37677-14-8

Basic information

• Product Name: MYRAC ALDEHYDE
• Synonyms: 1-(4-methyl-3-pentenyl)-4-formyl-1-cyclohexene;1-Formyl-4-isohexenyl-4-cyclohexene;1-Formyl-4-ixohexenyl-4-cyclohexene;3-Cyclohexene-1-carboxaldehyde, 4-(4-methyl-3-pentenyl)-;3-cyclohexene-1-carboxaldehyde,-(4-methyl-3-pentenyl)-;3-cyclohexene-1-carboxaldehyde,-(4-methyl-pentenyl)-;4-(4-Methyl-3-penten-1-yl)-3-cyclohexen-1-carboxaldehyde;4-(4-Methyl-3-pentenyl)-3-cyclohexene-1-carbaldehyde
• CAS NO: 37677-14-8
• Molecular Formula: C₁₃H₂₀O
• Molecular Weight: 192.3
• EINECS: 253-617-4
• Product Categories: Aroma Chemicals
• Mol File: 37677-14-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 273.7 °C at 760 mmHg
• Flash Point: 96.1 °C
• Appearance: /
• Density: 0.955 g/cm³
• Vapor Pressure: 0.00565mmHg at 25°C
• Refractive Index: 1.524
• CAS DataBase Reference: MYRAC ALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: MYRAC ALDEHYDE(37677-14-8)
• EPA Substance Registry System: MYRAC ALDEHYDE(37677-14-8)

Safety Data

• Hazardous Substances Data: 37677-14-8(Hazardous Substances Data)

Usage

Chemical Properties

MYRAC ALDEHYDE is prepared, together with its 3-isomer, by a Diels–Alder reaction ofmyrcene and acrolein.Themixture, d20 4 0.927–0.935, n20 D 1.488–1.492, has a fresh, fruity, slightly citrus-like odor and is used to perfume household products.

Occurrence

Has apparently not been reported to occur in nature

Preparation

From myrcene and acrolein (Arctander, 1969).

Hazard

Low toxicity by ingestion. A moderate skin and mild eye irritant.

Trade name

Myrac aldehyde (IFF), Myraldene (Givaudan), Myracal (DRT).

InChI:InChI=1/C13H20O/c1-11(2)4-3-5-12-6-8-13(10-14)9-7-12/h4,6,10,13H,3,5,7-9H2,1-2H3

Upstream product

• 123-35-3 7-methyl-3-methene-1,6-octadiene 
• 107-02-8 acrolein 

Downstream Products

• 40772-93-8 (±)-[4-(4-methyl-3-pentenyl)-3-cyclohexen-1-yl]methanol 
• 68991-97-9 (1,2,3,4,5,6,7,8-octahydro-8,8-dimethyl-2-naphthalenecarboxyaldehyde) 
• 73301-20-9 1-(4-methyl-3-pentenyl)cyclohexene 

Relevant articles and documents

Diels-Alder reaction of myrcene with carbonyl containing dienophiles supported on silica gel under microwave irradiation

Diels-Alder reactions of myrcene (7-methyl-3-methene-1,6-octadiene) with carbonyl containing dienophiles supported on silica gel under microwave irradiation have been studied.

Unsaturated aldehydes as alkene equivalents in the Diels-Alder reaction

A one-pot procedure is described for using α,β-unsaturated aldehydes as olefin equivalents in the Diels-Alder reaction. The method combines the normal electron demand cycloaddition with aldehyde dienophiles and the rhodium-catalyzed decarbonylation of aldehydes to afford cyclohexenes with no electron-with-drawing substituents. In this way, the aldehyde group serves as a traceless control element to direct the cycloaddition reaction. The Diels-Alder reactions are performed in a diglyme solution in the presence of a catalytic amount of boron trifluoride etherate. Subsequent quenching of the Lewis acid, addition of 0.3% of [Rh(dppp)2Cl] and heating to reflux achieves the ensuing decarbonylation to afford the product cyclohexenes. Under these conditions, acrolein, crotonaldehyde and cinnamaldehyde have been reacted with a variety of 1,3-dienes to afford cyclohexenes in overall yields between 53 and 88%. In these transformations, the three aldehydes serve as equivalents of ethylene, propylene and styrene, respectively.

Cycloaddition Of Carbonyl Compounds To Olefins At Aluminosilicate Catalysts

The use of zeolite catalysts in the reactions of allocimene and myrcene with α,β-unsaturated carbonyl compounds makes the reaction conditions milder and increases both the regio- and the stereoselectivity of the diene synthesis processes.In the reaction of certain polyenes with aldehydes at ascanite-bentonite clay a new reaction, leading to bicyclic ethers, was discovered.