EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

beta-apo-8'-carotenal
all-trans-beta-apo-8'-carotenal

Supplier Sponsors

Name:(2E,4E,6E,8E,10E,12E,14E,16E)-2,6,11,15-tetramethyl-17-(2,6,6-trimethylcyclohexen-1-yl)heptadeca-2,4,6,8,10,12,14,16-octaenal
CAS Number: 1107-26-2Picture of molecule3D/inchi
Other(deleted CASRN):2756-57-2
ECHA EINECS - REACH Pre-Reg:214-171-6
FDA UNII:V22N3E2U32
Nikkaji Web:J14.370G
Beilstein Number:2064131
MDL:MFCD00042626
XlogP3:9.40 (est)
Molecular Weight:416.64800000
Formula:C30 H40 O
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome or firefox)
Category:coloring agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
JECFA Food Additive: beta-Apo-8'-carotenal
GSFA Codex: beta-apo-8'-Carotenal (160e)
DG SANTE Food Additives:beta-apo-8'-carotenal
FDA Mainterm (SATF):1107-26-2 ; BETA-APO-8'-CAROTENAL
FDA Regulation:
FDA PART 73 -- LISTING OF COLOR ADDITIVES EXEMPT FROM CERTIFICATION
Subpart A--Foods
Sec. 73.90 [beta]-Apo-8'-carotenal.
 
Physical Properties:
Appearance:deep violet crystalline powder (est)
Assay: 96.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 575.00 to 576.00 °C. @ 760.00 mm Hg
Flash Point: 524.00 °F. TCC ( 273.33 °C. )
logP (o/w): 9.652 (est)
Shelf Life: 12.00 month(s) or longer if stored properly.
Storage:store under nitrogen.
Storage:refrigerate in tightly sealed containers. store under nitrogen.
air and light sensitive:store protected from air and light.
Soluble in:
 alcohol, slightly
 chloroform
 water, 2.17e-007 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Apocarotenal ≥95%
Odor: characteristic
Use: Apocarotenal is a carotenoid found in spinach and citrus fruits and plays a role as a precursor of vitamin A, which is formed f
DSM Nutritional
Apocarotenal
ExtraSynthese
For experimental / research use only.
apoCarotenal
Santa Cruz Biotechnology
For experimental / research use only.
trans-β-Apo-8'-Carotenal ≥96.0%
Sigma-Aldrich: Sigma
For experimental / research use only.
trans-β-Apo-8'-carotenal ≥96.0% (UV)
 
Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
None - None found.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
 
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:
oral-mouse LD50 > 10000 mg/kg
FAO Nutrition Meetings Report Series. Vol. 38B, Pg. 34, 1966.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
coloring agents
Recommendation for beta-apo-8'-carotenal usage levels up to:
 not for fragrance use.
 
Recommendation for beta-apo-8'-carotenal flavor usage levels up to:
 not for flavor use.
 
Safety References:
European Food Safety Authority (EFSA) reference(s):

Scientific Opinion on the re-evaluation of -apo-8-carotenal (E 160e) as a food additive
View page or View pdf

Request for a reconsideration of the ADI and a refined exposure assessment of -apo-8'-carotenal (E 160e)
View page or View pdf

EPI System: View
Chemical Carcinogenesis Research Information System:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):1107-26-2
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5478003
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
(2E,4E,6E,8E,10E,12E,14E,16E)-2,6,11,15-tetramethyl-17-(2,6,6-trimethylcyclohexen-1-yl)heptadeca-2,4,6,8,10,12,14,16-octaenal
Chemidplus:0001107262
RTECS:CD9115000 for cas# 1107-26-2
 
References:
 (2E,4E,6E,8E,10E,12E,14E,16E)-2,6,11,15-tetramethyl-17-(2,6,6-trimethylcyclohexen-1-yl)heptadeca-2,4,6,8,10,12,14,16-octaenal
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:1107-26-2
Pubchem (cid):5478003
Pubchem (sid):135017019
 
