norbixin
norbixen
 
Notes:
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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CAS Number: 542-40-5Picture of molecule3D/inchi
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 or firefox)
Category: natural substances and extractives
 
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DG SANTE Food Additives: norbixin
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Physical Properties:
Appearance: white crystalline (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Soluble in:
 water, 0.005225 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
 None found
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
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.
 
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):
The safety of annatto extracts (E 160b) as a food additive
View page or View pdf
Exposure assessment of annatto colouring principles bixin and norbixin (E 160b) when used as food additives
View page or View pdf
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
EPI System: View
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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
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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
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
KEGG (GenomeNet): C08608
HMDB (The Human Metabolome Database): HMDB35832
FooDB: FDB014600
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 found in nature
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Synonyms:
 annatto (e 160b)
norbixen
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
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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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