The chemistry and analysis of annatto food colouring: a review

References

• Aparnathi , KD and Sharma , RS . 1991 . Annatto colour for food: a review . Indian Food Packer March–April , : 13 – 27 .
   Google Scholar
• Association of Official Analytical Chemists (AOAC). 1980. Official methods of analysis, 11th ed. Washington, DC: AOAC
   Google Scholar
• Balaswamy , K , Prabhakara Rao , PGP , Satyanarayana , A and Rao , DG . 2006 . Stability of bixin in annatto oleoresin and dye powder during storage . LWT–Food Sci Tech , 39 : 952 – 956 .
   Web of Science ®Google Scholar
• Barber , MS , Hardisson , A , Jackman , LM and Weedon , BCL . 1961 . Studies in nuclear magnetic resonance. Part IV. Stereochemistry of the bixins . J Chem Soc. , : 1625 – 1630 .
   Web of Science ®Google Scholar
• Barbosa , MIMJ , Borsarelli , CD and Mercadante , AZ . 2005 . The light stability of spray-fried bixin encapsulated with different edible polysaccharide preparations . Food Res Int , 38 : 989 – 994 .
   Web of Science ®Google Scholar
• Bareth , A , Strohmar , W and Kitzelmann , E . 2002 . HPLC and spectrophotometric determination of annatto in cheese . Eur Food Res Tech , 215 : 359 – 364 .
   Web of Science ®Google Scholar
• Bernard , K and Grosjean , M . 1995 . “ Infrared spectroscopy ” . In Carotenoids, Vol. 1B: Spectroscopy , Edited by: Britton , G , Liaaen-Jensen , S and Pfander , H . 117 – 134 . Basel, , Switzerland : Birkhäuser .
   Google Scholar
• Berset , C and Marty , C . 1986 . Potential use of annatto in extrusion cooking . Lebensmittel-Wissenschaft Technologie , 19 : 126 – 131 .
   Google Scholar
• Bittencourt , C , Felicissimo , MP , Pireaux , J-J and Houssiau , L . 2005 . ToF-SIMS characterization of thermal modifications of bixin from Bixa orellana fruit . J Agricult Food Chem , 53 : 6195 – 6200 .
   PubMed Web of Science ®Google Scholar
• Breithaupt , D . 2004 . Simultaneous HPLC determination of carotenoids used as food coloring additives: applicability of accelerated solvent extraction . Food Chem , 86 : 449 – 456 .
   Web of Science ®Google Scholar
• Britton , G . 1995a . “ UV/visible spectroscopy ” . In Carotenoids, Vol. 1B: Spectroscopy , Edited by: Britton , G , Liaaen-Jensen , S and Pfander , H . 13 – 62 . Basel, , Switzerland : Birkhäuser .
   Google Scholar
• Britton , G . 1995b . Structure and properties of carotenoids in relation to function . Fed Am Soc Exp Biol J , 9 : 1551 – 1558 .
   PubMed Web of Science ®Google Scholar
• Budzikiewicz , H . 1974 . Mass spectra of carotenoids–labelling studies . Adv Mass Spectrom , 6 : 155 – 165 .
   Google Scholar
• Carvalho , PRN , Sarantópoulos , CIGJ , Shirose , I and da Silva , MG . 1993 . Study of the shelf-life of the colour (bixin) from annatto seeds (Bixa orellana, L.) . Coltanea Technologia , 23 : 98 – 104 .
   Google Scholar
• Chao , RR , Mulvaney , SJ , Sansom , DR , Hsieh , F-H and Tempesta , MS . 1991 . Supercritical CO2 extraction of annatto (Bixa orellana) pigments and some characteristics of the color extracts . J Food Sci , 56 : 80 – 83 .
   Web of Science ®Google Scholar
• Chatani , Y and Adachi , T . 1988 . Determination of norbixin in foods by HPLC after protease digestion . Kyoto-fu Eisei Kenkyusho Nenpo , 33 : 36 – 40 .
