4584-23-0

Basic information

• Product Name: 2,2,6-trimethyl-1-oxaspiro[2.5]oct-5-ene
• Synonyms: 2,2,6-trimethyl-1-oxaspiro[2.5]oct-5-ene;1-p-Menthene-4,8-epoxide;4,8-Epoxy-p-menth-1-ene;Terpinolene 4,8-epoxide;Terpinolene oxide
• CAS NO: 4584-23-0
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23344
• EINECS: 224-968-0
• Mol File: 4584-23-0.mol

Chemical Properties

• Boiling Point: 197.5°Cat760mmHg
• Flash Point: 67.3°C
• Appearance: /
• Density: 0.97g/cm³
• Vapor Pressure: 0.53mmHg at 25°C
• Refractive Index: 1.495
• CAS DataBase Reference: 2,2,6-trimethyl-1-oxaspiro[2.5]oct-5-ene(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,6-trimethyl-1-oxaspiro[2.5]oct-5-ene(4584-23-0)
• EPA Substance Registry System: 2,2,6-trimethyl-1-oxaspiro[2.5]oct-5-ene(4584-23-0)

Safety Data

• Hazardous Substances Data: 4584-23-0(Hazardous Substances Data)

Usage

Physical state

Colorless liquid

Odor

Floral

Common uses

Fragrance industry and flavoring agent in the food industry

Boiling point

High

Flash point

High

Safety precautions

May cause irritation to skin, eyes, and respiratory system if not handled properly.

InChI:InChI=1/C10H16O/c1-8-4-6-10(7-5-8)9(2,3)11-10/h4H,5-7H2,1-3H3

Upstream product

• 586-62-9 Terpinolene 
• 5989-54-8 (-)-(S)-limonene 

Downstream Products

• 1195-32-0 1-methyl-4-isopropenylbenzene 
• 18368-95-1 p-mentha-1,3,8-triene 
• 1197-01-9 p-cymene-8-ol 
• 99-87-6 4-methylisopropylbenzene 
• 562-74-3 TERPINEN-4-OL 
• 53312-55-3 p-mentha-1,4-dien-8-ol 
• 82538-84-9 1-(1'-hydroxy-1'-methylethyl)-4-methylcyclohexa-1,3-diene 
• 28233-65-0 1-isopropenyl-4-methyl-1,4-cyclohexadiene 
• 565-48-0 cis-1,8-terpine 
• 1753-42-0 1-isopropyl-4-methylcyclohexane-1,4-diol 
• 80-53-5 trans-terpin 
• 17948-61-7 cis-1,4-dihydroxy-1-isopropyl-4-methylcyclohexane 
• 35866-71-8 8-fluoro-p-menth-1-en-4-ol 
• 98-55-5 terpineol 

Relevant articles and documents

Synthesis of Aristoquinoline Enantiomers and Their Evaluation at the α3β4 Nicotinic Acetylcholine Receptor

The first synthesis of aristoquinoline (1), a naturally occurring nicotinic acetylcholine receptor (nAChR) antagonist, was accomplished using two different approaches. Comparison of the synthetic material's spectroscopic data to that of the isolated alkaloid identified a previously misassigned stereogenic center. An evaluation of each enantiomer's activity at the α3β4 nAChR revealed that (+)-1 is significantly more potent than (-)-1. This unexpected finding suggests that naturally occurring 1 possesses the opposite absolute configuration from indole-containing Aristotelia alkaloids.

PROCESS FOR THE EPOXIDATION OF A TETRASUBSTITUTED ALKENE

This invention relates to a process for the epoxidation of a tetrasubstituted alkene such as terpinolene to the corresponding epoxide such as terpinolene epoxide by reacting the tetrasubstituted alkene with peracetic acid prepared in situ from acetic anhydride and hydrogen peroxide in the presence of at least one buffering agent. Further, the invention relates to the use of an oxidizing agent comprising hydrogen peroxide and acetic anhydride for the in-situ epoxidation of a tetrasubstituted alkene.

PROCESS FOR THE EPOXIDATION OF A TETRASUBSTITUTED ALKENE

This invention relates to a process for the epoxidation of a tetrasubstituted alkene such as terpinolene to the corresponding epoxide such as terpinolene epoxideby reacting the tetrasubstituted alkene with performic acid prepared in situ from formic acid and hydrogen peroxide in the presence of at least one buffering agent. Further, the invention relates to the use of an oxidizing agent comprising hydrogenperoxide and formic acid for the in-situ epoxidation of a tetrasubstituted alkene.

