Irisone

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.

Description

Why do fresh home-grown tomatoes taste so much better than store-bought ones? The answer lies in a genetic modification that was introduced into commercial tomatoes to give them a longer shelf life. The downside of this mutation is that it reduces flavor and sugar development in the fruit.
Researchers in several nations led by Harry Klee at the University of Florida (Gainesville) and Sanwen Huang at the Chinese Academy of Agricultural Sciences (Beijing) determined how to modify mass-produced tomatoes?to restore desirable flavor components. The research team’s goal was to tell breeders which biochemicals are lacking in their tomatoes and to show them the markers they need to breed back in.
Based on the results of a human taste panel study, they identified 13 flavor molecules that are deficient in supermarket tomatoes. Two of the desired flavoring agents, geranylacetone?(upper images) and β-ionone (lower images), contribute “leafy” and “floral” flavors, respectively. The researchers then identified the regions of the tomato genome that are responsible for producing the 13 components.
Commenting on this study, James Giovannoni at the US Department of Agriculture said, “I don’t know if it’s possible to make a supermarket tomato that tastes exactly like it was grown in your own garden, but I have no doubt that this work can help breeders make supermarket tomatoes a lot better than they are now.”

Chemical properties

clear slightly yellow to yellow liquid

Chemical properties

β-Ionone has a characteristic violet-like odor, more fruity and woody than α-ionone

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

The Uses of Irisone

beta-Lonone is an essential oil extract from the leaves and flowers of Succisa Pratensis that shows antioxidant and antimicrobial activities against bacteria.

The Uses of Irisone

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.

Definition

ChEBI: Beta-ionone is an ionone that is but-3-en-2-one substituted by a 2,6,6-trimethylcyclohex-1-en-1-yl group at position 4. It has a role as an antioxidant and a fragrance.

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

Non flammable

Biochem/physiol Actions

Taste at 1-20 ppm