Chlorogenic acidCAS# 327-97-9 |
- Isochlorogenic acid
Catalog No.:BCN5910
CAS No.:534-61-2
- Neochlorogenic acid
Catalog No.:BCN4450
CAS No.:906-33-2
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
Cas No. | 327-97-9 | SDF | Download SDF |
PubChem ID | 1794427 | Appearance | White powder |
Formula | C16H18O9 | M.Wt | 354.31 |
Type of Compound | Phenylpropanoids | Storage | Desiccate at -20°C |
Synonyms | 3-O-Caffeoylquinic acid; Heriguard; NSC-407296 | ||
Solubility | DMSO : ≥ 32 mg/mL (90.32 mM) *"≥" means soluble, but saturation unknown. | ||
Chemical Name | (1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid | ||
SMILES | C1C(C(C(CC1(C(=O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O)O | ||
Standard InChIKey | CWVRJTMFETXNAD-JUHZACGLSA-N | ||
Standard InChI | InChI=1S/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 | ||
General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
||
About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
||
Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. |
Description | Chlorogenic acid, a phenolic compound found ubiquitously in plants, is an antioxidant and metal chelator, it has antiviral activity by inhibiting HBV replication, it inhibits the inflammatory reaction in HSE via the suppression of TLR2/TLR9-Myd88 signaling pathways. Some derivatives of chlorogenic acid are hypoglycemic agents and may affect lipid metabolism, chlorogenic acid can improve glucose tolerance, decrease some plasma and liver lipids, and improve mineral pool distribution in vivo. |
Targets | HBV | PEG | NO | NOS | ERK | ROS | COX |
In vitro | Chlorogenic acid enhances the effects of 5-fluorouracil in human hepatocellular carcinoma cells through the inhibition of extracellular signal-regulated kinases.[Pubmed: 25714249]Anticancer Drugs. 2015 Feb 24.There is an urgent need to search for novel chemosensitizers in the field of cancer therapy. Chlorogenic acid (CGA), a type of polyphenol present in the diet, has many biological activities.
|
In vivo | In vitro and in vivo antioxidant properties of chlorogenic acid and caffeic acid.[Pubmed: 20933071 ]Int J Pharm. 2011 Jan 17;403(1-2):136-8.Dietary polyphenols are thought to be beneficial for human health as antioxidants. Coffee beans contain a common polyphenol, Chlorogenic acid. Chlorogenic acid is the ester of caffeic acid and quinic acid. Although these polyphenols have received much attention, there is little evidence indicating a relationship between the effect and the rate of absorption.
Chlorogenic acid modifies plasma and liver concentrations of: cholesterol, triacylglycerol, and minerals in (fa/fa) Zucker rats.[Pubmed: 12550056]J Nutr Biochem. 2002 Dec;13(12):717-726.Chlorogenic acid, a phenolic compound found ubiquitously in plants, is an in vitro antioxidant and metal chelator. Some derivatives of Chlorogenic acid are hypoglycemic agents and may affect lipid metabolism. Concentrations of cholesterol and triacylglycerols are of interest due to their association with diseases such as non-insulin-dependent-diabetes- mellitus and obese insulin resistance.
|
Kinase Assay | Chlorogenic acid suppresses interleukin-1β-induced inflammatory mediators in human chondrocytes.[Pubmed: 25674248]Int J Clin Exp Pathol. 2014 Dec 1;7(12):8797-801.We investigated the anti-inflammatory properties of Chlorogenic acid (CGA) in interleukin-1β-induced chondrocytes. The nitric oxide (NO) and prostaglandin E2 (PGE2) were detected by Griess and Enzyme-linked immunosorbent assay (ELISA) respectively. Quantitative real-time PCR and western blot were performed to measure the expression of inducible NO synthase (iNOS) and cyclooxygenase (COX)-2. Our results indicate that Chlorogenic acid inhibited the production of NO and PGE2 as well as the expression of iNOS and COX-2 in chondrocytes. Our data suggest that Chlorogenic acid possess potential value in the treatment of OA. |
Cell Research | Involvement of TLR2 and TLR9 in the anti-inflammatory effects of chlorogenic acid in HSV-1-infected microglia.[Pubmed: 25744394]Life Sci. 2015 Mar 2. pii: S0024-3205(15)00105-8.There is no effective medication to date for herpes simplex virus encephalitis (HSE). In this study, we investigated the anti-inflammatory effect of Chlorogenic acid (CGA) on herpes simplex virus (HSV)-1-induced responses in BV2 microglia.
|
Animal Research | Anti-hepatitis B virus activity of chlorogenic acid, quinic acid and caffeic acid in vivo and in vitro.[Pubmed: 19463857 ]Antiviral Res. 2009 Aug;83(2):186-90.Chlorogenic acid and its related compounds are abundant plant polyphenols that have a diverse antiviral activity.
