7392-19-0

Basic information

• Product Name: LIMETOL
• Synonyms: 2,2,6-TRIMETHYL-6-VINYLTETRAHYDROPYRAN;FEMA 3735;LIMETOL;2,2,6-Trimethyl-6-vinyltetrahydro-2H-pyran;2,6,6-trimethoxy-2-vinyltetrahydropyran;2,6,6-trimethyl-2-ethenyltetrahydro-2H-pyran;2,6,6-trimethyl-2-ethenyltetrahydropyran;2,6,6-Trimethyl-2-vinyltetrahydropyran
• CAS NO: 7392-19-0
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.25
• EINECS: 230-983-3
• Mol File: 7392-19-0.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 171 °C at 760 mmHg
• Flash Point: 49.4 °C
• Appearance: /
• Density: 0.88 g/cm³
• Vapor Pressure: 4.89hPa at 25℃
• Storage Temp.: Amber Vial, Refrigerator, Under inert atmosphere
• Solubility: Chloroform (Sparingly), Ethyl Acetate (Slightly)
• Water Solubility: 449mg/L at 20℃
• Stability: Light Sensitive
• CAS DataBase Reference: LIMETOL(CAS DataBase Reference)
• NIST Chemistry Reference: LIMETOL(7392-19-0)
• EPA Substance Registry System: LIMETOL(7392-19-0)

Safety Data

• Hazardous Substances Data: 7392-19-0(Hazardous Substances Data)

Usage

Chemical Properties

2,6,6-Trimethyl-6-vinyltetrahydopyran has a musty, earthy, terpineolic odor.

Occurrence

Reported found in chestnut flower, muscat grapes and lime oil. Also reported found in grapefruit juice (Vitis labrusca L.) papaya (Carica papaya L.), white wine, black tea, purple passion fruit, yellow passion fruit, cherimoya, buchu oil, clary sage and loganberry.

Uses

Limetol, is the cyclized derivative of linalool (L465950), melanol, and other unsaturated alcohols, that was shown to give a product mixture that can be used in fragrance and perfumery industry.

Taste threshold values

Taste characteristics at 21 ppm: sweet, camphoraceous, woody and cooling with floral nuances.

InChI:InChI=1S/C10H18O/c1-5-10(4)8-6-7-9(2,3)11-10/h5H,1,6-8H2,2-4H3

Upstream product

• 13837-60-0 2-ethynyl-2,6,6-trimethyl-3,4,5,6-tetrahydro-(2H)-pyran 
• 56072-48-1 dimethyl-2,6 octadiene-6,7 ol-2 
• 57745-79-6 (Z)-N,N-diethyl-7-hydroxy-3,7-octenylamine 
• 115-95-7 linalool acetate 
• 78-70-6 3,7-dimethylocta-1,6-dien-3-ol 
• 29171-20-8 3,7-dimethyloct-6-en-1-yn-3-ol 
• 110-93-0 6-Methyl-hept-5-en-2-on 
• 95652-36-1 2-Methyl-2-(4-methyl-hexa-4,5-dienyl)-[1,3]dioxolane 
• 88974-48-5 1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octan-7-one 
• 73410-33-0 1-(2,6,6-Trimethyl-tetrahydro-pyran-2-yl)-ethanone 
• 38736-75-3 (+/-)-cinenic acid 
• 29210-77-3 2,6-dimethyloct-7-ene-2,6-diol 
• 64-17-5 ethanol 
• 87044-49-3 Dithiocarbonic acid S-methyl ester O-[1-(2,6,6-trimethyl-tetrahydro-pyran-2-yl)-ethyl] ester 

Downstream Products

• 13837-60-0 2-ethynyl-2,6,6-trimethyl-3,4,5,6-tetrahydro-(2H)-pyran 

Relevant articles and documents

Amberlyst-15-catalyzed efficient cyclization of γ-and δ-unsaturated alcohols: Green synthesis of oxygen heterocycles

Amberlyst-15 (H+) resin catalyzes efficient cationic endo-cyclization of-and-unsaturated alcohols to yield tetrahydro-(2H)-pyrans and oxepanes. The merits of the present protocol are good yield of the products under mild conditions, simple workup, and reusability of the resin.

A PRACTICAL SYNTHESIS OF MYRCENOL BY PALLADIUM COMPLEX-CATALYZED ELIMINATION REACTION

A Palladium complex-catalyzed elimination reaction of allyl amines was studied to establish a practical process for production of myrcenol.The catalytic elimination occurred smoothly with the cationic Pd(II) complexes.Among a variety phosphorous ligands, the tetramethylene and the pentamethylene diphosphine ligands proved to be the best ligand with respects to the catalytic activity and selectivity.

FACILE PREPARATION OF 2,6-DIMETHYL-2,6-TETRAHYDROPYRANCARBOLACTONE, A VERSATILE INTERMEDIATE FOR THE SYNTHESES OF (+/-)-FRONTALIN, (+/-)-CINENIC ACID, AND (+/-)-LINALOYL OXIDE

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