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Cryptochlorogenic acid

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Cryptochlorogenic acid Basic information

Product Name:
Cryptochlorogenic acid
Synonyms:
  • Cryptochlorogenic acid
  • 3,4-Dihydroxycinnamic acid 4-carboxy-2,4,6-trihydroxycyclohexyl ester
  • 4-Caffeoylquinic acid
  • Quinic acid 4-O-caffeate
  • Cryptochlorogenic acid,4-Caffeoylquinic acid
  • 4-Dicaffeoylquinic Acid
  • 4-Caffeoylquinic acid Quinic acid 4-O-caffeate
  • Cryptochlorogenic acid(4')
CAS:
905-99-7
MF:
C16H18O9
MW:
354.31
Product Categories:
  • chemical reagent
  • pharmaceutical intermediate
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).
  • standardized herbal extract
Mol File:
905-99-7.mol
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Cryptochlorogenic acid Chemical Properties

Boiling point:
694.9±55.0 °C(Predicted)
Density 
1.65
storage temp. 
2-8°C
solubility 
DMSO : 50 mg/mL (141.12 mM; Need ultrasonic)
form 
Solid
pka
4.07±0.50(Predicted)
color 
White-pale yellow
optical activity
[α]/D -76.0±5.0°, c = 0.5 in H2O
Stability:
Hygroscopic
InChI
InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(21)25-14-11(19)6-16(24,15(22)23)7-12(14)20/h1-5,11-12,14,17-20,24H,6-7H2,(H,22,23)/t11-,12-,14-,16+/m1/s1
InChIKey
GYFFKZTYYAFCTR-NCZKRNLISA-N
SMILES
O([C@H]1[C@@H](C[C@](C[C@H]1O)(O)C(=O)O)O)C(=O)C=CC1C=CC(=C(C=1)O)O
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Safety Information

WGK Germany 
3
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Cryptochlorogenic acid Usage And Synthesis

Chemical Properties

White needle-shaped crystals, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from Eucommia ulmoides, Lonicera japonica, and Honeysuckle.

Uses

Cryptochlorogenic acid may be used as a reference standard in the determination of cryptochlorogenic acid in the leaves of Hibiscus sabdariffa using high performance liquid chromatography coupled with mass spectrometry (HPLC-MS).

Uses

4-O-Caffeoylquinic acid has been used as a reference compound for the quantification in high performance liquid chromatography-diode array detector (HPLC-DAD).

Definition

ChEBI: A cinnamate ester obtained by formal condensation of the carboxy group of trans-caffeic acid with the 4-hydroxy group of (+)-quinic acid.

General Description

Cryptochlorogenic acid is a polyphenol, found in a variety of plants, which plays a crucial role in protection against various age-related diseases.

Biochem/physiol Actions

4-O-Caffeoylquinic acid (4-CQA) is a major active antioxidant marker in mulberry leaf extract. It is an inhibitor of ferroptosis hence, it is recognized as a potent anti-diabetic agent. 4-CQA plays an important role in the upregulation of nuclear factor (erythroid-derived 2)-like 2 (Nrf2) pathway.

in vivo


Pharmacokinetic parameters of Cryptochlorogenic acid after intragastric administration of Cryptochlorogenic acid at three dosages[2]

Dose (mg/kg)Cmax (μg/L)tmax (h)t1/2 (h)AUC0-t (μg?h/L)AUC0-∞ (μg?h/L)MRT0-t (h)MRT0-∞ (h)
100 6300.332.001938.911977.703.213.51
2001270.090.471.973071.873179.413.233.39
4002582.680.442.348825.329139.543.473.93

IC 50

HIF-1α

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