| 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: | 6983-79-5 | 3D/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
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Appearance: | dark red-brown to red-purple oily liquid (est) |
| Assay: | 10.00 to 100.00 %
|
| Food Chemicals Codex Listed: | No |
| Melting Point: | 198.00 °C. @ 760.00 mm Hg
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| Boiling Point: | 596.02 °C. @ 760.00 mm Hg (est)
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| 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 |
Organoleptic Properties:
| |
| Odor and/or flavor descriptions from others (if found). |
| |
| |
Cosmetic Information:
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. |
| Rung International |
| Annatto Oil Soluble ( 1.5% Bixin )
|
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
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| Dermal Toxicity: |
|
Not determined
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| Inhalation Toxicity: |
|
Not determined
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Safety in Use Information:
| Category: | coloring agents |
| Recommendation for annatto seed extract (oil-processed bixin) usage levels up to: | | | not for fragrance use.
|
| |
| Recommendation for annatto seed extract (oil-processed bixin) flavor usage levels up to: |
| | not for flavor use.
|
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 |
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 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| | annatto D | | | bixa orellana seed extract (oil-processed bixin) | | | c.i. 75120 (oil-processed bixin) | | | ci 75120 (oil-processed bixin) | | | natural orange 4 (oil-processed bixin) |
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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