24720-09-0

Basic information

• Product Name: (E)-1-(2,6,6-TRIMETHYL-CYCLOHEX-2-ENYL)-BUT-2-EN-1-ONE
• Synonyms: (2E)-1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-2-buten-1-one;1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-,(E)-2-Buten-1-one;1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-trans-2-Buten-1-one;2-Buten-1-one, 1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (E)-;2-Buten-1-one,1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-,(E)-;6,6-trimethyl-2-cyclohexen-1-yl)-1-((e)-2-buten-1-on;trans-2-Buten-1-one, 1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-;(E)-1-(2,6,6-TRIMETHYL-CYCLOHEX-2-ENYL)-BUT-2-EN-1-ONE
• CAS NO: 24720-09-0
• Molecular Formula: C₁₃H₂₀O
• Molecular Weight: 192.3
• EINECS: 246-430-4
• Product Categories: ketone Flavor
• Mol File: 24720-09-0.mol

Chemical Properties

• Boiling Point: 267.1 °C at 760 mmHg
• Flash Point: 100 °C
• Appearance: /
• Density: 0.898 g/cm³
• Vapor Pressure: 0.0083mmHg at 25°C
• Refractive Index: n20/D 1.496
• Water Solubility: 140mg/L at 20℃
• CAS DataBase Reference: (E)-1-(2,6,6-TRIMETHYL-CYCLOHEX-2-ENYL)-BUT-2-EN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1-(2,6,6-TRIMETHYL-CYCLOHEX-2-ENYL)-BUT-2-EN-1-ONE(24720-09-0)
• EPA Substance Registry System: (E)-1-(2,6,6-TRIMETHYL-CYCLOHEX-2-ENYL)-BUT-2-EN-1-ONE(24720-09-0)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• Hazardous Substances Data: 24720-09-0(Hazardous Substances Data)

Usage

Uses

Used in Fragrance Industry:
(E)-1-(2,6,6-TRIMETHYL-CYCLOHEX-2-ENYL)-BUT-2-EN-1-ONE is used as a fragrance ingredient for its floral rose, apple fruity, and black currant aroma. Its high strength odor makes it suitable for creating a strong and pleasant scent in various fragrance products.
Used in Flavor Industry:
In the flavor industry, (E)-1-(2,6,6-TRIMETHYL-CYCLOHEX-2-ENYL)-BUT-2-EN-1-ONE is used as a flavoring agent for its fruity and floral notes. It can be used to enhance the taste and aroma of various food and beverage products, adding a unique and pleasant flavor profile.
Used in Cosmetics Industry:
(E)-1-(2,6,6-TRIMETHYL-CYCLOHEX-2-ENYL)-BUT-2-EN-1-ONE is used as a scent additive in the cosmetics industry. Its strong and pleasant aroma can be incorporated into various cosmetic products, such as perfumes, lotions, and creams, to provide a desirable scent and enhance the overall sensory experience for the user.
Used in Aromatherapy:
In aromatherapy, (E)-1-(2,6,6-TRIMETHYL-CYCLOHEX-2-ENYL)-BUT-2-EN-1-ONE is used as an essential oil for its calming and uplifting properties. Its floral and fruity aroma can help create a relaxing and invigorating atmosphere, promoting mental well-being and stress relief.
Used in the Production of Fine Chemicals:
(E)-1-(2,6,6-TRIMETHYL-CYCLOHEX-2-ENYL)-BUT-2-EN-1-ONE can also be used as a starting material or intermediate in the synthesis of various fine chemicals, such as pharmaceuticals, agrochemicals, and specialty chemicals. Its unique chemical structure and properties make it a valuable component in the development of new and innovative products.

