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

β-Ionone has a characteristic violet-like odor, more fruity and woody than α-ionone. May be prepared by condensing citral with acetone to form pseudoionone, which is then cyclized by acid-type reagents.

Chemical Properties

Different sources of media describe the Chemical Properties of 14901-07-6 differently. You can refer to the following data:
1. β-Ionone has a characteristic violet-like odor, more fruity and woody than α-ionone
2. clear slightly yellow to yellow liquid

Occurrence

Reported found in the distillate from flowers of Boronia megatisma Nees. Also reported found in apricot, orange juice, lemon peel oil, guava, grapes, melon, papaya, peach, raspberry, blackberry, carrot, peas, bell pepper, tomato, ginger, peppermint and spearmint oil, milk powder, beef, hop oil, cognac, whiskies, grape wines, tea, passion fruit, plum, beans, mushroom, starfruit, almonds, mango, fenugreek, tamarind, apple and pear brandy, rice bran, quince, prickly pear, sweet potato, buckwheat, corn oil, corn tortillas, loquat, mountain papaya, clary sage and other sources

Uses

Different sources of media describe the Uses of 14901-07-6 differently. You can refer to the following data:
1. beta-Lonone is an essential oil extract from the leaves and flowers of Succisa Pratensis that shows antioxidant and antimicrobial activities against bacteria.
2. β-Ionone 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).

Preparation

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

Aroma threshold values

Detection: 0.007 to 205 ppb

Taste threshold values

Taste characteristics art 10 ppm: woody, sweet, fruity, berry-like with a green berry background

General Description

Colorless to light yellow liquid with an odor of cedar wood. In very dilute alcoholic solution the odor resembles odor of violets. Used in perfumery.

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 
• 75-52-5 nitromethane 
• 141-10-6 pseudoionone 
• 7664-93-9 sulfuric acid 
• 7446-70-0 aluminium trichloride 
• 7732-18-5 water 
• 64-19-7 acetic acid 
• 7235-40-7 beta-carotene 
• 122258-61-1 4-methoxy-β-ionone 

Downstream Products

• 112949-42-5 (+/-)-3,7-dimethyl-1t-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-1,6ξ,8-trien-4-yn-3-ol 
• 85763-13-9 3.5-dioxo-1t-(2.2.6-trimethyl-cyclohexen-⁽⁶⁾-yl)-hexen-⁽¹⁾-oic acid-⁽⁶⁾-methyl ester 
• 55089-94-6 1-(4,5-dihydro-thiazol-2-yl)-2-methyl-4t-(2,6,6-trimethyl-cyclohex-1-enyl)-but-3-en-2-ol 
• 21666-52-4 C₁₆H₂₆O 
• 93155-15-8 (E)-2-Hydroxy-3-methoxy-3-methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-pent-4-enoic acid 
• 1062-12-0 β-Jonylidenaethyl-triphenyl-phosphonium-chlorid 
• 5452-61-9 Ethyl-β-jonylidenacetat 
• 4941-93-9 β-Jonyliden-essigsaeure 
• 17974-55-9 (2E,4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate 
• 22255-47-6 (E)-2-(3-methylbuta-1,3-dienyl)-1,3,3-trimethyl-cyclohex-1-ene 
• 92861-25-1 1-<2,6,6-Trimethyl-cyclohexenyl-(1)>-3-ethylmercapto-butadien-(1,3) 
• 94710-63-1 β-Jonon-diethylthioketal 
• 114582-51-3 (7E)-9-(3'-methyl-1'-butynyl)-β-ionol 
• 80255-08-9 1-(2',6',6'-trimethyl-1'-cyclohexenyl)-1-undecene-3-6-dione 

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

Scalable synthesis of the aroma compounds d6-β-ionone and d6-β-cyclocitral for use as internal standards in stable isotope dilution assays

C13 Norisoprenoids are important aroma compounds in wine, giving positive attributes to the overall wine aroma even when found at very low levels. β-Ionone is considered one of the most important aroma compounds giving violet, woody and raspberry aromas to wine, fruits and vegetables in which it is found. Due to its potent aroma at low levels, precise analytical methods are desired for its quantification. Stable isotope dilution assay (SIDA) is one of the most important of these methods but requires the use of isotopically labelled standards. Herein, we describe the scalable synthesis of d6-β-ionone and d6-β-cyclocitral, another aroma compound with smokey and fruity notes, starting from the relatively inexpensive deuterated starting material d6-acetone.