4951-97-7

Usage

Type of compound

Organic compound

Structure

Ketone with a cyclobutyl ring and an ethyl group attached to one of the carbon atoms

Classification

Flavoring agent

Industry use

Food industry (to impart a buttery flavor) and fragrance industry (as a component of perfumes and scented products)

Physical state

Colorless liquid

Odor

Strong

Synthesis

Organic chemical reactions

Safety precautions

Handle with care, harmful if ingested or inhaled in large quantities

InChI:InChI=1/C10H18O/c1-5-8-6-9(7(2)11)10(8,3)4/h8-9H,5-6H2,1-4H3/t8-,9-/m0/s1

Upstream product

• 4795-86-2 (1R)-(+)-cis-pinane 
• 7785-70-8 (+)-α-pinene 
• 473-55-2 2,6,6-trimethylbicyclo[3.1.1]heptane 

Relevant academic research and scientific papers

FRAGRANCE COMPOSITIONS FROM TERTIARY TERPENE ALCOHOLS

Cyclic ethers or chloroketones useful as fragrance components or intermediates are made by reacting a saturated, tertiary terpene alcohol with hypochloric acid under conditions effective to promote oxidation. trans-Pinanol gives predominantly 6,9-dimethyl-7-oxatricyclo[4.3.0.03,9]-nonane, while cis-pinanol yields almost exclusively 1-acetyl-3-(2-chloroethyl)-2,2-dimethyl-cyclobutane, a new and versatile intermediate for making cyclobutane derivatives having interesting and diverse aromas.

Studies on the Oxidation of cis- and trans-Pinane with Molecular Oxygen

The pinanes are preferably attacked at the tertiary C-H bond in 2-position, but products of the oxidative attack at the secondary C-H-bonds in 3- and 4-position are also found.At 100 deg C cis-pinane is attacked more easily than trans-pinane (kcis : ktrans = 6.4), the relative rates of attack at the secondary C-H bonds in positions 3 and 4 with respect to the tertiary C-H bond in 2-position were also determined (in cis-pinane ksec : ktert = 0.027; in trans-pinane ksec : ktert = 0.20).After the attack at the 2-C-H bond the radical formed can either react with oxygen to form the corresponding cis- and trans-peroxy radicals and further to give cis- and trans-2-hydroperoxy pinane or fragmentate to the monocyclic radical derived from α-terpinene, giving as a final products α-terpinene hydroperoxide and the bicyclic 8-hydroperoxy 4,4,8-trimethyl 2,3-dioxabicyclononane.The corresponding alcohols were found after reduction with sodium sulphite.The oxidation at position 2 of the pinanes delivers not only the cis- and trans-hydroperoxide but also, as short-lived intermediates, the corresponding 2-pinanyloxy radicals.These radicals fragmentate forming a carbon radical with cyclobutane structure whose oxidation products were identified.Besides fragmentation of the 2-pinanyloxy radical also an intramolecular H-transfer from the methyl group in 9-position to the oxygen of the trans-pinanyloxy radical takes place leading to 9-hydroperoxy trans-pinane-2-ol.