4,6,6-Trimethylbicyclo(3.1.1)hept-3-en-2-one
Basic information
- CAS
18309-32-5- Standard SMILES
CC1=CC(=O)C2CC1C2(C)C- InChIKey
DCSCXTJOXBUFGB-UHFFFAOYSA-N- Molecular formula
- C10H14O
- Average molar mass
- 150.22 g/mol
- Monoisotopic mass
- 150.10446507
Overview
4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one is a carbobicyclic compound that is bicyclo[3.1.1]heptane which is substituted by an oxo group at position 2 and by methyl groups at positions 4, 6 and 6, and which contains a double bond between positions 3 and 4. It is a carbobicyclic compound, a cyclic ketone and an enone.
Names & identifiers
- Preferred name
- 4,6,6-Trimethylbicyclo(3.1.1)hept-3-en-2-one
- IUPAC
- 4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one
- English name
- Verbenone
- Molecular formula
- C10H14O
- Molecular weight
- 150.22
Names & synonyms
4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-oneCHEBI:783154,6,6-Trimethylbicyclo(3.1.1)hept-3-en-2-oneRefChem:507895dl-Verbenone2-Pinen-4-oned-VerbenoneNSC6832Verbinone2,6,6-trimethylbicyclo[3.1.1]hept-2-en-4-oneST069322Verbenone, (d)-
Show more names
Nsc36846VerbenoneVerbenone,(d)(+)-VERBENONE(R)-(+)-VerbenoneVerbenone, (+)- vone(1r,5r)-(+)-2-pinen-4-on(1R,5R)-(+)-2-Pinen-4-one
Verbenone, (L)-5480-12-6(1S,5S)-VerbenoneNSC 6831(-)-cis-verbenoneNSC 36846Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-, (1R)-4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one, (1R,5R)-
Database identifiers
- CAS
18309-32-5、5480-12-6、80-57-9- PubChem CID
- 29025
- DTXSID
DTXSID2048115- ChEBI
Properties
Computed structural properties
- XLogP
- 1.6
- Topological polar surface area
- 17.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 248
Experimental & physicochemical properties
SpringerMaterials PropertiesOptical coefficient
LogP2.23
Physicochemical properties
- Melting point
- 6.5 ° · 6.5°
- alpha
- 18 · D18 +249.62°
- Boiling point
- 12 · bp12 102-105°; bp760 227-228°
- Density
- 20 · d20 0.9780
- refractive index
- 18 · nD18 1.4957
- storage temp.
- 0 · Store at 0-8 °C
- solubility
- Chloroform (Sparingly), Methanol (Slightly)
- form
- Oil
- color
- Colourless to Pale Yellow
- Cosmetics Ingredients Functions
- PERFUMING
- InChI
- InChI=1S/C10H14O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-8H,5H2,1-3H3/t7-,8+/m1/s1
- InChIKey
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 69.8% (90 of 129) of all reports.
Warning
H302 (30.2%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P270, P272, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 129 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationChemical: Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-, (1R)-
Other Safety InformationIMAP assessments - Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-, (1R)-: Environment tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (30.2%)
Safety data
- tsca
- TSCA listed
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H315-H319
- Precautionary statements
- P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362
Chemistry & industry
Additional notes
DefinitionChEBI: (R)-(+)-verbenone is a 4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one in which both chiral centres have R configuration. It is a component of Spanish verbena oil, from Verbena triphylla. It has a role as a plant metabolite. It is a terpenoid and a 4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one. It is an enantiomer of a (S)-(-)-verbenone.
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Related reactions
1 records
Compound notes
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