432-24-6

Basic information

• Product Name: alpha-Cyclociral
• Synonyms: alpha-Cyclociral;1-formyl-2,6,6-trimethyl-2-cyclohexene;2,6,6-Trimethylcyclohex-2-ene-1-carbaldehyde;2,6,6-Trimethyl-cyclohex-2-enecarbaldehyde;a-Cyclocitral;2-Cyclohexene-1-carboxaldehyde, 2,6,6-trimethyl-;PSEUDOCYCLOCITRAL;2,6,6-Trimethyl-2-cyclohexene-1-carbaldehyde
• CAS NO: 432-24-6
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23
• EINECS: 207-080-8
• Product Categories: Chiral Reagents
• Mol File: 432-24-6.mol

Chemical Properties

• Boiling Point: 78-810C/5.4Torr
• Flash Point: 64.5 °C
• Appearance: Pale Yellow Oil
• Density: 0.935 g/cm³
• Vapor Pressure: 0.382mmHg at 25°C
• Refractive Index: 1.5
• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• Stability: Light Sensitive
• CAS DataBase Reference: alpha-Cyclociral(CAS DataBase Reference)
• NIST Chemistry Reference: alpha-Cyclociral(432-24-6)
• EPA Substance Registry System: alpha-Cyclociral(432-24-6)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• Hazardous Substances Data: 432-24-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Alpha-Cyclocitral is used as a key intermediate in the synthesis of various organic compounds. Its chemical properties allow it to participate in a range of reactions, making it a versatile building block for creating new molecules with specific functions and applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, alpha-Cyclocitral is used as a starting material for the development of new drugs. Its unique chemical structure can be modified and combined with other molecules to create potential therapeutic agents that target specific diseases or conditions.
Used in Fragrance Industry:
Due to its distinct chemical properties, alpha-Cyclocitral is also used in the fragrance industry as a component in the creation of various scents. Its ability to contribute to the overall aroma profile of a fragrance makes it a valuable asset in the development of new and innovative perfumes and scented products.
Used in Flavor Industry:
In addition to its applications in the fragrance industry, alpha-Cyclocitral is also utilized in the flavor industry. Its unique taste and aroma characteristics can be incorporated into the development of new flavors for the food and beverage sector, enhancing the sensory experience of consumers.

Synthesis Reference(s)

Tetrahedron Letters, 14, p. 377, 1973 DOI: 10.1016/S0040-4039(01)95666-7

InChI:InChI=1/C10H16O/c1-8-5-4-6-10(2,3)9(8)7-11/h5,7,9H,4,6H2,1-3H3

Upstream product

• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 6627-74-3 (+/-)-α-cyclogeraniol 
• 564-24-9 (+/-)-α-cyclogeranic acid 
• 61899-98-7 2,6,6-trimethylcyclohex-2-en-1-ylidene ketene 
• 432-25-7 2,6,6-trimethylcyclohex-1-enecarbaldehyde 
• 78842-52-1 N-(β-cyclocitrylidene)aniline 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 91056-62-1 2,6,6-trimethyl-cyclohex-3-enecarbaldehyde 
• 81708-96-5 C₁₁H₁₉N 
• 20013-73-4 2,6,6-trimethylcyclohex-2-en-1-one 
• 60714-17-2 1,1-dimethyl-2,3-bis(methylene)cyclohexane 
• 72172-57-7 (E)-2,7-dimethyl-2,6-octadienal 
• 4698-08-2 (E)-geranic acid 
• 72008-24-3 4,8,8-trimethyl-1-oxaspiro[2.5]oct-4-ene 

Downstream Products

• 432-25-7 2,6,6-trimethylcyclohex-1-enecarbaldehyde 
• 37384-70-6 3-(2,6,6-trimethyl-cyclohex-2-enyl)-acrylic acid ethyl ester 
• 118798-06-4 1-(3-Hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-ethanone 
• 176325-26-1 3-(4-methoxyphenethenyl)-2,4,4-trimethyl-1-cyclohexene 
• 627079-44-1 2-(3-methoxyphenyl)-1-(2,6,6-trimethylcyclohex-2-enyl)ethanol 
• 74408-55-2 3-(1-Butenyl)-2,4,4-trimethylcyclohexene 
• 78995-99-0 6,6-dimethyl-1-(hydroxymethyl)-2-(methyl-d3)-1-cyclohexene-3,3-d2 
• 99427-82-4 C₁₀H₁₂⁽²⁾H₅Br 
• 78996-15-3 (E)-retinoic acid-4,4,18,18,18-d5 
• 78995-96-7 ethyl (E)-retinoate-4,4,18,18,18-d5 
• 78995-97-8 <6,6-dimethyl-2-(methyl-d3)-1-cyclohexen-3,3-d2-1-yl>methyltriphenylphosphonium bromide 
• 78842-55-4 2-[1,3]dioxolan-2-yl-1,3,3-trimethyl-cyclohexene 
• 78842-54-3 α-cyclocitral ethylene acetal 
• 78842-52-1 N-(β-cyclocitrylidene)aniline 

