515-00-4

Basic information

• Product Name: (-)-MYRTENOL, 97
• Synonyms: (6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)methanol;2-Pinen-10-ol;6,6-dimethyl-2-oxymethlybicyclo-[1.1.3]hept-2-ene (myrtenol);6,6-dimethyl-bicyclo[3.1.1]hept-2-ene-2-methano;6,6-dimethyl-Bicyclo[3.1.1]hept-2-ene-2-methanol;(-)-MYRTENOL, 97;(-)-pin-2-ene-10-ol;(-)-MYRTENOL 97%
• CAS NO: 515-00-4
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23344
• EINECS: 208-193-5
• Product Categories: Alphabetical Listings;Flavors and Fragrances;M-N
• Mol File: 515-00-4.mol
• Article Data: 39

Chemical Properties

• Boiling Point: 221-222 °C(lit.)
• Flash Point: 89 °C
• Appearance: /
• Density: 0.954 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0179mmHg at 25°C
• Refractive Index: n20/D 1.496(lit.)
• PKA: 14.77±0.10(Predicted)
• CAS DataBase Reference: (-)-MYRTENOL, 97(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-MYRTENOL, 97(515-00-4)
• EPA Substance Registry System: (-)-MYRTENOL, 97(515-00-4)

Safety Data

• Safety Statements: S24/25:Avoid contact with skin and eyes.
• Hazardous Substances Data: 515-00-4(Hazardous Substances Data)

Usage

Chemical Properties

Myrtenol has a camphoraceous, minty, medicinal, woody odor

Occurrence

Reported found in cranberry, bilberry, blackberry, raspberry, strawberry, Virginia tobacco, mandarin and lime peel oil, melon, ginger, peppermint and Scotch spearmint oil, pepper, parsley, Gruyere cheese, hop oil, Bourbon vanilla, cognac, tea, laurel, myrtle leaf, myrtle oil, buchu oil, lemon balm, lamb’s lettuce, Roman chamomile oil, eucalyptus oil and mastic gum and leaf oil.

Uses

Myrtenol (cas# 515-00-4) is used in mosquito attractant compositions.

Preparation

Can be obtained in d,l-form from α-pinene with SeO2 in ethanol.

Taste threshold values

Taste characteristics at 50 ppm: cooling, minty, camphoraceous, green mentholic spice with a medicinal nuance.

InChI:InChI=1/C10H16O/c1-10(2)8-4-3-7(6-11)9(10)5-8/h3,8-9,11H,4-6H2,1-2H3

Upstream product

• 80-56-8 Pinene 
• 177698-19-0 Beta-pinene 
• 80-56-8 rac-α-pinene 
• 6931-54-0 β-pinene oxide 
• 50-00-0 formaldehyd 
• 88738-37-8 2-(2-Methoxy-ethoxymethoxymethyl)-6,6-dimethyl-bicyclo[3.1.1]hept-2-ene 
• 88738-38-9 2-Methoxymethoxymethyl-6,6-dimethyl-bicyclo[3.1.1]hept-2-ene 
• 104948-20-1 2-Benzyloxymethyl-6,6-dimethyl-bicyclo[3.1.1]hept-2-ene 
• 22321-84-2 trans-pinocarveyl hydroperoxide 
• 22321-84-2 pinocarveyl hydroperoxide 
• 58434-29-0 myrtenyl hydroperoxide 
• 564-94-3 6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde 
• 564-94-3 (+/-)-(1S,5R)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde 
• 127-91-3 (1R/S,5R/S)-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptane 

Downstream Products

• 17066-59-0 phthalic acid mono-((1S)-pin-2-en-10-yl ester) 
• 17066-59-0 (+/-)-O-(2-Carboxy-benzoyl)-myrtenol 
• 72928-52-0 myrtenyl formate 
• 564-94-3 6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde 
• 473-01-8 trans-myrtanol 
• 473-01-8 ((1S*,2R*,5S*)-6,6-dimethylbicyclo[3.1.1]heptan-2-yl)methanol 
• 564-94-3 (+/-)-(1S,5R)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carbaldehyde 
• 35670-93-0 myrtenyl acetate 
• 123464-09-5 allyl<(1R)-(-)-myrtenoxy>dimethylsilane 
• 119793-77-0 5-(6,6-Dimethyl-bicyclo[3.1.1]hept-2-en-2-ylmethylsulfanyl)-1-phenyl-1H-tetrazole 
• 177698-19-0 Beta-pinene 
• 4080-46-0 2⁽¹⁰⁾,3-pinadiene 
• 18368-95-1 p-mentha-1,3,8-triene 
• 99-87-6 4-methylisopropylbenzene 

Relevant articles and documents

Selective Catalytic Isomerization of β-Pinene Oxide to Perillyl Alcohol Enhanced by Protic Tetraimidazolium Nitrate

A series of tetraimidazolium salts with different anions was prepared and applied in the isomerization of β-pinene oxide. After examining the activity of different catalysts, a remarkable enhancement of the selectivity of perillyl alcohol (47 %) was obtained over [PEimi][HNO3]4 under mild reaction conditions and using DMSO as the solvent. Furthermore, noncovalent interactions between solvent molecules and the catalyst were found by FT-IR spectroscopy and confirmed by computational chemistry. The homogeneous catalyst showed excellent stability and was reused up to six times without significant loss.

New sustainable synthetic routes to cyclic oxyterpenes using the ecocatalyst toolbox

Cyclic oxyterpenes are natural products that are mostly used as fragrances, flavours and drugs by the cosmetic, food and pharmaceutical industries. However, only a few cyclic oxyterpenes are accessible via chemical syntheses, which are far from being ecofriendly. We report here the synthesis of six cyclic oxyterpenes derived from ?-pinene while respecting the principles of green and sustainable chemistry. Only natural or biosourced catalysts were used in mild conditions that were optimised for each synthesis. A new generation of ecocatalysts, derived from Mn-rich water lettuce, was prepared via green processes, characterised by MP-AES, XRPD and TEM analyses, and tested in catalysis. The epoxidation of ?-pinene led to the platform molecule, ?-pinene oxide, with a good yield, illustrating the efficacy of the new generation of ecocatalysts. The opening ?-pinene oxide was investigated in green conditions and led to new and regioselective syntheses of myrtenol, 7-hydroxy-α-terpineol and perillyl alcohol. Successive oxidations of perillyl alcohol could be performed using no hazardous oxidant and were controlled using the new generation of ecocatalysts generating perillaldehyde and cuminaldehyde.

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.