2244-16-8

Basic information

• Product Name: 2-Methyl-4-(1 -methylethenyl)-2-cyclohexene-1 -one
• Synonyms: 2-Cyclohexen-1-one,2-methyl-5-(1-methylethenyl)-, (S)-;p-Mentha-6,8-dien-2-one, (S)-(+)- (8CI);(+)-Carvone;(S)-(+)-Carvone;(S)-(+)-p-Mentha-6,8-dien-2-one;(S)-Carvone;Carvone, (+)-;D-(+)-Carvone;D-Carvone;Talent;d-1-Methyl-4-isopropenyl-6-cyclohexen-2-one
• CAS NO: 2244-16-8
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.21756
• EINECS: 218-827-2
• Mol File: 2244-16-8.mol
• Article Data: 75

Chemical Properties

• Melting Point: 88.9℃
• Boiling Point: 230.5 °C at 760 mmHg
• Flash Point: 88.9 °C
• Appearance: colourless or pale yellow liquid
• Density: 0.94 g/cm³
• Vapor Pressure: 0.0656mmHg at 25°C
• Refractive Index: 1.481
• Water Solubility: <0.1 g/100 mL at 25℃
• CAS DataBase Reference: 2-Methyl-4-(1 -methylethenyl)-2-cyclohexene-1 -one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methyl-4-(1 -methylethenyl)-2-cyclohexene-1 -one(2244-16-8)
• EPA Substance Registry System: 2-Methyl-4-(1 -methylethenyl)-2-cyclohexene-1 -one(2244-16-8)

Safety Data

• Safety Statements: S24/25:
• Hazardous Substances Data: 2244-16-8(Hazardous Substances Data)

Usage

General Description

2-Methyl-4-(1-methylethenyl)-2-cyclohexene-1-one, also known as Limonene 1,2-epoxide, is a type of organic compound related to terpenes. In its pure form, it is a colorless liquid. It is primarily found in many plants and fruits, most notably citrus rinds. The compound is named after lemons as it is a major component of the oil from this citrus fruit. It is used commercially in a range of products from edible citrus flavourings to biodegradable solvents in cleaning products and fragrances, due to its pleasant lemon-like odor. It is also studied for potential health benefits, such as antimicrobial, anti-inflammatory, and possible anti-cancer properties.

InChI:InChI=1/C10H14O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9H,1,5-6H2,2-3H3/t9-/m1/s1

Upstream product

• 7632-16-8 (2S,4S)-carveol 
• 2102-58-1 (+)-trans-carveol 
• 80124-30-7 oxime (4S)-4-isopropenyl-1-methylcyclohex-1-en-6-one 
• 6617-33-0 (1E,6R)-4,7,7-trimethylbicyclo[4.1.0]hept-4-en-3-one 
• 127911-61-9 (2S,3S,5R)-5-Isopropenyl-2-methyl-3-trimethylsilanyl-cyclohexanone 
• 4700-99-6 (+)-trans-p-mentha-5,8-dien-2-ol 
• 104111-76-4 (+)-trans-p-mentha-5,8-dien-2-one 
• 104049-42-5 3β-acetoxycaran-4-one 
• 34182-03-1 (+/-)-5-(1-hydroxy-1-methylethyl)-2-methyl-2-cyclohexen-1-one 
• 99-49-0 Carvone 
• 5989-27-5 D-limonene 
• 224967-21-9 (2S,3S,5S)-2-methyl-3-(tert-butyldimethylsiloxy)-5-(2-propenyl)cyclohexanone 
• 203719-53-3 (-)-limonene oxide 
• 16826-23-6 (1R,2S,5S)-2-methyl-3-oxo-5-(prop-1-en-2-yl)cyclohexanecarbonitrile 

Downstream Products

• 499-75-2 carvacrol 
• 74105-52-5 (S)-8-methoxy-p-menth-6-en-2-one 
• 103989-85-1 (R)-5-isopropenyl-1,2-dimethyl-cyclohexa-1,3-diene 
• 69392-27-4 1-methyl-6-methylene-4-(prop-1-en-2-yl)cyclohex-1-ene 
• 103986-54-5 (S)-5-isopropenyl-2,3-dimethyl-cyclohexa-1,3-diene 
• 85710-64-1 5-isopropenyl-1,2-dimethyl-cyclohex-2-enol 
• 672898-51-0 (5S)-2-methyl-5-(2-methyloxiran-2-yl)cyclohex-2-en-1-one 
• 123772-01-0 6-isopropenyl-3-methyl-2-oxo-cyclohex-3-enecarbaldehyde 
• 56423-47-3 2-methyl-5-(prop-1-en-2-yl)phenol 
• 4581-65-1 (+-)-carvone semicarbazone 
• 99-48-9 5-Isopropenyl-2-methyl-cyclohex-2-enol 
• 7632-16-8 (2S,4S)-carveol 
• 2102-58-1 (+)-trans-carveol 
• 16826-23-6 5-isopropenyl-2-methyl-3-oxo-cyclohexanecarbonitrile 

Relevant articles and documents

A glandular trichome-specific monoterpene alcohol dehydrogenase from Artemisia annua

The major components of the isoprenoid-rich essential oil of Artemisia annua L. accumulate in the subcuticular sac of glandular secretory trichomes. As part of an effort to understand isoprenoid biosynthesis in A. annua, an expressed sequence tag (EST) collection was investigated for evidence of genes encoding trichome-specific enzymes. This analysis established that a gene denoted Adh2, encodes an alcohol dehydrogenase and shows a high expression level in glandular trichomes relative to other tissues. The gene product, ADH2, has up to 61% amino acid identity to members of the short chain alcohol dehydrogenase/reductase (SDR) superfamily, including Forsythia × intermedia secoisolariciresinol dehydrogenase (49.8% identity). Through in vitro biochemical analysis, ADH2 was found to show a strong preference for monoterpenoid secondary alcohols including carveol, borneol and artemisia alcohol. These results indicate a role for ADH2 in monoterpenoid ketone biosynthesis in A. annua glandular trichomes.

Tuning of α-Silyl Carbocation Reactivity into Enone Transposition: Application to the Synthesis of Peribysin D, E-Volkendousin, and E-Guggulsterone

A reliable method for enone transposition has been developed with the help of silyl group masking. Enantio-switching, substituent shuffling, and Z-selectivity are the highlights of the method. The developed method was applied for the first total synthesis of peribysin D along with its structural revision. Formal synthesis of E-guggulsterone and E-volkendousin was also claimed using a short sequence.

Scalable Aerobic Oxidation of Alcohols Using Catalytic DDQ/HNO3

A selective, practical, and scalable aerobic oxidation of alcohols is described that uses catalytic amounts of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and HNO3, with molecular oxygen serving as the terminal oxidant. The method was successfully applied to the oxidation of a wide range of benzylic, propargylic, and allylic alcohols, including two natural products, namely, carveol and podophyllotoxin. The conditions are also applicable to the selective oxidative deprotection of p-methoxybenzyl ethers.