| 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
|
| ECHA EINECS - REACH Pre-Reg: | 208-810-8 |
| XlogP3-AA: | 7.20 (est) |
| Molecular Weight: | 380.48396000 |
| Formula: | C24 H28 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 powder (est) |
| Assay: | 15.00 to 100.00 %
|
| Food Chemicals Codex Listed: | No |
| Boiling Point: | 640.00 to 641.00 °C. @ 760.00 mm Hg (est)
|
| Flash Point: | 671.00 °F. TCC ( 355.10 °C. ) (est)
|
| logP (o/w): | 5.532 (est) |
| Soluble in: |
| | alkaline water | | | alcohol, slightly | | | water, 0.005225 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. |
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: |
intraperitoneal-mouse LD50 700 mg/kg Scientia Pharmaceutica. Vol. 47, Pg. 39, 1979.
|
| Dermal Toxicity: |
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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 (alkali-processed norbixin, acid precipitated) usage levels up to: | | | not for fragrance use.
|
| |
| Recommendation for annatto seed extract (alkali-processed norbixin, acid precipitated) 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 |
Safety and efficacy of cis-norbixin di-potassium salt (annatto F) for cats and dogs 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 |
| Cancer 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,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 F | | | bixa orellana seed extract (alkali-processed norbixin, acid precipitated) | | | c.i. 75120 (alkali-processed norbixin, acid precipitated) | | | ci 75120 (alkali-processed norbixin, acid precipitated) | | | natural orange 4 (alkali-processed norbixin, acid precipitated) |
Articles:
| Info: | EVALUATION OF CERTAIN FOOD ADDITIVES AND CONTAMINANTS |
| PubMed: | Gum arabic and Fe²⁺ synergistically improve the heat and acid stability of norbixin at pH 3.0-5.0. |
| PubMed: | Studies on interaction of norbixin with DNA: multispectroscopic and in silico analysis. |
| PubMed: | Short communication: norbixin and bixin partitioning in Cheddar cheese and whey. |
| 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: | Inhibition of cyclophosphamide-induced oxidative stress in rat brain by polar and non-polar extracts of Annatto (Bixa orellana) seeds. |
| PubMed: | Probing the binding between norbixin and dairy proteins by spectroscopy methods. |
| PubMed: | Effect of bixin and norbixin on the expression of cytochrome P450 in HepG2 cell line. |
| 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: | Prooxidant activity of norbixin in model of acute gastric ulcer induced by ethanol in rats. |
| PubMed: | Annatto prevents retinal degeneration induced by endoplasmic reticulum stress in vitro and in vivo. |
| PubMed: | Raman spectroscopic determination of norbixin and tartrazine in sugar. |
| PubMed: | Characteristics of activated carbon and carbon nanotubes as adsorbents to remove annatto (norbixin) in cheese whey. |
| PubMed: | Bixin and norbixin have opposite effects on glycemia, lipidemia, and oxidative stress in streptozotocin-induced diabetic rats. |
| PubMed: | Contact sensitizing potential of annatto extract and its two primary color components, cis-bixin and norbixin, in female BALB/c mice. |
| PubMed: | Bixin and norbixin protect against DNA-damage and alterations of redox status induced by methylmercury exposure in vivo. |
| 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: | Digestive stability and transport of norbixin, a 24-carbon carotenoid, across monolayers of Caco-2 cells. |
| PubMed: | Effect of temperature and concentration on benzoyl peroxide bleaching efficacy and benzoic acid levels in whey protein concentrate. |
| PubMed: | Toxicity of the hyperglycaemic-inducing extract of the annatto (Bixa orellana) in the dog. |
| PubMed: | Induction of liver monooxygenases by annatto and bixin in female rats. |
| PubMed: | Extraction of an hyperglycaemic principle from the annatto (Bixa orellana), a medicinal plant in the West Indies. |
| PubMed: | Decolorization of Cheddar cheese whey by activated carbon. |
| 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: | Time-of-flight secondary ion mass spectrometry and X-ray photoelectron spectroscopy analyses of Bixa orellana seeds. |
| PubMed: | Inhibitory effect of apocarotenoids on the activity of tyrosinase: Multi-spectroscopic and docking studies. |
| PubMed: | A synergistic effect of Cu(2+) and norbixin on DNA damage. |
| PubMed: | Bixin and norbixin in human plasma: determination and study of the absorption of a single dose of Annatto food color. |
| 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: | Cold enzymatic bleaching of fluid whey. |
