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
Density	0.93 gcm −3 (20 ° C)
Solubility in water	0.064 g/L
Hazards
Main hazards	irritant, environmental hazard
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H315, H317, H319, H411, H412
GHS precautionary statements	P261, P264, P272, P273, P280, P302+352, P305+351+338, P321, P332+313, P333+313, P337+313, P362, P363, P391, P501
	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 an isomer of methyl ionone. Alpha-isomethyl ionone can be colorless or pale-straw coloured liquid.[2] Its primary scent is flowery and secondary scent is violet. It may also have a woody or orris-like scent.[3] and is often used in flavouring and 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,[5] and other branded products such as Fidji by Guy Laroche.[6] Perfume fragrances that alpha-isomethyl ionone is used in are for example, amber, chypre, violet, mimosa, reseda, iris, orris, cyclamen, chypre, berries, woody notes, ylang-ylang, leather, orange, nut, pistachio, muscatel, and tobacco.[6]

Alpha-isomethyl ionone can be refined to Cetone alpha[7] which is also used as a fragrance compound. The difference between alpha-isomethyl ionone and cetone alpha is thatt cetone alpha has a stronger and more intense scent.[3]

Properties

Chanel No.5 Perfume

Alpha-isomethyl ionone consists of terpenes with three consecutive isoprene units. They are extremely weak base. It's pKa value (strongest acidic) is 19.7 and it's pKa vlaue (strongest basic) is -4.8.[8] The percentage of alpha-isomethyl ionone used in perfumes are approximately ranging from 0.1% to 11.9%, with an average of 1.1%. For example, in It is usually used in conjunction with hydroxycitronellal, woody notes, copaiba, N-methyl Ionone, Ionone, or Vetiver.[6]

Synthesis

The synthesis of alpha-isomethyl ionone involves a cross- aldol condensation of citral with methyl ethyl ketone[9] A high temperature and strong alkali is used. The ratio between the n-form and iso-form is controlled in order to obtain methyl pseudo-ionone and allow ring formation to occur. Iso-forms is then synthesized consequently.[10]

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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.
"Alpha Isomethyl Ionone". Perfumes World. Retrieved 9 July 2020.
"ChemBK". Cetone alpha. Retrieved 24 June 2020.
"3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one". Foodb. Retrieved 9 July 2020.
"Encyclopedia of Food and Colour additives". Google Books. Retrieved 13 July 2020.
"ALPHA-ISO-METHYLIONONE". Chemical Book. Retrieved 24 June 2020.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

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

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

[Cetone-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.

[fragrance-6] "Alpha Isomethyl Ionone". Perfumes World. Retrieved 9 July 2020.

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

[8] "3-Methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one". Foodb. Retrieved 9 July 2020.

[9] "Encyclopedia of Food and Colour additives". Google Books. Retrieved 13 July 2020.

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