Cynaropicrin

Base Information

• Chemical Name: Cynaropicrin
• CAS No.: 35730-78-0
• Molecular Formula: C₁₉H₂₂O₆
• Molecular Weight: 346.38
• European Community (EC) Number: 689-765-5
• UNII: M9233789I9
• DSSTox Substance ID: DTXSID20957143
• Nikkaji Number: J17.402E
• Wikipedia: Cynaropicrin
• Wikidata: Q15410905
• ChEMBL ID: CHEMBL374146
• Mol file: 35730-78-0.mol

Synonyms:cynaropicrin

Chemical Property of Cynaropicrin

Chemical Property:

• Refractive Index: 1.571
• Boiling Point: 566.2 °C at 760 mmHg
• PKA: 13.52±0.10(Predicted)
• Flash Point: 203.8 °C
• PSA: 93.06000
• Density: 1.28 g/cm³
• LogP: 1.05760
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 346.14163842
• Heavy Atom Count: 25
• Complexity: 690

Purity/Quality:

98% ^*data from raw suppliers

Cynaropicrin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=C1CC(C2C(C3C1CC(C3=C)O)OC(=O)C2=C)OC(=O)C(=C)CO
• Isomeric SMILES: C=C1C[C@@H]([C@@H]2[C@@H]([C@@H]3[C@H]1C[C@@H](C3=C)O)OC(=O)C2=C)OC(=O)C(=C)CO
• Uses: Cynaropicrin can inhibit lipopolysaccharide-induced TNF-α release from either murine or human macrophage cells in a dose-dependent manner with the IC50 values of 8.24 and 3.18 μM, respectively. It can also inhibit the increase of cartilage degradation factor (MMP13) and suppresses NF-κB signaling.

Technology Process of Cynaropicrin

There total 26 articles about Cynaropicrin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

(3aR,4S,6aR,8S,9aR,9bR)-8-((tert-butyldimethylsilyl)oxy)-3,6,9-trimethylene-2-oxododecahydroazuleno[4,5-b]furan-4-yl 2-(((triisopropylsilyl)oxy)methyl)acrylate → cynaporicrin (35932-39-9,35730-78-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 4h; Inert atmosphere;

DOI:10.1016/j.bmcl.2015.10.065

Reference yield: 23.0%

(3aR,4S,6aR,8S,9aR,9bR)-8-(methoxymethoxy)-3,6,9-trimethylene-2-oxododecahydroazuleno[4,5-b]furan-4-yl 2-(((triisopropylsilyl)oxy)methyl)acrylate → cynaporicrin (35932-39-9,35730-78-0)

Guidance literature:

With pyridinium p-toluenesulfonate; In tert-butyl alcohol; for 44h; Inert atmosphere; Reflux;

DOI:10.1016/j.bmcl.2015.10.065

Reference yield:

C27H30O7 → cynaporicrin (35932-39-9,35730-78-0)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In aq. phosphate buffer; dichloromethane; at 0 ℃; for 4h; pH=7;

DOI:10.1039/d1ob00657f

upstream raw materials:

chlorojanerin

Downstream raw materials:

aguerin B

deacylcynaropicrin

8α-acetoxyzaluzanin D

Refernces

• 1、 Sato, Takuya,Hara, Shihori,Sato, Makiko,Ogawa, Keita,Adams, Michael,Usuki, Toyonobu. "Synthesis of cynaropicrin-d4". . p. 5504 - 5507. Retrieved 2015/11/18.