35044-68-9

Basic information

• Product Name: ALPHA-DAMASCONE
• Synonyms: ALPHA-DAMASCONE;2-Buten-1-one, 1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-;B-Damascone;1-(2,6,6-Trimethyl-1-cyclohexenyl)-2-butene-1-one;1-(2-Butenoyl)-2,6,6-trimethyl-1-cyclohexene;3,4-Dihydro-3,4,7-megastigmatrien-7-one
• CAS NO: 35044-68-9
• Molecular Formula: C₁₃H₂₀O
• Molecular Weight: 192.2973
• Mol File: 35044-68-9.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 271.2±10.0 °C(Predicted)
• Appearance: /
• Density: 0.907±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: ALPHA-DAMASCONE(CAS DataBase Reference)
• NIST Chemistry Reference: ALPHA-DAMASCONE(35044-68-9)
• EPA Substance Registry System: ALPHA-DAMASCONE(35044-68-9)

Safety Data

• Hazardous Substances Data: 35044-68-9(Hazardous Substances Data)

Usage

Description

ALPHA-DAMASCONE is a colorless to pale yellow liquid with a powerful floral and complex fruity note, reminiscent of plum, rose, and blackcurrant. It is found as a volatile constituent in many natural materials, such as rose oils and extracts.

Uses

Used in Perfumery:
ALPHA-DAMASCONE is used as a fragrance ingredient in perfume compositions, particularly in rose perfumes, to impart a natural and complex fruity scent.
Used in Flavor Industry:
ALPHA-DAMASCONE is used as a flavoring agent in the flavor industry to add naturalness and body to various food products. It is found in a variety of foods, including bilberry, butter, milk, caviar, chicken fat, cooked beef and mutton, cured pork, pork and beef fat, roasted filberts and peanuts, pecans, potato chips, soybean, coriander leaf and seed, and kiwifruit.
Used in the Synthesis of Damascones:
ALPHA-DAMASCONE can be used as a starting material in the synthesis of other damascones, which are also used in perfumery and flavor industries. One synthetic route to the damascones starts with an appropriate cyclogeranic acid derivative, which is reacted with an allyl magnesium halide to give 2,6,6-trimethylcyclohexenyl diallyl carbinol. ALPHA-DAMASCONE, upon pyrolysis, yields the desired l-(2,6,6-trimethylcyclohexenyl)-3-buten-l-one, and damascone is obtained by rearrangement of the double bond in the side chain.

Preparation

Various methods: recently from ionone izoxazoles, also from 7,8-dehydro-β-ionole.

Upstream product

• 35124-05-1 2,6,6-Trimethyl-α-(1-propenyl)-1-cyclohexene-1-methanol 
• 472-80-0 beta-Ionol 
• 141-79-7 4-methyl-pent-3-en-2-one 
• 1197-92-8 1-(2,6,6-trimethyl-cyclohex-1-enyl)-ethanone 
• 75-07-0 acetaldehyde 
• 25915-53-1 2,6,6-trimethyl-3-cyclohexenyl methyl ketone 
• 39900-16-8 2,6,6-trimethyl-1-[3-hydroxy-butan-1-oyl]-cyclohex-1-ene 
• 39900-12-4 1-(2,6,6-trimethyl-1-cyclohexenyl)-1,3-butanedione 
• 39190-06-2 β-ionone isoxazole 
• 79-77-6 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one 
• 124572-60-7 β-ionone epoxyhydrazone 
• 38448-31-6 β-ionone epoxide 
• 23726-90-1 (Z)-2,6,6-Trimethyl-α-(1-propenyl)-1-cyclohexene-1-methanol 

Downstream Products

• 23696-85-7 1-(2,6,6-trimethyl-1,3-cyclohexadiene-1-yl)-2-butene-1-one 

Relevant articles and documents

Synthesis process of beta-damascenone

The invention belongs to the technical field of chemical synthesis of perfume essences and in particular relates to a novel synthesis process for industrial production of beta-damascenone. The synthesis process comprises the following steps: by taking 1,3-pentadiene as a starting material, performing a Diels-Alder addition reaction on the 1,3-pentadiene with 4-methyl-3-pentene-2-one under catalysis of AlCl3 firstly so as to generate 1-(2,6,6,-trimethyl cyclohexyl-3-alkenyl)-butanone; under the catalysis of a solid super strong acid catalyst, performing olefin isomerization so as to obtain 1-(2,6,6,-trimethyl cyclohexyl-1-alkenyl)-butanone; and finally, performing a hydroxyaldehyde condensation reaction with acetaldehyde, so as to generate a target product, namely beta-damascenone. The synthesis process provided by the invention has the main advantages that the raw material cost is low, the energy consumption is low, a gas-phase reaction catalyzed by the solid super strong acid catalystis implemented in an olefin isomerization production process, the product purity is high, no reaction solvent is needed, a very small amount of wastewater or waste gas is generated, and in addition,the catalyst is good in reuse performance.

1 - (2, 6, 6 - trimethyl - cyclohexenyl) - 2 - butene - 1 - ketone

The invention provides a 1-(2,6,6-trimethyl-cyclohexenyl)-2-buten-1-one preparation method, which comprises that 1-(2,6,6-trimethyl-3-cyclohexenyl)-1,3-butanedione is subjected to isomerization to obtained an isomerized product; and the isomerized product reacts to obtain 1-(2,6,6-trimethyl-cyclohexenyl)-2-buten-1-one, wherein the 1-(2,6,6-trimethyl-cyclohexenyl)-2-buten-1-one comprises 1-(2,6,6-trimethyl-cyclohex-1-enyl)-2-buten-1-one and 1-(2,6,6-trimethyl-cyclohex-2-enyl)-2-buten-1-one. According to the present invention, the 1-(2,6,6-trimethyl-3-cyclohexenyl)-1,3-butanedione is adopted as the raw material, such that the oxidation of the alcohol into the ketone is avoided compared with the prior art, and the environmental pollution is low; and the route is simple, and the scale production is easily achieved.

A β- malaysian ketene method for the preparation of perfume

The invention discloses a preparation method of beta-damascenone spice. The preparation method comprises the following steps: (1) by taking beta-ionone as an initial raw material, carrying out a reaction with hydroxylamine hydrochloride in an alkaline environment to obtain beta-ionone oxime; (2) carrying out a reaction on beta-ionone oxime and halogens and metal salt thereof to obtain a beta-ionone oxime isoxazole derivative; (3) acting on the eta-ionone oxime isoxazole derivative and sodium to generate beta-dihydrodamascenone; and (4) carrying out an oxidizing halogenating reaction on beta-dihydrodamascenone and free radicals of halogens and carrying out an elimination reaction of removing halogen hydride under the alkaline environment to obtain the beta-damascenone. The preparation method disclosed by the invention is cheap and easily available in raw materials, simple to operate, mild in reaction condition, high in yield of reactions and low in cost, and the solvent used can be recycled, so that the preparation method is a method suitable for industrially producing beta-damascenone spice.