(1alpha,2alpha,5alpha)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one Property

Melting point:

202-206 °C

Boiling point:

90 °C(Press: 12 Torr)

Density 

0.960 g/cm3(Temp: 22 °C)

solubility 

Insoluble in water, soluble in alcohol and oils.

form 

oily liquid

Specific Gravity

0.97

color 

Colorless or very pale yellowish

Odor

Warm-camphoraceous, Cedarleaf-like, slightly spicy odor of moderate to poor tenacity.

LogP

2.343 (est)

EPA Substance Registry System

Bicyclo[3.1.1]heptan-3-one, 2,6,6-trimethyl-, (1R,2S,5S)-rel- (547-60-4)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P330Rinse mouth.

P501Dispose of contents/container to..…

(1alpha,2alpha,5alpha)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one Chemical Properties,Usage,Production

Uses

Pinocamphone has been made available mainly for the purpose of supplying the main component of Hyssop oil, which is relatively expensive and occasionally scarce on the market. It is a minor, but highly appreciated ingredient in certain topnote compositions for fine perfumes, and it is also used to a minor extent in flavor compositions for seasonings, etc. Apart from this special application, there is no significant use for the subject material in perfumes or flavors.

Preparation

1) from alpha-PinerIe, via Nitrosopinene, reduced to the title material with Zinc dust or catalytic hydrogenation.
2) from Verbanone - also obtained by synthetic way.
3) from Pinonic acid ethyl ether.
4) by isolation from Hyssop oil (40-45% of the oil).

Definition

ChEBI: (-)-Pinocamphone is a monoterpenoid.