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
• Article Data: 13

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

Description

Alpha-Cyclocitral, with the CAS number 432-24-6, is a pale yellow oil compound that is primarily utilized in the field of organic synthesis. It is known for its unique chemical properties that make it a valuable component in various chemical reactions and processes.

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

• 72008-24-3 4,8,8-trimethyl-1-oxaspiro[2.5]oct-4-ene 
• 6627-74-3 (+/-)-α-cyclogeraniol 
• 78842-52-1 N-(β-cyclocitrylidene)aniline 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 91056-62-1 2,6,6-trimethyl-cyclohex-3-enecarbaldehyde 
• 107-86-8 3,3-dimethyl acrylaldehyde 
• 432-25-7 2,6,6-trimethylcyclohex-1-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 
• 514-95-4 1,5,5-trimethyl-6-methylene-cyclohexene 
• 72172-57-7 (E)-2,7-dimethyl-2,6-octadienal 
• 4698-08-2 (E)-geranic acid 
• 28043-10-9 methyl 2,6,6-trimethyl-cyclohex-2-en-1-yl carboxylate 

Downstream Products

• 90858-28-9 (+/-)-6-(2-Methoxy-5-isopropylstyryl)-1,5,5-trimethylcyclohexene 
• 564-24-9 (+/-)-α-cyclogeranic acid 
• 432-25-7 2,6,6-trimethylcyclohex-1-enecarbaldehyde 
• 471-90-9 2,6,6-trimethyl-cyclohex-1-enecarboxylic acid 
• 78995-98-9 pentadeuterio-β-cyclocitral 
• 126456-65-3 ethyl 3-(2,6,6-trimethyl-2-cyclohexenyl)-2-propenoate 
• 92186-90-8 E-5-carbomethoxy-2-methyl-4-penten-2-ol 
• 28897-23-6 1-(2,6,6-trimethyl-2-cyclohexenyl)-3-buten-1-ol 
• 6627-74-3 (+/-)-α-cyclogeraniol 
• 59444-43-8 dl-4-Benzoxy-β-cyclocitral 
• 59444-44-9 1-benzoyloxy-2,6,6-trimethyl-cyclohex-2-enecarbaldehyde 
• 178488-23-8 3-(3,4-dimethoxyphenylethenyl)-2,4,4-trimethyl-1-cyclohexene 
• 118798-24-6 1-(2,6,6-trimethyl-cyclohex-2-enyl)-ethan-1-ol 
• 627079-41-8 2-(3,4-methylenedioxyphenyl)-1-(2,6,6-trimethylcyclohex-2-enyl)ethanol 

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.

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.

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.