Alpha-isomethyl ionone

Alpha-isomethyl ionone
Names
	IUPAC name (3E)-3-methyl-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-one
	Other names 3-methyl-a-ionone; 3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one;
Identifiers
CAS Number	127-51-5;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3183353;
ECHA InfoCard	100.004.407
EC Number	204-846-3;
PubChem CID	5372174;
UNII	9XP4LC555B;
CompTox Dashboard (EPA)	DTXSID7027047 ;
	InChI InChI=1S/C14H22O/c1-10-7-6-8-14(4,5)13(10)9-11(2)12(3)15/h7,9,13H,6,8H2,1-5H3/b11-9+ Key: JRJBVWJSTHECJK-PKNBQFBNSA-N;
	SMILES CC(=O)C(\C)=C\C1C(C)=CCCC1(C)C;
Properties
Chemical formula	C14H22O
Molar mass	206.3239
Appearance	liquid
Solubility in water	0.064 g/L
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

Alpha-isomethyl ionone is a synthetically made and naturally occurring organic compound found in Brewer's yeasts or the species known as Saccharomyces cerevisiae.[1] The compound is a type of ionone. Alpha-isomethyl ionone can be colorless, pale-straw coloured liquid or voilet.[2] It has a flowery orris-like scent [3] and is often used in cosmetic industries for example, aftershave lotions, bath products, hair care products, moisturizers, perfumes, shampoos and skin care products.[4] It is also an ingredient used in Channel No. 5 Perfume. [5]

Alpha-isomethyl ionone can be refined to Cetone alpha [6] which is also used as a fragrance compound.

Properties

Alpha-isomethyl ionone compound consists of terpenes with three consecutive isoprene units. They are extremely weak basic.

Synthesis

The synthesis of alpha-isomethyl ionone involves the condensation of Citral with Methyl ethyl ketone. A high temperature and strong alkali is used. The ratio between the n-form and iso-form is also controlled. This is used to obtain methyl pseudo-ionone and allow ring formation to occur and iso-forms to be synthesized.[7]

References

"alpha-Isomethyl-ionone (YMDB01634)". YMDB. Retrieved 29 May 2020.
"Alpha-Isomethyl Ionone". Cosmetic Info. Retrieved 29 May 2020.
"Frangrance Demo Formula". TGSC Information System. Retrieved 24 June 2020.
"Alfa-Isomethyl ionone". Chemo Technique Diagnostics. Retrieved 29 May 2020.
Kennedy, James. "Visual Ingredients Chanel No. 5" (PDF). James Kennedy Monash. Retrieved 29 May 2020.
"ChemBK". Cetone alpha. Retrieved 24 June 2020.
"ALPHA-ISO-METHYLIONONE". Chemical Book. Retrieved 24 June 2020.

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[1] "alpha-Isomethyl-ionone (YMDB01634)". YMDB. Retrieved 29 May 2020.

[2] "Alpha-Isomethyl Ionone". Cosmetic Info. Retrieved 29 May 2020.

[3] "Frangrance Demo Formula". TGSC Information System. Retrieved 24 June 2020.

[4] "Alfa-Isomethyl ionone". Chemo Technique Diagnostics. Retrieved 29 May 2020.

[5] Kennedy, James. "Visual Ingredients Chanel No. 5" (PDF). James Kennedy Monash. Retrieved 29 May 2020.

[6] "ChemBK". Cetone alpha. Retrieved 24 June 2020.

[7] "ALPHA-ISO-METHYLIONONE". Chemical Book. Retrieved 24 June 2020.