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Purity: ≥98%
Chlorogenic acid (3-O-Caffeoylquinic acid; Heriguard; NSC-407296) is a naturally occuring phenolic compound found in coffee and tea. It has antioxidant activity, antibacterial, hepatoprotective, cardioprotective, anti-inflammatory, antipyretic, neuroprotective, anti-obesity, antiviral, anti-microbial, anti-hypertension. Chlorogenic acid is an important biosynthetic intermediate in lignin biosynthesis. This compound, known as an antioxidant, may also slow the release of glucose into the bloodstream after a meal. The term chlorogenic acids can also refer to a related family of esters of hydroxycinnamic acids (caffeic acid, ferulic acid and p-coumaric acid) with quinic acid. Chlorogenic acids contain no chlorine.
| ln Vitro |
In CoCl2-induced hypoxic A549 cells, HIF-1α protein levels can be decreased by 10 μM of chlorogenic acid for 16 hours, but HIF-1α mRNA levels are unaffected [1]. Hypoxia is inhibited by chlorogenic acid (10 μM, 24 h). Huh7 cell proliferation is inhibited by chlorogenic acid (25, 50 μM, 24 h), which also decreases cell migration and number [4]. Induces HUVEC cell migration, thoracic and vascular endothelial cell tube formation [1].
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| ln Vivo |
kg, lateral wall) has a protective effect against experimental reflux esophagitis [3]. Chlorogenic acid (10 mg/kg, intravenous injection) prevents endotoxin death and induced TNF-α release in LPS-intoxicated C57BL/6 nozzles and improves acute liver injury in LPS/GalN-challenged mice [2]. Intraperitoneal injection of chlorogenic acid (25–200 mg/kg) can inhibit tumor growth in NOD/SCID mice with Huh7 or H446 cells [4].
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| Animal Protocol |
Animal/Disease Models: Rat experimental reflux esophagitis (RE) [1]
Doses: 10, 30, 100 mg/kg Route of Administration: Oral Experimental Results:Reduce esophageal lipid peroxidation (marker: MDA) and increase reflux esophagitis Prototype glutathione/oxidized glutathione ratio. Inhibits the increase in serum TNF-α levels and the expression of iNOS and COX-2 proteins. Animal/Disease Models: LPS/GalN-challenged mice [2] Doses: 10 mg/kg Route of Administration: intravenous (iv) (iv)injection Experimental Results: The survival rate of LPS/GalN-intoxicated mice increased. Inhibits LPS/GalN-induced NF-κB p65 or c-Jun phosphorylation without affecting p-IRF3 levels in liver lobules. |
| References |
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| Additional Infomation |
Chlorogenic acid is a cinnamate ester obtained by formal condensation of the carboxy group of trans-caffeic acid with the 3-hydroxy group of quinic acid. It is an intermediate metabolite in the biosynthesis of lignin. It has a role as a plant metabolite and a food component. It is a cinnamate ester and a tannin. It is functionally related to a (-)-quinic acid and a trans-caffeic acid. It is a conjugate acid of a chlorogenate.
Chlorogenic Acid has been used in trials studying the treatment of Advanced Cancer and Impaired Glucose Tolerance. Chlorogenic Acid has been reported in Camellia sinensis, Meum athamanticum, and other organisms with data available. Chlorogenic Acid is a polyphenol and the ester of caffeic acid and quinic acid that is found in coffee and black tea, with potential antioxidant and chemopreventive activities. Chlorogenic acid scavenges free radicals, which inhibits DNA damage and may protect against the induction of carcinogenesis. In addition, this agent may upregulate the expression of genes involved in the activation of the immune system and enhances activation and proliferation of cytotoxic T-lymphocytes, macrophages, and natural killer cells. Chlorogenic acid also inhibits the activity of matrix metalloproteinases. A naturally occurring phenolic acid which is a carcinogenic inhibitor. It has also been shown to prevent paraquat-induced oxidative stress in rats. (From J Chromatogr A 1996;741(2):223-31; Biosci Biotechnol Biochem 1996;60(5):765-68). See also: Arctium lappa Root (part of); Cynara scolymus leaf (part of); Lonicera japonica flower (part of) ... View More ... |
| Molecular Formula |
C16H18O9
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| Molecular Weight |
354.309
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| Exact Mass |
354.095
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| CAS # |
327-97-9
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| Related CAS # |
Neochlorogenic acid;906-33-2;Chlorogenic acid-13C3
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| PubChem CID |
1794427
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| Appearance |
White to off-white solid powder
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| Density |
1.7±0.1 g/cm3
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| Boiling Point |
665.0±55.0 °C at 760 mmHg
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| Melting Point |
210 °C (dec.)(lit.)
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| Flash Point |
245.5±25.0 °C
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| Vapour Pressure |
0.0±2.1 mmHg at 25°C
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| Index of Refraction |
1.690
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| LogP |
-0.36
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| Hydrogen Bond Donor Count |
6
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| Hydrogen Bond Acceptor Count |
9
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
25
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| Complexity |
534
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| Defined Atom Stereocenter Count |
4
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| SMILES |
C1[C@H]([C@H]([C@@H](C[C@@]1(C(=O)O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O)O
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| InChi Key |
CWVRJTMFETXNAD-XYXZIBEBSA-N
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| InChi Code |
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
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| Chemical Name |
(1S,3R,4R,5R)-3-{[(2Z)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexanecarboxylic acid
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| Synonyms |
3-O-Caffeoylquinic acid; Heriguard; NSC-407296; NSC407296; NSC 407296; 3(34Dihydroxycinnamoyl)quinate; 3(34Dihydroxycinnamoyl)quinic acid; 3Caffeoylquinate; 3Caffeoylquinic acid; 3CQA; 3OCaffeoylquinic acid; Chlorogenate; Heriguard; 3transCaffeoylquinic acid
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~282.24 mM)
H2O : ≥ 20 mg/mL (~56.45 mM) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.06 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (7.06 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (7.06 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.8224 mL | 14.1119 mL | 28.2239 mL | |
| 5 mM | 0.5645 mL | 2.8224 mL | 5.6448 mL | |
| 10 mM | 0.2822 mL | 1.4112 mL | 2.8224 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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