Mass Spectra of Carotenoids - Labelling Studies

Budzikiewicz, H.

doi:10.1016/b978-0-08-026224-6.50014-0

Cited by 13 publications

(5 citation statements)

References 20 publications

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“…A comprehensive review on the use of mass spectrometry in the study of carotenoids 816 in general may be found elsewhere (Enzell and Back, 1990). This work cites earlier 817 reviews and studies that consolidate the importance of the technique not only for 818 elucidation of structure but also for analytical research, not least those carried out by 819 Vetter et al, (1971), Budzikiewicz, (1974) and Enzell and Wahlberg, (1980). The 820 study, similar analytical conditions were used to characterize the 17-carbon major 844 thermal degradation product of annatto (Scotter, 1995).…”

Section: Mass Spectrometry(ms) 815mentioning

confidence: 85%

The chemistry and analysis of annatto food colouring: a review

Scotter

2009

Food Additives & Contaminants: Part A

149

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International audienceAnnatto food colouring (E160b) has a long history of use in the food industry for the colouring of a wide range of food commodities. The principle colouring components of annatto is the oil-soluble diapo carotenoid bixin, which is the methyl ester of the dicarboxylic acid norbixin, which is soluble in aqueous alkali. Bixin and norbixin therefore exhibit not only physicochemical properties normally associated with carotenoids but also certain anomalous properties that have an impact on the stability, food colouring applications and importantly the analysis of annatto. This review summarizes the key aspects of the structural determination of bixin (and norbixin) with special attention to cis-trans isomerization and how this links with its chemical structure, spectroscopic properties and stability. The oxidative, thermal and photo stability of annatto and the subsequent implications for its use in the colouring of foods, food processing, and the analysis of foods and beverages are discussed along with important mechanistic, thermodynamic and kinetic aspects. The main analytical techniques used for the chemical characterization of annatto i.e. spectrophotometry, NMR, chromatography (particularly HPLC) and mass spectrometry are reviewed in detail and other methods discussed. This links in with a review of the methods available for the detection and measurement of annatto in colour formulations and foods and beverages, which highlights the importance of the need for a good understanding and knowledge of the chemistry of bixin and norbixin in order to meet new analytical challenges

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Section: Mass Spectrometry(ms) 815mentioning

confidence: 85%

The chemistry and analysis of annatto food colouring: a review

Scotter

2009

Food Additives & Contaminants: Part A

149

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“…Violaxanthin (1), auroxanthin (2), and cycloviolaxanthin (3) (9,10). Furthermore, a series of product ions resulting from the cleavage of C-C bonds in the polyene chain, from the epoxy end group such as m/z 221 (c ion: attributed to cleavage between C10 and C11), 352 (g-H ion: attributed to cleavage between C14′ and C13′ accompanied by a hydrogen transfer to the C13′ side) and 419 (i ion: attributed to cleavage between C9′ and C8′) was detected.…”

Section: Resultsmentioning

confidence: 99%

Characterization of epoxy carotenoids by fast atom bombardment collision‐induced dissociation MS/MS

Maoka

Fujiwara

Hashimoto

et al. 2004

Lipids

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The characterization and structure of epoxy carotenoids possessing 5,6-epoxy, 5,8-epoxy and 3,6-epoxy end groups conjugated to the polyene chain were investigated using high-energy fast atom bombardment collision-induced dissociation MS/MS methods. In addition to [M - 80](+*), a characteristic fragment ion of an epoxy carotenoid, product ions resulting from the cleavage of C-C bonds in the polyene chain from the epoxy end group, such as m/z 181 (b ion) and 121 (c ion), were detected. On the other hand, diagnostic ions of m/z 286 (e-H ion) and 312 (f-H ion) were observed, not in the 5,6-epoxy or 5,8-epoxy carotenoid but in the 3,6-epoxy carotenoid. These fragmentation patterns can be used to distinguish 3,6-epoxy carotenoids from 5,6-epoxy or 5,8-epoxy carotenoids. The structure of an epoxy carotenoid, 3,6-epoxy-5,6-dihydro-7',8'-didehydro-beta,beta-carotene-5,3'-diol (8), isolated from oyster, was characterized using FAB CID-MS/MS by comparing fragmentation patterns with those of related known compounds.

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“…However, for quantitative analysis of carotenoids, ultraviolet (UV)-visible spectrophotometry is still the most convenient method (8)(9), by measuring the absorbent at different wavelengths. In addition, nuclear magnetic resonance (10) and mass spectroscopy (11) were proved to be useful in identification of carotenoids.…”

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confidence: 99%

Quantitative analysis of palm carotene using fourier transform infrared and near infrared spectroscopy

Moh

Man

Badlishah

et al. 1999

J Americ Oil Chem Soc

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β-Carotene content is usually determined by using ultraviolet (UV)-visible spectrophotometry at 446 nm. In this study, two spectroscopic techniques, namely, Fourier transform infrared (FTIR) and near infrared (NIR) spectroscopy, have been investigated and compared to UV-visible spectrophotometry to measure the β-carotene content of crude palm oil (CPO). Calibration curves ranging from 200 to 800 ppm were prepared by extracting β-carotene from original CPO using open-column chromatography. Separate partial least squares calibration models were developed for predicting β-carotene based on the spectral region from 976 to 926 cm −1 for FTIR spectroscopy and 546 to 819 nm for NIR spectroscopy. The correlation coefficient (R 2 ) and standard error of calibration obtained were 0.972 and 25.2 for FTIR and 0.952 and 23.6 for NIR techniques, respectively. The validation set gave R 2 of 0.951 with standard error of performance (SEP) of 25.78 for FTIR technique and R 2 of 0.979 with SEP of 19.96 for NIR technique. The overall reproducibility and accuracy did not give comparable results to that of spectrophotometric method; however, the standard deviation of prediction was still within ±5% β-carotene content over the range tested. Because of their rapidness and simplicity, both FTIR and NIR techniques provide alternative means of measuring β-carotene content in CPO. In addition, these two spectroscopic techniques are environmentally friendly since no solvent is involved.Paper no. J8796 in JAOCS 76, 249-254 (February 1999).

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Mass Spectra of Carotenoids - Labelling Studies

Cited by 13 publications

References 20 publications

The chemistry and analysis of annatto food colouring: a review

The chemistry and analysis of annatto food colouring: a review

Characterization of epoxy carotenoids by fast atom bombardment collision‐induced dissociation MS/MS

Quantitative analysis of palm carotene using fourier transform infrared and near infrared spectroscopy

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