(3aR,4S,6E,10E,11aR)-4-(Acetyloxy)-3a,4,5,8,9,11a-hexahydro-6,10-dimethyl-3-methylenecyclodeca(b)furan-2(3H)-one
Basic information
- CAS
24164-12-3- Standard SMILES
C=C1C(=O)O[C@@H]2/C=C(\C)CC/C=C(\C)C[C@H](OC(C)=O)[C@@H]12- InChIKey
UPNVKIZABMRHNR-DUUXJKDPSA-N- Molecular formula
- C17H22O4
- Average molar mass
- 290.4 g/mol
- Monoisotopic mass
- 290.15180918
Overview
Tulipinolide is a germacranolide based on a 2,3,3a,4,5,8,9,11a-octahydrocyclodeca[b]furan-4-yl skeleton. It has a role as a metabolite and an allergen.
Names & identifiers
- Preferred name
- (3aR,4S,6E,10E,11aR)-4-(Acetyloxy)-3a,4,5,8,9,11a-hexahydro-6,10-dimethyl-3-methylenecyclodeca(b)furan-2(3H)-one
- IUPAC
- [(3aR,4S,6E,10E,11aR)-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] acetate
- English name
- (3aR,4S,6E,10E,11aR)-4-Acetoxy-3a,4,5,8,9,11a-hexahydro-6,10-dimethyl-3-methylenecyclodeca[b]furan-2(3H)-one
- Molecular formula
- C17H22O4
- Molecular weight
- 290.35
Names & synonyms
Tulipinolide24164-12-3CHEBI:9776DTXSID90415129(3aR,4S,6E,10E,11aR)-6,10-dimethyl-3-methylidene-2-oxo-2,3,3a,4,5,8,9,11a-octahydrocyclodeca[b]furan-4-yl acetate[(3aR,4S,6E,10E,11aR)-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] acetate((3aR,4S,6E,10E,11aR)-6,10-dimethyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca(b)furan-4-yl) acetate(3aR,4S,6E,10E,11aR)-6,10-dimethyl-3-methylidene-2-oxo-2,3,3a,4,5,8,9,11a-octahydrocyclodeca(b)furan-4-yl acetateRefChem:1050145DTXCID60365980(3aR,4S,6E,10E,11aR)-4-(Acetyloxy)-3a,4,5,8,9,11a-hexahydro-6,10-dimethyl-3-methylenecyclodeca(b)furan-2(3H)-oneEPITULIPINOLIDE
Show more names
Cyclodeca[b]furan-2(3H)-one, 4-(acetyloxy)-3a,4,5,8,9,11a-hexahydro-6,10-dimethyl-3-methylene-, (3aR,4S,6E,10E,11aR)-
8alpha-acetoxycostunolideSCHEMBL29934342(3aR,4S,6E,10E,11aR)-4-Acetoxy-3a,4,5,8,9,11a-hexahydro-6,10-dimethyl-3-methylenecyclodeca[b]furan-2(3H)-oneC09564Q27108492(3aR,4S,11aR)-6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl acetate
Properties
Computed structural properties
- XLogP
- 2.4
- Topological polar surface area
- 52.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 527
Chemistry & industry
Additional notes
DefinitionChEBI: A germacranolide based on a 2,3,3a,4,5,8,9,11a-octahydrocyclodeca[b]furan-4-yl skeleton.
Related reactions
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Compound notes
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