   Google Scholar
• Collingwood Williams W. 1925. Annual report of the County Analyst for the year 1925. Notes from the Reports of Public Analysts:28–29
   Google Scholar
• Collins , P . 1992 . The role of annatto in food . Food Ingred Process Int. , February : 23 – 27 .
   Google Scholar
• Corradi , C and Micheli , G . 1981 . A rapid research and identification method for the natural colorant E160b bixin, norbixin (Oriana, annatto) in food products . Industrie Alimentari , May : 372 – 375 .
   Google Scholar
• Dale , J . 1954 . Empirical relationships of the minor bands in the absorption spectra of polyenes . Acta Chemica Scandinavica , 8 : 1235 – 1256 .
   Google Scholar
• Dendy , DAV . 1966 . The assay of annatto preparations by thin-layer chromatography . J Sci Food Agricult. , 17 : 75 – 76 .
   Web of Science ®Google Scholar
• Ellis Richards PA. 1923. Annual report of the County Analyst for the year 1923. Notes from the Reports of Public Analysts:428
   Google Scholar
• Englert , G . 1995 . “ NMR spectroscopy ” . In Carotenoids, Vol. 1B: Spectroscopy , Edited by: Britton , G , Liaaen-Jensen , S and Pfander , H . 147 – 260 . Basel, , Switzerland : Birkhäuser .
   Google Scholar
• Enzell , C and Wahlberg , I . 1980 . “ Carotenoids ” . In Biomedical applications of mass spectrometry–first supplementary volume , Edited by: Waller , GR and Dermer , OC . 407 – 438 . Chichester : Wiley .
   Google Scholar
• Enzell , CR and Back , S . 1995 . “ Mass spectrometry ” . In Carotenoids, Vol. 1B: Spectroscopy , Edited by: Britton , G , Liaaen-Jensen , S and Pfander , H . 261 – 320 . Basel, , Switzerland : Birkhäuser .
   Google Scholar
• European Commission . 1994 . European Parliament and Council Directive 94/36/EC, of 30 June 1994 on colours for use in foodstuffs . Off J Eur Comm. L , 237 : 13 – 29 .
   Google Scholar
• European Commission . 1995 . Commission Directive 95/45/EC, of 26 July 1995 laying down specific criteria of purity concerning colours for use in foodstuffs . Off J Eur Comm , L226 : 1 – 44 .
   Google Scholar
• European Commission. 2006. Commission of the European Communities. Proposal for a Regulation of the European Parliament and of the Council establishing a common authorisation procedure for food additives, food enzymes and food flavourings. 28.7.2006 COM(2006) 423 Final. 2006/0143 (COD). Brussels (Belgium): European Commission
   Google Scholar
• European Union. 2008. European Union raid Alert System [internet]; [cited 2008 Jan 9]. Available from: http://ec.europa.eu/food/food/rapidalert/index_en.htm/ (http://ec.europa.eu/food/food/rapidalert/index_en.htm/)
   Google Scholar
• Felicissimo , MP , Bittencourt , C , Houssiau , L and Pireaux , JJ . 2004 . Time-of-flight secondary ion mass spectrometry and X-ray photoelectron spectroscopy analyses of Bixa orellana seeds . J Agricult Food Chem , 52 : 1810 – 1814 .
   PubMed Web of Science ®Google Scholar
• Ferreira , VLP , Teixera Neto , RO , Moura , SCSR and De Silva , MS . 1999 . Kinetics of colour degradation of water soluble commercial annatto solutions under thermal treatments . Ciencia Tecnologia Alimentos , 19 : 37 – 42 .