A PROCESS FOR THE PREPARATION OF TERPINOLENE EPOXIDE

The present invention relates to a process for the preparation of terpinolene epoxide by epoxidation of terpinolene.

Structure-Odor Activity Studies on Monoterpenoid Mercaptans Synthesized by Changing the Structural Motifs of the Key Food Odorant 1-p-Menthene-8-thiol

1-p-Menthene-8-thiol (1) has been discovered as the key odorant in grapefruit juice several decades ago and contributes to the overall odor of the fruit with an extremely low odor threshold of 0.000034 ng/L in air. This value is among the lowest odor thresholds ever reported for a food odorant. To check whether modifications in the structure of 1 would lead to changes in odor threshold and odor quality, 34 mercapto-containing p-menthane and 1-p-menthene derivatives as well as several aromatic and open-chain mercapto monoterpenoids were synthesized. Eighteen of them are reported for the first time in the literature, and their odor thresholds and odor qualities as well as analytical data are supplied. A comparison of the sensory data with those of 1 showed that hydrogenation of the double bond led to a clear increase in the odor threshold. Furthermore, moving the mercapto group into the ring always resulted in higher odor thresholds compared to thiols with a mercapto group in the side chains. Although all tertiary thiols always exhibited low odor thresholds, none of the 31 compounds reached the extremely low threshold of 1. Also, none of the synthesized mercapto monoterpenoids showed a similar odor quality resembling grapefruit. Although the saturated and aromatic analogues exhibited similar scents as 1, the aromas of the majority of the other compounds were described as sulfury, rubber-like, burned, soapy, or even mushroom-like. NMR and MS data as well as retention indices of the 23 newly reported sulfur-containing compounds might aid in future research to identify terpene-derived mercaptans possibly present in trace levels in foods.

Spectroscopic, calorimetric, and catalytic evidences of hydrophobicity on Ti-MCM-41 silylated materials for olefin epoxidations

Hydrophobic Ti-MCM-41 samples prepared by post-synthesis silylation treatment demonstrate to be highly active and selective catalysts in olefins epoxidation by using organic hydroperoxides as oxidizing agents in liquid phase reaction systems. Epoxide yields show important enhancements with increased silylation degrees of the Ti-mesoporous samples. Catalytic studies are combined and correlated with spectroscopic techniques (e.g. XRD, XANES, UV-Visible, 29Si MAS-NMR) and calorimetric measurements to better understand the changes in the surface chemistry of Ti-MCM-41 samples due to the post-synthesis silylation treatment and to ascertain the role of these trimethylsilyl groups incorporated in olefin epoxidation. In such manner, the effect of the organic moieties on solids, and both water and glycol molecules contents on the catalytic activity and selectivity are analyzed in detail. Results show that the hydrophobicity level of the samples is responsible for the decrease in water adsorption and, consequently, the negligible formation of the non-desired glycol during the catalytic process. Thus, catalyst deactivation by glycol poisoning of Ti active sites is greatly diminished, this increasing catalyst stability and leading to practically quantitative production of the corresponding epoxide. The extended use of these hydrophobic Ti-MCM-41 catalysts together with organic hydroperoxides for the highly efficient and selective epoxidation of natural terpenes is also exemplified.

Chemoenzymatic synthesis of homochiral (R)- and (S)-karahanaenol from (R)-limonene

Terpinolene oxide, a monoterpene belonging to the p-menthane group, is easily derived from naturally abundant (R)-limonene. It was isomerized with montmorillonite clay catalyst to karahanaenone (2,2,5-trimethylcyclohept-4- en-1-one) by ring enlargement. The enantiomers of the corresponding alcohol, karahanaenol (2,2,5-trimethylcyclohept-4-en-1-ol), known for their individual organoleptic properties, were resolved through Pseudomonas cepacia lipase mediated enantiospecific alcoholysis of its acetate derivative.

Comparison of amine additives most effective in the new methyltrioxorhenium-catalyzed epoxidation process

Three different heterocyclic amine additives, pyridine, 3-cyanopyridine and pyrazole are compared in the methyltrioxorhenium (MTO) catalyzed epoxidation of olefins using aqueous hydrogen peroxide.

The Diepoxides of Terpinolene

The structures of the racemic 1,2:4,8-diepoxy-p-menthanes, the diepoxides of terpinolene, are revised.The major isomer has the trans relationship between the two epoxides.