79-69-6

Basic information

• Product Name: IRONE
• Synonyms: (3E)-4-(2,5,6,6-Tetramethyl-2-cyclohexen-1-yl)-3-buten-2-one;3-Buten-2-one, 4-(2,5,6,6-tetramethyl-2-cyclohexen-1-yl)-;3-Buten-2-one, 4-(2,5,6,6-tetramethyl-2-cyclohexen-1-yl)-, cis-;4-(2,5,6,6-tetramethyl-2-cyclohexen-1-yl)-3-buten-2-on;4-(2,5,6,6-tetramethyl-2-cyclo-hexen-1-yl)-3-buten-2-one;4-(2,5,6,6-tetramethyl-2-cyclohexen-1-yl)-3-Buten-2-one;alpha-Ionone, 6-methyl-;alpha-Irone
• CAS NO: 79-69-6
• Molecular Formula: C₁₄H₂₂O
• Molecular Weight: 206.32
• EINECS: 201-219-6
• Product Categories: ketone Flavor;Chiral Building Blocks;Ketones;Organic Building Blocks
• Mol File: 79-69-6.mol
• Article Data: 1

Chemical Properties

• Melting Point: <25 °C
• Boiling Point: 285.19°C (rough estimate)
• Flash Point: 118.4oC
• Appearance: /
• Density: 0.934 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.00419mmHg at 25°C
• Refractive Index: n20/D 1.492
• Merck: 13,5111
• BRN: 1343498
• CAS DataBase Reference: IRONE(CAS DataBase Reference)
• NIST Chemistry Reference: IRONE(79-69-6)
• EPA Substance Registry System: IRONE(79-69-6)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 2
• RTECS: EN0335000
• Hazardous Substances Data: 79-69-6(Hazardous Substances Data)

Usage

Description

α-Irone has a characteristic orris and violet-like odor. The commercially prepared product corresponds generally to the α-isomer.

Chemical Properties

Different sources of media describe the Chemical Properties of 79-69-6 differently. You can refer to the following data:
1. α- Irone has a rich, floral and natural character and constitutes an important element in orris and violet compositions as well as being useful when an exotic nuance is required. α-Irone is extremely diffusive, and it gives volume and tenacity to compositions. In combination with α-irisone (1:20, respectively) gives a natural orris effect.
2. Yellowish liquid; Soluble in alcohol. A mixture of three isomers (α-, βand γ-irone).

Occurrence

Reported found in orris root, raspberry and flowers of Pittosporum sp

Uses

Perfumery, violet odor. The α isomer is also used as a flavoring agent.

Definition

ChEBI: A methyl ketone that is alpha-ionone in which a hydrogen at position 5 of the cyclohex-2-en-1-yl ring is substituted by a methyl group.

Preparation

By intramolecular thermal H-ene reaction of an allysilane.

Taste threshold values

Taste characteristics at 10 ppm: woody, fruity, raspberry, orris, and berry with seedy nuances.

General Description

Irone is a bioactive compound that is produced by an endophytic fungus in the rhizomes of Iris germanica.

Purification Methods

If large amounts are available, then fractionate through a Podbielniak column (p 10) or an efficient spinning band column, but small amounts are distilled using a Kügelrohr apparatus. The 4-phenylsemicarbazone has m 174-175o (165-165.5o). [IR: Seidel & Ruzicka Helv Chim Acta 35 1826 1952, Naves Helv Chim Acta 31 1280 1948, Lecomte & Naves J Chim Phys 53 462 1956, Beilstein 7 IV 378.]

InChI:InChI=1/C14H22O/c1-10-6-7-11(2)14(4,5)13(10)9-8-12(3)15/h6,8-9,11,13H,7H2,1-5H3/b9-8+

Upstream product

• 645-68-1 pseudoirone 
• 72074-86-3 (+-)-4t-(2,5t,6,6-Tetramethyl-cyclohex-2-en-r-yl)-but-3-en-2-on 
• 58307-67-8 3,6,7-trimethyl-6-octen-1-en-3-ol 
• 3899-32-9 (E)-3,6,7-trimethylocta-2,6-dien-1-ol 
• 687-68-3 5,6-dimethyl-5-hepten-2-one 
• 52567-96-1 3,6,7-trimethyl-oct-6-en-1-yn-3-ol 

Downstream Products

• 62430-55-1 optically inactive 2,2'-dimethyl-ε,ε-carotene 

Relevant articles and documents

Precursors for fragrant ketones and fragrant aldehydes

The present invention refers to fragrance precursors of formula I for a fragrant ketone of formula II and one or more fragrant aldehydes or ketones of formula III and IV, These fragrance precursors are useful in perfumery, especially in the fine and functional perfumery.