|
Chlorogenic acid Dilution Calculator
Chlorogenic acid Molarity Calculator
1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
1 mM | 2.8224 mL | 14.1119 mL | 28.2239 mL | 56.4477 mL | 70.5597 mL |
5 mM | 0.5645 mL | 2.8224 mL | 5.6448 mL | 11.2895 mL | 14.1119 mL |
10 mM | 0.2822 mL | 1.4112 mL | 2.8224 mL | 5.6448 mL | 7.056 mL |
50 mM | 0.0564 mL | 0.2822 mL | 0.5645 mL | 1.129 mL | 1.4112 mL |
100 mM | 0.0282 mL | 0.1411 mL | 0.2822 mL | 0.5645 mL | 0.7056 mL |
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. |
Calcutta University
University of Minnesota
University of Maryland School of Medicine
University of Illinois at Chicago
The Ohio State University
University of Zurich
Harvard University
Colorado State University
Auburn University
Yale University
Worcester Polytechnic Institute
Washington State University
Stanford University
University of Leipzig
Universidade da Beira Interior
The Institute of Cancer Research
Heidelberg University
University of Amsterdam
University of Auckland
TsingHua University
The University of Michigan
Miami University
DRURY University
Jilin University
Fudan University
Wuhan University
Sun Yat-sen University
Universite de Paris
Deemed University
Auckland University
The University of Tokyo
Korea University
Chlorogenic acid(NSC-407296; 3-O-Caffeoylquinic acid) is one of the most abundant polyphenols in the human diet, has been reported to inhibit cancer cell growth and a major anti-inflammatory constituent of lonicerae flos extract. IC50 value: Target: in vitro: CGA significantly decreases the hypoxia-induced HIF-1α protein level in A549 cells, without changing its mRNA level. CGA was, however, found to suppress the transcriptional activity of HIF-1α under hypoxic conditions, leading to a decrease in the expression of its downstream target VEGF [1]. CGA inhibited various TLR agonist-, IL-1α-, or high-mobility group box-1-stimulated autophosphorylation (activation) of IRAK4 in peritoneal macrophages from C57BL/6 or C3H/HeJ mice via directly affecting the kinase activity of IRAK4, a proximal signal transducer in the MyD88-mediated innate immunity that enhances transcriptional activity of NF-κB or AP-1 [2]. in vivo: CGA can block hypoxia-stimulated angiogenesis in vitro and VEGF-stimulated angiogenesis in vivo using HUVEC cells in a mouse model [1]. CGA consequently attenuated protein or mRNA levels of NF-κB/AP-1 target genes encoding TNF-α, IL-1α, IL-6, and high-mobility group box-1 in vivo under endotoxemia or ALI [2]. CGA (10, 30 and 100 mg/kg) and omeprazole (positive control, 10 mg/kg) were administered orally 48 h after the RE operation for 12 days. CGA reduced the severity of esophageal lesions, and this beneficial effect was confirmed by histopathological observations. CGA reduced esophageal lipid peroxidation and increased the reduced glutathione/oxidized glutathione ratio. CGA attenuated increases in the serum level of tumor necrosis factor-α, and expressions of inducible nitric oxide synthase and cyclooxygenase-2 protein [3].
References:
[1]. Park JJ, et al. Chlorogenic acid inhibits hypoxia-induced angiogenesis via down-regulation of the HIF-1α/AKT pathway. Cell Oncol (Dordr). 2015 Jan 6.
[2]. Park SH, et al. IRAK4 as a Molecular Target in the Amelioration of Innate Immunity-Related Endotoxic Shock and Acute Liver Injury by Chlorogenic Acid. J Immunol. 2015 Feb 1;194(3):1122-30.
[3]. Kang JW, et al. Protective Effects of Chlorogenic Acid against Experimental Reflux Esophagitis in Rats. Biomol Ther (Seoul). 2014 Sep;22(5):420-5.
