annatto seed extract (solvent-extracted bixin)
annatto B
 
Notes:
None found
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Name: (2E,4E,6E,8E,10E,12E,14E,16Z,18E)-20-methoxy-4,8,13,17-tetramethyl-20-oxoicosa-2,4,6,8,10,12,14,16,18-nonaenoic acid
CAS Number: 6983-79-5Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 230-248-7
XlogP3-AA: 7.50 (est)
Molecular Weight: 394.51090000
Formula: C25 H30 O4
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: coloring agents
 
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 FDA/DG SANTE Petitions, Reviews, Notices:
EU SANCO Annatto, Bixin, Norbixin View - review
JECFA Food Additive: Annatto extract (solvent-extracted bixin)
GSFA Codex: Annatto extracts, bixin-based (160b(i))
DG SANTE Food Additives: annatto B
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Physical Properties:
Appearance: dark red-brown to red-purple powder (est)
Assay: 85.00 to 100.00 % 
Food Chemicals Codex Listed: No
Melting Point: 198.00 °C. @ 760.00 mm Hg
Boiling Point: 596.02 °C. @ 760.00 mm Hg (est)
Flash Point: 388.00 °F. TCC ( 197.80 °C. ) (est)
logP (o/w): 6.170 (est)
Soluble in:
 acetone
 alcohol, slightly
 water, 0.0007697 mg/L @ 25 °C (est)
Insoluble in:
 water
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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:
Chr. Hansen A/S
Annatto
Flavor: characteristic
Annatto is the international food and beverage industry’s preferred natural color in orange shades ranging from light, yellowish orange to deep, dark orange. Chr. Hansen offers a full range of annatto natural color solutions including water-soluble, oil-soluble, acid-stable and encapsulated formulations, all with good light and heat stability.
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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: coloring agents
Recommendation for annatto seed extract (solvent-extracted bixin) usage levels up to:
 not for fragrance use.
 
Recommendation for annatto seed extract (solvent-extracted bixin) 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
EPI System: View
Chemical Carcinogenesis Research Information System: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
National Institute of Allergy and Infectious Diseases: Data
 (2E,4E,6E,8E,10E,12E,14E,16Z,18E)-20-methoxy-4,8,13,17-tetramethyl-20-oxoicosa-2,4,6,8,10,12,14,16,18-nonaenoic acid
Chemidplus: 0006983795
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References:
 (2E,4E,6E,8E,10E,12E,14E,16Z,18E)-20-methoxy-4,8,13,17-tetramethyl-20-oxoicosa-2,4,6,8,10,12,14,16,18-nonaenoic acid
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 5281226
Pubchem (sid): 135048012
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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
FDA Listing of Food Additive Status: View
FDA Color Additive Status ListView
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
 annatto seed
Search Trop  Picture
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Synonyms:
 annatto B
 bixa orellana seed extract (solvent-extracted bixin)
 c.i. 75120 (solvent-extracted bixin)
 ci 75120 (solvent-extracted bixin)
 natural orange 4 (solvent-extracted bixin)
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Articles:
Info: EVALUATION OF CERTAIN FOOD ADDITIVES AND CONTAMINANTS
PubMed: Annatto prevents retinal degeneration induced by endoplasmic reticulum stress in vitro and in vivo.
PubMed: Systemic administration of the apocarotenoid bixin protects skin against solar UV-induced damage through activation of NRF2.
PubMed: De novo transcriptome sequencing in Bixa orellana to identify genes involved in methylerythritol phosphate, carotenoid and bixin biosynthesis.
PubMed: Bixin loaded solid lipid nanoparticles for enhanced hepatoprotection--preparation, characterisation and in vivo evaluation.
PubMed: Aprotic solvents effect on the UV-visible absorption spectra of bixin.
PubMed: DFT and ENDOR Study of Bixin Radical Cations and Neutral Radicals on Silica-Alumina.
PubMed: Short communication: norbixin and bixin partitioning in Cheddar cheese and whey.
PubMed: Bixin protects hepatocytes against 1,2-dimethylhydrazine-induced genotoxicity but does not suppress DNA damage and pre-neoplastic lesions in the colon of Wistar rats.
PubMed: Inhibition of cyclophosphamide-induced oxidative stress in rat brain by polar and non-polar extracts of Annatto (Bixa orellana) seeds.
PubMed: Protective effect of bixin on carbon tetrachloride-induced hepatotoxicity in rats.
PubMed: Effect of bixin and norbixin on the expression of cytochrome P450 in HepG2 cell line.
PubMed: Inhibition of Cholesterol and Polyunsaturated Fatty Acids Oxidation through the Use of Annatto and Bixin in High-Pressure Processed Fish.
PubMed: Characterisation and stability evaluation of bixin nanocapsules.