   Google Scholar
• Food and Agricultural Organization/World Health Organization (FAO/WHO). 1981. Specifications for identity and purity of food additives (carrier solvents, emulsifiers and stabilizers, enzyme preparations, flavouring agents, food colours, sweetening agents, and other food additives). Food and Nutrition Paper No. 19. Rome (Italy): FAO
   Google Scholar
• Food and Agricultural Organization/World Health Organization (FAO/WHO). 1996. Compendium of food additive specifications, addendum 4. Food and Nutrition Paper No. 52, Add. 4. Rome (Italy): FAO
   Google Scholar
• Food Standards Agency (FSA). 2006. Study on illegal dyes in imported foods. 12th December [internet]; [cited 2009 Jan 8]. Available from: http://www.food.gov.uk/ (http://www.food.gov.uk/)
   Google Scholar
• Francis , BJ . 1965 . The separation of annatto pigments by thin-layer chromatography with special reference to the use of analytical-grade reagents . Analyst , 90 : 374
   Web of Science ®Google Scholar
• Galindo-Cuspinera , V and Rankin , SA . 2005 . Bioautography and chemical characterization of antimicrobial compound(s) in commercial water-soluble annatto extracts . J Agricult Food Chem , 53 : 2524 – 2529 .
   PubMed Web of Science ®Google Scholar
• Gloria , MBA , Vale , SR and Bobbio , PA . 1995 . Effect of water activity on the stability of bixin in annatto extract-microcrystalline cellulose model system . Food Chem , 52 : 389 – 391 .
   Web of Science ®Google Scholar
• Guaratini , T , Vessechi , RL , Lavarda , FC , Maia , Campos , Naal , PMBG , Gates , PH and Lopes , NP . 2004 . New chemical evidence for the ability to generate radical molecular ions of polyenes from ESI and HR-MALDI mass spectrometry . Analyst , 129 : 1223 – 1226 .
   PubMed Web of Science ®Google Scholar
• Haberli , A and Pfander , H . 1999 . Synthesis of bixin and three minor carotenoids from annatto (Bixa orellana) . Helvetica Chimica Acta , 82 : 696 – 706 .
   Web of Science ®Google Scholar
• Haila , KM , Lievonen , SM and Heinonen , MI . 1996 . Effects of lutein, lycopene, annatto and g-tocopherol on autoxidation of triglycerides . J Agricult Food Chem , 44 : 2096 – 2100 .
   Web of Science ®Google Scholar
• Hammond , EG , Chang , J and Reinbold , GW . 1975 . Colorimetric method for residual annatto in dry whey . J Dairy Sci , 58 : 1365
   Web of Science ®Google Scholar
• Haas , U and Vinha , CA . 1995 . Qualitative and semiquantitative analysis of annatto and its content in food additives by photoacoustic spectrometry . Analyst , 120 : 351 – 354 .
   Web of Science ®Google Scholar
• Heiduschka , A and Panzer , A . 1917 . Zur Kenntnis des Bixins . Berichte der Deutschen Chemischen Gesellschaft , 50 : 546 – 554, 1525 .
   Google Scholar
• Henry , BS . 1992 . “ Natural food colours ” . In Natural food colorants , Edited by: Hendry , GAF and Houghton , JD . 39 – 78 . London, , UK : Blackie .
   Google Scholar
• Herzig , J and Faltis , F . 1923 . Zur Kenntnis des Bixins . Justus Liebigs Annalen Chemie , 431 : 40 – 70 .
   Google Scholar
• Hudson , BS and Kohler , BE . 1974 . Linear polyene electronic structure and spectroscopy . Ann Rev Phys Chem , 25 : 437 – 460 .
   Web of Science ®Google Scholar
• Hudson , B , Kohler , BE and Schulten , K . 1982 . Linear polyene electronic-structure and potential surfaces . Excited States , 6 : 1 – 95 .
   Google Scholar
• Iversen , S and Lam , J . 1953 . Uber den farbstoff in annatto-butterfarben . Zeitschrift Lebensmittel Untersuchung Forschung , 97 : 1 – 7 .
