80-57-9

Basic information

• Product Name: 4,6,6-TRIMETHYLBICYCLO[3.1.1]HEPT-3-EN-2-ONE
• Synonyms: 4,6,6-trimethyl-bicyclo[3.1.1]hept-3-en-2-on;Berbenone;VERBENONE;2-PINEN-4-ONE;4,6,6-TRIMETHYLBICYCLO[3.1.1]HEPT-3-EN-2-ONE;2-Pinen-4-one, 4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one;2,6,6-Trimethylbicyclo[3.1.1]hepta-2-ene-4-one;Pina-2-ene-4-one
• CAS NO: 80-57-9
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.22
• EINECS: 201-292-4
• Mol File: 80-57-9.mol
• Article Data: 93

Chemical Properties

• Melting Point: 6.5 °C
• Boiling Point: 227-228 °C(lit.)
• Flash Point: 85 °C
• Appearance: /
• Density: 0.975 g/mL at 20 °C(lit.)
• Refractive Index: n20/D 1.496(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4,6,6-TRIMETHYLBICYCLO[3.1.1]HEPT-3-EN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6,6-TRIMETHYLBICYCLO[3.1.1]HEPT-3-EN-2-ONE(80-57-9)
• EPA Substance Registry System: 4,6,6-TRIMETHYLBICYCLO[3.1.1]HEPT-3-EN-2-ONE(80-57-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22-43
• Safety Statements: 36/37
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 80-57-9(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid; minty, spicy aroma.

Occurrence

Reported found in Artemisia diffusa Krasch. ex poljak oil, Iran (13.0%); rosemary oil, Egypt (12.33%); rosemary oil corsica (10.7%); rosemary oil co2 extract (8.36%); rosemary oil, spain (6.3%); wormwood oil, cuba (2.47%); hinoki root oil (2.44%), rosemary oil, France (1.03–5.08%), etc.

Aroma threshold values

Medium strength odor, camphoreous type.

InChI:InChI=1/C10H14O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-8H,5H2,1-3H3/t7-,8+/m1/s1

Upstream product

• 80-56-8 Pinene 
• 1845-30-3 trans-verbenol 
• 7785-70-8 (+)-α-pinene 
• 7785-26-4 (-)-α-pinene 
• 924265-28-1 (1R,2R,4R,6S)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.0^2,4]octan-5-one 
• 80-56-8 rac-α-pinene 
• 1820-09-3 Verbenol 
• 473-67-6 trans-Verbenol 
• 38693-73-1 Thioverbenon 
• 177698-18-9 α-pinene 
• 18172-67-3 beta-pinene 
• 135503-45-6 (1R,3S,5R)-6,6-dimethyl-3-(phenylseleno)bicyclo<3.1.1>heptan-2-one 
• 35408-03-8 (+)-apoverbenone 
• 38651-65-9 (1R,5S)-(+)-nopinone 

Downstream Products

• 18881-04-4 (S)-cis-Verbenol 
• 154966-65-1 (1S,5R)-4,6,6-trimethyl-3-phenylthiobicyclo<3.1.1>hept-3-en-2-one 
• 22571-78-4 (+)-cis-pinononoic acid 
• 80-57-9 (-)-Verbenone 
• 149404-74-0 (4R,5R)-1-Acetoxy-4-isopropenyl-5-methyl-5-vinylcyclohex-1-ene 
• 188918-50-5 (1S,3R)-3-[(tert-butoxycarbonyl)amino]-2,2-dimethylcyclobutane-1-carboxylic acid 
• 1017279-96-7 benzyl (1S,3R)-3-acetyl-2,2-dimethylcyclobutyl-1-carbamate 
• 1017279-76-3 (1R,3S)-3-(((benzyloxy)carbonyl)amino)-2,2-dimethylcyclobutan-1-carboxylic acid 
• 1261253-81-9 benzyl ((1S,3R)-2,2-dimethyl-3-(morpholin-4-carbonyl)cyclobutyl)carbamate 
• 1261253-85-3 benzyl (1S,3R)-2,2-dimethyl-3-(piperidine-1-carbonyl)cyclobutylcarbamate 
• 1261253-89-7 benzyl (1S,3R)-2,2-dimethyl-3-(pyrrolidine-1-carbonyl)cyclobutylcarbamate 
• 188918-42-5 (1S,3R)-3-((benzyloxy)carbonyl)-2,2-dimethylcyclobutane-1-carboxylic acid 

