Cynaropicrin
Basic information
- CAS
35730-78-0- Standard SMILES
C=C(CO)C(=O)O[C@H]1CC(=C)[C@@H]2C[C@H](O)C(=C)[C@@H]2[C@H]2OC(=O)C(=C)[C@@H]21- InChIKey
KHSCYOFDKADJDJ-NQLMQOPMSA-N- Molecular formula
- C19H22O6
- Average molar mass
- 346.4 g/mol
- Monoisotopic mass
- 346.14163842
Overview
Cynaropicrin is a sesquiterpene lactone.
Names & identifiers
- Preferred name
- Cynaropicrin
- IUPAC
- [(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
- English name
- cynaropicrin
- Molecular formula
- C19H22O6
- Molecular weight
- 346.37
Names & synonyms
Cynaropicrin35730-78-02-Propenoic acid, 2-(hydroxymethyl)-, (3aR,4S,6aR,8S,9aR,9bR)-dodecahydro-8-hydroxy-3,6,9-tris(methylene)-2-oxoazuleno(4,5-b)furan-4-yl esterM9233789I9[(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-enoate2-Propenoic acid, 2-(hydroxymethyl)-, dodecahydro-8-hydroxy-3,6,9-tris(methylene)-2-oxoazuleno(4,5-b)furan-4-yl ester, (3aR-(3aalpha,4alpha,6aalpha,8beta,9aalpha,9bbeta))-((3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno(4,5-b)furan-4-yl) 2-(hydroxymethyl)prop-2-enoate((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[(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoateRefChem:34088689-765-5Cynaropikrin
Show more names
Cynaropicrin-RMCynaropicrin(AS)
Properties
Computed structural properties
- XLogP
- 0.6
- Topological polar surface area
- 93.1 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 4
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 690
Physicochemical properties
- Boiling point
- 566.2 · 566.2±50.0 °C(Predicted)
- Density
- 1.28 · 1.28±0.1 g/cm3 (20 ºC 760 Torr)
- storage temp.
- -20 °C, · -20°C, protect from light
- solubility
- 50 · DMSO:50.0(Max Conc. mg/mL);144.35(Max Conc. mM)
- pka
- 13.52 · 13.52±0.10(Predicted)
- form
- Oil
- color
- Off-white to light yellow
- biological source
- plant
- Major Application
- metabolomicsvitamins, nutraceuticals, and natural products
- InChI
- 1S/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
- InChIKey
- KHSCYOFDKADJDJ-NQLMQOPMSA-N
- SMILES
- O1[C@@H]2[C@@H]3[C@@H](C[C@@H](C3=C)O)C(=C)C[C@@H]([C@H]2C(=C)C1=O)OC(=O)C(=C)CO
- LogP
- 1.34 · 1.340 (est)
- FDA UNII
- 9233789 I9 · M9233789I9
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesSkin Sens. 1 (100%)
Safety data
- wgk
- WGK 3
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H317
- Hazard Classifications
- Skin Sens. 1
- Precautionary statements
- P261-P272-P280-P333+P313-P362+P364-P501
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Substances that are toxic to cells; they may be involved in immunity or may be contained in venoms. These are distinguished from CYTOSTATIC AGENTS in degree of effect. Some of them are used as CYTOTOXIC ANTIBIOTICS. The mechanism of action of many of these are as ALKYLATING AGENTS or MITOSIS MODULATORS.
Applications
UsesCynaropicrin 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.
Additional notes
DefinitionChEBI: Cynaropicrin is a sesquiterpene lactone.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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