Synthesis Reference(s)

The Journal of Organic Chemistry, 55, p. 1106, 1990 DOI: 10.1021/jo00290a057Tetrahedron Letters, 23, p. 335, 1982 DOI: 10.1016/S0040-4039(00)86824-0

Flammability and Explosibility

Notclassified

InChI:InChI=1/C13H20O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5,7-8,12H,6,9H2,1-4H3/b7-5+

Upstream product

• 14505-74-9 α-cyclocitral 
• 5674-01-1 2-methylallylmagnesium chloride 
• 123-73-9 crotonaldehyde 
• 78-79-5 isoprene 
• 39190-09-5 3-methyl-5-[2,6,6-trimethyl-cyclohex-2-en-1-yl]-isoxazole 
• 887256-12-4 4'-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3'-buten-2'-ketoxime 
• 590-13-6 (Z)-1-propenyl bromide 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 408534-44-1 C₁₆H₂₂N₂O₂S 
• 35076-50-7 γ-damascol 
• 41169-33-9 3,5,5-trimethylcyclohexa-1,3-diene 
• 503-47-9 1,3,3-trimethyl-1-cyclohexene 
• 29481-98-9 1,3-dimethyl-2-cyclohexen-1-ol 
• 1193-18-6 3-methylcyclohexen-2-one 

Downstream Products

• 39872-57-6 Isodamascone 
• 23726-94-5 (Z)-1-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-2-buten-1-one 
• 878665-06-6 3-benzyloxy-1-(2,6,6-trimethyl-cyclohex-2-enyl)-butan-1-one 
• 130285-75-5 3-methyl-4-nitro-1-(2',6',6'-trimethylcyclohex-1-en-1-yl)butan-1-one 
• 104751-86-2 3-methyl-4-nitro-1-(2',6',6'-trimethylcyclohex-2-en-1-yl)butan-1-one 
• 51769-15-4 3-hydroxy-α-damascone 
• 43126-29-0 (E)-megastigma-4,8-diene-3,7-dione 
• 1447716-76-8 C₁₅H₂₂O₃ 
• 1447716-75-7 (S)-(+)-4-hydroxy-β-damascone 
• 1019850-29-3 3-(2-hydroxy-ethylsulfanyl)-1-(2,6,6-trimethyl-cyclohex-2-enyl)-butan-1-one 
• 804565-47-7 3-{[3-(triethoxysilyl)propyl]thio}-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-butanone 
• 851387-51-4 3-{[3-(triethoxysilyl)propyl]amino}-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-butanone 
• 104751-91-9 (3β,5α,5aβ,8aβ,8bβ)-(+/-)-4,5,5a,6,7,8,8a,8b,-octahydro-3,6,6,8b-tetramethyl-3H-naphth<1,8-cd>isoxazol-5-ol acetate 
• 104751-91-9 (3α,5α,5aβ,8aβ,8bβ)-(+/-)-4,5,5a,6,7,8,8a,8b,-octahydro-3,6,6,8b-tetramethyl-3H-naphth(1,8-cd)isoxazol-5-ol acetate 

Relevant articles and documents

Preparation process of alpha-damascenone

The invention relates to a preparation process of alpha-damascenone. The preparation process of the alpha-damascenone comprises the following steps: taking alpha-ionone, namely a compound A, as a rawmaterial, reacting the alpha-ionone with hydroxylamine hydrochloride to obtain alpha-oximes of ionones, namely a compound B; carrying out epoxidation on double bonds in the compound B to obtain alpha-epoxidized oximes of ionones, namely a compound C; dehydrating the compound C under the effect of acid to obtain alpha-ionone isoxazole derivative, namely a compound D; and carrying out reduction on the compound D to obtain a final product E which is the alpha-damascenone. The alpha-ionone is used as the raw material, the alpha-damascenone can be prepared by only four steps, the preparation process of the alpha-damascenone has the characteristics of short reaction period, low preparation cost, high yield of various steps and easiness in follow-up treatment, and is suitable for industrial production, and a gap of domestic industrial production of the product at present is filled.

New preparation methods for α-damascone, γ-damascone, and β-damascenone using pyronenes

γ- and δ-Pyronenes are terpenic synthons easily available from myrcene. They are used as intermediates in the synthesis of α-damascone, γ-damascones, and β-damascenone. Copyright Taylor & Francis Group, LLC.