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 Substances Added to Food (formerly EAFUS):View
CHEBI:View
KEGG (GenomeNet):C19728
HMDB (The Human Metabolome Database):HMDB36886
FooDB:FDB015844
FDA Listing of Food Additive Status:View
FDA Color Additive Status ListView
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
FAO:-apo-8'-CAROTENAL
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 egg yolk
Search PMC Picture
 marigold
Search PMC Picture
 orange peel
Search Trop Picture
 orange pericarp
Search Trop Picture
 spinach
Search Trop Picture
 
Synonyms:
 c.i. 40820
8'-apo-beta-caroten-8'-al
8'apo-beta,psi-carotenal
all-trans-beta-apo-8'-carotenal
apocarotenal
apo-beta,psi-carotenal, 8'
 ci 40820
 food orange 6
(2E,4E,6E,8E,10E,12E,14E,16E)-2,6,11,15-tetramethyl-17-(2,6,6-trimethylcyclohexen-1-yl)heptadeca-2,4,6,8,10,12,14,16-octaenal
 

Articles:

PubMed:Novel carotenoid cleavage dioxygenase catalyzes the first dedicated step in saffron crocin biosynthesis.
PubMed:Tackling the challenge of selective analytical clean-up of complex natural extracts: the curious case of chlorophyll removal.
PubMed:Dynamics of the time-resolved stimulated Raman scattering spectrum in presence of transient vibronic inversion of population on the example of optically excited trans-β-apo-8'-carotenal.
PubMed:Analysis of carotenoid isomerase activity in a prototypical carotenoid cleavage enzyme, apocarotenoid oxygenase (ACO).
PubMed:Substrate specificity of purified recombinant human β-carotene 15,15'-oxygenase (BCO1).
PubMed:Determination of egg yolk xanthophylls by isocratic high-performance liquid chromatography.
PubMed:A novel carotenoid cleavage activity involved in the biosynthesis of Citrus fruit-specific apocarotenoid pigments.
PubMed:Acyclic carotenoid and cyclic apocarotenoid cleavage by an orthologue of lignostilbene-α,β-dioxygenase in Rhodopseudomonas palustris.
PubMed:Structural basis of carotenoid cleavage: from bacteria to mammals.
PubMed:The ORF slr0091 of Synechocystis sp. PCC6803 encodes a high-light induced aldehyde dehydrogenase converting apocarotenals and alkanals.
PubMed:New insight into the cleavage reaction of Nostoc sp. strain PCC 7120 carotenoid cleavage dioxygenase in natural and nonnatural carotenoids.
PubMed:Microcapsules containing antioxidant molecules as scavengers of reactive oxygen and nitrogen species.
PubMed:The formation, occurrence, and function of β-apocarotenoids: β-carotene metabolites that may modulate nuclear receptor signaling.
PubMed:In vivo and in vitro studies on the carotenoid cleavage oxygenases from Sphingopyxis alaskensis RB2256 and Plesiocystis pacifica SIR-1 revealed their substrate specificities and non-retinal-forming cleavage activities.
PubMed:Characterization of an apo-carotenoid 13,14-dioxygenase from Novosphingobium aromaticivorans that converts β-apo-8'-carotenal to β-apo-13-carotenone.
PubMed:Separation and quantification of 15 carotenoids by reversed phase high performance liquid chromatography coupled to diode array detection with isosbestic wavelength approach.
PubMed:Application of centrifugal precipitation chromatography and high-speed counter-current chromatography equipped with a spiral tubing support rotor for the isolation and partial characterization of carotenoid cleavage-like enzymes in Enteromorpha compressa (L.) Nees.
PubMed:Dietary 9-cis-β,β-carotene fails to rescue vision in mouse models of leber congenital amaurosis.
PubMed:Carotenoid composition in Rhinacanthus nasutus (L.) Kurz as determined by HPLC-MS and affected by freeze-drying and hot-air-drying.
PubMed:Beta-carotene reduces body adiposity of mice via BCMO1.
PubMed:Carotene and novel apocarotenoid concentrations in orange-fleshed Cucumis melo melons: determinations of β-carotene bioaccessibility and bioavailability.