   Google Scholar
• Joint Expert Committee on Food Additives (JECFA). 2002. Joint FAO/WHO Expert Committee on Food Additives, 2002: List of substances scheduled for evaluation and request for data. Rome (Italy). p. 10–12
   Google Scholar
• Jondiko , IJO and Pattenden , G . 1989 . Terpenoids and an apocarotenoid from seeds of Bixa orellana . Phytochemistry , 28 : 3159 – 3162 .
   Web of Science ®Google Scholar
• Jukes , DJ . 2008 . Food Law-Reading , Reading, , (UK) : Department of Food Biosciences, University of Reading [internet]; [cited 2008 Dec 8]. . Available from: http://www.rdg.ac.uk/foodlaw/main.htm/
   Google Scholar
• Karrer , P , Benz , P , Morf , R , Raudnitz , H , Stoll , M and Takahashi , T . 1932 . Konstitution des Safranfarbstoffs Crocetin, Synthese des Perhydro-bixin-äthylesters und Perhydro-norbixins. Vorläufige Mitteilung . Helvetica Chimica Acta , 15 : 1218 – 1399 .
   Google Scholar
• Karrer , P , Helfenstein , A , Widmer , R and Van Itallie , TB . 1929 . Über Bixin. (XIII. Mitteilung über Pflanzenfarbstoffe) . Helvetica Chimica Acta , 12 : 741 – 756 .
   Google Scholar
• Karrer , P and Jucker , E . 1950 . “ Chapter V. Cis-trans isomerism of carotenoids ” . In Carotenoids , 38 – 42 . Basel, , Switzerland : Birkhäuser .
   Google Scholar
• Kelly , DR , Edwards , AA , Parkinson , JA , Olovsson , G , Trotter , J , Jones , S , Abdul Malik , KM , Hursthouse , MB and Hibbs , DE . 1996 . NMR, MS and X-ray crystal structure determination of the bixin family of apocarotenoids . J Chem Res. M , : 2640 – 2697 .
   Google Scholar
• Kiokias , S and Gordon , MH . 2003 . Antioxidant properties of annatto carotenoids . Food Chem , 83 : 523 – 529 .
   Web of Science ®Google Scholar
• Kohler , BE . 1977 . Visual chromophore electronic structure . Biophys Struct Mech , 3 : 101 – 106 .
   PubMedGoogle Scholar
• Kohler , BE . 1995 . “ Electronic structure of carotenoids ” . In Carotenoids, Vol. 1B: Spectroscopy , Edited by: Britton , G , Liaaen-Jensen , S and Pfander , H . 1 – 12 . Basel, , Switzerland : Birkhäuser .
   Google Scholar
• Kovary , K , Louvain , TS , Costa e Silva , MC , Albano , F , Pires , BBM , Laranj , GAT , Lage , CLA and Felzenszwalb , I . 2001 . I. Biochemical behaviour of norbixin during in vitro DNA damage induced by reactive oxygen species . Br J Nutr , 85 : 431 – 440 .
   PubMed Web of Science ®Google Scholar
• Kuhn , R and Winterstein , A . 1932 . Die dihydroverbindung der isomeren bixine und die elektronen-konfiguration der polyene . Berichte Deutschen Chemischen Gesellschaft , 65 : 646 – 651 .
   Google Scholar
• Lancaster , FE and Lawrence , JF . 1995 . Determination of annatto in high-fat dairy products, margarine and hard candy by solvent extraction followed by high-performance liquid chromatography . Food Addit Contam , 12 : 9 – 19 .
   PubMed Web of Science ®Google Scholar
• Lancaster , FE and Lawrence , JF . 1996 . High performance liquid chromatographic separation of carminic acid, α-bixin, and α- and β-norbixin, and the determination of carminic acid in foods . J Chromatograph A , 732 : 394 – 398 .
