Cryptochlorogenic acid
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
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
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 | 630 | 0.33 | 2.00 | 1938.91 | 1977.70 | 3.21 | 3.51 |
| 200 | 1270.09 | 0.47 | 1.97 | 3071.87 | 3179.41 | 3.23 | 3.39 |
| 400 | 2582.68 | 0.44 | 2.34 | 8825.32 | 9139.54 | 3.47 | 3.93 |
IC 50
HIF-1α
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