Physicochemical Properties
| Molecular Formula | C₁₆H₁₈O₉ |
| Molecular Weight | 354.31 |
| Exact Mass | 354.095 |
| CAS # | 905-99-7 |
| PubChem CID | 9798666 |
| Appearance | White to off-white solid powder |
| Density | 1.7±0.1 g/cm3 |
| Boiling Point | 694.9±55.0 °C at 760 mmHg |
| Flash Point | 256.8±25.0 °C |
| Vapour Pressure | 0.0±2.3 mmHg at 25°C |
| Index of Refraction | 1.690 |
| LogP | -0.97 |
| Hydrogen Bond Donor Count | 6 |
| Hydrogen Bond Acceptor Count | 9 |
| Rotatable Bond Count | 5 |
| Heavy Atom Count | 25 |
| Complexity | 520 |
| Defined Atom Stereocenter Count | 2 |
| SMILES | C1[C@H](C([C@@H](CC1(C(=O)O)O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O |
| InChi Key | GYFFKZTYYAFCTR-JUHZACGLSA-N |
| InChi Code | 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)/b4-2+/t11-,12-,14-,16+/m1/s1 |
| Chemical Name | (1α,3R,4α,5R)-4-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-1,3,5-trihydroxy-cyclohexanecarboxylic acid |
| Synonyms | 4-Caffeoylquinic acid Cryptochlorogenic acid 4-O-Caffeoylquinic Acid |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| References |
[1]. Wang Jing, ea al.Simultaneous determination of chlorogenic acid,cryptochlorogenic acid,caffeic acid,naringin,hesperidin and linarin in Xiao′erjinning oral liquid by an HPLC method. China Journal of Chinese Materia Medica, 2010-13. [2]. Cryptochlorogenic acid attenuates LPS-induced inflammatory response and oxidative stress via upregulation of the Nrf2/HO-1 signaling pathway in RAW 264.7 macrophages. Int Immunopharmacol. 2020;83:106436. [3]. Cryptochlorogenic acid and its metabolites ameliorate myocardial hypertrophy through a HIF1α-related pathway. Food Funct. 2022;13(4):2269-2282. Published 2022 Feb 21. |
| Additional Infomation |
4-O-trans-caffeoylquinic acid is a cinnamate ester obtained by formal condensation of the carboxy group of trans-caffeic acid with the 4-hydroxy group of (+)-quinic acid. It has a role as a metabolite and a hepatoprotective agent. It is a cinnamate ester and a cyclitol carboxylic acid. It is functionally related to a (+)-quinic acid and a trans-caffeic acid. Cryptochlorogenic acid has been reported in Erigeron breviscapus, Hypericum perforatum, and other organisms with data available. See also: Cryptochlorogenic acid (annotation moved to). |
Solubility Data
| Solubility (In Vitro) | DMSO : ~50 mg/mL (~141.12 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.06 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 2.5 mg/mL (7.06 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (7.06 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.8224 mL | 14.1119 mL | 28.2239 mL | |
| 5 mM | 0.5645 mL | 2.8224 mL | 5.6448 mL | |
| 10 mM | 0.2822 mL | 1.4112 mL | 2.8224 mL |