Relevant articles and documents

Synthesis and biological activity of novel (Z)- and (E)-verbenone oxime esters

Twenty-seven (Z)- and (E)-verbenone derivatives bearing an oxime ester moiety were designed and synthesized in search of novel bioactive molecules. Their structures were confirmed by UV-Vis, FTIR, NMR, ESI-MS, and elemental analysis. The antifungal and herbicidal activities of the target compounds were preliminarily evaluated. As a result, compound (E)-4n (R = b-pyridyl) exhibited excellent antifungal activity with growth inhibition percentages of 92.2%, 80.0% and 76.3% against Alternaria solani, Physalospora piricola, and Cercospora arachidicola at 50 g/mL, showing comparable or better antifungal activity than the commercial fungicide chlorothalonil with growth inhibition of 96.1%, 75.0% and 73.3%, respectively, and 1.7 5.5-fold more growth inhibition than its stereoisomer (Z)-4n (R = b-pyridyl) with inhibition rates of 22.6%, 28.6% and 43.7%, respectively. In addition, seven compounds displayed significant growth inhibition activity of over 90% against the root of rape (Brassica campestris) at 100 g/mL, exhibiting much better herbicidal activity than the commercial herbicide flumioxazin with a 63.0% growth inhibition. Among these seven compounds, compound (E)-4n (R = b-pyridyl) inhibited growth by 92.1%, which was 1.7-fold more than its stereoisomer (Z)-4n (R = b-pyridyl) which inhibited growth by 54.0%.

Individual stereoisomers of verbenol and verbenone express bioactive features

Naturally occurring terpene core compounds have been used extensively in both pharmaceutical and cosmetic industry. However, since chirality of these compounds has profound influence on the level of their bioactivity, the aim of the present study was to a

Cubic CuxZrO100-x as an efficient and selective catalyst for the oxidation of aromatics active methyl, alcohol, and amine groups

The local structure of a supported active metal plays a vital role in determining the desired product's selectivity in heterogeneous catalysis. Herein, we have developed a simple protocol for the synthesis of Cu doped on cubic ZrO2 mixed metal oxide catalysts and used it for the selective oxidation of various functional groups. The catalyst was synthesized by varying the wt.% of Cu (1–20%) on ZrO2 by co-precipitation, followed by hydrothermal treatment. The X-ray diffraction pattern of the catalysts confirmed the formation of the cubic phase of ZrO2, and the growth of CuO occurred along the (1 1 1) plane. The microscopy analysis revealed the uniform distribution of Cu on the ZrO2 surface, while XPS analysis confirmed the presence of copper in the +2 oxidation state. The synthesized catalyst with 2 wt% loading of Cu on ZrO2 showed excellent liquid-phase oxidation properties and gave good to best conversion of active methyl groups, alcohols, and amines with high selectivities to corresponding ketones, aldehydes, and amides, respectively, under milder reaction conditions. Furthermore, the synthesized catalyst showed a broader substrate scope for the various substituted active methyl groups, alcohols, and amines with good conversion and selectivity.

Selective Allylic Oxidation of Terpenic Olefins Using Co-Ag Supported on SiO2 as a Novel, Efficient, and Recyclable Catalyst

Co-Ag supported on the SiO2 catalyst was synthesized by the sol-gel method and characterized using XRD, FT-IR, TG-DTG, BET, CV, and SEM/EDX analysis. The catalytic performance of the resulting catalyst was examined by the oxidation of mono and sesquiterpenic olefins using hydrogen peroxide and tert-butyl peroxide as oxidant agents. Various parameters such as catalyst amount, temperature, and solvents have been studied. The Co-Ag supported on the SiO2 catalyst showed a high activity, selectivity, and recyclability for the selected oxidation reaction.