| Name: | (2E,4E,6E,8E,10E,12E,14E,16E,18E)-19-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-1-[(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]-4,8,13,17-tetramethylnonad |
| CAS Number: | 465-42-9 |  3D/inchi
|
| Other(deleted CASRN): | 113359-44-7 |
| ECHA EINECS - REACH Pre-Reg: | 207-364-1 |
| FDA UNII: | 420NY1J57N |
| Nikkaji Web: | J5.891B |
| Beilstein Number: | 2493991 |
| MDL: | MFCD03423725 |
| XlogP3-AA: | 10.60 (est) |
| Molecular Weight: | 584.88392000 |
| Formula: | C40 H56 O3 |
| 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: | deep red needles (est) |
| Assay: | 95.00 to 100.00
|
| Food Chemicals Codex Listed: | No |
| Boiling Point: | 726.00 to 727.00 °C. @ 760.00 mm Hg (est)
|
| Flash Point: | 765.00 °F. TCC ( 407.20 °C. ) (est)
|
| logP (o/w): | 9.467 (est) |
| Soluble in: |
| | water, 1.113e-009 mg/L @ 25 °C (est) |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
Safety Information:
| Preferred SDS: View |
| |
| 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
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| Dermal Toxicity: |
|
Not determined
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| Inhalation Toxicity: |
|
Not determined
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Safety in Use Information:
| Category: | | coloring agents |
| Recommendation for capsanthin usage levels up to: | | | not for fragrance use.
|
| |
| Recommendation for capsanthin 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 paprika extract (E 160c) as a food additive
View page or View pdf
|
Outcome of the consultation with Member States and EFSA on the basic substance application for paprika extract, capsanthin, capsorubin E 160 c (admissibility accepted when named Capsicum spp. spice) for use in plant protection as repellent to various invertebrates, mammals and birds
View page or View pdf
|
| EPI System: View |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :5281228 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| (2E,4E,6E,8E,10E,12E,14E,16E,18E)-19-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-1-[(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]-4,8,13,17-tetramethylnonad |
| Chemidplus:0000465429 |
References:
| | (2E,4E,6E,8E,10E,12E,14E,16E,18E)-19-[(4R)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-1-[(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]-4,8,13,17-tetramethylnonad |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 5281228 |
| Pubchem (sid): | 135228485 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| (3R,3'S,5'R)-3,3'- | dihydroxy-beta,kappa-caroten-6'-one | | 3,3'- | dihydroxy-beta,kappa-caroten-6'one | | (2E,4E,6E,8E,10E,12E,14E,16E,18E)-19-[(4R)-4- | hydroxy-2,6,6-trimethylcyclohexen-1-yl]-1-[(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]-4,8,13,17-tetramethylnonad |
Articles:
| PubMed:Cross-linking of soybean protein isolate-chitosan coacervate with transglutaminase utilizing capsanthin as the model core. |
| PubMed:[Spectral characterization for capsanthin molecule with in vitro oxidative defense reaction]. |
| PubMed:Alteration of flower color in Iris germanica L. 'Fire Bride' through ectopic expression of phytoene synthase gene (crtB) from Pantoea agglomerans. |
| PubMed:The bioefficacy of microemulsified natural pigments in egg yolk pigmentation. |
| PubMed:Fluorescent nanomicelles for selective detection of Sudan dye in Pluronic F127 aqueous media. |
| PubMed:De novo transcriptome analysis of Liriodendron chinense petals and leaves by Illumina sequencing. |
| PubMed:Antioxidant activity and content of chlorophylls and carotenoids in raw and heat-processed Jalapeño peppers at intermediate stages of ripening. |
| PubMed:Determination of egg yolk xanthophylls by isocratic high-performance liquid chromatography. |
| PubMed:Assessment of free radicals scavenging activity of seven natural pigments and protective effects in AAPH-challenged chicken erythrocytes. |
| PubMed:Biochemistry and molecular biology of carotenoid biosynthesis in chili peppers (Capsicum spp.). |
| PubMed:Paprika Pigments Attenuate Obesity-Induced Inflammation in 3T3-L1 Adipocytes. |