PubMed:Antioxidant activity of β-carotene compounds in different in vitro assays.
PubMed:Contribution of major lipophilic antioxidants to the antioxidant activity of basil extracts: an EPR study.
PubMed:Evaluation of certain food additives and contaminants.
PubMed:{beta}-Apocarotenoids do not significantly activate retinoic acid receptors {alpha} or {beta}.
PubMed:Hydrophobicity of residue 108 specifically affects the affinity of human beta-carotene 15,15'-monooxygenase for substrates with two ionone rings.
PubMed:Qualitative and quantitative differences in the carotenoid composition of yellow and red peppers determined by HPLC-DAD-MS.
PubMed:Cloning and functional characterization of carotenoid cleavage dioxygenase 4 genes.
PubMed:Total synthesis of (3R,3'R,6'R)-lutein and its stereoisomers.
PubMed:Excited-state dynamics of 12'-apo-beta-caroten-12'-al and 8'-apo-beta-caroten-8'-al in supercritical CO2, N2O, and CF3H.
PubMed:In vitro characterization of a recombinant Blh protein from an uncultured marine bacterium as a beta-carotene 15,15'-dioxygenase.
PubMed:Substrate specificity of a recombinant chicken beta-carotene 15,15'-monooxygenase that converts beta-carotene into retinal.
PubMed:Functional characterization of FaCCD1: a carotenoid cleavage dioxygenase from strawberry involved in lutein degradation during fruit ripening.
PubMed:Effect of Leu/Met variation at residue 450 on isomerase activity and protein expression of RPE65 and its modulation by variation at other residues.
PubMed:Activity of a cationic carotenoid derivative in a mouse model of protoporphyria.
PubMed:Excentral cleavage of beta-carotene in vivo in a healthy man.
PubMed:Influence of solubility-enhancing fusion proteins and organic solvents on the in vitro biocatalytic performance of the carotenoid cleavage dioxygenase AtCCD1 in a micellar reaction system.
PubMed:Retinal biosynthesis in fungi: characterization of the carotenoid oxygenase CarX from Fusarium fujikuroi.
PubMed:Studies of carotenoid one-electron reduction radicals.
PubMed:Beta-carotene and apocarotenals promote retinoid signaling in BEAS-2B human bronchioepithelial cells.
PubMed:Effects of quercetin on beta-apo-8'-carotenal-induced DNA damage and cytochrome P1A2 expression in A549 cells.
PubMed:Carotenoid radical anions and their protonated derivatives.
PubMed:Identification of carotenoid cleavage dioxygenases from Nostoc sp. PCC 7120 with different cleavage activities.
PubMed:The carotenase AtCCD1 from Arabidopsis thaliana is a dioxygenase.
PubMed:Synthetic carotenoid derivatives prevent photosensitised killing of retinal pigment epithelial cells more effectively than lutein.
PubMed:Improved high performance liquid chromatographic method for determination of carotenoids in the microalga Chlorella pyrenoidosa.
PubMed:Key role of conserved histidines in recombinant mouse beta-carotene 15,15'-monooxygenase-1 activity.
PubMed:Electrospray tandem mass spectrometric analysis of zeaxanthin and its oxidation products.
PubMed:Retinal biosynthesis in Eubacteria: in vitro characterization of a novel carotenoid oxygenase from Synechocystis sp. PCC 6803.
PubMed:Structural requirements for efficient cellular photoprotection by carotenoid derivatives.
PubMed:Induction of 1,N(2)-etheno-2'-deoxyguanosine in DNA exposed to beta-carotene oxidation products.
PubMed:Method development and analysis of retail foods and beverages for carotenoid food colouring materials E160a(ii) and E160e.
PubMed:Induction of liver monooxygenases by annatto and bixin in female rats.
PubMed:Feedback regulation of beta,beta-carotene 15,15'-monooxygenase by retinoic acid in rats and chickens.
PubMed:[Initial stages of trisporic acid synthesis in Blakeslea trispora].
