| 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 |  
| FDA UNII:  | Search |  
| XlogP3-AA: | 7.20 (est) |  
| Molecular Weight: | 380.48396000 |  
| Formula: | C24 H28 O4 |  
| BioActivity Summary: | listing |  
| NMR Predictor: | Predict (works with chrome, Edge 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: |  85.00 to 100.00 
 |  
| Food Chemicals Codex Listed:  | No |  
| Boiling Point: |  640.37 °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) |  
 
  
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 Nor Bixin Powder ( 1.5% Nor - 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
 |  
| Dermal Toxicity:  |  
| 
Not determined
 |  
| Inhalation Toxicity:  |  
| 
Not determined
 |  
 
  
Safety in Use Information: 
| Category:  |  | coloring agents |  
| Recommendation for annatto seed extract (solvent-extracted norbixin) usage levels up to:  |  |   | not for fragrance use.
 |  
|   |  
| Recommendation for annatto seed extract (solvent-extracted norbixin) 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 |  
| AIDS Citations:Search |  
| 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 C |  |   | bixa orellana seed extract (solvent-extracted norbixin) |  |   | c.i. 75120 (solvent-extracted norbixin) |  |   | ci 75120 (solvent-extracted norbixin) |  |   | natural orange 4 (solvent-extracted norbixin) |  
 
  
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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