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Cryptochlorogenic acid

$252

  • Brand : BIOFRON

  • Catalogue Number : BD-D1345

  • Specification : 98%(HPLC)

  • CAS number : 905-99-7

  • Formula : C16H18O9

  • Molecular Weight : 354.309

  • PUBCHEM ID : 9798666

  • Volume : 20MG

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Catalogue Number

BD-D1345

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

2-8℃

Molecular Weight

354.309

Appearance

White crystal

Botanical Source

Eucommia ulmoides,Lonicera japonica Thunb.,Lonicera japonica Thunb./Coffea sp. (coffee), Cynara scolymus (artichoke) heads, Cydonia oblonga (quince fruit), Helianthus sp. (sunflowers), Ipomoea batatas (sweet potato) tubers and Prunus domestica (prune)

Structure Type

Simple Phenylpropanoids

Category

Standards;Natural Pytochemical;API

SMILES

C1C(C(C(CC1(C(=O)O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O

Synonyms

4-O-CAFFEOYL QUINIC ACID/4-(3,4-Dihydroxycinnamoyl)quinic acid/(1S,3R,4S,5R)-4-{[(2E)-3-(3,4-Dihydroxyphenyl)-2-propenoyl]oxy}-1,3,5-trihydroxycyclohexanecarboxylic acid/(3R,5R)-4-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,3,5-trihydroxycyclohexane-1-carboxylic acid/4-O-trans-caffeoylquinic acid/(1S,3R,4S,5R)-4-{[(2E)-3-(3,4-Dihydroxyphenyl)prop-2-enoyl]oxy}-1,3,5-trihydroxycyclohexanecarboxylic acid/4-Caffeoylquinic acid/4-O-(E)-caffeoylquinic acid/4-O-Caffeoylquinic acid/Cryptochlorogenic acid/Cyclohexanecarboxylic acid, 4-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1,3,5-trihydroxy-, (1α,3α,4α,5β)-

IUPAC Name

(3R,5R)-4-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,3,5-trihydroxycyclohexane-1-carboxylic acid

Density

1.7±0.1 g/cm3

Solubility

Methanol; Ethanol; Acetone

Flash Point

256.8±25.0 °C

Boiling Point

694.9±55.0 °C at 760 mmHg

Melting Point

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2918290000

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:905-99-7) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

27405173

Abstract

The degradation kinetics of chlorogenic acid (5-CQA), cryptochlorogenic acid (4-CQA), and neochlorogenic acid (3-CQA) in aqueous solution at 37 degrees C and different pH values (7.05, 7.96, 9.25) were investigated in the present work. The results indicated that 3-, 4- and 5-CQA tended to remain stable in acidic pH circumstance, and unstable in neutral and alkaline pH circumstance. With the increase of the alkalinity, the degradation of 3-, 4- and 5-CQA was increased leading to a less amount of total CQA and was satisfactorily described by the Weibull equation. Meanwhile, caffeic acid was not detected after the degradation of CQA. Moreover, the degradation of 3-CQA and 5-CQA tended to be converted to 4-CQA, and the degradation of 4-CQA tended to be converted to 3-CQA rather than 5-CQA. The comparison of the degradation kinetics parameters of 3-, 4- and 5-CQA at neutral and alkaline pH values showed that the orders of the rate constant (k) values were 4-CQA > 3-CQA > 5-CQA, while the orders of the degradation half life (t½) values were 4-CQA < 3-CQA < 5-CQA, indicating the orders of the stabilities of 3-, 4- and 5-CQA at 37 degrees C and neutral and alkaline pH values were 4-CQA < 3-CQA < 5-CQA.

Title

[Degradation kinetics of chlorogenic acid, cryptochlorogenic acid, and neochlorogenic acid at neutral and alkaline pH values].

Author

Zhu P, Miao XL, Chen Y.

Publish date

2016 Jan

PMID

32234671

Abstract

Phenolic acids are found in natural plants, such as caffeic acid, rosmarinic acid, and chlorogenic acid. They have long been used as pharmacological actives, owing to their anti-inflammatory and antioxidant activities. Cryptochlorogenic acid (CCGA) is a special isomer of chlorogenic acid; the pharmacological effects and related molecular mechanisms of CCGA have been poorly reported. In the present study, the antioxidant and anti-inflammatory effects of CCGA in RAW 264.7 macrophages and the underlying mechanisms were investigated. The results revealed that CCGA dose-dependently inhibited LPS-induced production of NO, TNF-α, and IL-6 and blocked iNOS, COX-2, TNF-α, and IL-6 expressions. CCGA also significantly increased the GSH/GSSG ratio and SOD activity and reduced the MDA level. Moreover, CCGA suppressed the nuclear translocation of NF-κB by hindering the phosphorylation of IκB kinase (IKK) and degrading IκB. It also downregulated the phosphorylation of MAPKs. Our results indicated that CCGA significantly inhibited NF-κB activation by controlling the expression of pro-inflammatory factors and promoting the nuclear transfer of Nrf2. In conclusion, CCGA could attenuate LPS-induced inflammatory symptoms by modulating NF-κB/MAPK signaling cascades and inhibit LPS-induced oxidative stress via Nrf2 nuclear translocation.

Copyright © 2020 Elsevier B.V. All rights reserved.

KEYWORDS

Anti-inflammatory; Antioxidant; Cryptochlorogenic acid; MAPK; NF-κB; Nrf2

Title

Cryptochlorogenic acid attenuates LPS-induced inflammatory response and oxidative stress via upregulation of the Nrf2/HO-1 signaling pathway in RAW 264.7 macrophages.

Author

Zhao XL1, Yu L1, Zhang SD1, Ping K1, Ni HY1, Qin XY1, Zhao CJ1, Wang W1, Efferth T2, Fu YJ3.

Publish date

2020 Mar 29

PMID

24842397

Abstract

A simple, specific and sensitive ultra-performance liquid chromatography tandem mass spectrometry (UPLC-MS/MS) method was established and validated for simultaneous determination of neochlorogenic acid, chlorogenic acid, cryptochlorogenic acid and geniposide in rat plasma using puerarin as an internal standard (IS). Plasma samples were pretreated by a one-step direct protein precipitation procedure with acetonitrile after acidified using as little as 50 μL plasma. Chromatographic separation was performed on an Acquity BEH C18 column (100 × 2.1 mm, 1.7 µm) at a flow rate of 0.2 mL/min by a gradient elution, using 0.2% acetic acid-methanol as mobile phase. The detection was performed on a triple quadrupole tandem mass spectrometer by multiple reaction monitoring via electrospray ionization source with negative ion mode. Calibration curves showed good linearity (r > 0.995) over wide concentration ranges. The intra- and inter-day precisions were <15%, and the accuracy was within ±8.0%. The validated method was successfully applied to a pharmacokinetic study of the four bioactive components in rats after intravenous administration of Reduning injection. Copyright © 2014 John Wiley & Sons, Ltd.

KEYWORDS

Reduning injection; UPLC-MS/MS; chlorogenic acid isomers; geniposide; pharmacokinetics

Title

Simultaneous determination of neochlorogenic acid, chlorogenic acid, cryptochlorogenic acid and geniposide in rat plasma by UPLC-MS/MS and its application to a pharmacokinetic study after administration of Reduning injection.

Author

Wang Y1, Wen J, Zheng W, Zhao L, Fu X, Wang Z, Xiong Z, Li F, Xiao W.

Publish date

2015 Jan


Description :

Cryptochlorogenic acid is a natural product.