Cynaropicrin , CAS No.35730-78-0

Item Number
C646868
Grouped product items
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C646868-1mg
1mg
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$70.90
C646868-5mg
5mg
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C646868-10mg
10mg
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$270.90

Phenols

Basic Description

SynonymsCynaropicrin | 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)-
Biochemical and Physiological MechanismsCynaropicrin 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 TempProtected from light,Store at -20°C
Shipped InIce 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

Associated Targets(Human)

MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-MEL-2 (46422 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-OV-3 (52876 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A549 (127892 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HEK293 (82097 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KB (17409 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCT-15 (51914 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RELA Tchem Nuclear factor NF-kappa-B p65 subunit (627 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

murA UDP-N-acetylglucosamine 1-carboxyvinyltransferase (389 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypanosoma brucei (78846 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mus musculus (284745 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypanosoma brucei rhodesiense (7991 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
L6 (7924 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Sitophilus granarius (35 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trogoderma granarium (29 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Tribolium confusum (93 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Names and Identifiers

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
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

Certificates

Certificate of Analysis(COA)

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Chemical and Physical Properties

SolubilityDMSO : ≥ 50 mg/mL (144.35 mM)
Flash Point(°F)Not applicable
Flash Point(°C)Not applicable

Safety and Hazards(GHS)

Pictogram(s) GHS07
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.

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