin, bone and muscle, and has the function of promoting metabolism and preventing decline, it can be used to prevent the decline of bones and muscles caused by weightlessness in space. At the same time, it is found that chlorogenic acid of Eucommia ulmoides has obvious anti-free radical effect both in vivo and in vitro.
inhibition of mutation and antitumor
- Modern pharmacological experiments have proved that eucommia ulmoides chlorogenic acid has anti-cancer and anti-cancer effects. Japanese scholars have studied the mutagenicity inhibition of Eucommia ulmoides chlorogenic acid, it was found that the effect was related to the anti variant components such as chlorogenic acid, which revealed the important significance of chlorogenic acid in tumor prevention. 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 activated enzymes; chlorogenic acid can also reduce the utilization of carcinogens and its transport in the liver to achieve anti-cancer, anti-cancer effects. Chlorogenic acid has a significant inhibitory effect on colorectal cancer, liver cancer and laryngeal cancer, and is considered to be an effective chemical protective agent for cancer.
cardiovascular protection
chlorogenic acid, as a free radical scavenger and antioxidant, has been proved by a large number of experiments. The biological activity of chlorogenic acid can protect the cardiovascular system. Isochlorogenic acid B has a strong effect on promoting the release of prostacyclin (PGI2) and anti-platelet aggregation in rats; the inhibition rate of antibody induced SRS-A release to guinea pig lung fragments was 62.3%. Isochlorogenic acid C also promoted the release of pgi2. In addition, isochlorogenic acid B had a strong inhibitory effect on the biosynthesis of platelet thrombosis and the damage of endothelin induced by hydrogen peroxide.
hypotensive effect
after years of clinical trials confirmed that eucommia ulmoides chlorogenic acid has obvious antihypertensive effect, and the curative effect is stable, non-toxic, no side effects. Research at the University of Wisconsin found that the effective components of Eucommia ulmoides Green are Pinitol diglucoside, aucubin, chlorogenic acid, and Eucommia chlorogenic acid polysaccharides.
Other biological activities
due to chlorogenic acid on hyaluronic acid (HAase) and glucose -6-phosphatase (Gl-6-Pase) has a special inhibitory effect, so chlorogenic acid for wound healing, skin health and moisture, lubrication of joints, to prevent inflammation and the balance of blood sugar in the body regulation and so have certain curative effect. Chlorogenic acid has a strong inhibitory and killing effect on a variety of diseases and Virus. Chlorogenic acid has pharmacological effects such as lowering blood pressure, anti-bacterial, anti-viral, anti-inflammatory, increasing white blood cells, preventing diabetes, significantly increasing gastrointestinal peristalsis and promoting gastric secretion, and has obvious curative effect on acute pharyngitis. Studies have shown that oral chlorogenic acid can significantly stimulate the secretion of bile, with the effect of gallbladder and liver protection; It can also effectively inhibit the hemolysis of rat red blood cells induced by H2O2.
Last Update：2022-01-01 08:48:49
(1S,3R,4R,5R)-3-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid - Uses and synthesis methods
physical and chemical properties
Chlorogenic acid, also known as "chlorogenic acid", "coffee tannic acid", "coffee tannic acid", is a phenylpropanoid compound produced by the shikimic acid pathway in the process of aerobic respiration of plants. Caffeoylquinic acid derivatives, strong antioxidant ability, it also has the functions of anti-HIV, anti-tumor cells, antibacterial, improving central excitation, choleretic, anti-teratogenic, anti-allergic and regulating the activity of cytochrome P450 ligase.
Origin of chlorogenic acid
according to literature records, chlorogenic acid was first found in coffee seeds. as early as 1837, Robiquet and Boutron scientists found its existence when looking for acidic substances in crude coffee extract (with green pigment). at that time, this substance had a green color in aqueous solution containing ferric Chloride. in 1846, payen found that it changed from yellow to green after contacting oxygen in an alkaline solution containing amines, so the substance was officially named [chlorogenic acid, Chlorogenic acid]]. Chloro-The prefix comes from Greek, the original meaning is light green, and the root-genic means the source, so chlorogenic acid Chlorogenic means the green extract derived from coffee.
However, it was not until 1909 that high-purity chlorogenic acid crystals were obtained by Gorter from coffee seeds. This is the first time it has been presented to the world with its true face. Gorter also established a color reaction based on ferric chloride (Ferric Chloride) as a rapid screening method for chlorogenic acid, and found that chlorogenic acid not only appears in coffee seeds, but also in coffee leaves, rubber tree latex Sap and sunflower seeds can be found in it. From now on. Chlorogenic acid is not only found in coffee, almost all higher plants can make it, such as apples, sweet potatoes, tomatoes, pears, apricot peaches, roxen flowers, oranges, etc. It can be seen in its existence. The content of chlorogenic acid in coffee is the highest.
Toxicity
Chlorogenic acid has a sensitizing effect on humans and can cause allergic reactions such as asthma and dermatitis, but there is no such reaction after oral administration, because chlorogenic acid can be converted into non-sensitizing substances by small intestinal secretions. Chlorogenic acid has little toxicity. LD50 for young rats is greater than 1 g/kg and intraperitoneal injection is greater than 0.25 g/kg.
Production method
1. It is naturally found in plants such as the whole herb of the Loniceraceae plant (javanica Reinw., Sambucus) and the flowers of the Lichellaceae plant (L., Lythrum salicaria). It can also be obtained by chemical synthesis.
2. Tobacco: FC,54;FC,53;FC,BU,6. Isolated from green coffee beans.
category
Toxic substances
Toxicity classification
Poisoning
Acute toxicity
abdominal cavity-rat LDL0: 4000 mg/kg
flammability hazard characteristics
Flammable; fire scene releases spicy and irritating smoke
storage and transportation features
The warehouse is low temperature, ventilated and dry
Fire extinguishing agent
Water, carbon dioxide, dry powder, sand
Last Update：2024-04-09 15:16:18
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