   PubMed Web of Science ®Google Scholar
• Lauro , GJ . 1991 . A primer on natural colours . Cereal Food World , 36 : 949 – 953 .
   Web of Science ®Google Scholar
• Levy , LW , Regalado , E , Navarette , S and Watkins , RH . 1997 . Bixin and norbixin in human plasma: determination and study of the absorption of a single dose of annatto food color . Analyst , 122 : 977 – 980 .
   PubMed Web of Science ®Google Scholar
• Levy , LW and Rivadeneira , DM . 2000 . “ Annatto ” . In Natural food colorants: science and technology , Edited by: Lauro , GJ and Francis , FJ . 115 – 152 . New York, NY : Marcel Dekker .
   Google Scholar
• Luf , W and Brandl , E . 1988 . The detection of the annatto dyestuff norbixin/bixin in cheese using derivative spectroscopy and high-performance liquid chromatography . Zeitschrift Lebensmittel-Untersuchung -Forschung , 186 : 327 – 332 .
   PubMedGoogle Scholar
• Lunde , K and Zechmeister , L . 1954 . Infrared spectra and cis-trans configurations of some carotenoid pigments . J Am Chem Soc , 77 : 1647 – 1653 .
   Web of Science ®Google Scholar
• Lyng , SM , Passos , M and Fontana , JD . 2005 . Bixin and alpha-cyclodextrin inclusion complex and stability tests . Process Biochem , 40 : 865 – 872 .
   Web of Science ®Google Scholar
• Martinez-Tomé , M , Jimenéz , AM , Ruggieri , S , Frega , N , Strabbioli , R and Murcia , MA . 2001 . Antioxidant properties of Mediterranean spices compared with common food additives . J Food Protect , 64 : 1412 – 1419 .
   PubMed Web of Science ®Google Scholar
• McKeown , GG . 1961 . Paper chromatography of bixin and related compounds . J Assoc Off Analyt Chem , 45 : 347 – 351 .
   Google Scholar
• McKeown , GG . 1963 . Composition of oil-soluble food colours. II. Thermal degradation of bixin . J Assoc Off Analyt Chem , 46 : 790 – 796 .
   Google Scholar
• McKeown , GG . 1965 . Composition of oil-soluble annatto food colors. III. Structure of the yellow pigment formed by the thermal degradation of bixin . J Assoc Off Analyt Chem , 48 : 835 – 837 .
   Google Scholar
• McKeown , GG and Mark , E . 1962 . The composition of oil-soluble annatto food colors . J Assoc Off Analyt Chem , 45 : 761 – 766 .
   Google Scholar
• McNeal , JE . 1976 . Qualitative tests for added colouring matter in meat products . J Assoc Off Analyt Chem , 59 : 570
   PubMedGoogle Scholar
• Mercadante , AZ . 2001 . “ Composition of carotenoids from annatto ” . In Chemistry and physiology of selected food colorants. Symposium Series Number 775 , Edited by: Ames , JM and Hofmann , TS . 92 – 101 . Washington, DC : ACS .
   Google Scholar
• Mercadante , AZ , Steck , A and Pfander , H . 1997a . Isolation and structure elucidation of minor carotenoids from annatto (Bixa orellana) seeds . Phytochemistry , 46 : 1379 – 1383 .
   Web of Science ®Google Scholar
• Mercadante , AZ , Steck , A and Pfander , H . 1997b . Isolation and identification of new apocarotenoids from annatto (Bixa orellana) seeds . J Agricult Food Chem , 45 : 1050 – 1054 .
   Web of Science ®Google Scholar
• Mercadante , AZ , Steck , A and Pfander , H . 1999 . Three minor carotenoids from annatto (Bixa orellana) . Phytochemistry , 52 : 135 – 139 .
   Web of Science ®Google Scholar
• Mercadante , AZ , Steck , A , Rodriguez-Amaya , D , Pfander , H and Britton , G . 1996 . Isolation of methyl 9′-Z-apo-6′-lycopenoate from Bixa orellana . Phytochemistry , 41 : 1201 – 1203 .
