| Name: | (2E,4E,6E,8E,10E,12E,14E,16E,18E)-4,8,13,17-tetramethylicosa-2,4,6,8,10,12,14,16,18-nonaenedioic acid |
| CAS Number: | 542-40-5 |  3D/inchi
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| ECHA EINECS - REACH Pre-Reg: | 208-810-8 |
| FDA UNII: | E8M59E17AI |
| Nikkaji Web: | J12.714K |
| XlogP3-AA: | 7.20 (est) |
| Molecular Weight: | 380.48396000 |
| Formula: | C24 H28 O4 |
| NMR Predictor: | Predict (works with chrome, Edge or firefox) |
Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Appearance: | white crystalline (est) |
| Assay: | 95.00 to 100.00
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| Food Chemicals Codex Listed: | No |
| Soluble in: |
| | water, 0.005225 mg/L @ 25 °C (est) |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
Safety Information:
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| Hazards identification |
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| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
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| Pictogram | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
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Not determined
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | | natural substances and extractives |
| Recommendation for norbixin usage levels up to: | | | not for fragrance use.
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| Recommendation for norbixin flavor usage levels up to: |
| | not for flavor use.
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Safety References:
European Food Safety Authority (EFSA) reference(s):
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The safety of annatto extracts (E 160b) as a food additive
View page or View pdf
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Exposure assessment of annatto colouring principles bixin and norbixin (E 160b) when used as food additives
View page or View pdf
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Safety of annatto E and the exposure to the annatto colouring principles bixin and norbixin (E 160b) when used as a food additive
View page or View pdf
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| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :5281249 |
| National Institute of Allergy and Infectious Diseases:Data |
| (2E,4E,6E,8E,10E,12E,14E,16E,18E)-4,8,13,17-tetramethylicosa-2,4,6,8,10,12,14,16,18-nonaenedioic acid |
| Chemidplus:0000542405 |
References:
| | (2E,4E,6E,8E,10E,12E,14E,16E,18E)-4,8,13,17-tetramethylicosa-2,4,6,8,10,12,14,16,18-nonaenedioic acid |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 5281249 |
| Pubchem (sid): | 135050098 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| | annatto (e 160b) | | nor | bixen | | 6,6'- | diapo-psi,psi-carotene dioic acid | | 4,8,13,17- | tetramethyl-2,4,6,8,10,12,14,16,18-eicosanonaene dioic acid | | (2E,4E,6E,8E,10E,12E,14E,16E,18E)-4,8,13,17- | tetramethylicosa-2,4,6,8,10,12,14,16,18-nonaenedioic acid |
Articles:
| PubMed:Norbixin, an apocarotenoid derivative activates PPAR? in cardiometabolic syndrome: Validation by in silico and in vivo experimental assessment |
| PubMed:Mechanism behind the degradation of aqueous norbixin upon storage in light and dark environment |
| PubMed:Safety of annatto E and the exposure to the annatto colouring principles bixin and norbixin (E 160b) when used as a food additive |
| PubMed:Bromoacetate Olefination Protocol for Norbixin and Julia-Kocienski Olefination for Its Ester Syntheses |
| PubMed:Addition of norbixin microcapsules obtained by spray drying in an isotonic tangerine soft drink as a natural dye |
| PubMed:Studies on interaction of norbixin with DNA: multispectroscopic and in silico analysis |
| PubMed:Characterization and assessment of the genotoxicity and biocompatibility of poly (hydroxybutyrate) and norbixin membranes |
| PubMed:Effect of norbixin-based poly(hydroxybutyrate) membranes on the tendon repair process after tenotomy in rats |
| PubMed:Short communication: norbixin and bixin partitioning in Cheddar cheese and whey |
| PubMed:Norbixin Protects Retinal Pigmented Epithelium Cells and Photoreceptors against A2E-Mediated Phototoxicity In Vitro and In Vivo |
| PubMed:Incorporation of bixin in aqueous media: Self-formulation with sorbitol ester of norbixin |
| PubMed:Systemic administration of the di-apocarotenoid norbixin (BIO201) is neuroprotective, preserves photoreceptor function and inhibits A2E and lipofuscin accumulation in animal models of age-related mac |
| PubMed:Norbixin ingestion did not induce any detectable DNA breakage in liver and kidney but caused a considerable impairment in plasma glucose levels of rats and mice |
| PubMed:Short communication: Sensitive detection of norbixin in dried dairy ingredients at concentrations of less than 1 part per billion |
| PubMed:Effect of bixin and norbixin on the expression of cytochrome P450 in HepG2 cell line |
| PubMed:Exposure assessment of annatto colouring principles bixin and norbixin (E˙160b) when used as food additives |
| PubMed:Effect of low intensity photobiomodulation associated with norbixin-based poly (hydroxybutyrate) membrane on post-tenotomy tendon repair. In vivo study |
| PubMed:Antigenotoxic and antimutagenic potential of an annatto pigment (norbixin) against oxidative stress |
