beta-apo-8'-carotenal

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

CAS: 1107-26-2 C30 H40 O MW: 416.64800000

Identification

Namebeta-apo-8'-carotenal
IUPAC(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 Number1107-26-2
EINECS214-171-6
FDA UNIIV22N3E2U32
Molecular FormulaC30 H40 O
Molecular Weight416.64800000
MDL NumberMFCD00042626
Nikkaji NumberJ14.370G
Beilstein2064131
XlogP39.40 (est)

Regulatory

JECFA Food Additivebeta-Apo-8'-carotenal
GSFA Codexbeta-apo-8'-Carotenal (160e)
DG SANTE Food Additivesbeta-apo-8'-carotenal
FDA Mainterm (SATF)1107-26-2 ; BETA-APO-8'-CAROTENAL
FDA RegulationFDA PART 73 -- LISTING OF COLOR ADDITIVES EXEMPT FROM CERTIFICATION

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., refrigerate in tightly sealed containers. store under nitrogen.
air and light sensitive store protected from air and light.
Soluble in alcohol, slightly
Insoluble in water

No sensory data available

Safety Information

Preferred SDSView
European informationMost important hazard(s):
Oral/Parenteral Toxicityoral-mouse LD50 > 10000 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorycoloring agents
Recommendation for beta-apo-8'-carotenal usage levels up tonot for fragrance use.
Recommendation for beta-apo-8'-carotenal flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

egg yolk PMC marigold PMC orange peel orange pericarp spinach

Synonyms

c.i. 40820 8'-apo-beta- caroten-8'-al 8'apo-beta,psi- carotenal all-trans-beta-apo-8'- carotenal apo carotenal 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 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.