(4R,9S,11aS)-4,9-dihydroxy-6-methyl-3,10-dimethylidene-2H,3H,3aH,4H,7H,8H,9H,10H,11H,11aH-cyclodeca[b]furan-2-one

• ChemBase ID: 179757
• Molecular Formular: C15H20O4
• Molecular Mass: 264.3169
• Monoisotopic Mass: 264.13615912
• SMILES: C1(=O)C(=C)C2[C@@H](O1)CC(=C)[C@H](CCC(=C[C@H]2O)C)O
• Canonical SMILES: CC1=C[C@@H](O)C2[C@H](CC(=C)[C@H](CC1)O)OC(=O)C2=C
• InChI: InChI=1S/C15H20O4/c1-8-4-5-11(16)9(2)7-13-14(12(17)6-8)10(3)15(18)19-13/h6,11-14,16-17H,2-5,7H2,1H3/b8-6+/t11-,12+,13-,14?/m0/s1
• InChIKey: KNEQPJSDSYNUHP-FPTOJPCGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,9S,11aS)-4,9-dihydroxy-6-methyl-3,10-dimethylidene-2H,3H,3aH,4H,7H,8H,9H,10H,11H,11aH-cyclodeca[b]furan-2-one
• IUPAC Traditional name: (4R,9S,11aS)-4,9-dihydroxy-6-methyl-3,10-dimethylidene-2H,3H,3aH,4H,7H,8H,9H,10H,11H,11aH-cyclodeca[b]furan-2-one
• Synonyms: 1,6-Dihydroxy-4,10(14),11(13)-germacratrien-12,8-olide; Tanachin

Database IDs

• CAS Number: 60362-95-0
• PubChem SID: 164235667
• PubChem CID: 9992972

CALCULATED PROPERTIES

• Acid pKa: 6.6218963
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.2667314
• LogD (pH = 7.4): 0.47061834
• Log P: 1.2981274
• Molar Refractivity: 71.9601 cm^3
• Polarizability: 28.189013 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Product Information

• Biological Source: Constit. of Tanacetum pseudoachillea
• Application(s): Phytoncide

REFERENCES

• Yunusov, A.I. et al., Khim. Prir. Soedin., 1976, 12, 263; 462; Chem. Nat. Compd. (Engl. Transl.), 1976, 12, 236; 408, (Tanachin)
• El-Feraly, F.S. et al., J.C.S. Perkin 1, 1983, 355, (synth)
• Makhmudov, M.K. et al., Khim. Prir. Soedin., 1989, 25, 198; Chem. Nat. Compd. (Engl. Transl.), 1989, 25, 168, (cryst struct)
• Sanz, J.F. et al., J. Nat. Prod., 1991, 54, 591, (pmr, cmr)