| PubMed:Biochemical behaviour of norbixin during in vitro DNA damage induced by reactive oxygen species |
| PubMed:Safety and efficacy of cis-norbixin di-potassium salt (annatto F) for cats and dogs |
| PubMed:Evaluation of bone repair after application of a norbixin membrane scaffold with and without laser photobiomodulation (? 780˙nm) |
| PubMed:Bixin and norbixin in human plasma: determination and study of the absorption of a single dose of Annatto food color |
| PubMed:Prooxidant activity of norbixin in model of acute gastric ulcer induced by ethanol in rats |
| PubMed:Gum arabic and Feŭ? synergistically improve the heat and acid stability of norbixin at pH 3.0-5.0 |
| PubMed:Short communication: Development of a novel method for the extraction of norbixin from whey and its subsequent quantification via high performance liquid chromatography |
| PubMed:Study on decomposition products of norbixin during bleaching with hydrogen peroxide and a peroxidase by means of UPLC-UV and mass spectrometry |
| PubMed:Digestive stability and transport of norbixin, a 24-carbon carotenoid, across monolayers of Caco-2 cells |
| PubMed:Probing the binding between norbixin and dairy proteins by spectroscopy methods |
| PubMed:The biotechnology (genetic transformation and molecular biology) of Bixa orellana L. (achiote) |
| PubMed:Bixin and norbixin protect against DNA-damage and alterations of redox status induced by methylmercury exposure in vivo |
| PubMed:Contact sensitizing potential of annatto extract and its two primary color components, cis-bixin and norbixin, in female BALB/c mice |
| PubMed:Colorants in cheese manufacture: Production, chemistry, interactions, and regulation |
| PubMed:Bixin and norbixin have opposite effects on glycemia, lipidemia, and oxidative stress in streptozotocin-induced diabetic rats |
| PubMed:Determination of bixin and norbixin in meat using liquid chromatography and photodiode array detection |
| PubMed:Raman spectroscopic determination of norbixin and tartrazine in sugar |
| PubMed:A synergistic effect of Cu(2+) and norbixin on DNA damage |
| PubMed:Characteristics of activated carbon and carbon nanotubes as adsorbents to remove annatto (norbixin) in cheese whey |
| PubMed:[Detection of the annatto dye norbixin/bixin in cheese using derivative spectroscopy and high performance liquid chromatography (HPLC)] |
| PubMed:Tiered intake assessment for food colours |
| PubMed:Immobilization of peroxidase on textile carrier materials and their application in the bleaching of colored whey |
| PubMed:Water-in-oil-in-water emulsion obtained by glass microfluidic device for protection and heat-triggered release of natural pigments |
| PubMed:Dietary supplementation with annatto food-coloring extracts increases the resistance of human erythrocytes to hemolysis |
| PubMed:Decolorization of Cheddar cheese whey by activated carbon |
| PubMed:Generalized and rapid supramolecular solvent-based sample treatment for the determination of annatto in food |
| PubMed:Effect of temperature and concentration on benzoyl peroxide bleaching efficacy and benzoic acid levels in whey protein concentrate |
| PubMed:A thirteen-week oral toxicity study of annatto extract (norbixin), a natural food color extracted from the seed coat of annatto (Bixa orellana L.), in Sprague-Dawley rats |
| PubMed:The effect of bleaching agents on the degradation of vitamins and carotenoids in spray-dried whey protein concentrate |
| PubMed:Hydrophilization of bixin by lipase-catalyzed transesterification with sorbitol |
| PubMed:High-performance liquid chromatographic separation of carminic acid, alpha- and beta-bixin, and alpha- and beta-norbixin, and the determination of carminic acid in foods |
| PubMed:Achiote (Bixa orellana L.): a natural source of pigment and vitamin E |
| PubMed:Development of carotenoid storage cells in Bixa orellana L. seed arils |
| PubMed:Short-Term Bixin Supplementation of Healthy Subjects Decreases the Susceptibility of LDL to Cu(2+)-Induced Oxidation Ex Vivo |
| PubMed:Irradiance and light quality affect two annatto (Bixa orellana L.) cultivars with contrasting bixin production |
| PubMed:Determination of annatto in high-fat dairy products, margarine and hard candy by solvent extraction followed by high-performance liquid chromatography |
| PubMed:Alternative bleaching methods for Cheddar cheese whey |
| PubMed:The effects of photodynamic therapy with blue light and papain-based gel associated with Urucum, on collagen and fibroblasts: a spectroscopic and cytotoxicity analysis |
| PubMed:Invited review: Annatto usage and bleaching in dairy foods |
| PubMed:Beyond AREDS Formulations, What Is Next for Intermediate Age-Related Macular Degeneration (iAMD) Treatment? Potential Benefits of Antioxidant and Anti-inflammatory Apocarotenoids as Neuroprotectors |
| PubMed:Absence of liver tumor promoting effects of annatto extract (norbixin), a natural carotenoid food color, in a medium-term liver carcinogenesis bioassay using male F344 rats |
| PubMed:Using full chloroplast genomes of 'red' and 'yellow' Bixa orellana (achiote) for kmer based identification and phylogenetic inference |
| PubMed:Cold enzymatic bleaching of fluid whey |