- H-Nle-OH
Catalog No.:BCC3295
CAS No.:327-57-1
- MHY1485
Catalog No.:BCC6404
CAS No.:326914-06-1
- Shz 1
Catalog No.:BCC6334
CAS No.:326886-05-9
- FAAH inhibitor 1
Catalog No.:BCC4254
CAS No.:326866-17-5
- Edpetiline
Catalog No.:BCN6771
CAS No.:32685-93-1
- H-Glu(OtBu)-OtBu.HCl
Catalog No.:BCC2934
CAS No.:32677-01-3
- Mesoridazine Besylate
Catalog No.:BCC3975
CAS No.:32672-69-8
- Fraxamoside
Catalog No.:BCN5247
CAS No.:326594-34-7
- Boc-Ser-OH
Catalog No.:BCC3439
CAS No.:3262-72-4
- Oleuropein
Catalog No.:BCN5246
CAS No.:32619-42-4
- Kaempferol 3-neohesperidoside
Catalog No.:BCN5245
CAS No.:32602-81-6
- GRI 977143
Catalog No.:BCC2401
CAS No.:325850-81-5
- TCS-PIM-1-4a
Catalog No.:BCC5461
CAS No.:327033-36-3
- TDZD-8
Catalog No.:BCC4258
CAS No.:327036-89-5
- VU 0285683
Catalog No.:BCC6154
CAS No.:327056-22-4
- Cyclohexanecarboxylic acid
Catalog No.:BCN3443
CAS No.:98-89-5
- tcY-NH2
Catalog No.:BCC5770
CAS No.:327177-34-4
- Heliosupine
Catalog No.:BCN1980
CAS No.:32728-78-2
- Phorbol 13-acetate
Catalog No.:BCN7231
CAS No.:32752-29-7
- Macrocarpal L
Catalog No.:BCN5248
CAS No.:327601-97-8
- BIO 5192
Catalog No.:BCC8002
CAS No.:327613-57-0
- Macrocarpal O
Catalog No.:BCN7371
CAS No.:327622-65-1
- Protopanaxatriol
Catalog No.:BCC9245
CAS No.:32773-56-1
- Labetalol HCl
Catalog No.:BCC5489
CAS No.:32780-64-6
Anti-hepatitis B virus activity of chlorogenic acid, quinic acid and caffeic acid in vivo and in vitro.[Pubmed:19463857]
Antiviral Res. 2009 Aug;83(2):186-90.
Chlorogenic acid and its related compounds are abundant plant polyphenols that have a diverse antiviral activity. In this study, HepG2.2.15 cells and duck hepatitis B virus infection model were used as in vitro and in vivo models to evaluate their anti-HBV activity. In the cell model, all the three compounds inhibited HBV-DNA replication as well as HBsAg production. Chlorogenic acid and caffeic acid also reduced serum DHBV level in DHBV-infected duckling model. Moreover, the anti-HBV activity of crude extracts of coffee beans, which have a high content of Chlorogenic acid, was studied. Both the extracts of regular coffee and that of decaffeinated coffee showed inhibitory effect on HBV replication.
Chlorogenic acid suppresses interleukin-1beta-induced inflammatory mediators in human chondrocytes.[Pubmed:25674248]
Int J Clin Exp Pathol. 2014 Dec 1;7(12):8797-801. eCollection 2014.
We investigated the anti-inflammatory properties of Chlorogenic acid (CGA) in interleukin-1beta-induced chondrocytes. The nitric oxide (NO) and prostaglandin E2 (PGE2) were detected by Griess and Enzyme-linked immunosorbent assay (ELISA) respectively. Quantitative real-time PCR and western blot were performed to measure the expression of inducible NO synthase (iNOS) and cyclooxygenase (COX)-2. Our results indicate that CGA inhibited the production of NO and PGE2 as well as the expression of iNOS and COX-2 in chondrocytes. Our data suggest that CGA possess potential value in the treatment of OA.
Involvement of TLR2 and TLR9 in the anti-inflammatory effects of chlorogenic acid in HSV-1-infected microglia.[Pubmed:25744394]
Life Sci. 2015 Apr 15;127:12-8.
AIMS: There is no effective medication to date for herpes simplex virus encephalitis (HSE). In this study, we investigated the anti-inflammatory effect of Chlorogenic acid (CGA) on herpes simplex virus (HSV)-1-induced responses in BV2 microglia. MAIN METHODS: The cellular model was established with BV2 cells stimulated by HSV-1 and then treated with CGA at different concentrations. Cell viability was assayed by the MTT assay. The mRNA expression of Toll-like receptor (TLR)-2, TLR9 and myeloid differentiation factor88 (Myd88) was assayed by real-time quantitative PCR, and the protein expression was assayed by flow cytometry or Western blotting. Tumor necrosis factor-alpha (TNF-alpha) and interleukin (IL)-6 were measured by ELISA as well as real-time quantitative PCR. Nuclear NF-kappaB p65 protein was assayed by Western blotting. KEY FINDINGS: The cell survival rate was significantly improved after CGA treatment, and CGA prevented increases in TLR2, TLR9 and Myd88 following HSV-1 challenge in BV2 cells both at the mRNA and protein levels. Moreover, CGA could attenuate HSV-induced TNF-alpha and IL-6 release into the supernatant. The mRNA levels of TNF-alpha and IL-6 were also significantly inhibited by CGA. The expression of NF-kappaB p65 increased significantly in the nucleus in HSV-1-stimulated microglia but could be reduced by CGA. SIGNIFICANCE: CGA inhibits the inflammatory reaction in HSE via the suppression of TLR2/TLR9-Myd88 signaling pathways. CGA may serve as an anti-inflammatory agent and provide a new strategy for treating HSE.
