1,3-Dicaffeoylquinic acidCAS# 19870-46-3 |
- 1,5-Dicaffeoylquinic acid
Catalog No.:BCN5913
CAS No.:30964-13-7
Quality Control & MSDS
3D structure
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| Cas No. | 19870-46-3 | SDF | Download SDF |
| PubChem ID | 6474640 | Appearance | White-beige powder |
| Formula | C25H24O12 | M.Wt | 516.5 |
| Type of Compound | Phenylpropanoids | Storage | Desiccate at -20°C |
| Synonyms | 1,3-O-Dicaffeoylquinic acid; 1,5-Dicaffeoylquinic acid | ||
| Solubility | DMSO : ≥ 23 mg/mL (44.53 mM) *"≥" means soluble, but saturation unknown. | ||
| Chemical Name | (1S,3R,4R,5R)-1,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxycyclohexane-1-carboxylic acid | ||
| SMILES | C1C(C(C(CC1(C(=O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)OC(=O)C=CC3=CC(=C(C=C3)O)O)O)O | ||
| Standard InChIKey | YDDUMTOHNYZQPO-PSEXTPKNSA-N | ||
| 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. |
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| 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. |
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| 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 | 1,3-Dicaffeoylquinic acid is a caffeoylquinic acid derivative that exhibits antioxidant activity and radical scavenging activity.It can significantly inhibit hOAT3 transport under similar conditions. |
| Targets | ROS | hOAT3 |
| In vitro | Antioxidant activity of 1,3-dicaffeoylquinic acid isolated from Inula viscosa.[Reference: WebLink]Food Research International, 2009 , 42 (9) :1273-1280.Inula viscosa is a perennial herbaceous plant used topically in folk medicine as an anti-scabies, anti-inflammatory, and wound-healing agent. |
| In vivo | Interaction of Natural Dietary and Herbal Anionic Compounds and Flavonoids with Human Organic Anion Transporters 1 (SLC22A6), 3 (SLC22A8), and 4 (SLC22A11).[Pubmed: 23573138]Evid Based Complement Alternat Med. 2013;2013:612527.Active components of complementary/alternative medicines and natural supplements are often anionic compounds and flavonoids. As such, organic anion transporters (OATs) may play a key role in their pharmacokinetic and pharmacological profiles, and represent sites for adverse drug-drug interactions. |
1,3-Dicaffeoylquinic acid Dilution Calculator
1,3-Dicaffeoylquinic acid Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 1.9361 mL | 9.6805 mL | 19.3611 mL | 38.7222 mL | 48.4027 mL |
| 5 mM | 0.3872 mL | 1.9361 mL | 3.8722 mL | 7.7444 mL | 9.6805 mL |
| 10 mM | 0.1936 mL | 0.9681 mL | 1.9361 mL | 3.8722 mL | 4.8403 mL |
| 50 mM | 0.0387 mL | 0.1936 mL | 0.3872 mL | 0.7744 mL | 0.9681 mL |
| 100 mM | 0.0194 mL | 0.0968 mL | 0.1936 mL | 0.3872 mL | 0.484 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. | |||||
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1,3-Dicaffeoylquinic acid is a caffeoylquinic acid derivative, and activates PI3K/Akt.
In Vitro:1,3-Dicaffeoylquinic acid shows increased neuronal cell viability against Aβ(42) toxicity in a concentration-dependent manner in neurons. 1,3-Dicaffeoylquinic acid activates both phosphoinositide 3-kinase (PI3K)/Akt and extracellular regulated protein kinase 1/2 (Erk1/2) with stimulating their upstream tyrosine kinase A (Trk A). 1,3-Dicaffeoylquinic acid's anti-apoptotic potential is related to the enhanced inactivating phosphorylation of glycogen synthase kinase 3β (GSK3β) and the modulation of expression of apoptosis-related protein Bcl-2/Bax[2]. 1,3-Dicaffeoylquinic acid (10 μM, 20 μM, 50 μM, and 100 μM) significantly increases cell viablity before OGD/reperfusion, and prevents the depletion of GSH under OGD/reperfusion insult. 1,3-Dicaffeoylquinic acid induces nuclear translocation of Nrf2 in OGD/reperfusion treated astrocytes, and induces increased GCL activity, and the effect is lost in Nrf2 siRNA-transfected cells[3].
In Vivo:1,3-Dicaffeoylquinic acid (32.0 mg/kg, p.o.) and 1-O-ABL are absorbed very quickly in Wistar rats. The maximum plasma concentrations for 1,3-Dicaffeoylquinic acid and 1-O-ABL are 44.5 ± 7.1 and 19.1 ± 6.9 ng/mL, respectively[1].
References:
[1]. Wang Z, et al. An LC-MS/MS method for simultaneous determination of 1,5-dicaffeoylquinic acid and 1-O-acetylbritannilactone in rat plasma and its application to a pharmacokinetic study.
[2]. Xiao HB, et al. 1,5-dicaffeoylquinic acid protects primary neurons from amyloid β 1-42-induced apoptosis via PI3K/Akt signaling pathway. Chin Med J (Engl). 2011 Sep;124(17):2628-35.
[3]. Cao X, et al. 1, 5-Dicaffeoylquinic acid-mediated glutathione synthesis through activation of Nrf2 protects against OGD/reperfusion-induced oxidative stress in astrocytes. Brain Res. 2010 Aug 6;1347:142-8.
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Interaction of Natural Dietary and Herbal Anionic Compounds and Flavonoids with Human Organic Anion Transporters 1 (SLC22A6), 3 (SLC22A8), and 4 (SLC22A11).[Pubmed:23573138]
Evid Based Complement Alternat Med. 2013;2013:612527.
Active components of complementary/alternative medicines and natural supplements are often anionic compounds and flavonoids. As such, organic anion transporters (OATs) may play a key role in their pharmacokinetic and pharmacological profiles, and represent sites for adverse drug-drug interactions. Therefore, we assessed the inhibitory effects of nine natural products, including flavonoids (catechin and epicatechin), chlorogenic acids (1,3- and 1,5-dicaffeoylquinic acid), phenolic acids (ginkgolic acids (13 : 0), (15 : 1), and (17 : 1)), and the organic acids ursolic acid and 18 beta -glycyrrhetinic acid, on the transport activity of the human OATs, hOAT1 (SLC22A6), hOAT3 (SLC22A8), and hOAT4 (SLC22A11). Four compounds, 1,3- and 1,5-dicaffeoylquinic acid, ginkgolic acid (17 : 1), and 18 beta -glycyrrhetinic acid, significantly inhibited hOAT1-mediated transport (50 mu M inhibitor versus 1 mu M substrate). Five compounds, 1,3- and 1,5-dicaffeoylquinic acid, ginkgolic acids (15 : 1) and (17 : 1), and epicatechin, significantly inhibited hOAT3 transport under similar conditions. Only catechin inhibited hOAT4. Dose-dependency studies were conducted for 1,3-Dicaffeoylquinic acid and 18 beta -glycyrrhetinic acid on hOAT1, and IC50 values were estimated as 1.2 +/- 0.4 mu M and 2.7 +/- 0.2 mu M, respectively. These data suggest that 1,3-Dicaffeoylquinic acid and 18 beta -glycyrrhetinic acid may cause significant hOAT1-mediated DDIs in vivo; potential should be considered for safety issues during use and in future drug development.