| PubMed:Bioautography and chemical characterization of antimicrobial compound(s) in commercial water-soluble annatto extracts |
| PubMed:The use of lactoperoxidase for the bleaching of fluid whey |
| PubMed:Annatto-entrapped casein-chitosan complexes improve whey color quality after acid coagulation of milk |
| PubMed:The effect of microfiltration on color, flavor, and functionality of 80% whey protein concentrate |
| PubMed:Comparative Cold Shock Expression and Characterization of Fungal Dye-Decolorizing Peroxidases |
| PubMed:Annatto carotenoids attenuate oxidative stress and inflammatory response after high-calorie meal in healthy subjects |
| PubMed:Characterization of the principal colouring components of annatto using high performance liquid chromatography with photodiode-array detection |
| PubMed:Inhibitory effect of apocarotenoids on the activity of tyrosinase: Multi-spectroscopic and docking studies |
| PubMed:Evaluation of certain food additives and contaminants |
| PubMed:Effects of saffron˙and its constituents,˙crocin-1, crocin-2, and crocetin on à-synuclein fibrils |
| PubMed:Effect of natural pigments on the oxidative stability of sausages stored under refrigeration |
| PubMed:Genetic, evolutionary and phylogenetic aspects of the plastome of annatto (Bixa orellana L.), the Amazonian commercial species of natural dyes |
| PubMed:Variants of PpuLcc, a multi-dye decolorizing laccase from Pleurotus pulmonarius expressed in Pichia pastoris |
| PubMed:Analysis of annatto (Bixa orellana) food coloring formulations. 2. Determination of aromatic hydrocarbon thermal degradation products by gas chromatography |
| PubMed:Neuron-glial cell communication in the traumatic stress-induced immunomodulation |
| PubMed:Sensory and Functionality Differences of Whey Protein Isolate Bleached by Hydrogen or Benzoyl Peroxide |
| PubMed:Chitosan microspheres containing the natural urucum pigment |
| PubMed:Carotenoids and ?-cyclodextrin inclusion complexes: Raman spectroscopy and theoretical investigation |
| PubMed:In vitro scavenging capacity of annatto seed extracts against reactive oxygen and nitrogen species |
| PubMed:Bixin activates PPARà and improves obesity-induced abnormalities of carbohydrate and lipid metabolism in mice |
| PubMed:Partial replacement of nitrite by annatto as a colour additive in sausage |
| PubMed:Effect of bleaching permeate from microfiltered skim milk on 80% serum protein concentrate |
| PubMed:Studies on application of annatto (Bixa orellena L.) dye formulations in dairy products |
| PubMed:The effect of starter culture and annatto on the flavor and functionality of whey protein concentrate |
| PubMed:Biosynthesis of the food and cosmetic plant pigment bixin (annatto) |
| PubMed:Short communication: The influence of solids concentration and bleaching agent on bleaching efficacy and flavor of sweet whey powder |
| PubMed:Reactive oxygen species mediate lethality induced by far-UV in Escherichia coli cells |
| PubMed:Influence of storage, heat treatment, and solids composition on the bleaching of whey with hydrogen peroxide |
| PubMed:Evaluation of certain food additives and contaminants. Eightieth report of the Joint FAO/WHO Expert Committee on Food Additives |
| PubMed:Bixin regulates mRNA expression involved in adipogenesis and enhances insulin sensitivity in 3T3-L1 adipocytes through PPARgamma activation |
| PubMed:Effect of bleaching whey on sensory and functional properties of 80% whey protein concentrate |
| PubMed:Novel method for the determination of added annatto colour in extruded corn snack products |
| PubMed:Method development and analysis of retail foods for annatto food colouring material |
| PubMed:Annatto constituent cis-bixin has selective antimyeloma effects mediated by oxidative stress and associated with inhibition of thioredoxin and thioredoxin reductase |
| PubMed:Effect of temperature and bleaching agent on bleaching of liquid Cheddar whey |
| PubMed:Next generation sequencing and de novo transcriptome analysis of Costus pictus D. Don, a non-model plant with potent anti-diabetic properties |
| PubMed:Structural analysis of the synaptic protein neuroligin and its beta-neurexin complex: determinants for folding and cell adhesion |
| PubMed:Influence of bleaching on flavor of 34% whey protein concentrate and residual benzoic acid concentration in dried whey proteins |
| PubMed:The effect of bleaching agent on the flavor of liquid whey and whey protein concentrate |
| PubMed:Active food packaging of cellulose acetate: Storage stability, protective effect on oxidation of riboflavin and release in food simulants |
| PubMed:Characterizing endogenous and exogenous peroxidase activity for bleaching of fluid whey and retentate |
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Water-soluble food colour. Commercial forms contain mixts. of isomers and their Me esters. Used to colour butter, margarine and other fat-related products
Bixin is an apocarotenoid found in annatto, a natural food coloring obtained from the seeds of the achiote tree (Bixa orellana). Upon exposure to alkali, the methyl ester is hydrolyzed to produce the dicarboxylic acid norbixin, a water-soluble derivative. (Wikipedia)
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