Composition of Oil-Soluble Annatto Food Colors. III. Structure of the Yellow Pigment Formed by the Thermal Degradation of Bixin

Mckeown, G G

doi:10.1093/jaoac/48.4.835

Cited by 9 publications

(13 citation statements)

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“…Extraction with aqueous alkali (the form used in the dairy industry, e.g., for cheese color) saponifies bixin's methyl group on bixin, yielding norbixin as the principal colorant (Giuliano et al, 2003;Mortenson et al, 2008). Both bixin and norbixin naturally occur in the cis form but can be converted to the trans form by light and heat (McKeown 1963(McKeown , 1965. The trans forms of both…”

Section: Extraction Of Annattomentioning

confidence: 99%

Invited review: Annatto usage and bleaching in dairy foods

Kang

Campbell

Bastian³

et al. 2010

Journal of Dairy Science

103

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Annatto is a yellow/orange colorant that is widely used in the food industry, particularly in the dairy industry. Annatto, consisting of the carotenoids bixin and norbixin, is most commonly added to produce orange cheese, such as Cheddar, to achieve a consistent color over seasonal changes. This colorant is not all retained in the cheese, and thus a percentage remains in the whey, which is highly undesirable. As a result, whey is often bleached. Hydrogen peroxide and benzoyl peroxide are the 2 bleaching agents currently approved for bleaching whey in the United States. Recent studies have highlighted the negative effect of bleaching on whey flavor while concurrently there is a dearth of current studies on bleaching conditions and efficacy. Recent international mandates have placed additional concern on the use of benzoyl peroxide as a bleaching agent. This review discusses the advantages, disadvantages, regulatory concerns, flavor implications, and optimal usage conditions of 2 widely used bleaching agents, hydrogen peroxide and benzoyl peroxide, as well as a few alternative methods including lipoxygenase, peroxidase, and lactoperoxidase systems.

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Section: Extraction Of Annattomentioning

confidence: 99%

Invited review: Annatto usage and bleaching in dairy foods

Kang

Campbell

Bastian³

et al. 2010

Journal of Dairy Science

103

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“…For example, at relatively high (.708C) temperatures, carotenoids can undergo a series of degradation reactions to produce a range of products including aromatic compounds, principally xylene and toluene. The main aromatic thermal degradation product of the apocarotenoid colouring component of annatto (E160b) has been identified as m-xylene (McKeown, 1963(McKeown, , 1965Scotter, 1995). m-Xylene has been found in commercial annatto food-colouring preparations up to a level of 200 mg/kg (Scotter et al 2000) and has been detected in the headspace of heated foodstuffs containing annatto (Scotter, unpublished results).…”

Section: Other Non-nutrientsmentioning

confidence: 99%

A critical assessment of some biomarker approaches linked with dietary intake

Crews¹,

Alink²,

Andersen

et al. 2001

Br J Nutr

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“…Most studies on bixin stability focused on thermal degradation (10,11), direct illumination (12), and the water activity solvent effect (13). In the thermal degradation of bixin, the main products formed were all-trans-bixin, a C17 carotenoid (transmonomethyl ester of 4,8-dimethyl tetradecahexaenedioic acid) and volatile compounds, especially xylene (5,10).…”

Section: Introductionmentioning

confidence: 99%

Model Studies on the Photosensitized Isomerization of Bixin

Montenegro

Rios

Mercadante

et al. 2003

J. Agric. Food Chem.

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The photosensitized isomerization reaction of the natural cis carotenoid bixin (methyl hydrogen 9'-cis-6, 6'-diapocarotene-6, 6'-dioate) with rose bengal or methylene blue as the sensitizer in acetonitrile/methanol (1:1) solution was studied using UV-vis spectroscopy, high-performance liquid chromatography (HPLC), and time-resolved spectroscopic techniques, such as laser-flash photolysis and singlet oxygen phosphorescence detection. In both N(2)- and air-saturated solutions, the main product formed was all-trans-bixin. The observed isomerization rate constants, k(obs), decreased in the presence of air or with increase in the bixin concentration, suggesting the participation of the excited triplet state of bixin, (3)Bix, as precursor of the cis--> trans process. On the other hand, bixin solutions in the absence of sensitizer and/or light did not degrade, indicating that the ground state of bixin is stable to thermal isomerization at room temperature. Time-resolved spectroscopic experiments confirmed the formation of the excited triplet state of bixin and its deactivation by ground state bixin and molecular oxygen quenching processes. The primary isomerization products only degraded in the presence of air and under prolonged illumination conditions, probably due to the formation of oxidation products by reaction with singlet molecular oxygen. An energy-transfer mechanism was used to explain the observed results for the bixin transformations, and the consequences for food color are discussed.

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Composition of Oil-Soluble Annatto Food Colors. III. Structure of the Yellow Pigment Formed by the Thermal Degradation of Bixin

Cited by 9 publications

References 0 publications

Invited review: Annatto usage and bleaching in dairy foods

Invited review: Annatto usage and bleaching in dairy foods

A critical assessment of some biomarker approaches linked with dietary intake

Model Studies on the Photosensitized Isomerization of Bixin

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