14398-36-8

Basic information

• Product Name: [S-(E)]-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one
• Synonyms: [S-(E)]-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one;(3E)-4-[(S)-2,6,6-Trimethyl-2-cyclohexen-1-yl]-3-buten-2-one;(E)-4-[(1S)-2,6,6-Trimethyl-2-cyclohexenyl]-3-butene-2-one;(E)-4-[(S)-2,6,6-Trimethyl-2-cyclohexen-1α-yl]-3-buten-2-one;(E)-4-[(S)-2,6,6-Trimethyl-2-cyclohexenyl]-3-butene-2-one;(S)-α-Ionone;Einecs 238-362-9
• CAS NO: 14398-36-8
• Molecular Formula: C₁₃H₂₀O
• Molecular Weight: 192.2973
• EINECS: 238-362-9
• Mol File: 14398-36-8.mol
• Article Data: 34

Chemical Properties

• Boiling Point: 257.6°C at 760 mmHg
• Flash Point: 111.9°C
• Appearance: /
• Density: 0.935g/cm³
• Vapor Pressure: 0.0144mmHg at 25°C
• Refractive Index: 1.511
• CAS DataBase Reference: [S-(E)]-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: [S-(E)]-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one(14398-36-8)
• EPA Substance Registry System: [S-(E)]-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one(14398-36-8)

Safety Data

• Hazardous Substances Data: 14398-36-8(Hazardous Substances Data)

Usage

Description

[S-(E)]-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one, also known as Citral, is an organic compound belonging to the enones class. It is a yellow liquid with a strong odor and is naturally found in plants. Citral is recognized for its antimicrobial and antioxidant properties, making it a versatile compound with applications in various industries.

Uses

Used in Fragrance Industry:
Citral is used as a key component in the fragrance industry due to its strong and distinctive odor. It contributes to the creation of various scents for perfumes, colognes, and other aromatic products.
Used in Flavoring Industry:
In the flavoring industry, Citral is employed as a flavoring agent for various food products. Its natural occurrence and distinctive taste make it a popular choice for enhancing the flavor of different culinary items.
Used in Pharmaceutical Industry:
Citral has potential applications in the pharmaceutical industry, particularly in the development of new drugs. Its unique chemical structure and properties make it a promising candidate for research and development in drug formulation.
Used in Antimicrobial Applications:
Due to its antimicrobial properties, Citral is used in various industrial and consumer products to inhibit the growth of harmful microorganisms, ensuring cleanliness and safety.
Used in Antioxidant Applications:
Citral's antioxidant properties make it useful in the development of products that require protection against oxidative damage, such as cosmetics, skincare, and other personal care items.
Used in the Food Industry:
In the food industry, Citral is used as a flavoring agent to enhance the taste and aroma of various food products, contributing to a more enjoyable and flavorful eating experience.
It is important to handle Citral with care, as it is flammable and may cause irritation upon contact with skin or eyes. Proper safety measures should be taken during its use and storage to ensure the safety of individuals and the environment.

InChI:InChI=1/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h6-8,12H,5,9H2,1-4H3

Upstream product

• 64-17-5 ethanol 
• 79-77-6 (E)-β-ionone 
• 141-52-6 sodium ethanolate 
• 141-10-6 pseudoionone 
• 6627-74-3 (+/-)-α-cyclogeraniol 
• 472-20-8 β-cyclogeraniol 
• 52340-45-1 4c-(2,6,6-trimethyl-cyclohex-2-enyl)-but-3-en-2-one 
• 13927-47-4 (3E,5Z)-6,10-dimethyl-3,5,9-undecatrien-2-one 
• 141-10-6 pseudoionone 
• 25312-34-9 alpha-ionol 
• 28102-24-1 (Z)-2,6,6-Trimethyl-α-(1-propenyl)-2-cyclohexene-1-methanol 
• 157552-18-6 5-Hydroxy-3-oxo-5-(2,6,6-trimethyl-cyclohex-1-enyl)-pentanoic acid tert-butyl ester 
• 62692-61-9 5E-6,10-dimethylundeca-3,5,9-trien-2-one 
• 14505-74-9 α-cyclocitral 

