19620-37-2

Basic information

• Product Name: 4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-one
• Synonyms: 4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-one;4-Hydroxy-2,6,6-trimethyl-2-cyclohexen-1-one;Einecs 243-192-3
• CAS NO: 19620-37-2
• Molecular Formula: C₉H₁₄O₂
• Molecular Weight: 154.20626
• EINECS: 243-192-3
• Mol File: 19620-37-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 258.8°Cat760mmHg
• Flash Point: 107.2°C
• Appearance: /
• Density: 1.03g/cm³
• Vapor Pressure: 0.00198mmHg at 25°C
• Refractive Index: 1.486
• CAS DataBase Reference: 4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-one(19620-37-2)
• EPA Substance Registry System: 4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-one(19620-37-2)

Safety Data

• Hazardous Substances Data: 19620-37-2(Hazardous Substances Data)

Usage

Uses

2,6,6-Trimethylcyclohex-2-en-4-ol-1-one is an carotenoid degradation product found in paprika powder.

InChI:InChI=1/C9H14O2/c1-6-4-7(10)5-9(2,3)8(6)11/h4,7,10H,5H2,1-3H3

Upstream product

• 118467-12-2 6,6-Dimethyl-2-phenylsulfanyl-cyclohex-2-enone 
• 102676-97-1 1-(2,6,6-trimethyl-1,3-cyclohexadienyl)ethanol 
• 41436-46-8 2,6,6-trimethyl-cyclohexa-1,3-dien-1-yl methyl ketone 
• 20548-02-1 trans (4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexanone 
• 116-26-7 safranal 
• 102677-02-1 methyl 6,7,7-trimethyl-2,3-dioxabicyclo<2.2.2>oct-5-enyl ketone 
• 118467-19-9 2,6,6-Trimethyl-2-phenylsulfanyl-cyclohex-3-enone 
• 1125-21-9 2,6,6-trimethyl-2-cyclohexene-1,4-dione 

Downstream Products

• 254963-54-7 (+/-)-4-oxo-3,5,5-trimethyl-2-cyclohexenyl chloroacetate 
• 254963-55-8 (R)-4-oxo-3,5,5-trimethyl-2-cyclohexenyl chloroacetate 
• 254963-53-6 (S)-4-oxo-3,5,5-trimethyl-2-cyclohexenyl chloroacetate 
• 76686-09-4 (+)-(R)-4-Hydroxy-2,6,6-trimethyl-2-cyclohexen-1-one 
• 64809-50-3 (4S)-4-hydroxy-2,6,6-trimethyl-cyclohex-2-en-one 
• 107536-93-6 (+/-)-4-acetoxy-2,6,6-trimethyl-2-cyclohexenone 
• 13487-30-4 2,6,6-trimethylcyclohexa-2,4-dienone 
• 99901-26-5 2-(2-oxobut-3-yl)-2,6,6-trimethyl-3-cyclohexen-1-one 

Relevant articles and documents

Selective Base-free Transfer Hydrogenation of α,β-Unsaturated Carbonyl Compounds using iPrOH or EtOH as Hydrogen Source

Commercially available Ru-MACHOTM-BH is an active catalyst for the hydrogenation of several functional groups and for the dehydrogenation of alcohols. Herein, we report on the new application of this catalyst to the base-free transfer hydrogenation of carbonyl compounds. Ru-MACHOTM-BH proved to be highly active and selective in this transformation, even with α,β-unsaturated carbonyl compounds as substrates. The corresponding aliphatic, aromatic and allylic alcohols were obtained in excellent yields with catalyst loadings as low as 0.1–0.5 mol % at mild temperatures after very short reaction times. This protocol tolerates iPrOH and EtOH as hydrogen sources. Additionally, scale up to multi-gram amounts was performed without any loss of activity or selectivity. An outer-sphere mechanism has been proposed and the computed kinetics and thermodynamics of crotonaldehyde and 1-phenyl-but-2-en-one are in perfect agreement with the experiment.

A New Access to 2,6,6-Trimethylcyclohexa-2,4-dienone from 4-Oxoisophorone

2,6,6-Trimethylcyclohexa-2,4-dienone (1), a versatile starting material for the preparation of some carotenoids and several natural products, was efficiently (73 percent yield) prepared from oxoisophorone 3.After conversion of 3 to the alcohol 4 or the acetate 5, H2O was eliminated (4 -> 1) under acidic distillative conditions, whereas AcOH could be eliminated (5 -> 1) under Pd(O) catalysis.

The Catalytic Reduction of Aldehydes and Ketones with 2-Propanol over Hydrous Zirconium Oxide

Reduction of aldehydes with 2-propanol proceeded efficiently by catalysis with hydrous zirconium oxide to give the corresponding alcohols.Most ketones also were reduced efficiently, but conjugated or sterically hindered ketones resisted the reduction.The reduction was carried out with primary, secondary, or tertiary alcohols, and only secondary alcohols served as hydrogen donors.Kinetic experiments have indicated that the reaction rate is first-order dependence on each of the concentrations of the carbonyl compound, 2-propanol, and the catalyst.An observation of the primary isotope effect has suggested that a step of hydride transfer from absorbed 2-propanol to absorbed carbonyl compound constitutes the rate-determining step for the reduction.