Tomentosin
Basic information
- CAS
33649-15-9- Standard SMILES
C=C1C(=O)O[C@@H]2C[C@H](C)C(CCC(C)=O)=CC[C@H]12- InChIKey
AVFIYMSJDDGDBQ-CUOATXAZSA-N- Molecular formula
- C15H20O3
- Average molar mass
- 248.32 g/mol
- Monoisotopic mass
- 248.1412445
Overview
Tomentosin is a sesquiterpene lactone.
Names & identifiers
- Preferred name
- Tomentosin
- IUPAC
- (3aR,7S,8aR)-7-methyl-3-methylidene-6-(3-oxobutyl)-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one
- English name
- Tomentosin
- Molecular formula
- C15H20O3
- Molecular weight
- 248.32
Names & synonyms
Tomentosin(3aR,7S,8aR)-7-methyl-3-methylidene-6-(3-oxobutyl)-4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-2-one(3aR,7S,8aR)-7-methyl-3-methylidene-6-(3-oxobutyl)-4,7,8,8a-tetrahydro-3aH-cyclohepta(b)furan-2-oneRefChem:933185(3aR,7S,8aR)-7-methyl-3-methylene-6-(3-oxobutyl)-4,7,8,8a-tetrahydro-3aH-cyclohepta(b)furan-2-one33649-15-9(3aR,7S,8aR)-7-Methyl-3-methylene-6-(3-oxobutyl)-3,3a,4,7,8,8a-hexahydro-2H-cyclohepta[b]furan-2-oneXanthalongi6-Deacetoxybritanlin GC09562Tomentosin (Parthenium)2H-Cyclohepta(b)furan-2-one, 3,3a,4,7,8,8a-hexahydro-7-methyl-3-methylene-6-(3-oxobutyl)-, (3aR,7S,8aR)-
Show more names
(3aα)-3-Methylene-6-(3-oxobutyl)-7β-methyl-3,3aα,4,7,8,8aα-hexahydro-2H-cyclohepta[b]furan-2-one(3aR)-3,3aα,4,7,8,8aα-Hexahydro-7β-methyl-3-methylene-6-(3-oxobutyl)-2H-cyclohepta[b]furan-2-one
2H-Cyclohepta[b]furan-2-one, 3,3a,4,7,8,8a-hexahydro-7-methyl-3-methylene-6-(3-oxobutyl)-, (3aR,7S,8aR)-CHEBI:9631orb1981768orb3054532CHEMBL1164483SCHEMBL12476412DTXSID10955274HY-N8284
Database identifiers
- CAS
33649-15-9- PubChem CID
- 155173
- DTXSID
DTXSID10955274- ChEMBL
CHEMBL1164483- ChEBI
CHEBI:9631- Nikkaji
- J146.457D
Properties
Computed structural properties
- XLogP
- 1.9
- Topological polar surface area
- 43.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 3
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 419
Physicochemical properties
- Melting point
- 121 · 121-122 °C(Solv: methanol (67-56-1))
- Boiling point
- 416.2 · 416.2±45.0 °C(Predicted)
- Density
- 1.08 · 1.08±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- Soluble in DMSO (50 mg/ml)
- form
- oil
- color
- Yellow
- Stability
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 2 month.
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319
- Precautionary statements
- 501 · P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319
- Precautionary statements
- P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330
Chemistry & industry
Applications
DescriptionExtracts of Inula which contain tomentosin (33649-15-9) have been used for centuries in traditional medicine for the treatment of inflammation.1 It suppresses the production of inflammatory mediators in RAW264.7 cells by inhibiting NFkB activation.2 It induces telomere shortening and caspase-dependent apoptosis in cervical cancer cells3 and induces apoptosis in human osteosarcoma MG-63 cells4. It causes G2/M arrest and apoptosis in human melanoma cell lines.5
UsesTomentosin is a antiphlogistic sesquiterpene lactone that can be isolated from Inula falconeri.Tomentosin induces apoptosis and inhibits proliferation, migration and invasion of pancreatic cancer cells[1].
Additional notes
DefinitionChEBI: Tomentosin is a sesquiterpene lactone.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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