Relevant articles and documents

Synthesis method of alpha-cyclocitral

The invention discloses a synthesis method of alpha-cyclocitral. The method comprises the steps of (1) carrying out Diels-Alder reaction on 1,3-pentadiene and methylcrotonaldehyde under the catalysisof lewis acid to obtain a 2,6,6-trimethyl-3-cyclohexenyl formaldehyde crude product; (2) carrying out isomerization reaction on the 2,6,6-trimethyl-3-cyclohexenyl formaldehyde crude product obtained in step (1) under the catalysis of a catalyzer to generate an alpha-cyclocitral crude product. The method provided by the invention is easy to get reaction raw materials, mild in conditions, easy to control, free of generating byproducts, simple in process, favorable in industrial production, green and environmentally friendly.

Method for preparing cyclocitral by micro-structural reactors

The invention discloses a method for preparing cyclocitral by micro-structural reactors. The method comprises steps as follows: a liquid raw material citral and organic amine in a mole ratio being 1: (0.8-1.5) are simultaneously pumped into a tubular reactor or one micro-structural reactor for an amination reaction, the reaction temperature of the reactor is controlled in a range of 10-20 DEG C, a flow velocity of a reaction liquid is controlled, the reaction liquid is enabled to totally stay in the reactor for 0.1-25 min, and obtained aldimine and concentrated sulfuric acid are injected into another micro-structural reactor and subjected to a ring closing reaction; a reaction product is neutralized by a sodium hydroxide solution and is subjected to acidic hydrolysis, liquid separation, reduced pressure distillation and drying, and a pale yellow oily product, namely, cyclocitral, is obtained. According to the method, the reaction time is short, the reaction temperature is accurate and controllable, and product selectivity and yield are high. The method adopts simple steps, and is convenient to operate and high in practicability.

Synthesis of three putative kairomones of the beech leaf-mining weevil Orchestes fagi (L.)

The beech leaf-mining weevil, Orchestes fagi (L.), also known as the beech flea weevil, is a common and widespread pest of beech, Fagus sylvatica L., in its native Europe. It now appears to be well established in Nova Scotia, Canada. We report a novel synthesis of 9-geranyl-p-cymene and syntheses of 9-geranyl-α-terpinene and 1,1-dimethyl-3-methylene-2-vinylcyclohexane, making partial use of known methods. All three of these compounds are found in beech leaf volatiles and/or wood and are putative kairomones of the beech leaf-mining weevil.

Nitriles and carbonyl groups as acceptors in titanocene-catalyzed radical cyclizations

A catalytic approach to the titanocene-mediated radical cyclization of epoxy nitriles and epoxy carbonyl compounds to hydroxy ketones and diols is described. The reaction is sensitive to the substitution pattern of the catalyst and especially useful for the preparation of cyclobutanones. It can also be used for nitrile group transfer. Georg Thieme Verlag Stuttgart.

Improved synthesis of methyl 3-oxo-2,6,6-trimethylcyclohex-1-ene-1- carboxylate, an A-ring intermediate for (±)strigol

Methyl 3-oxo-2,6,6-trimethylcyclohex-1-ene-1-carboxylate was synthesised over eight steps from the starting material of citral instead of α-ionone. KMnO4, HC(OEt)3 and O2/TEMPO/CuCl were substituted for NaIO4, CH3I and pyridinium chlorochromate, respectively. Every step was simplified and gave a 48% overall yield. The procedure is suitable for large scale production.

Isolation, synthesis, and anti-tumor activities of a novel class of podocarpic diterpenes

A novel unusual 17-carbon diterpenoid, named (+)-7-deoxynimbidiol, was isolated from the stalks of Celastrus hypoleucus (Oliv.) Warb. Its racemate and derivatives were synthesized, and the inhibitory activities of these compounds against four cultured human-tumor cell lines were evaluated. The structure-activity relationship was discussed.

Synthesis of olivacene, a constituent of Archilejeunea olivacea

A simple synthesis of olivacene 1, a naturally occurring sesquiterpenoid hydrocarbon isolated from Archilejeunea olivacea has been described.

γ-Pyronene, a synthon derived from saffron and intermediary precursor of synthesis of forskolin and strigol

γ-Pyronene, a terpenic synthon available from myrcene, is an excellent raw material for the preparation of numerous intermediates used in the synthesis of perfumes, retinoids and biological derivatives such as forskolin or strigol.

Epoxy-pyronene: Obtention of cyclocitrals from ionones and precursor of new terpenic compounds

The selective obtention of epoxy-pyronene from δ-pyronene has been realized using metachloroperbenzoic acid. The isomerization of this epoxidic compound with Lewis and protonic acids and on active alumina has been studied leading to cyclocitrals. Ionones are obtained from epoxy-pyronene by homologation with various C3 units, in the presence of paratoluenesulfonic acid in order to obtain β-cyclocitral in situ. New terpenic compounds with the cyclogeranyl skeleton were obtained from epoxy-pyronene by reduction followed by homologation.