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SKU | Size | Availability | Price | Qty |
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C646868-1mg | 1mg | Available within 8-12 weeks(?) Production requires sourcing of materials. We appreciate your patience and understanding. | $70.90 | |
C646868-5mg | 5mg | Available within 8-12 weeks(?) Production requires sourcing of materials. We appreciate your patience and understanding. | $170.90 | |
C646868-10mg | 10mg | Available within 8-12 weeks(?) Production requires sourcing of materials. We appreciate your patience and understanding. | $270.90 |
Phenols
Synonyms | Cynaropicrin | 35730-78-0 | Cynaropikrin | 2-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 ester | CHEBI:4038 | CHEMBL374146 | M9233789I9 | UNII-M9233789I9 | [(3aR,4S,6aR,8S,9aR,9bR)- |
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Biochemical and Physiological Mechanisms | Cynaropicrin is a sesquiterpene lactone which can inhibit tumor necrosis factor ( TNF-α ) release with IC 50 s of 8.24 and 3.18 μM for murine and human macrophage cells, respectively. Cynaropicrin also inhibits the increase of cartilage degradation factor |
Storage Temp | Protected from light,Store at -20°C |
Shipped In | Ice chest + Ice pads |
Product Description | Cynaropicrin is a sesquiterpene lactone which can inhibit tumor necrosis factor ( TNF-α ) release with IC 50 s of 8.24 and 3.18 μM for murine and human macrophage cells, respectively. Cynaropicrin also inhibits the increase of cartilage degradation factor ( MMP13 ) and suppresses NF-κB signaling. In Vitro Cynaropicrin strongly inhibits lipopolysaccharide-induced TNF-α release from either murine or human macrophage cells in a dose-dependent manner with the IC 50 values of 8.24 and 3.18 μM, respectively. Cynaropicrin shows significant inhibitory effects toward all mitogenic signals with the IC 50 values of 1.20 (concanavalin A), 1.02 (phytohemagglutinin) and 0.90 μM (lipopolysaccharide), respectively. Cynaropicrin suppresses CTLL-2 cell proliferation in a dose-dependent manner and the 50% inhibitory concentration (IC 50 ) of Cynaropicrin for CTLL-2 cell growth is 0.91 μM. The increased mRNA expression of MMP13 induced by TNF-α is similarly inhibited in a concentration-dependent manner by Cynaropicrin. The increased mRNA expression of HIF-2α induced by IL-1β in SW1353 is inhibited in a concentration-dependent manner by Cynaropicrin. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Form:Oil IC50& Target:MMP13|NF-κB |
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IUPAC Name | [(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 |
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INCHI | 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 |
InChi Key | KHSCYOFDKADJDJ-NQLMQOPMSA-N |
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 |
PubChem CID | 119093 |
Molecular Weight | 346.37 |
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Solubility | DMSO : ≥ 50 mg/mL (144.35 mM) |
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Flash Point(°F) | Not applicable |
Flash Point(°C) | Not applicable |
Pictogram(s) | GHS07 |
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Signal | Warning |
Hazard Statements | H317:May cause an allergic skin reaction |
Precautionary Statements | P261:Avoid breathing dust/fume/gas/mist/vapors/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of water. P272:Contaminated work clothing should not be allowed out of the workplace. P333+P313:IF SKIN irritation or rash occurs: Get medical advice/attention. P362+P364:Take off contaminated clothing and wash it before reuse. |