Downstream Products

• 4359-32-4 trans-1-(2,4-dimethyl-[1,3]dioxolan-2-yl)-2-(2,6,6-trimethyl-cyclohex-2-enyl)-ethylene 
• 25312-34-9 alpha-ionol 
• 37384-69-3 3-(2,6,6-trimethyl-2-cyclohexen-1-yl)-2-propenoic acid 
• 13720-37-1 dihydro-α-ionol 
• 446293-91-0 4-(2,6,6-trimethyl-cyclohex-1-enyl)-butan-2-ol 
• 31499-72-6 7,8-dihydro-α-ionone 
• 57461-21-9 (3E)-4-(2,3,6-trimethylphenyl)but-3-en-2-one 
• 79734-43-3 3,5,5-trimethyl-4-[(E)-3-oxo-1-butenyl]-2-cyclohexen-1-one 
• 52340-45-1 4c-(2,6,6-trimethyl-cyclohex-2-enyl)-but-3-en-2-one 
• 4361-23-3 trans-tetrahydroionol 
• 6138-85-8 tetrahydroionone 
• 127-41-3 trans-α-ionone 
• 133399-20-9 (+/-)-4t-(2,6,6-trimethyl-cyclohex-2-enyl)-but-3-en-2-one semicarbazone 
• 37677-81-9 4-(2,3-epoxy-2,6,6-trimethylcyclohexyl)-3-buten-2-one 

Relevant articles and documents

The Synthesis of Optically Active Enriched (+)-(6R)-α-Ionone

Starting with the readily available (-)-(S)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-one (2) an optically active enriched sample of (+)-(6R)-α-ionone (1) (85percent enantiomeric excess) was synthesized.

Controlled release of encapsulated bioactive volatiles by rupture of the capsule wall through the light-induced generation of a gas

The encapsulation of photolabile 2-oxoacetates in core-shell microcapsules allows the light-induced, controlled release of bioactive compounds. On irradiation with UVA light these compounds degrade to generate an overpressure of gas inside the capsules, which expands or breaks the capsule wall. Headspace measurements confirmed the light-induced formation of CO and CO2 and the successful release of the bioactive compound, while optical microscopy demonstrated the formation of gas bubbles, the cleavage of the capsule wall, and the leakage of the oil phase out of the capsule. The efficiency of the delivery system depends on the structure of the 2-oxoacetate, the quantity used with respect to the thickness of the capsule wall, and the intensity of the irradiating UVA light.

ω-Sulfonic-perfluoroalkylated poly(styrene-maleic anhydride)/silica hybridized nanocomposite as a new kind of solid acid catalyst

A new kind of ω-sulfonic-perfluoroalkylated poly(styrene-maleic anhydride)/silica hybrid nanocomposite FSMA/SiO2 has been synthesized under mild conditions by perfluoroalkylation of styrene-maleic anhydride copolymer (SMA) with ω-fluorosulfonylperfluorodiacyl peroxides (SFAP), and followed in turn by aminolysis using (3-aminopropyl)triethoxysilane (APTES), alkali hydrolysis, gelation with tetraethoxysilane (TEOS) and finally acidification. The hybrid solid acid FSMA/SiO2 with terminal perfluoroalkylsulfonic and carboxyl groups was characterized by FTIR, SEM, TEM, TGA, XPS, EDX, acidimetry and nitrogen sorption technique. Its pore structure, acid strength and acid amount were easily modulated by controlling the gelation and perfluoroalkylation conditions. The catalytic activity and selectivity, as well as reusability of FSMA/SiO2 were tested in three important reactions, namely, cyclization of pseudoionone, condensation of indole and esterification of benzoic acid. Owing to the higher exchange capacity than that of Nafion/SiO2, and the stronger acidity than that of Amberlyst-15, the nanocomposite FSMA/SiO2 showed higher activity and selectivity than these commercial solid acids in the reactions.