[1R-(1α,3α,4α,5β)]-3-[[3-(3,4-dihydroxyphenyl)-1-oxoallyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid
[1R-(1α,3α,4α,5β)]-3-[[3-(3,4-dihydroxyphenyl)-1-oxoallyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid
CAS: 906-33-2
Molecular Formula: C16H18O9
[1R-(1α,3α,4α,5β)]-3-[[3-(3,4-dihydroxyphenyl)-1-oxoallyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid - Names and Identifiers
[1R-(1α,3α,4α,5β)]-3-[[3-(3,4-dihydroxyphenyl)-1-oxoallyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid - Physico-chemical Properties
| Molecular Formula | C16H18O9 |
| Molar Mass | 354.31 |
| Density | 1.65±0.1 g/cm3(Predicted) |
| Melting Point | 204-206 °C (decomp) |
| Boling Point | 665.0±55.0 °C(Predicted) |
| Specific Rotation(α) | -36° |
| Flash Point | 245.5°C |
| Solubility | Easily soluble in hot water, ethanol and acetone, and can be completely dissolved. Very slightly soluble in ethyl acetate. |
| Vapor Presure | 1.38E-18mmHg at 25°C |
| Appearance | White powder |
| Color | White to Off-White |
| pKa | 3.90±0.50(Predicted) |
| Storage Condition | 2-8°C |
| Stability | Hygroscopic |
| Refractive Index | 1.69 |
| MDL | MFCD10566639 |
| Physical and Chemical Properties | Easily soluble in hot water, ethanol and acetone, and can be completely dissolved. Very slightly soluble in ethyl acetate. from honeysuckle |
| In vitro study | Neochlorogenic acid (NCA) shows a reduction of lipopolysaccharide (LPS)-induced NO production by suppressing iNOS and COX-2 protein expression and production of pro-inflammatory cytokines, such as TNF-α and IL-1β, in BV2 microglia cells. In addition, phosphorylated p38 MAPK and NF-κB p65 are also inhibited by Neochlorogenic acid in activated microglia. iNOS and COX-2 levels are increased in LPS-induced BV2 cells, but this increase is significantly inhibited after treatment with 50 and 100 μM Neochlorogenic acid. |
[1R-(1α,3α,4α,5β)]-3-[[3-(3,4-dihydroxyphenyl)-1-oxoallyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid - Risk and Safety
| WGK Germany | 3 |
| HS Code | 29182900 |
[1R-(1α,3α,4α,5β)]-3-[[3-(3,4-dihydroxyphenyl)-1-oxoallyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic acid - Reference Information
| Plant Source: | honeysuckle |
| chlorogenic acid | chlorogenic acid is also called "chlorogenic acid" and "coffee tannic acid". Formula C16H18O9. Molecular weight 354.32. 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 is an important factor in plant metabolism. Chlorogenic acid and its isomer isochlorogenic acid and neochlorogenic acid also exist in the fruit, leaves and other tissues of dicotyledonous plants. Chlorogenic acid is 3-caffeic acid quinine acid. The new chlorogenic acid is 5-caffeic acid quinine acid. Isochlorogenic acid contains three kinds of caffeoylquinine acids, respectively 4, 5-dicaffeoylquinine acid, 3, 4-dicaffeoylquinine acid, 3, 5-dicaffeoylquininic acid. |
| Application | chlorogenic acid widely exists in plant medicine, and has many activities, such as cholagogic effect of Artemisia capillaris; hemostatic and leukocyte-elevating effects of ramie. Herbage, Eucommia ulmoides leaf, water keel, chelate, pomelo, corn leaf, cabbage, coffee, tea and so on all contain chlorogenic acid. Honeysuckle contains a variety of chlorogenic acid compounds, chlorogenic acid, isochlorogenic acid, new chlorogenic acid, caffeic acid and so on. The content of chlorogenic acid was the highest in flower buds. Chlorogenic acid and caffeic acid contained in Flos lonicerae have significant hemostatic effect, and can shorten the coagulation time and bleeding time. Chlorogenic acid and caffeic acid are also effective hemostatic components of ramie root. Chlorogenic acid is not resistant to high temperature, long time heating will destroy and reduce the efficacy. Traditional hemostatic silver flower charcoal, may be related to this. |
| biological activity | Neochlorogenic acid is a natural polyphenolic compound found in dried fruits and other plants. Neochlorgenic acid inhibits TNF-α and IL-1β production. Neochlorogenic acid inhibits iNOS and COX-2 protein expression. Neochlorogenic acid also inhibits phosphorylated NF-κB p65 and p38 MAPK activation. |
| Use | for content determination/identification/pharmacological experiments. Pharmacological Efficacy: has a wide range of antibacterial effect, but in vivo can be inactivated by protein. |
Last Update：2024-05-07 14:32:28
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