SYNTHESIS OF α-DAMASCONE AND 1-(2,6,6-TRIMETHYL-2-TETRAHYDROPYRANYL)-2-ALKEN-1-ONES

α-Damascone was obtained by the reaction of α-cyclocitral with allyl bromide in the presence of zinc, followed by oxidation of the obtained alcohol with chromic acid to the ketone and isomerization of the latter with triethylamine as catalyst.The analogous synthesis of β-damascone from 1-(4,6,6-trimethyl-1,3-cyclohexadienyl)-2-buten-1-one was impossible on account of complications at the oxidation stage.The rearrangement of the acetylenic alcohols with polyvanadioorganosiloxane as catalyst led to 1-(2,6,6-trimethyl-2-tetrahydropyranyl)-2-alken-1-ones.

Reaction of Ester Enolates with Nucleophiles. Stereocontrolled Formation of Ketone and Aldehyde Enolates

Lithium enolates of carboxylic and thiocarboxylic esters react with nucleophiles to afford ketone and aldehyde enolates and subsequently their enol silyl ethers diastereoselectively.This reaction is applied to the synthesis of γ-damascone, α-damascone, β-safranal, and artemisia ketone.

HYDROLYSE ACIDO-CATALYSEE D'UN SULFURE DE DIENYLE APPLICATION A LA SYNTHESE DE LA gamma-DAMSCONE

A new synthetic route to γ-Damascone 1 starting with methyl-γ-dithiocyclogeranate 2 is described.Addition of HMPT was found necessary to perform the carbophilic addition of allylmagnesium bromide on dithioester 2.A dienylsulfide, 6,6-dimethyl-2-methylene-(1-methylthio-1,3-butadiene)-1-yl cyclohexane 3 resulted from this addition, and not the expected dithioketal.Following a number of described conditions, hydrolysis of 3 to γ-damascone 1 proved to be unsatisfactory.These initial attempts but showed the necessity for an acidic medium.This finding allowed the development of a new, very mild method of hydrolysis of dienylsulfides to unsaturated ketones.

172. β-Cleavage of Bis(homoallylic) Potassium Alkoxides. Two-Step Preparation of Propenyl Ketones from Carboxylic Esters. Synthesis of ar-Turmerone, α-Damascone, β-Damascone, and β-Damascenone

The transformation of 36 bis(homoallylic) alcohols VII to alkenones IX and X via β-cleavage of their potassium alkoxides VIIa in HMPA has been investigated (cf.Scheme 2).These studies have established an order of β-cleavage for 2-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1,1-dimethyl-2-propenyl, and benzyl groups in alkoxides 49a-56a and have allowed a comparison between the β-cleavage reaction and the oxy-Cope rearrangement in alkoxides 74a-83a.As illustrative synthetic applications, a two-step preparation of propenyl ketones 15-42 from carboxylic esters is described, together with syntheses of ar-turmerone (48), α-damascone ((E)-71), β-damascone ((E)-109), and β-damascenone ((E)-111).

SYNTHESIS WITH ORGANOBORANES. 2. SYNTHESIS OF α- AND γ-DAMASCONE

Selective synthesis of α- and γ-damascone, using allylic organoboranes as key intermediates, are described.

GRIGNARD AND HYDRIDE ADDITION TO A KETENE INTERMEDIATE: A NOVEL ACCESS TO α-DAMASCONE AND α-CYCLOCITRAL

α-Damascone (1), a rose fragrance chemical, was synthesized by an allylmagnesium chloride addition to ketene 7 as key step.When the same ketene 7 was reduced by two different aluminium hydride reagents, α-cyclocitral was obtained.The presumed intermediates, enolates II and III, were first trapped as silyl enol ethers and then hydrolyzed with D2O to give the expected α-monodeuterated carbonyl compounds.Mixed aluminium hydride reduction of ketenes is recommended as a facile entry into the chemistry of aldehyde enolates.

Synthesis of (E)-1-Propenyl Ketones from Carboxylic Esters and Carboxamides by Use of Mixed Organolithium-Magnesium Reagents

The novel reagents formed by combination of allylmagnesium chloride and a strong non-nucleophilic lithium base (LiNR2) convert non- or slowly enolizable carboxylic esters or carboxamides into 2-propenyl ketones which are protected from further reaction by their in situ conversion into enolates.This modified Grignard reaction is applied to efficient syntheses of α-damascone, β-damascone, β-damascenone, and various other (E)-1-propenyl ketones.