   Web of Science ®Google Scholar
• Mínguez-Mosquera , MI , Hornero-Méndez , D and Garrido-Fernández , J . 1995 . Detection of bixin, lycopene, canthaxanthin and β-apo-8′-carotenal in products derived from red pepper . J AOAC Int , 78 : 491 – 496 .
   PubMed Web of Science ®Google Scholar
• Mínguez-Mosquera , MI and Jaren-Galan , M . 1995 . Kinetics of the decoloring of carotenoid pigments . J Sci Food Agricult , 67 : 153 – 161 .
   Web of Science ®Google Scholar
• Ministry of Agriculture, Fisheries and Food (MAFF). 1989. Response to comments received on its Final Report on the Review of the Colouring Matter in Food Regulations 1973, Fd/FAC/6, Food Advisory Committee. London (UK): HMSO
   Google Scholar
• Ministry of Agriculture, Fisheries and Food (MAFF). 1993. Dietary intake of food additives in the UK: initial surveillance. Food Surveillance Paper Number 37. London: HMSO
   Google Scholar
• Montenegro , MA , Rios A de , O , Mercadante , AZ , Nazareno , MA and Borsarelli , CD . 2004 . Model studies on the photosensitized isomerisation of bixin . J Agricult Food Chem , 52 : 367 – 373 .
   PubMed Web of Science ®Google Scholar
• Moss , GP . 1976 . Carbon-13 NMR spectra of carotenoids . Pure Appl Chem , 47 : 97 – 102 .
   Web of Science ®Google Scholar
• Najar , SV , Bobbio , FO and Bobbio , PA . 1988 . Effects of light, air, anti-oxidants and pro-oxidants on annatto extracts (Bixa orellana) . Food Chem , 29 : 283 – 289 .
   Web of Science ®Google Scholar
• Navaz Diaz , A and Ramos Peinado , MC . 1992 . Fluorimetric determination of curcumin in yogurt and mustard . J Agricult Food Chem , 40 : 56 – 59 .
   Web of Science ®Google Scholar
• Nishizawa , M , Chonan , T , Sekijo , I and Sugii , Y . 1983 . Studies on the analysis of natural dyes: analysis of annatto extract and gardenia yellow dye in foods and natural dye preparations . Hokkaidoritsu Eisei Kenkyusho , 33 : 32 – 34 .
   Google Scholar
• Noppe , H , Abuin Martinez , S , Verheyden , K , Van Loco , J , Companyó Beltran , R and De Brabander , HF . 2009 . Determination of bixin and norbixin in meat using liquid chromatography and photodiode array detection . Food Addit Contam , 26 : 17 – 24 .
   Web of Science ®Google Scholar
• Nordic Working Group on Food Toxicology and Risk Assessment (NNT). 2008. Nordic Food Additives Database [Internet] Available from: http://www.norfad.dk/ (http://www.norfad.dk/)
   Google Scholar
• Pattenden , G , Way , JE and Weedon , BCL . 1970 . Carotenoids and related compounds. Part XXVI. Synthesis of methyl natural bixin . J Chem Soc. , : 235 – 241 .
   Google Scholar
• Pettersson , A and Jonsson , L . 1990 . Separation of cis-trans isomers of alpha- and beta-carotene by adsorption HPLC and identification with diode-array detection . J Micronutr Anal , 8 : 23 – 41 .
   Google Scholar
• Prentice-Hernández , C and Rusig , O . 1999 . Effect of light on the stability of a microencapsulated extract obtained from annatto (Bixa orellana L.) . Braz J Food Tech , 2 : 185 – 189 .
   Google Scholar
• Prentice-Hernández , C , Rusig , O and Carvalho , PRN . 1993 . Influence of heating time on the thermal-degradation of bixin in alkaline extracts of annatto (Bixa orellana) . Arquivos Biologica Tecnologica , 36 : 819 – 828 .
