1,3-Dicaffeoylquinic acid - CAS 19870-46-3
Category: Inhibitor
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Molecular Formula:
C25H24O12
Molecular Weight:
516.45
COA:
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Targets:
PI3K
Description:
1,3-Dicaffeoylquinic acid, a caffeoylquinic acid derivative found in artichoke, acts as an anti-hyperlipidemic agent and activates PI3K/Akt.
Synonyms:
(1S,3R,4R,5R)-1,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxycyclohexane-1-carboxylic acid; 1,3-dicaffeoylquinic acid
Solubility:
DMSO: ≥ 23 mg/mL
Storage:
Store in a cool and dry place (or refer to the Certificate of Analysis).
MSDS:
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Boiling Point:
819.9±65.0 ℃ at 760 Torr
InChIKey:
YDDUMTOHNYZQPO-PSEXTPKNSA-N
InChI:
1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20-,23-,25+/m1/s1
Canonical 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
1.Determination of phenolic compounds in dietary supplements and tea blends containing Echinacea by liquid chromatography with coulometric electrochemical detection.
Luo W;Ang CY;Gehring TA;Heinze TM;Lin LJ;Mattia A J AOAC Int. 2003 Mar-Apr;86(2):202-8.
Analytical methodologies with ultrasonic extraction and liquid chromatography (LC) were developed for the determination of phenolic compounds in dietary supplements containing Echinacea. The phenolic compounds determined by these methods included caftaric acid, chlorogenic acid, cynarin, echinacoside, and cichoric acid. Samples from tablets, capsules, and bags of tea blends were extracted by sonication for < or = 30 min with methanol-water (60 + 40). The extracts were centrifuged and filtered, and the filtrates were diluted and analyzed by LC using a reversed-phase column and coulometric electrochemical (EC) detection. The mobile phase was acetonitrile-ammonium formate buffer, pH 3.5 (15.3 + 84.7) containing tetrabutyl ammonium hydrogen sulfate as an ion-pairing reagent. Extraction conditions (e.g., composition of the extraction solvent and sonication time) were optimized for different types of samples. Intra- and interday analytical variations were determined, and intraday analyses were performed by 2 independent analysts using 2 different LC systems. Results were generally comparable. The LC method with EC detection showed better sensitivity and selectivity when compared with LC with ultraviolet detection, although results were similar for the 2 methods for major compounds, i.
2.Caffeoylquinic acids in Centella asiatica protect against amyloid-β toxicity.
Gray NE;Morré J;Kelley J;Maier CS;Stevens JF;Quinn JF;Soumyanath A J Alzheimers Dis. 2014;40(2):359-73. doi: 10.3233/JAD-131913.
The accumulation of amyloid-β (Aβ) is a hallmark of Alzheimer's disease and is known to result in neurotoxicity both in vivo and in vitro. We previously demonstrated that treatment with the water extract of Centella asiatica (CAW) improves learning and memory deficits in Tg2576 mice, an animal model of Aβ accumulation. However the active compounds in CAW remain unknown. Here we used two in vitro models of Aβ toxicity to confirm this neuroprotective effect and identify several active constituents of the CAW extract. CAW reduced Aβ-induced cell death and attenuated Aβ-induced changes in tau expression and phosphorylation in both the MC65 and SH-SY5Y neuroblastoma cell lines. We confirmed and quantified the presence of several mono- and dicaffeoylquinic acids (CQAs) in CAW using chromatographic separation coupled to mass spectrometry and ultraviolet spectroscopy. Multiple dicaffeoylquinic acids showed efficacy in protecting MC65 cells against Aβ-induced cytotoxicity. Isochlorogenic acid A and 1,5-dicaffeoylquinic acid were found to be the most abundant CQAs in CAW, and the most active in protecting MC65 cells from Aβ-induced cell death. Both compounds showed neuroprotective activity in MC65 and SH-SY5Y cells at concentrations comparable to their levels in CAW.
3.[Compounds from fraction with cardiovascular activity of Chrysanthemum indicum].
Sun Y;Ma X;Liu J Zhongguo Zhong Yao Za Zhi. 2012 Jan;37(1):61-5.
In order to investigate the chemical constituents from the fraction with cardiovascular activtiy of Chrysanthemum indicum, the isolation and purification of compounds from this active fraction were performed, and the chemical structures were elucidated by spectral analysis and comparison of the spectral data with those reported in the literature. As a result, twelve compounds were obtained and identified as (2S) -eriodictyol-7-O-beta-D-glucuronide (1), (2S) -eriodictyol-7-O-beta-D-glucoside (2), (2S) -hesperetin-7-O-beta-D-glucuronide (3), luteolin-7-O-beta-D-glucoside (4), luteolin-7-O-beta-D-glucuronide (5), diosmetin-7-O-beta-D-glucuronide (6), quercetin -7-O-beta-D-glucoside (7), (2S)-eriodict-dicaffeoylquinate (8), 3, 5-dicaffeoylquinic acid(9), 3, 5-cis-dicaffeoylquinic acid (10), 1, 5-dicaffeoylquinic acid (11), and 1, 3-dicaffeoylquinic acid (12). The above result indicated that flavonoids were the ma-dicaffeoylquinate (8), 3, 5-dicaffeoylquinic acid (9), 3, 5-cis-dicaffeoylquinic acid (10), 1, 5-dicaffeoylquinic acid (11), and 1, 3-dicaffeoylquinic acid (12). The above result indicated that flavonoids were the major components of the active fraction. Compounds 2, 3, 7, 8 and 10 were obtained from this genus for the first time, and compounds 5, 6, 9, 11, and 12 were first isolated from C.
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CAS 19870-46-3 1,3-Dicaffeoylquinic acid

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