78617-27-3

Basic information

• Product Name: 3,5-Cyclohexadiene-1,2-dione,3-methyl-6-(1-methylethyl)-(9CI)
• Synonyms: 3,5-Cyclohexadiene-1,2-dione,3-methyl-6-(1-methylethyl)-(9CI)
• CAS NO: 78617-27-3
• Molecular Formula: C₁₀H₁₂O₂
• Molecular Weight: 164.20108
• Product Categories: ISOPROPYL
• Mol File: 78617-27-3.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,5-Cyclohexadiene-1,2-dione,3-methyl-6-(1-methylethyl)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Cyclohexadiene-1,2-dione,3-methyl-6-(1-methylethyl)-(9CI)(78617-27-3)
• EPA Substance Registry System: 3,5-Cyclohexadiene-1,2-dione,3-methyl-6-(1-methylethyl)-(9CI)(78617-27-3)

Safety Data

• Hazardous Substances Data: 78617-27-3(Hazardous Substances Data)

Upstream product

• 499-75-2 carvacrol 
• 89-83-8 thymol 
• 490-06-2 3-isopropyl-6-methyl-1,2-benzenediol 

Relevant articles and documents

Structure-Odor Activity Studies on Derivatives of Aromatic and Oxygenated Monoterpenoids Synthesized by Modifying p-Cymene

Thymoquinone was recently reported as having a unique pencil-like odor and being the impact compound for the cedar-like and cedar wood-based product smell such as pencils. The compounds thymol and carvacrol are structurally related odorants commonly found in plants and foods such as thyme and oregano, also having a significant contribution to their overall aroma. However, a systematic elucidation of the sensory properties in this class of oxygenated, aromatic monoterpenoids has not been carried out. To close this gap and gain new insights into structure-odor relationships leading to pencil-like and woody odors, 19 structurally related derivatives of p-cymene starting from thymol and carvacrol were synthesized and characterized. The compounds had odor thresholds ranging from 2.0 ng/L air to 388.8 ng/L air, being lowest for thymol and carvacrol and highest for thymohydroquinone. The compounds smelled mostly thyme-like, oregano-like, and pencil-like with phenolic, earthy, and medicinal variations in their odor character, which could be successfully linked to structural motifs.

A Catalyst-Controlled Aerobic Coupling of ortho-Quinones and Phenols Applied to the Synthesis of Aryl Ethers

ortho-Quinones are underutilized six-carbon-atom building blocks. We herein describe an approach for controlling their reactivity with copper that gives rise to a catalytic aerobic cross-coupling with phenols. The resulting aryl ethers are generated in high yield across a broad substrate scope under mild conditions. This method represents a unique example where the covalent modification of an ortho-quinone is catalyzed by a transition metal, creating new opportunities for their utilization in synthesis.

COMPARATIVE OXIDATION OF PHENOLS WITH BENZENESELENINIC ANHYDRIDE AND WITH BENZENESELENINIC ACID

Oxidation of phenols by benzeneseleninic acid 2 in methylene dichloride leads to the para-quinones, whereas oxidation by benzeneseleninic anhydride 1 is confirmed to afford the corresponding ortho-quinones.Addition of indole, as a phenylselenium (II) trapping agent, inhibits the formation of phenylselenoquinones in the oxidation with 1 or 2.