   Google Scholar
• Preston , HD and Rickard , MD . 1980 . Extraction and chemistry of annatto . Food Chem , 5 : 47 – 56 .
   Web of Science ®Google Scholar
• Ramamurthy , MK and Bhalerao , VR . 1964 . A thin-layer chromatographic method for identifying annatto and other food colours . Analyst , 89 : 740 – 744 .
   Web of Science ®Google Scholar
• Rao , PGP , Jyothirmayi , T , Balaswamy , K , Satyanarayana , A and Rao , DG . 2005 . Effect of processing conditions on the stability of annatto (Bixa orellana L.) dye incorporated into some foods . LWT–Food Sci Tech , 38 : 779 – 784 .
   Web of Science ®Google Scholar
• Reith , JF and Gielen , JW . 1971 . Properties of bixin and norbixin and the composition of annatto extracts . J Food Sci , 36 : 861 – 864 .
   Web of Science ®Google Scholar
• Rios , ADO , Borsarelli , CD and Mercadante , AZ . 2005 . Thermal degradation kinetics of bixin in an aqueous model system . J Agricult Food Chem , 53 : 2307 – 2311 .
   PubMed Web of Science ®Google Scholar
• Rios , ADO and Mercadante , AZ . 2004 . Novel method for the determination of added annatto colour in extruded corn snack products . Food Addit Contam , 21 : 125 – 133 .
   PubMedGoogle Scholar
• Rios , ADO , Mercadante , AZ and Borsarelli , D . 2007 . Triplet state energy of the carotenoid bixin determined by photoacoustic calorimetry . Dyes Pigment , 74 : 561 – 565 .
   Web of Science ®Google Scholar
• Rouseff , RL . 1988 . High performance liquid chromatographic separation and spectral characterisation of the pigments in turmeric and annatto . J Food Sci , 53 : 1823 – 1826 .
   Web of Science ®Google Scholar
• Satyanarayana , A , Prabhakara Rao , P , Balaswamy , K , Velu , V and Rao , DG . 2006 . Application of annatto dye formulations in different fruit and vegetable products . J Food Serv , 17 : 1 – 5 .
   Google Scholar
• Satyanarayana , A , Prabhakara Rao , PG and Rao , DG . 2003 . Chemistry, processing and toxicology of annatto (Bixa orellana L.) . J Food Sci Tech , 40 : 131 – 141 .
   Web of Science ®Google Scholar
• Scheidt , K and Liaaen-Jensen , S . 1995 . “ Isolation and analysis ” . In Carotenoids Vol. 1A: Isolation and analysis , Edited by: Britton , G , Liaaen-Jensen , S and Pfander , H . 81 – 108 . Basel, , Switzerland : Birkhäuser .
   Google Scholar
• Scott , AI . 1964 . “ Application of spectral data to the investigation of gross molecular structure. Interpretation of the ultraviolet spectra of natural products ” . In International series of monographs on organic chemistry , 228 – 312 . London, , UK : Pergamon .
   Google Scholar
• Scotter , MJ . 1995 . Characterisation of the coloured thermal degradation products of bixin from annatto and a revised mechanism for their formation . Food Chem , 53 : 177 – 185 .
   Web of Science ®Google Scholar
• Scotter , MJ , Appleton , GP and Castle , L . 2001 . Kinetics and yields for the formation of coloured and aromatic thermal degradation products of annatto in foods . Food Chem , 74 : 365 – 375 .
   Web of Science ®Google Scholar
• Scotter , MJ , Castle , L , Honeybone , C and Nelson , C . 2002 . Method development and analysis of retail foods for annatto food colouring material . Food Addit Contam , 19 : 205 – 222 .
