14901-07-6

Basic information

• Product Name: Irisone
• Synonyms: 3-Buten-2-one, 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (E)-;4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-on;4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one (beta-ionone);4-(2,6,6-trimethyl-1-cyclohexene-1-yl)-3-buten-2-one;4-(2,6,6-Trimethyl-1-cyclohexen-l-yl)-3-buten-2-one;4-(2,6,6-trimethyl-cyclohex-1-enyl)-but-3-en-2-one;5,7-Megastigmadien-9-one;beta-Ionene
• CAS NO: 14901-07-6
• Molecular Formula: C13H20O
• Molecular Weight: 192.3
• EINECS: 201-224-3
• Product Categories: Pharmaceutical Intermediates;Biochemistry;Monocyclic Monoterpenes;Terpenes
• Mol File: 14901-07-6.mol
• Article Data: 61

Chemical Properties

• Melting Point: -49°C
• Boiling Point: 126-128 °C12 mm Hg(lit.)
• Flash Point: 230 °F
• Appearance: Clear slightly yellow to yellow/Liquid
• Density: 0.945 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.706Pa at 25℃
• Refractive Index: n20/D 1.52(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 0[at 20 ℃]
• Water Solubility: SLIGHTLY SOLUBLE
• Stability: Light Sensitive
• Merck: 14,5056
• BRN: 1909544
• CAS DataBase Reference: Irisone(CAS DataBase Reference)
• NIST Chemistry Reference: Irisone(14901-07-6)
• EPA Substance Registry System: Irisone(14901-07-6)

Safety Data

• Hazard Codes: Xi,N
• Statements: 38-51/53-36/37/38
• Safety Statements: 61-36/37/39-27-26-24/25
• RIDADR: UN 3082 9/PG 3
• WGK Germany: 2
• RTECS: EN0500000
• Hazardous Substances Data: 14901-07-6(Hazardous Substances Data)

Usage

Description

Irisone, also known as β-Ionone, is a colorless to light yellow liquid with a characteristic violet-like odor, more fruity and woody than α-ionone. It is derived from various natural sources and is used in the perfumery industry due to its distinct cedar wood-like aroma. In very dilute alcoholic solutions, the odor of Irisone resembles the scent of violets.

Uses

Used in Perfumery:
Irisone is used as a fragrance ingredient for its distinct cedar wood-like odor with a hint of violets, adding depth and complexity to perfume compositions.
Used in Flavor and Fragrance Industry:
Irisone is used as a flavor and fragrance compound due to its woody, sweet, fruity, and berry-like taste with a green berry background. It is commonly found in the distillate from flowers of Boronia megatisma Nees and various other natural sources, contributing to the unique taste and aroma profiles of different products.
Used in Analytical Chemistry:
Irisone may be used as a reference standard in the determination of β-ionone in wine using solid-phase extraction followed by gas chromatography with mass spectrometry (GC-MS), ensuring accurate analysis and quality control in the beverage industry.
Used in the Food Industry:
Irisone is used as an additive in the food industry to enhance the flavor and aroma of various products, such as fruits, beverages, and dairy products, due to its versatile taste and scent characteristics.
Used in the Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, Irisone's antioxidant and antimicrobial activities against bacteria suggest potential applications in the pharmaceutical industry for the development of new drugs or as additives in the formulation of health products.

Preparation

By condensing citral with acetone to form pseudoionone, which is then cyclized by acid-type reagents.

Air & Water Reactions

Slightly water soluble .

Reactivity Profile

Irisone may react vigorously with oxidizing agents. May react exothermically with reducing agents to release hydrogen gas.

Health Hazard

ACUTE/CHRONIC HAZARDS: Toxic. May cause allergic reaction.

Flammability and Explosibility

Nonflammable

Biochem/physiol Actions

Taste at 1-20 ppm

InChI:InChI=1/C13H20O/c1-10-6-5-7-12(13(10,3)4)9-8-11(2)14/h7-10H,5-6H2,1-4H3/b9-8+/t10-/m1/s1

Upstream product

• 141-10-6 pseudoionone 
• 127-41-3 alpha-ionone 
• 14505-74-9 α-cyclocitral 
• 67-64-1 acetone 
• 432-25-7 2,6,6-trimethylcyclohex-1-enecarbaldehyde 
• 141-52-6 sodium ethanolate 
• 472-80-0 beta-Ionol 
• 62692-61-9 5E-6,10-dimethylundeca-3,5,9-trien-2-one 
• 627-79-2 6,10-dimethyl-undeca-3,5,9-trien-2-one semicarbazone 
• 86119-84-8 phosphoric acid 
• 7664-93-9 sulfuric acid 
• 75-52-5 nitromethane 
• 141-10-6 pseudoionone 
• 7446-70-0 aluminium trichloride 