PubMed: Bixin activates PPARα and improves obesity-induced abnormalities of carbohydrate and lipid metabolism in mice.
PubMed: Induction of liver monooxygenases by annatto and bixin in female rats.
PubMed: Bixin action in the healing process of rats mouth wounds.
PubMed: The antiatherogenic effect of bixin in hypercholesterolemic rabbits is associated to the improvement of lipid profile and to its antioxidant and anti-inflammatory effects.
PubMed: Protective effect of bixin on cisplatin-induced genotoxicity in PC12 cells.
PubMed: Effects of thermal denaturation on binding between bixin and whey protein.
PubMed: Effects of pH on the molecular binding between β-lactoglobulin and bixin.
PubMed: Bixin and norbixin have opposite effects on glycemia, lipidemia, and oxidative stress in streptozotocin-induced diabetic rats.
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: Contact sensitizing potential of annatto extract and its two primary color components, cis-bixin and norbixin, in female BALB/c mice.
PubMed: Interaction of curcumin and bixin with β-cyclodextrin: complexation methods, stability, and applications in food.
PubMed: Bixin and norbixin protect against DNA-damage and alterations of redox status induced by methylmercury exposure in vivo.
PubMed: Annatto constituent cis-bixin has selective antimyeloma effects mediated by oxidative stress and associated with inhibition of thioredoxin and thioredoxin reductase.
PubMed: Binding between bixin and whey protein at pH 7.4 studied by spectroscopy and isothermal titration calorimetry.
PubMed: Simultaneous extraction and analysis by high performance liquid chromatography coupled to diode array and mass spectrometric detectors of bixin and phenolic compounds from annatto seeds.
PubMed: Extraction of an hyperglycaemic principle from the annatto (Bixa orellana), a medicinal plant in the West Indies.
PubMed: Bixin regulates mRNA expression involved in adipogenesis and enhances insulin sensitivity in 3T3-L1 adipocytes through PPARgamma activation.
PubMed: Studies on application of annatto (Bixa orellena L.) dye formulations in dairy products.
PubMed: Time-of-flight secondary ion mass spectrometry and X-ray photoelectron spectroscopy analyses of Bixa orellana seeds.
PubMed: Toxicity of the hyperglycaemic-inducing extract of the annatto (Bixa orellana) in the dog.
PubMed: Evaluation of the clastogenicity and anticlastogenicity of the carotenoid bixin in human lymphocyte cultures.
PubMed: Model studies on the photosensitized isomerization of bixin.
PubMed: Analysis of binding interaction between the natural apocarotenoid bixin and human serum albumin by circular dichroism and fluorescence spectroscopy.
PubMed: Antioxidant action of bixin against cisplatin-induced chromosome aberrations and lipid peroxidation in rats.
PubMed: Bixin and norbixin in human plasma: determination and study of the absorption of a single dose of Annatto food color.
PubMed: [Analysis of the uncertainty of the easily oxidized substance of the injector by titration].
PubMed: Thermal degradation kinetics of bixin in an aqueous model system.
PubMed: Biosynthesis of the food and cosmetic plant pigment bixin (annatto).
PubMed: Inhibitory effect of apocarotenoids on the activity of tyrosinase: Multi-spectroscopic and docking studies.
PubMed: Next generation sequencing and de novo transcriptome analysis of Costus pictus D. Don, a non-model plant with potent anti-diabetic properties.
PubMed: Circular dichroism and absorption spectroscopic data reveal binding of the natural cis-carotenoid bixin to human alpha1-acid glycoprotein.
PubMed: Generalized and rapid supramolecular solvent-based sample treatment for the determination of annatto in food.
PubMed: Hypoglycaemic activity of Bixa orellana extract in the dog.
PubMed: ToF-SIMS characterization of thermal modifications of bixin from Bixa orellana fruit.
PubMed: Protective effect of curcumin, ellagic acid and bixin on radiation induced genotoxicity.
PubMed: Detection of bixin, lycopene, canthaxanthin, and beta-apo-8'-carotenal in products derived from red pepper.
PubMed: The coupled reactions between methyl linoleate and bixin or tocopherol during oxidation by lipoxidase.
PubMed: Determination of bixin and norbixin in meat using liquid chromatography and photodiode array detection.
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: [Detection of the annatto dye norbixin/bixin in cheese using derivative spectroscopy and high performance liquid chromatography (HPLC)].
PubMed: Protective effect of curcumin, ellagic acid and bixin on radiation induced toxicity.
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: Characterization of bixin by LC-MS and LC-NMR.
PubMed: In vitro scavenging capacity of annatto seed extracts against reactive oxygen and nitrogen species.
PubMed: Identification and expression pattern of a new carotenoid cleavage dioxygenase gene member from Bixa orellana.
PubMed: Characteristic Parameters of MTF of the Retina-Brain System.