In vitro and in vivo antioxidant properties of chlorogenic acid and caffeic acid.[Pubmed:20933071]
Int J Pharm. 2011 Jan 17;403(1-2):136-8.
Dietary polyphenols are thought to be beneficial for human health as antioxidants. Coffee beans contain a common polyphenol, Chlorogenic acid. Chlorogenic acid is the ester of caffeic acid and quinic acid. Although these polyphenols have received much attention, there is little evidence indicating a relationship between the effect and the rate of absorption. In this study, we focused on the beneficial effects of Chlorogenic acid and caffeic acid, a major metabolite of Chlorogenic acid. We carried out in vitro and in vivo experiments. In the in vitro study, caffeic acid had stronger antioxidant activity than that of Chlorogenic acid. The uptake of Chlorogenic acid by Caco-2 cells was much less than that of caffeic acid. The physiological importance of an orally administered compound depends on its availability for intestinal absorption and subsequent interaction with target tissues. We then used an intestinal ischemia-reperfusion model to evaluate antioxidant activities in vivo. We found that both Chlorogenic acid and caffeic acid had effects on intestinal ischemia-reperfusion injury. Since caffeic acid has a stronger antioxidant activity than that of Chlorogenic acid and Chlorogenic acid is hydrolyzed into caffeic acid in the intestine, it is possible that caffeic acid plays a major role in the protective effect of Chlorogenic acid against ischemia-reperfusion injury.
Chlorogenic acid modifies plasma and liver concentrations of: cholesterol, triacylglycerol, and minerals in (fa/fa) Zucker rats.[Pubmed:12550056]
J Nutr Biochem. 2002 Dec;13(12):717-726.
Chlorogenic acid, a phenolic compound found ubiquitously in plants, is an in vitro antioxidant and metal chelator. Some derivatives of Chlorogenic acid are hypoglycemic agents and may affect lipid metabolism. Concentrations of cholesterol and triacylglycerols are of interest due to their association with diseases such as non-insulin-dependent-diabetes- mellitus and obese insulin resistance. As little is known about the effects of Chlorogenic acid in vivo, studies using obese, hyperlipidemic, and insulin resistant (fa/fa) Zucker rats were conducted to test the effect of Chlorogenic acid on fasting plasma glucose, plasma and liver triacylglycerols and cholesterol concentrations. Aditionally, the effects of Chlorogenic acid on selected mineral concentrations in plasma, spleen, and liver were determined. Rats were implanted with jugular vein catheters. Chlorogenic acid was infused (5 mg/Kg body weight/day) for 3 weeks via intravenous infusion. Chlorogenic acid did not promote sustained hypoglycemia and significantly lowered the postprandial peak response to a glucose challenge when compared to the same group of rats before Chlorogenic acid treatment. In Chlorogenic acid-treated rats, fasting plasma cholesterol and triacylglycerols concentrations significantly decreased by 44% and 58% respectively, as did in liver triacylglycerols concentrations (24%). We did not find differences (p > 0.05) in adipose triacylglycerols concentration. Significant differences (p < 0.05) in the plasma, liver, and spleen concentration of selected minerals were found in Chlorogenic acid-treated rats. In vivo, Chlorogenic acid was found to improve glucose tolerance, decreased some plasma and liver lipids, and improve mineral pool distribution under the conditions of this study.
Chlorogenic acid enhances the effects of 5-fluorouracil in human hepatocellular carcinoma cells through the inhibition of extracellular signal-regulated kinases.[Pubmed:25714249]
Anticancer Drugs. 2015 Jun;26(5):540-6.
There is an urgent need to search for novel chemosensitizers in the field of cancer therapy. Chlorogenic acid (CGA), a type of polyphenol present in the diet, has many biological activities. The present study is designed to explore the influence of CGA on the effects of 5-fluorouracil (5-FU) on human hepatocellular carcinoma cells (HepG2 and Hep3B). Treatment with 5-FU induced the inhibition of hepatocellular carcinoma cells' proliferation, and the combined treatment with CGA enhanced this inhibition. 5-FU also increased the production of reactive oxygen species (ROS). The combination of 5-FU and CGA led to a more prominent production of ROS and significantly inactivated ERK1/2, although CGA and 5-FU exerted no significant changes when used alone. A previous report has shown that ROS are upstream mediators that inactivate ERK in hepatocellular carcinoma cells. Combined with our results, this indicates that the combination of 5-FU and CGA leads to the inactivation of ERK through the overproduction of ROS. This mediates the enhancement of 5-FU-induced inhibition of hepatocellular carcinoma cells' proliferation, that is, CGA sensitizes hepatocellular carcinoma cells to 5-FU treatment by the suppression of ERK activation through the overproduction of ROS. CGA has shown potential as a chemosensitizer of 5-FU chemotherapy in hepatocellular carcinoma.