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Quinic acid

$43

  • Brand : BIOFRON

  • Catalogue Number : BF-Q3001

  • Specification : 98%

  • CAS number : 77-95-2

  • Formula : C7H12O6

  • Molecular Weight : 192.17

  • PUBCHEM ID : 6508

  • Volume : 25mg

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Catalogue Number

BF-Q3001

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

-20℃

Molecular Weight

192.17

Appearance

White crystalline powder

Botanical Source

Schisandra chinensis,Crataegus pinnatifida

Structure Type

Others

Category

Standards;Natural Pytochemical;API

SMILES

C1C(C(C(CC1(C(=O)O)O)O)O)O

Synonyms

(1R,3R,4R,5R)-(-)-quinic acid/Kinicacid/(1S,3R,4s)-1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid/[1R-(1a,3a,4a,5b)]-1,3,4,5-Tetrahydroxycyclohexanecarboxylic Acid/CHINIC ACID/l-Chinic acid/D-(-)-quinic acid/5beta)]-alph/(-)-quinic acid/Chinasaure/Cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-, (1α,3α,4α)-/l-Kinic acid

IUPAC Name

(3R,5R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid

Density

1.8±0.1 g/cm3

Solubility

Methanol; Acetontrile

Flash Point

233.1±25.2 °C

Boiling Point

438.4±45.0 °C at 760 mmHg

Melting Point

165-170 °C

InChl

InChl Key

WGK Germany

RID/ADR

HS Code Reference

2918190000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:77-95-2) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

PMID

27513177

Abstract

(-)-Quinic acid possess eight possible stereoisomers, which occur both naturally and as products of thermal food processing. In this contribution, we have selectively synthesized four isomers, namely, epi-quinic acid, muco-quinic acid, cis-quinic acid, and scyllo-quinic acid, to develop a tandem LC-MS method identifying all stereoisomeric quinic acids. Four derivatives have been unambiguously characterized by single-crystal X-ray crystallography. The missing diastereomers of quinic acid were obtained by nonselective isomerization of (-)-quinic acid using acetic acid/concentrated H2SO4 allowing chromatographic separation and assignment of all diastereomers of quinic acid. We report for the first time that a full set of stereoisomers are reliably distinguishable on the basis of their tandem mass spectrometric fragment spectra as well as their elution order. A rationale for characteristic fragmentation mechanisms is proposed. In this study, we also observed that muco-quinic acid, scyllo-quinic acid, and epi-quinic acid are present in hydrolyzed Guatemalan roasted coffee sample as possible products of roasting.

KEYWORDS

cis-quinic acid; coffee; epi-quinic acid; muco-quinic acid; scyllo-quinic acid

Title

Synthesis, Structure, and Tandem Mass Spectrometric Characterization of the Diastereomers of Quinic Acid.

Author

Deshpande S1, Matei MF1, Jaiswal R1, Bassil BS1, Kortz U1, Kuhnert N1.

Publish date

2016 Sep 28

PMID

31166006

Abstract

BACKGROUND AND PURPOSE:
Quinic acid (QA) is an abundant natural compound from plant sources which may improve metabolic health. However, little attention has been paid to its effects on pancreatic beta-cell functions, which contribute to the control of metabolic health by lowering blood glucose. Strategies targeting beta-cell signal transduction are a new approach for diabetes treatment. This study investigated the efficacy of QA to stimulate beta-cell function by targeting the basic molecular machinery of metabolism-secretion coupling.

EXPERIMENTAL APPROACH:
We measured bioenergetic parameters and insulin exocytosis in a model of insulin-secreting beta-cells (INS-1E), together with Ca2+ homeostasis, using genetically encoded sensors, targeted to different subcellular compartments. Islets from mice chronically infused with QA were also assessed.

KEY RESULTS:
QA triggered transient cytosolic Ca2+ increases in insulin-secreting cells by mobilizing Ca2+ from intracellular stores, such as endoplasmic reticulum. Following glucose stimulation, QA increased glucose-induced mitochondrial Ca2+ transients. We also observed a QA-induced rise of the NAD(P)H/NAD(P)+ ratio, augmented ATP synthase-dependent respiration, and enhanced glucose-stimulated insulin secretion. QA promoted beta-cell function in vivo as islets from mice infused with QA displayed improved glucose-induced insulin secretion. A diet containing QA improved glucose tolerance in mice.

CONCLUSIONS AND IMPLICATIONS:
QA modulated intracellular Ca2+ homeostasis, enhancing glucose-stimulated insulin secretion in both INS-1E cells and mouse islets. By increasing mitochondrial Ca2+ , QA activated the coordinated stimulation of oxidative metabolism, mitochondrial ATP synthase-dependent respiration, and therefore insulin secretion. Bioactive agents raising mitochondrial Ca2+ in pancreatic beta-cells could be used to treat diabetes.

© 2019 The British Pharmacological Society.

Title

The plant product quinic acid activates Ca2+ -dependent mitochondrial function and promotes insulin secretion from pancreatic beta cells.

Author

Heikkila E1, Hermant A1, Thevenet J1, Bermont F1, Kulkarni SS1, Ratajczak J1, Santo-Domingo J1, Dioum EH1, Canto C1, Barron D1, Wiederkehr A1, De Marchi U1.

Publish date

2019 Sep


Description :

D-(-)-Quinic acid is a cyclohexanecarboxylic acid and is implicated in the perceived acidity of coffee.