PubMed: Energized state of mitochondria as revealed by the spectral change of bound bixin.
PubMed: Spectral changes of bixin upon interaction with respiring rat liver mitochondria.
PubMed: The induced reaction between methyl linoleate and bixin during oxidation by lipoxidase.
PubMed: THE PREPARATION OF BIXIN.
PubMed: Development of carotenoid storage cells in Bixa orellana L. seed arils.
PubMed: RNA-Seq analysis and annotation of a draft blueberry genome assembly identifies candidate genes involved in fruit ripening, biosynthesis of bioactive compounds, and stage-specific alternative splicing.
PubMed: Carotenoids inhibit proliferation and regulate expression of peroxisome proliferators-activated receptor gamma (PPARγ) in K562 cancer cells.
PubMed: Development of a novel PPARγ ligand screening system using pinpoint fluorescence-probed protein.
PubMed: Evaluation of certain food additives and contaminants.
PubMed: Optical characterization in annatto and commercial colorific.
PubMed: Determination of annatto in high-fat dairy products, margarine and hard candy by solvent extraction followed by high-performance liquid chromatography.
PubMed: Method development and analysis of retail foods for annatto food colouring material.
PubMed: Effect of annatto seed and coriander leaves as natural antioxidants in fish meatballs during frozen storage.
PubMed: Effect of carotenoids on the respiratory burst of rat peritoneal macrophages.
PubMed: Unraveling new genes associated with seed development and metabolism in Bixa orellana L. by expressed sequence tag (EST) analysis.
PubMed: Carotenoids enhance gap junctional communication and inhibit lipid peroxidation in C3H/10T1/2 cells: relationship to their cancer chemopreventive action.
PubMed: Invited review: Annatto usage and bleaching in dairy foods.
PubMed: Capillary NMR detection in separation science.
PubMed: Evaluation of the developmental toxicity of annatto in the rat.
PubMed: Suppressive effect of carotenoids on the luminol dependent chemiluminescence of the stimulated rat macrophages.
PubMed: Effect of dietary supplementation with carotenoids on xenobiotic metabolizing enzymes in the liver, lung, kidney and small intestine of the rat.
PubMed: Antigenotoxic and antimutagenic potential of an annatto pigment (norbixin) against oxidative stress.
PubMed: Analysis of annatto (Bixa orellana) food coloring formulations. 2. Determination of aromatic hydrocarbon thermal degradation products by gas chromatography.
PubMed: Effects of Singlet Oxygen Quenchers and pH on the Bacterially Induced Hypersensitive Reaction in Tobacco Suspension Cell Cultures.
PubMed: Cellular toxicity of elsinochrome phytotoxins produced by the pathogenic fungus, Elsinoë fawcettii causing citrus scab.
PubMed: Relative inhibition of lipid peroxidation, cyclooxygenase enzymes, and human tumor cell proliferation by natural food colors.
PubMed: Absence of carcinogenic and anticarcinogenic effects of annatto in the rat liver medium-term assay.
PubMed: Subacute toxicity assessment of annatto in rat.
PubMed: Novel method for the determination of added annatto colour in extruded corn snack products.
PubMed: Dietary supplementation with a natural carotenoid mixture decreases oxidative stress.
PubMed: Effect of natural food colorings on immunoglobulin production in vitro by rat spleen lymphocytes.
PubMed: Diverse carotenoids protect against chemically induced neoplastic transformation.
PubMed: [Determination of the pigmenting carotenoids in feeds and premixes for laying hens and broilers (author's transl)].
PubMed: Isolation and purification of RNA from tissues rich in polyphenols, polysaccharides, and pigments of annatto (Bixa orellana L.).
PubMed: Chitosan microspheres containing the natural urucum pigment.
PubMed: To dye or not to dye: biochemistry of annatto unveiled.
PubMed: FT-IR study of some seco- and apocarotenoids.
PubMed: Modified atmosphere packaged cheddar cheese shreds: influence of fluorescent light exposure and gas type on color and production of volatile compounds.
PubMed: In vitro antimutagenic and in vivo anticlastogenic effects of carotenoids and solvent extracts from fruits and vegetables rich in carotenoids.
PubMed: Retinoic acid and beta-carotene inhibit fibronectin synthesis and release by fibroblasts; antagonism to phorbol ester.
PubMed: Characterization of the principal colouring components of annatto using high performance liquid chromatography with photodiode-array detection.
PubMed: Carotenoids up-regulate connexin43 gene expression independent of their provitamin A or antioxidant properties.
PubMed: Carotenoids, tocopherols and thiols as biological singlet molecular oxygen quenchers.
PubMed: [Analysis of the seed Bixa orellana, L. (annatto) and the waste generated in the extraction of its pigments].
PubMed: Controlled release of metformin hydrochloride and repaglinide from sandwiched osmotic pump tablet.
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