PubMed:FT-IR study of some seco- and apocarotenoids.
PubMed:Quantitative determination of 13C-labeled and endogenous beta-carotene, lutein, and vitamin A in human plasma.
PubMed:Girard's reagent P derivative of beta-Apo-8'-carotenal: a potent photoprotective agent.
PubMed:beta-carotene is converted primarily to retinoids in rats in vivo.
PubMed:Co-oxidation of beta-carotene catalyzed by soybean and recombinant pea lipoxygenases.
PubMed:Isolation of 9Z beta-carotene from Dunaliella bardawil and its stereoselective synthesis.
PubMed:Dietary carotenoids inhibit aflatoxin B1-induced liver preneoplastic foci and DNA damage in the rat: role of the modulation of aflatoxin B1 metabolism.
PubMed:The influence of two carotenoid food dyes on clastogenic activities of cyclophosphamide and dioxidine in mice.
PubMed:Relative stability of carotenoid radical cations and homologue tocopheroxyl radicals. A real time kinetic study of antioxidant hierarchy.
PubMed:Ah receptor-dependent CYP1A induction by two carotenoids, canthaxanthin and beta-apo-8'-carotenal, with no affinity for the TCDD binding site.
PubMed:Enzymatic oxidation of beta-apo-8'-carotenol to beta-apo-14'-carotenal by an enzyme different from beta-carotene-15,15'-dioxygenase.
PubMed:Modulation of aflatoxin B1 carcinogenicity, genotoxicity and metabolism in rat liver by dietary carotenoids: evidence for a protective effect of CYP1A inducers.
PubMed:Effects of provitamin A or non-provitamin A carotenoids on liver xenobiotic-metabolizing enzymes in mice.
PubMed:Carotenoid analysis of several dark-green leafy vegetables associated with a lower risk of cancers.
PubMed:Rat intestinal beta-carotene dioxygenase activity is located primarily in the cytosol of mature jejunal enterocytes.
PubMed:beta-Apo-8'-carotenal, but not beta-carotene, is a strong inducer of liver cytochromes P4501A1 and 1A2 in rat.
PubMed:Detection of bixin, lycopene, canthaxanthin, and beta-apo-8'-carotenal in products derived from red pepper.
PubMed:Isolation and identification of singlet oxygen oxidation products of beta-carotene.
PubMed:Dietary carotenoids influenced biochemical but not morphological changes in adult male rats fed a choline-deficient diet.
PubMed:Metabolism of carotenoid analogs in humans.
PubMed:Carotenoids as cellular antioxidants.
PubMed:Retinoic acid can be produced from excentric cleavage of beta-carotene in human intestinal mucosa.
PubMed:Enzymatic conversion of beta-carotene into beta-apo-carotenals and retinoids by human, monkey, ferret, and rat tissues.
PubMed:Characterization of products formed during the autoxidation of beta-carotene.
PubMed:[Effect of carotenoids on selected indicators of cellular immunity in cockerels receiving food with high level of vitamin A].
PubMed:Localization of chicken parathyroid glands through vital staining.
PubMed:Retinoids and related compounds. XI. Synthesis and stereochemistry of (+/-)-C22-acetylenic and allenic apocarotenals.
PubMed:[Detection of the annatto dye norbixin/bixin in cheese using derivative spectroscopy and high performance liquid chromatography (HPLC)].
PubMed:The polarized UV-absorption spectra and the crystal structure of two different monoclinic crystal forms of the retinal homologue beta-8'-apocarotenal.
PubMed:Peroral challenge tests with food additives in urticaria and atopic dermatitis.
PubMed:Relative value of carotenoids as precursors of vitamin A.
PubMed:Carotenoids as food colorants.
PubMed:Charge-transfer complexes of some linear conjugated polyenes.
PubMed:Studies on the relative biopotencies and intestinal absorption of different apo-beta-carotenoids in rats and chickens.
 
Notes:
Constit. of orange peel, spinach, marigolds and egg yolks. Colour additive
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