Parthenolide

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title: "Parthenolide" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["adiponectin-receptor-agonists", "epoxides", "histone-deacetylase-inhibitors", "sesquiterpene-lactones"] topic_path: "general/adiponectin-receptor-agonists" source: "https://en.wikipedia.org/wiki/Parthenolide" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 409336852 | Name = | ImageFile = Parthenolide.svg | OtherNames = | IUPACName = (1aR,4E,7aS,10aS,10bR)-2,3,6,7,7a,8,10a,10b-octahydro-1a,5-dimethyl-8-methylene-oxireno[9,10]cyclodeca[1,2-b]furan-9(1aH)-one | SystematicName = | Section1 = {{Chembox Identifiers | Abbreviations = | CASNo_Ref = | CASNo = 20554-84-1 | EINECS = | PubChem = 5420805 | RTECS = LY4220000 | UNII_Ref = | UNII = 2RDB26I5ZB | InChI = | ChEBI_Ref = | ChEBI = | ChEMBL_Ref = | ChEMBL = 540445 | KEGG_Ref = | KEGG = | ChemSpiderID_Ref = | ChemSpiderID = 20126246 | SMILES = C/C/1=C\CC[C@@]2(C@@H[C@@H]3C@@HC(=C)C(=O)O3)C | InChI2 = 1/C15H20O3/c1-9-5-4-8-15(3)13(18-15)12-11(7-6-9)10(2)14(16)17-12/h5,11-13H,2,4,6-8H2,1,3H3/b9-5+/t11-,12-,13-,15+/m0/s1 | InChIKey = KTEXNACQROZXEV-SLXBATTEBY | StdInChI_Ref = | StdInChI = 1S/C15H20O3/c1-9-5-4-8-15(3)13(18-15)12-11(7-6-9)10(2)14(16)17-12/h5,11-13H,2,4,6-8H2,1,3H3/b9-5+/t11-,12-,13-,15+/m0/s1 | StdInChIKey_Ref = | StdInChIKey = KTEXNACQROZXEV-SLXBATTESA-N}} | Section2 = {{Chembox Properties | C=15|H=20|O=3 | Appearance = | Density = | MeltingPtC = 113 to 115 | BoilingPt = | Solubility = | SolubleOther = | Solvent = | pKa = | pKb = | IsoelectricPt = | SpecRotation = | RefractIndex = | Viscosity = | Dipole = | Section3 = {{Chembox Structure | CrystalStruct = | Coordination = | MolShape = | Dipole = | Section4 = {{Chembox Thermochemistry | DeltaHf = | DeltaHc = | Entropy = | HeatCapacity = | Section5 = {{Chembox Pharmacology | ATCCode = | Bioavail = | Metabolism = | HalfLife = | Excretion = | PregCat = | AdminRoutes = | Section6 = {{Chembox Explosive | ShockSens = | FrictionSens = | DetonationV = | REFactor = | Section7 = {{Chembox Hazards | MainHazards = | NFPA-H = | NFPA-F = | NFPA-R = | NFPA-S = | HPhrases = | PPhrases = | GHS_ref = | FlashPt = | AutoignitionPt = | ExploLimits = | PEL = | Section9 = {{Chembox Related | OtherAnions = | OtherCations = | OtherFunction = | OtherFunction_label = | OtherCompounds =

Parthenolide is a sesquiterpene lactone of the germacranolide class which occurs naturally in the plant feverfew (Tanacetum parthenium), after which it is named, and in the closely related tansy (Tanacetum vulgare). It is found in highest concentration in the flowers and fruit. Parthenolide's molecular structure depiction is often incorrect regarding the stereochemistry of the epoxide, although X-ray single crystal structures are available.

Lack of solubility in water and bioavailability limits the potential of parthenolide as a drug.

References

References

  1. (2009). "Tanacetum vulgare: antiherpes virus activity of crude extract and the purified compound parthenolide". Phytother Res.
  2. (1976). "Crystal and molecular structure of parthenolide [4,5-epoxygermacra-1(10),11(13)-dien-12,6-olactone]". Journal of the Chemical Society, Perkin Transactions 2.
  3. (2013-10-18). "Protection-Group-Free Semisyntheses of Parthenolide and Its Cyclopropyl Analogue". The Journal of Organic Chemistry.

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adiponectin-receptor-agonistsepoxideshistone-deacetylase-inhibitorssesquiterpene-lactones