Beta-ionone

Simkin, A. J., S. H. Schwartz et al. (2004a). The tomato carotenoid cleavage dioxygenase 1 genes contribute to the formation of the flavor volatiles beta-ionone, pseudoionone, and geranylacetone. Plant J. 40(6) 882-892. 

Simkin, A. J., B. A. Underwood et al. (2004b). Circadian regulation of the PhCCDl carotenoid cleavage dioxygenase controls emission of beta-ionone, a fragrance volatile of petunia flowers. Plant Physiol. 136(3) 3504-3514. 

NT393 Eujimori, T., R. K. Asuga, and M. NT404 Nouchi. Isolation of R-(-)-3-hydroxy-beta-ionone from burley tobacco. Agr Biol Chem 1974 38 891. 

Lawsonia inermis L. Zhi Jia Hua (Henna) (flower) Alpha-ionone, beta-ionone, gallic acid, lawsone.50 Antibiotic, antitumor, anthelmintic, astringent, bactericidal, fungicidal, sedative. 

The molecular encapsulation of flavors with cyclo-dextrins was found to improve the resistence of light sensitive flavor constituents against daylight and ultraviolet irradiation. The photodecomposition of adsorbed and complexed flavors was tested both in the solid state and in aqueous solutions. The results of the light stability tests are demonstrated in the example of complexed and adsorbed citral,beta-ionone and cinnamaldehyde formulations /Table III./. 

Carotenoids Beta-Ionone Beta-Cyclocitral + 2-Propanone... 

Polysaccharides, including starches and dextrins, have been shown to reduce the volatility of aroma compounds, such as limonene, isoamyl acetate, ethyl hexanoate and beta-ionones.237... 

Several of the carotenoids are now commercially synthesized and used as food colors. A possible method of synthesis is described by Borenstein and Bunnell (1967). Beta-ionone is obtained from lemon grass oil and converted into a C14 aldehyde. The C14 aldehyde is changed to a C16 aldehyde, then to a C19 aldehyde. Two moles of the C19 aldehyde are condensed with acetylene dimagnesium bromide and, after a series of reactions, yield p-carotene. 

A-3 It is a yellow color oil, insoluble in water but soluble in alcohol, chloroform etc. It consists of beta ionone ring with side chain of long chain unsaturated alcohol. It is unstable in the presence of heat, light, acid and oxidation while stable in alkaline media and also upon reduction. 

CIC The main flavouring components are alpha-and beta-ionone with their floral, violet and typical perfumy, raspberry, woody character. l-(4-hydroxyphenyl)butan-2-one imparts the fruity, sweet raspberry body. (Z)-3-hexenal is responsible for the fresh, green topnote and 2,5-dimethyl-4 hydroxy-furan-3(2H)-one adds the overripe, almost cooked fruit jammy body. 

CIC The fatty aldehydes octanal, nonanal, decanal together with the corresponding fatty acids and their ethyl esters are responsible for the characteristic fatty aldehydic flavour of the skin. (E)-2-hexenal, hexanal and (E)-2-pentenal contribute to the refreshing character, supported by the high acidity of the juice. Methyl-2-methyl bu-tanoate, methyl-3-methyl butanoate and methyl hexanoate impart a fresh, fruity note, rounded off with traces of methyl benzoate, methyl salicylate and the sweet floral note of beta-ionone and damascenone. 

CIC The powerful odour is dominated by 2-isobutyl thiazole and 3-pentanethiol. The green notes are lipid degradation products like (E)-2-hexenal, hexanal and higher unsaturated aldehydes, the pineapple-pear like fruity notes are derived from methyl hexanoate, ethyl-2-hexenoate and hexyl acetate. The spicy cinnamon notes are represented by 3-phenyl propyl acetate, cinnamyl acetate, methyl cinnamate, ethyl cinna-mate and ciimamaldehyde. Gamma-decalactone and 2,5-dimethyl-4-hydroxy-furan-3(2H)-one and 3-hydroxy-2-butanone add the sweet, creamy body. Beta-famesene, citronellol, 2-phenylethanol, beta-ionone add the sweet, floral, quincelike part and methyl benzoate and ethyl benzoate impart a characteristic medicinal, exotic topnote. 

CIC Green, fruity, fatty esters like (Z)-3-hexenyl butyrate, (Z)-3-hexenyl hexanoate, 2-ethyl hexenoate, 2-ethyl-octenoate form the basic fruity body. Nerol oxide and edulan add an ethereal, fresh, green, sharp, floral topnote. The floral note (mainly in the purple variety) is represented by linalool with a complex of ionone derivatives, mainly beta-ionone, dihydro-beta-ionone, theaspirone, damascenone. The key components for the green, exotic, sulfury topnote of the yellow variety are 2-methyl-4-propyl-l,3-oxathiane and 3-methylthio-l-hexanol. 

CIC The floral fruity perfume is the result of a balanced mixture of famesene, linalool, ethyl-2-methyl-2-butenoate, ethyl (E)-2-(Z)-4-decadienoate, derivatives around beta-ionone (theaspirone, theaspirane (E,E)-6,8-megastigmadien-4-one) and... 

Isoe S., Hyeon S.B. and Sakan T. (1969) Photo-oxygenation of carotenoids. I. The formation of dihydroactinidiolide and beta-ionone from beta-carotene. Tetrahedron Lett. (4), 279-81. 

F F compounds are usually not a significant part of plants. Typically they comprise <1%, sometimes much less than 1%, of the plant s total weight. They form from precursors that may constitute a large proportion of the plant. Maltol, a burnt sugar note, has carbohydrates as its precursor, vanillin has lignin as its precursor, beta-ionone, used in berry flavors, has carotenoids as its precursor, and the green notes, hexanal and (E)-2-hexenal, have the fatty acids, linoleic acid and linolenic acid, respectively, as their precursors. 

Nostocionone, 3-oxo-beta-ionone, and indole alkaloids, 270 Notoamides F-K, 267-269, 267/... 

Esehenmoser W, Uebelhart R Eugster CH (1981) Synthesis and chirality of the enantiomeric 6-hydroxy-alpha-ionones and of cis and trawi 5,6-di-hydroxy-5,6-dihydro-beta-ionones. Helv Chim Acta 64 2681-2690... 

Mikhlin, E.D., V.P. Radina, A.A. Dmitrovskii et ah, 1983. Antifungal and antimicrobial activity of beta-ionone and vitamin A derivatives. Prikladnaja biochimija i mikrobiologija, 19 795-803. 

Beta-ionone.—Specific gravity at 15° C., 0 9488 refractive index at 16 8° 0., 1 52070 (Ohuit) optically it is inactive also. 

LaRoe, E. G., and P. A. Shipley Whiskey Composition Formation of alpha- and beta-Ionone by the Thermal Decomposition of beta-Carotene. J. Agric. Food Chem. 18, 174 (1970). 

In addition to the character impact compound of raspberry, 4-(4-hydroxy-phenyl)-butan-2-one (raspberry ketone), alpha- and beta-ionone, geraniol, and linalool were concluded to be of importance in raspberry aroma (30). Its odor threshold was measured at 1-10 ig/kg. The ionones have chemical stracture similarities and potencies comparable to P-damascenone (11). 

Sakamoto, M., Wada, A., Akai, A., Ito, M., Goshima, T, and Takahashi, T., Evidence for the archaebacterial-type conformation about the bond between the beta-ionone ring and the polyene chain of the chromophore retinal in chlamyrhodopsin, FEBS Lett., 434,3,335, 1998. 

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