(3aS,9aS,9bS)-6,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

• ChemBase ID: 154820
• Molecular Formular: C15H16O3
• Molecular Mass: 244.28574
• Monoisotopic Mass: 244.10994437
• SMILES: CC1=C2[C@@H]([C@@H]3[C@@H](CC1)C(=C)C(=O)O3)C(=CC2=O)C
• Canonical SMILES: CC1=CC(=O)C2=C(C)CC[C@@H]3[C@@H]([C@@H]12)OC(=O)C3=C
• InChI: InChI=1S/C15H16O3/c1-7-4-5-10-9(3)15(17)18-14(10)13-8(2)6-11(16)12(7)13/h6,10,13-14H,3-5H2,1-2H3/t10-,13-,14-/m0/s1
• InChIKey: SKNVIAFTENCNGB-BPNCWPANSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aS,9aS,9bS)-6,9-dimethyl-3-methylidene-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione
• IUPAC Traditional name: (3aS,9aS,9bS)-6,9-dimethyl-3-methylidene-3aH,4H,5H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione
• Synonyms: 11,13-Dehydroleucodin; Dehydroleucodin; Leucodin; Lidbeckialactone; Mesatlantin E; NSC 180034; [3aS-(3aalpha,9aalpha,9bbeta)]-3,3a,4,5,9a,9b-hexahydro-6,9-dimethyl-3-methylene-azuleno[4,5-b]furan-2,7-dione; dehydro-; Dehydroleucodine

Database IDs

• CAS Number: 36150-07-9
• MDL Number: MFCD06794926
• PubChem SID: 162248958
• PubChem CID: 73440

CALCULATED PROPERTIES

• Acid pKa: 15.133956
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.6081917
• LogD (pH = 7.4): 2.6081917
• Log P: 2.6081917
• Molar Refractivity: 68.5197 cm^3
• Polarizability: 26.285416 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥30 mg/mL
• Apperance: white to off-white powder

Safety Information

• Storage Condition: desiccated; protect from light; under inert gas
• German water hazard class: 3
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C15H16O3

DETAILS

Sigma Aldrich - D4196

Biochem/physiol Actions
Dehydroleucodine is a sesquiterpene lactone isolated from Artemisia douglasiana Besser; mast cell stabilizers. An extract from the plant is widely used in Cuyo region (Argentina) as folk medicine for the treatment of gastric ailments. The compound prevents gastric and duodenal damages in response to necrosis-inducing agents. Stabilization of mast cells may be a key mechanism to protect the gastrointestinal tract from injury and ulceration. Recently, it was established that dehydroleucodine and xanthatin inhibit mast cell degranulation induced by compound 48/80.