Downstream Products

• 37836-28-5 (2E,4E,6E)-5-Methyl-7-(2,6,6-trimethyl-cyclohex-1-enyl)-hepta-2,4,6-trienoic acid 
• 112949-42-5 (+/-)-3,7-dimethyl-1t-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-1,6ξ,8-trien-4-yn-3-ol 
• 102550-87-8 (+/-)-7-hydroxy-3,7-dimethyl-9t-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2t,8-dien-4-ynoic acid ethyl ester 
• 2302-89-8 4-(2,6,6-trimethyl-cyclohex-1-enyl)-but-3-en-2-one semicarbazone 
• 36595-79-6 1,3,3-trimethyl-2-(3-methyl-penta-1,3-dienyl)-cyclohexene 
• 51547-40-1 1.1.3-trimethyl-2-(2³-metho-penten-(2¹)-ylol-(2³))-cyclohexene-⁽²⁾ 
• 3917-41-7 (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal 
• 446293-91-0 4-(2,6,6-trimethyl-cyclohex-1-enyl)-butan-2-ol 
• 2302-90-1 4t-(2,6,6-trimethyl-cyclohex-1-enyl)-but-3-en-2-one thiosemicarbazone 
• 2302-90-1 4-(2,6,6-trimethyl-cyclohex-1-enyl)-but-3-en-2-one thiosemicarbazone 
• 56013-05-9 (RS)-(E)-2-methyl-4-(2',6',6'-trimethyl-1'-cyclohexenyl)-3-butenal 
• 85763-13-9 3.5-dioxo-1t-(2.2.6-trimethyl-cyclohexen-⁽⁶⁾-yl)-hexen-⁽¹⁾-oic acid-⁽⁶⁾-methyl ester 

Relevant articles and documents

An unexpected generation of magnetically separable Se/Fe3O4 for catalytic degradation of polyene contaminants with molecular oxygen

Selenization of Fe2O3 with NaHSe led to Se/Fe3O4. The unexpected generation of Fe3O4 attributed to the reduction conditions of the reaction, and the resulted magnetic features of the materi

Carotenoid-cleavage activities of crude enzymes from pandanous amryllifolius

Carotenoid degradation products, known as norisoprenoids, are aroma-impact compounds in several plants. Pandan wangi is a common name of the shrub Pandanus amaryllifolius. The genus name Pandanus is derived from the Indonesian name of the tree, pandan. In Indonesia, the leaves from the plant are used for several purposes, e.g., as natural colorants and flavor, and as traditional treatments. The aim of this study was to determine the cleavage of β-carotene and β-apo-8-carotenal by carotenoidcleavage enzymes isolated from pandan leaves, to investigate dependencies of the enzymatic activities on temperature and pH, to determine the enzymatic reaction products by using Headspace Solid Phase Microextraction Gas Chromatography/Mass Spectrophotometry (HS-SPME GC/MS), and to investigate the influence of heat treatment and addition of crude enzyme on formation of norisoprenoids. Crude enzymes from pandan leaves showed higher activity against β-carotene than β-apo-8-carotenal. The optimum temperature of crude enzymes was 70°, while the optimum pH value was 6.We identified bionone as the major volatile reaction product from the incubations of two different carotenoid substrates, β-carotene and β-apo-8-carotenal. Several treatments, e.g., heat treatment and addition of crude enzymes in pandan leaves contributed to the norisoprenoid content. Our findings revealed that the crude enzymes from pandan leaves with carotenoid-cleavage activity might provide a potential application, especially for biocatalysis, in natural-flavor industry.

Method for preparing beta-ionone through cyclization

The invention discloses a method for preparing beta-ionone through cyclization. The method comprises the following steps: with pseudoionone as a raw material, performing cyclization on the pseudoionone through a catalyst, namely concentrated sulfuric acid

Iodine/water-mediated deprotective oxidation of allylic ethers to access α,β-unsaturated ketones and aldehydes

The first iodine/water-mediated deprotective oxidation of allylic ethers to access α,β-unsaturated ketones and aldehydes was achieved. The reaction tolerates a wide range of functionalities. Furthermore, this protocol was found to be applicable to the oxidative transformation of allylic acetates. The proposed mechanism involves an oxygen transfer from solvent water to the carbonyl products.