   PubMed Web of Science ®Google Scholar
• Scotter , MJ , Thorpe , SA , Reynolds , SL , Wilson , LA and Strutt , PR . 1994 . Characterization of the principal colouring components of annatto using high performance liquid chromatography with photodiode array detection . Food Addit Contam , 11 : 301 – 315 .
   PubMed Web of Science ®Google Scholar
• Scotter , MJ , Wilson , LA , Appleton , GP and Castle , L . 1998 . Analysis of annatto (Bixa orellana) food colouring formulations. 1. Determination of colouring components and coloured thermal degradation products by high-performance liquid chromatography with photodiode array detection . J Agricult Food Chem , 46 : 1031 – 1038 .
   Web of Science ®Google Scholar
• Scotter , MJ , Wilson , LA , Appleton , GP and Castle , L . 2000 . Analysis of annatto (Bixa orellana) food colouring formulations. 2. Determination of aromatic hydrocarbon thermal degradation products by gas chromatography . J Agricult Food Chem , 48 : 484 – 488 .
   PubMed Web of Science ®Google Scholar
• Silva , GS , Souza , AG , Botelho , JR , Silva , MCD and Silva , TMS . 2007 . Kinetics study of norbixin's first stage thermal decomposition, using dynamic method . J Therm Anal Calorimetr , 87 : 871 – 874 .
   Web of Science ®Google Scholar
• Silva , MCD , Bothelo , JR , Conceição , MM , Lira , BF , Couthino , MA , Dias , AF , Souza , AG and Filho , PFA . 2005 . Thermogravimetric investigations on the thermal degradation of bixin, derived from the seeds of annatto (Bixa orellana L.) . J Therm Anal Calorimetr , 79 : 277 – 281 .
   Web of Science ®Google Scholar
• Smith , PR , Blake , CJ and Porter , DC . 1983 . Determination of added natural colours in foods , III. Annatto. Research Report Number 431. Leatherhead, , (UK) : British Food Manufacturing Industries Research Association .
   Google Scholar
• Tennant , DR and O’Callaghan , MO . 2005 . Survey of usage and estimated intakes of annatto extracts . Food Res Int , 38 : 911 – 917 .
   Web of Science ®Google Scholar
• Tirimanna , ASL . 1980 . Study of the carotenoid pigments of Bixa orellana L. seeds by thin layer chromatography . Mikrochimica Acta (Vienna) , 2 : 11 – 16 .
   Google Scholar
• Van Breemen , RB . 1995 . Electrospray liquid-chromatography mass-spectrometry of carotenoids . Analyt Chem , 67 : 2004 – 2009 .
   Web of Science ®Google Scholar
• Vetter , W , Englert , G , Rigassi , N and Schwieter , U . 1971 . “ Spectroscopic methods ” . In Carotenoids , Edited by: Isler , O . 189 – 266 . Basel, , Switzerland : Birkhäuser .
   Google Scholar
• Vetter , W and Meister , W . 1985 . Fast atom bombardment mass-spectrum of beta-carotene . Organ Mass Spectroscop , 20 : 266 – 267 .
   Web of Science ®Google Scholar
• Weedon , BCL and Moss , GP . 1995 . “ Structure and nomenclature ” . In Carotenoids, Vol. 1A: Isolation and analysis , Edited by: Britton , G , Liaaen-Jensen , S and Pfander , H . 27 – 70 . Basel, , Switzerland : Birkhäuser .
   Google Scholar
• Zechmeister , L . 1960 . Cis-trans isomeric carotenoid pigments . Progr Chem Natur Prod , 18 : 223 – 349 .
   Google Scholar
• Zhao , W , Han , YS , Zhao , BL , Hirota , S , Hou , JW and Xin , WJ . 1998 . The effect of carotenoids on the respiratory burst of rat peritoneal macrophages . Biochim Biophys Acta Gen Subj , 1381 : 77 – 88 .
   PubMed Web of Science ®Google Scholar