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 |
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 |
Safety Description | S24/25 - Avoid contact with skin and eyes. |
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.
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 ℃).
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.
specific rotation | -36 ° (c=1, H2O) |
Solubility | Soluble in ethanol and acetone. |
Merck | 14,2142 |
EPA chemical information | Chlorogenic acid (327-97-9) |
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.
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.
mark of dangerous goods Xi
Hazard category code 68
Safety instructions 24/25
WGK Germany 3
RTECS# GU8480000
Hazard Note Irritant
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
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. 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.
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;
instrument;
chromatographic conditions:
take the product under the weight difference item, cut, mix, take about 0.5g, precision weighing, for the test article.
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.
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.
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]
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.
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.
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.
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.
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.
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.
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.