| PubMed: | Determination of bixin and norbixin in meat using liquid chromatography and photodiode array detection. |
| PubMed: | [Detection of the annatto dye norbixin/bixin in cheese using derivative spectroscopy and high performance liquid chromatography (HPLC)]. |
| PubMed: | Alternative bleaching methods for Cheddar cheese whey. |
| 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: | 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: | The use of lactoperoxidase for the bleaching of fluid whey. |
| PubMed: | Effect of bleaching permeate from microfiltered skim milk on 80% serum protein concentrate. |
| PubMed: | Effect of temperature and bleaching agent on bleaching of liquid Cheddar whey. |
| PubMed: | The effect of microfiltration on color, flavor, and functionality of 80% whey protein concentrate. |
| PubMed: | Bixin activates PPARα and improves obesity-induced abnormalities of carbohydrate and lipid metabolism in mice. |
| PubMed: | Sensory and Functionality Differences of Whey Protein Isolate Bleached by Hydrogen or Benzoyl Peroxide. |
| PubMed: | Influence of bleaching on flavor of 34% whey protein concentrate and residual benzoic acid concentration in dried whey proteins. |
| PubMed: | Short communication: The influence of solids concentration and bleaching agent on bleaching efficacy and flavor of sweet whey powder. |
| PubMed: | Influence of storage, heat treatment, and solids composition on the bleaching of whey with hydrogen peroxide. |
| PubMed: | Development of carotenoid storage cells in Bixa orellana L. seed arils. |
| PubMed: | Characterizing endogenous and exogenous peroxidase activity for bleaching of fluid whey and retentate. |
| PubMed: | Evaluation of certain food additives and contaminants. |
| PubMed: | Determination of annatto in high-fat dairy products, margarine and hard candy by solvent extraction followed by high-performance liquid chromatography. |
| PubMed: | Next generation sequencing and de novo transcriptome analysis of Costus pictus D. Don, a non-model plant with potent anti-diabetic properties. |
| PubMed: | Bixin regulates mRNA expression involved in adipogenesis and enhances insulin sensitivity in 3T3-L1 adipocytes through PPARgamma activation. |
| PubMed: | Bioautography and chemical characterization of antimicrobial compound(s) in commercial water-soluble annatto extracts. |
| PubMed: | The effect of starter culture and annatto on the flavor and functionality of whey protein concentrate. |
| PubMed: | Effect of bleaching whey on sensory and functional properties of 80% whey protein concentrate. |
| PubMed: | Method development and analysis of retail foods for annatto food colouring material. |
| PubMed: | The effect of bleaching agent on the flavor of liquid whey and whey protein concentrate. |
| PubMed: | Carotenoids and β-cyclodextrin inclusion complexes: Raman spectroscopy and theoretical investigation. |
| PubMed: | In vitro scavenging capacity of annatto seed extracts against reactive oxygen and nitrogen species. |
| PubMed: | Neuron-glial cell communication in the traumatic stress-induced immunomodulation. |
| PubMed: | Effect of natural pigments on the oxidative stability of sausages stored under refrigeration. |
| PubMed: | Evaluation of the clastogenicity and anticlastogenicity of the carotenoid bixin in human lymphocyte cultures. |
| PubMed: | Novel method for the determination of added annatto colour in extruded corn snack products. |
| PubMed: | Annatto constituent cis-bixin has selective antimyeloma effects mediated by oxidative stress and associated with inhibition of thioredoxin and thioredoxin reductase. |
| PubMed: | Invited review: Annatto usage and bleaching in dairy foods. |
| PubMed: | Reactive oxygen species mediate lethality induced by far-UV in Escherichia coli cells. |
| PubMed: | Biosynthesis of the food and cosmetic plant pigment bixin (annatto). |
| PubMed: | Analysis of annatto (Bixa orellana) food coloring formulations. 2. Determination of aromatic hydrocarbon thermal degradation products by gas chromatography. |
| PubMed: | Characterization of the principal colouring components of annatto using high performance liquid chromatography with photodiode-array detection. |
| PubMed: | Partial replacement of nitrite by annatto as a colour additive in sausage. |
| PubMed: | Structural analysis of the synaptic protein neuroligin and its beta-neurexin complex: determinants for folding and cell adhesion. |
| PubMed: | Chitosan microspheres containing the natural urucum pigment. |
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