35730-78-0

Basic information

• Product Name: cynaropicrin
• Synonyms: cynaropicrin;2-Hydroxymethylpropenoic acid (3aR,4S,6aβ,9aβ,9bα)-dodecahydro-8α-hydroxy-3,6,9-tris(methylene)-2-oxoazuleno[4,5-b]furan-4-yl ester;Cynaropikrin;[(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate;2-methylolacrylic acid [(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-2-keto-3,6,9-trimethylene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] ester;CYNAROPICRIN(SH)
• CAS NO: 35730-78-0
• Molecular Formula: C₁₉H₂₂O₆
• Molecular Weight: 346.377
• Mol File: 35730-78-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 566.2 °C at 760 mmHg
• Flash Point: 203.8 °C
• Appearance: /
• Density: 1.28±0.1 g/cm3 (20 ºC 760 Torr)
• Refractive Index: 1.571
• PKA: 13.52±0.10(Predicted)
• CAS DataBase Reference: cynaropicrin(CAS DataBase Reference)
• NIST Chemistry Reference: cynaropicrin(35730-78-0)
• EPA Substance Registry System: cynaropicrin(35730-78-0)

Safety Data

• Hazardous Substances Data: 35730-78-0(Hazardous Substances Data)

Usage

Description

Cynaropicrin is a natural compound derived from plants, specifically from the seeds of the Cynara cardunculus, which is a thistle species. It is known for its anti-inflammatory and immunosuppressive properties, making it a potential candidate for various pharmaceutical applications.

Uses

Used in Pharmaceutical Industry:
Cynaropicrin is used as an anti-inflammatory agent for its ability to inhibit lipopolysaccharide-induced TNF-α release from both murine and human macrophage cells in a dose-dependent manner. This property makes it a promising candidate for the treatment of inflammatory diseases.
Additionally, Cynaropicrin is used as an immunosuppressive agent due to its ability to suppress NF-κB signaling, which plays a crucial role in the regulation of immune responses and inflammation.
Furthermore, Cynaropicrin is used as a chondroprotective agent for its ability to inhibit the increase of cartilage degradation factor (MMP13), which is involved in the breakdown of cartilage in conditions like osteoarthritis.

InChI:InChI=1/C19H22O6/c1-8-5-14(24-18(22)9(2)7-20)16-11(4)19(23)25-17(16)15-10(3)13(21)6-12(8)15/h12-17,20-21H,1-7H2/t12-,13-,14-,15-,16+,17-/m0/s1

Upstream product

• 859843-12-2 (5R)-2-hydroxymethyl-5-isopropenyl-cyclohex-2-enone 

Downstream Products

• 35932-46-8 deacylcynaropicrin 
• 68370-45-6 aguerin B 
• 71305-80-1 8α-acetoxyzaluzanin D 

Relevant articles and documents

Total synthesis of cynaropicrin

Cynaropicrin is found in artichoke (Cynara scolymus) and is the source of its bitter taste and it is a sesquiterpene lactone with a 5-7-5 tricyclic skeleton, six chiral centers, and fourexo-olefins. This natural product has numerous attractive biological activities including the inhibition of NF-κB activation, antihepatitis C activity, and antitrypanosomal activity. In this study, the first total synthesis of cynaropicrin was achieved starting from (S)-α-pinene. The synthesis involved a stereoselective Favorskii rearrangement and an indium-promoted diastereoselective Barbier reaction.

SESQUITERPENE LACTONES IN MONGOLIAN Saussurea lipshitzii

Five known guaianolides were isolated from the areal part of Saussurea lipshitzii (Asteraceae) collected in South Gobi, Mongolia: cynaropicrin (I), janerin (II), chlorojanerin (III), 15-deschloro-15-acetoxychlorojanerin (IV), and 15-deschloro-15-hydroxychlorojanerin (V).The correlation between I-V and the β-configuration of the C-4/C-15 bond in II-V was shown by biomimetic chemical transformations, suggesting compound I as the possible common precursor.