(1S)-1α,5α-Dihydroxy-3β,4α-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1β-cyclohexanecarboxylic acid
(1S,3R,4R,5R)-3,4-Bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,5-dihydroxycyclohexane-1-carboxylic acid
CAS: 14534-61-3
Molecular Formula: C25H24O12
(1S)-1α,5α-Dihydroxy-3β,4α-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1β-cyclohexanecarboxylic acid - Names and Identifiers
(1S)-1α,5α-Dihydroxy-3β,4α-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1β-cyclohexanecarboxylic acid - Physico-chemical Properties
| Molecular Formula | C25H24O12 |
| Molar Mass | 516.45 |
| Density | 1?+-.0.1 g/cm3(Predicted) |
| Melting Point | >117°C (sub.) |
| Boling Point | 810.8±65.0 °C(Predicted) |
| Specific Rotation(α) | -225 (MeOH) |
| Flash Point | 274.9°C |
| Solubility | DMSO : 50 mg/mL (96.81 mM; Need ultrasonic) |
| Vapor Presure | 8.9E-28mmHg at 25°C |
| Appearance | White powder |
| Color | Off-White to Light Yellow |
| pKa | 3.70±0.50(Predicted) |
| Storage Condition | Sealed in dry,Store in freezer, under -20°C |
| Refractive Index | 1.719 |
| MDL | MFCD22375481 |
| Physical and Chemical Properties | Color-like crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents, from honeysuckle, honeysuckle, Eucommia. |
| In vitro study | 3,4-Dicaffeoylquinic acid acts as a greater primary antioxidant than its methanol extract, by having higher ferric reducing activity (EC 50 2.18 μg/ml), β-carotene bleaching activity (EC 50 23.85 μg/ml) and DPPH scavenging activity (EC 50 68.91 μg/ml). 3,4-Dicaffeoylquinic acid exhibits a remarkable dose-dependent inhibitory effect on NCI-H23 (human lung adenocarcinoma) cell lines (EC 50 3.26 μg/ml) and is found to be apoptotic in nature based on a clear indication of DNA fragmentation. 3,4-Dicaffeoylquinic acid also displays a concentration-dependent α-glucosidase inhibition with EC 50 241.80 μg/ml. |
(1S)-1α,5α-Dihydroxy-3β,4α-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1β-cyclohexanecarboxylic acid - Risk and Safety
| Safety Description | 24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| HS Code | 29189900 |
(1S)-1α,5α-Dihydroxy-3β,4α-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1β-cyclohexanecarboxylic acid - Reference Information
| Plant source: | Honeysuckle |
| overview | honeysuckle LoniceraeFlos is Lonicera LonicerajaponicaThunb. The dry flower buds or newly blooming flowers are commonly used Chinese medicines in my country. They have the effects of clearing away heat and detoxification, cooling and dispelling wind and heat. They are often used for diseases such as hot blood, toxic dysentery, wind-heat colds, carbuncle, boils, plague and fever. Honeysuckle contains a large number of organic acid compounds, the main pharmacological activities are antibacterial, anti-inflammatory, inhibition of platelet aggregation, antithrombotic, antioxidant and so on. Isochlorogenic acids A, B and C are dicaffeoyl quinic acid compounds, which are effective active ingredients in honeysuckle. They are a kind of organic acids formed by condensation of quinic acid and caffeic acid with different numbers through esterification reaction. Natural ingredients, widely exist in the plant kingdom. In the past 20 years, scholars at home and abroad have conducted in-depth research on the phytochemistry and pharmacology of dicaffeoylquinic acids, and found that they have some important biological activities and have great clinical application value. The main pharmacological activities include anti-oxidation, inhibition of oxygenase, anti-atherosclerosis, anti-atherosclerosis, anti-platelet active substances, blood lipid regulation, anti-inflammatory, anti-virus, inhibition of histamine release, anti-fibrosis, inhibition of smooth muscle contraction and other effects. Isochlorogenic acid B(isochlorogenicacidB,ICAB), also known as 3, 4-dicaffeoylquinic acid, is a polyphenolic compound extracted from the medicinal plant honeysuckle. Isochlorogenic acid B is one of the components of Shuanghuanglian oral liquid, and it is also an antioxidant substance in Reduning injection. At present, there are few pharmacological studies on isochlorogenic acid B. Studies have confirmed that isochlorogenic acid B has antioxidant, hepatoprotective and anti-neurodegenerative disease biological activity. In addition, molecular docking experiments show that isochlorogenic acid B may be a strong inhibitor of phosphodiesterase -5(phosphodiesteras-5,PDE-5) receptor. |
| Application | Isochlorogenic acid B has more phenolic hydroxyl groups than chlorogenic acid, and has been confirmed to have better antioxidant and anti-neurodegenerative diseases than chlorogenic acid Pharmacological effects. The protective effect of isochlorogenic acid B (isochlorogenic acid B) on acute liver injury induced by carbon tetrachloride (CCl4) in mice was studied experimentally. An experimental model of acute liver injury induced by CCl4 in mice was established and the protective effect of isochlorogenic acid B was evaluated. The levels of serum alanine aminotransferase (ALT), aspartate aminotransferase (AST), malondialdehyde (MDA) content in liver tissue, and the activities of superoxide dismutase (SOD) and glutathione peroxidase (GSH-Px) were measured. HE staining was used to observe the morphology of liver tissue cells. Western blotting was used to determine the effect of isochlorogenic acid B on the expression of nuclear factor E2 related factor 2(Nrf2), heme oxygenase-1 (HO-1) and quinone oxide reductase 1(NQO1) in liver cells of mice with liver injury. The results showed that each administration group (5, 10 and 20 mg/kg) of isochlorogenic acid B could inhibit the increase of ALT, AST and MDA in serum of mice induced by CCl4 to different degrees (P<0.01). The high dose group (20 mg/kg) of isochlorogenic acid B significantly increased SOD(P<0.01) and GSH-Px activity level (P<0.05) in liver cells and decreased MDA content. At the same time, isochlorogenic acid B can improve liver histopathological damage caused by CCl4. In addition, isochlorogenic acid B can promote the expression of Nrf2 and the nuclear translocation of Nrf2, thus promoting the expression of Nrf2 downstream target proteins HO-1 and NQO1. Therefore, isochlorogenic acid B has obvious hepatoprotective and enzyme-lowering effects on CCl4-induced acute liver injury in mice, and its mechanism of action may be related to its participation in regulating Nrf2 signaling pathway and relieving oxidative stress. |
| biological activity | 3,4-Dicaffeoylquinic acid is naturally isolated and has antioxidant, DNA protective, neuroprotective and liver protective properties. 3,4-Dicaffeoylquinic acid has apoptosis-mediated cytotoxicity and α-glucosidase (α-glucosidase) inhibition. 3,4-Dicaffeoylquinic acid has a unique antiviral mechanism, that is, to increase the virus clearance rate by increasing TRAIL. |
| use | isochlorogenic acid B has anti-platelet aggregation, antibacterial and anti-inflammatory effects. used for content determination/identification/pharmacological experiment, etc. Pharmacological effects: clearing away heat and detoxification, antibacterial and anti-inflammatory. |
Last Update：2024-04-09 20:52:54
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