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Eupalinolide B

CAT: 0804-HY-N0753-04Size: 50 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N0753-04Size:50 mg
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Description
Eupalinolide B is a germ sesquiterpene. Eupalinolide B can be isolated from Eupatorium lindleyanum. Eupalinolide B induces Apoptosis, elevates ROS, promotes Autophagy. regulates GSK-3β/β-catenin, targets UBE2D3 and TAK1, activates ROS-ER-JNK, inhibits NF-κB and MAPKs. Eupalinolide B has anticancer activity against pancreatic cancer and liver cancer. Eupalinolide B relieves rheumatoid arthritis, acute lung injury, periodontitis, depression[1][2][3][4][5][6][7].
CAS Number
877822-41-8
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Apoptosis; Autophagy; GSK-3; JNK; MAP3K; NF-κB; p38 MAPK; Reactive Oxygen Species (ROS) ; β-catenin
Type
Natural Products
Related Pathways
Apoptosis; Autophagy; Immunology/Inflammation; MAPK/ERK Pathway; Metabolic Enzyme/Protease; NF-κB; PI3K/Akt/mTOR; Stem Cell/Wnt
Applications
Cancer-programmed cell death
Field of Research
Cancer; Inflammation/Immunology; Neurological Disease
Assay Protocol
https://www.medchemexpress.com/eupalinolide-b.html
Purity
99.48
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
O=C(O[C@@H]1C/C(COC(C)=O)=C/C[C@H](OC(C)=O)/C(C)=C/[C@@]([C@]1([H])C2=C)([H])OC2=O)/C(C)=C/CO
Molecular Formula
C24H30O9
Molecular Weight
462.49
Precautions
H302, H315, H319, H335
References & Citations
[1]Yang NY, et al. Cytotoxic sesquiterpene lactones from Eupatorium lindleyanum. J Asian Nat Prod Res. 2007 Apr-Aug;9 (3-5) :339-45.|[2]Huang Q, et al. Eupalinolide B suppresses pancreatic cancer by ROS generation and potential cuproptosis. iScience. 2024 Jul 14;27 (8) :110496.|[3]Gu SL, et al. Eupalinolide B alleviates rheumatoid arthritis through the promotion of apoptosis and autophagy via regulating the AMPK/mTOR/ULK-1 signaling axis. Int Immunopharmacol. 2025 Feb 20;148:114179.|[4]Yang L, et al. Eupalinolide B attenuates lipopolysaccharide-induced acute lung injury through inhibition of NF-κB and MAPKs signaling by targeting TAK1 protein. Int Immunopharmacol. 2022 Oct;111:109148.|[5]Zhang Y, et al. Eupalinolide B inhibits hepatic carcinoma by inducing ferroptosis and ROS-ER-JNK pathway. Acta Biochim Biophys Sin (Shanghai) . 2022 Jul 25;54 (7) :974-986.|[6]Kuang W, et al. Eupalinolide B inhibits periodontitis development by targeting ubiquitin conjugating enzyme UBE2D3. MedComm (2020) . 2025 Jan 14;6 (1) :e70034.|[7]Wang TT, et al. Eupalinolide B alleviates corticosterone-induced PC12 cell injury and improves depression-like behaviors in CUMS rats by regulating the GSK-3β/β-catenin pathway. Biochem Pharmacol. 2025 May;235:116831.
Shipping Conditions
Blue Ice
Storage Conditions
-20°C (Powder, protect from light)
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

Eupalinolide A

Eupalinolide B has been reported in Eupatorium lindleyanum with data available.

CAS Number877822-41-8
PubChem CID71463992
IUPAC Name[(3aR,4R,6Z,9S,10E,11aR)-9-acetyloxy-6-(acetyloxymethyl)-10-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (E)-4-hydroxy-2-methylbut-2-enoate
Molecular FormulaC24H30O9
Molecular Weight462.5
XLogP1.2
Topological Polar Surface Area125
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count9
Rotatable Bond Count9
Heavy Atom Count33
Formal Charge0
Complexity909
SMILES
C/C/1=C\[C@@H]2[C@@H]([C@@H](C/C(=C/C[C@@H]1OC(=O)C)/COC(=O)C)OC(=O)/C(=C/CO)/C)C(=C)C(=O)O2
InChI
InChI=1S/C24H30O9/c1-13(8-9-25)23(28)32-21-11-18(12-30-16(4)26)6-7-19(31-17(5)27)14(2)10-20-22(21)15(3)24(29)33-20/h6,8,10,19-22,25H,3,7,9,11-12H2,1-2,4-5H3/b13-8+,14-10+,18-6-/t19-,20+,21+,22-/m0/s1
InChIKey
HPWMABTYJYZFLK-FHEQDPKSSA-N
Chemical Structure
2D Structure
2D structure of Eupalinolide A
CAS: 877822-41-8
CID: 71463992
Formula: C24H30O9
MW: 462.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight462.5
XLogP31.2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count9
Rotatable Bond Count9
Exact Mass462.18898253
Monoisotopic Mass462.18898253
Topological Polar Surface Area125 Ų
Heavy Atom Count33
Formal Charge0
Complexity909
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count3
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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