Ionone

The ionones, from greek ἴον ion "violet", are a series of closely related chemical substances that are part of a group of compounds known as rose ketones, which also includes damascones and damascenones. Ionones are aroma compounds found in a variety of essential oils, including rose oil. β-Ionone is a significant contributor to the aroma of roses, despite its relatively low concentration, and is an important fragrance chemical used in perfumery. The ionones are derived from the degradation of carotenoids.

Ionones
alpha-ionone
beta-ionone
gamma-ionone
Names
IUPAC names
α: (3E)-4-(2,6,6-Trimethylcyclohex-2-en-1-yl)but-3-en-2-one
β: (3E)-4-(2,6,6-Trimethylcyclohex-1-en-1-yl)but-3-en-2-one
γ: (3E)-4-(2,2-Dimethyl-6-methylenecyclohexyl)but-3-en-2-one
Other names
Cyclocitrylideneacetone, irisone, jonon
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h7-8,12H,1,5-6,9H2,2-4H3/b8-7+ Y
    Key: SFEOKXHPFMOVRM-BQYQJAHWSA-N Y
  • InChI=1/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h7-8,12H,1,5-6,9H2,2-4H3/b8-7+
    Key: SFEOKXHPFMOVRM-BQYQJAHWBW
  • O=C(\C=C\C1\C(=C)CCCC1(C)C)C
Properties
C13H20O
Molar mass 192.30 g/mol
Density α: 0.933 g/cm3
β: 0.945 g/cm3
Melting point β: −49 °C (−56 °F; 224 K)
Boiling point β: 126 to 128 °C (259 to 262 °F; 399 to 401 K) at 12 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

The combination of α-ionone and β-ionone is characteristic of the scent of violets and used with other components in perfumery and flavouring to recreate their scent.

The carotenes α-carotene, β-carotene, γ-carotene, and the xanthophyll β-cryptoxanthin, can all be metabolized to β-ionone, and thus have vitamin A activity because they can be converted by plant-eating animals to retinol and retinal. Carotenoids that do not contain the β-ionone moiety cannot be converted to retinol, and thus have no vitamin A activity.

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