annatto seed extract (alkali-processed norbixin, acid precipitated)
annatto F
 
Notes:
an annatto compound; 9-cis-norbixin is alpha-norbixin.
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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: 542-40-5Picture of molecule3D/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:
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 FDA/DG SANTE Petitions, Reviews, Notices:
EU SANCO Annatto, Bixin, Norbixin View - review
JECFA Food Additive: Annatto Extract (Alkali-Processed Norbixin, Acid Precipitated)
GSFA Codex: Annatto extracts, norbixin-based (160b(ii))
DG SANTE Food Additives: annatto F
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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
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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:
intraperitoneal-mouse LD50  700 mg/kg
Scientia Pharmaceutica. Vol. 47, Pg. 39, 1979.

Dermal Toxicity:
Not determined
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.
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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
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
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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
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 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)
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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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