Rotundifolone
Basic information
- CAS
35178-55-3- Standard SMILES
CC(C)=C1CC[C@]2(C)O[C@@H]2C1=O- InChIKey
AKASWINDKIEEBO-ZJUUUORDSA-N- Molecular formula
- C10H14O2
- Average molar mass
- 166.22 g/mol
- Monoisotopic mass
- 166.09937969
Overview
Rotundifolone is an oxacycle.
Names & identifiers
- Preferred name
- Rotundifolone
- IUPAC
- (1S,6S)-6-methyl-3-propan-2-ylidene-7-oxabicyclo[4.1.0]heptan-2-one
- English name
- [1S,6S,(+)]-6-Methyl-3-(1-methylethylidene)-7-oxabicyclo[4.1.0]heptane-2-one
- Molecular formula
- C10H14O2
- Molecular weight
- 166.22
Names & synonyms
Rotundifolone3564-96-3(1S,6S)-6-methyl-3-propan-2-ylidene-7-oxabicyclo[4.1.0]heptan-2-oneDTXSID301317536(1S,6S)-3-isopropylidene-6-methyl-7-oxabicyclo(4.1.0)heptan-2-one(1S,6S)-6-methyl-3-propan-2-ylidene-7-oxabicyclo(4.1.0)heptan-2-oneRefChem:179963DTXCID901747345Piperitenone oxideLippionecis-Piperitenone epoxidePiperitenone oxide [FHFI]
Show more names
(+-)-[1S,6S,(+)]-6-Methyl-3-(1-methylethylidene)-7-oxabicyclo[4.1.0]heptan-2-one7-Oxabicyclo[4.1.0]heptan-2-one, 6-methyl-3-(1-methylethylidene)-, (1S,6S)-[1S,6S,(+)]-6-Methyl-3-(1-methylethylidene)-7-oxabicyclo[4.1.0]heptane-2-one
(+-)-RotundifoloneFEMA No. 4199(+-)-Piperitenone oxideUNII-6FR5IOD112(+)-RotundifolonePiperitenone oxide, (+-)-6FR5IOD1127-Oxabicyclo(4.1.0)heptan-2-one, 6-methyl-3-(1-methylethylidene)-, (1S)-
Database identifiers
- CAS
35178-55-3、3564-96-3- PubChem CID
- 442497
- DTXSID
DTXSID301317536- ChEBI
CHEBI:8900- UNII
- 6FR5IOD112
- Nikkaji
- J16.191H
Properties
Computed structural properties
- XLogP
- 1.8
- Topological polar surface area
- 29.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 274
Experimental & physicochemical properties
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Physicochemical properties
- Melting point
- 27.5 °C · 27.5 °C
- Boiling point
- 80 · 80-85 °C(Press: 4 Torr)
- Density
- 1.0497 g/cm3 · 1.0497 g/cm3(Temp: 22 °C)
- FDA UNII
- 6 FR5IOD112 · 6FR5IOD112
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory InformationCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Chemistry & industry
Uses & manufacturing
Use ClassificationFlavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Applications
UsesPiperitenone oxide (lippione), a monoterpene, can be isolated from the n-hexane extract from spearmint (Mentha spicata) leaves. Piperitenone oxide is a potent inducer of differentiation in a RCM-1 human colon cancer cell line[1].
Additional notes
DefinitionChEBI: Rotundifolone is an oxacycle.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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