| PubMed:The effect of domestic processing on the content and bioaccessibility of carotenoids from chili peppers (Capsicum species). |
| PubMed:In vitro investigation of the bioaccessibility of carotenoids from raw, frozen and boiled red chili peppers (Capsicum annuum). |
| PubMed:Simultaneous determination of free capsorubin and capsanthin in red pepper powder using u-HPLC. |
| PubMed:Lower photostability of capsanthin dispersed in an aqueous solution. |
| PubMed:Characterization of 12 Capsicum varieties by evaluation of their carotenoid profile and pungency determination. |
| PubMed:[Potency of carotenoids found in vegetables and fruits]. |
| PubMed:A further analysis of the relationship between yellow ripe-fruit color and the capsanthin-capsorubin synthase gene in pepper (Capsicum sp.) indicated a new mutant variant in C. annuum and a tandem repeat structure in promoter region. |
| PubMed:Proteomic analysis of chromoplasts from six crop species reveals insights into chromoplast function and development. |
| PubMed:Effect of heat processing on the profile of pigments and antioxidant capacity of green and red jalapeño peppers. |
| PubMed:Cloning and functional characterization of a gene for capsanthin-capsorubin synthase from tiger lily (Lilium lancifolium Thunb. 'Splendens'). |
| PubMed:Separation and quantification of 15 carotenoids by reversed phase high performance liquid chromatography coupled to diode array detection with isosbestic wavelength approach. |
| PubMed:Analysis of native carotenoid composition of sweet bell peppers by serially coupled C30 columns. |
| PubMed:Putative supramolecular complexes formed by carotenoids and xanthophylls with ascorbic acid to reverse multidrug resistance in cancer cells. |
| PubMed:Influence of different drying methods on carotenoids and capsaicinoids of paprika (Cv., Jalapeno). |
| PubMed:Carotenoid accumulation in orange-pigmented Capsicum annuum fruit, regulated at multiple levels. |
| PubMed:Nitrocapsanthin and nitrofucoxanthin, respective products of capsanthin and fucoxanthin reaction with peroxynitrite. |
| PubMed:Carotenoids inhibit proliferation and regulate expression of peroxisome proliferators-activated receptor gamma (PPARγ) in K562 cancer cells. |
| PubMed:Phytochemicals and antioxidant activity of fruits and leaves of paprika (Capsicum Annuum L., var. special) cultivated in Korea. |
| PubMed:Carotenoid composition and vitamin A value in ají (Capsicum baccatum L.) and rocoto (C. pubescens R. & P.), 2 pepper species from the Andean region. |
| PubMed:Recent advances in the study on capsaicinoids and capsinoids. |
| PubMed:Effect of Capsicum carotenoids on growth and aflatoxins production by Aspergillus flavus isolated from paprika and chilli. |
| PubMed:Effect of Capsicum carotenoids on growth and ochratoxin A production by chilli and paprika Aspergillus spp. isolates. |
| PubMed:Purified canola lutein selectively inhibits specific isoforms of mammalian DNA polymerases and reduces inflammatory response. |
| PubMed:Reversal of multidrug resitance by natural substances from plants. |
| PubMed:Variability of Carotenoid Biosynthesis in Orange Colored Capsicum spp. |
| PubMed:Characterization of plant carotenoid cyclases as members of the flavoprotein family functioning with no net redox change. |
| PubMed:Production of single cell protein using waste capsicum powder produced during capsanthin extraction. |
| PubMed:Qualitative and quantitative differences in the carotenoid composition of yellow and red peppers determined by HPLC-DAD-MS. |
| PubMed:Dietary capsanthin, the main carotenoid in paprika (Capsicum annuum), alters plasma high-density lipoprotein-cholesterol levels and hepatic gene expression in rats. |
| PubMed:Carotenoid synthesis: retrospect and recent progress. |
| PubMed:Research of the (E/Z)-isomerization of carotenoids in Pécs since the 1970s. |
| PubMed:Total synthesis of cucurbitaxanthin A, cycloviolaxanthin and capsanthin 3,6-epoxide by applying a regioselective ring opening of tetrasubstituted epoxides. |
| PubMed:Reversal of multidrug resistance by synthetic and natural compounds in drug-resistant MCF-7 cell lines. |
| PubMed:A density functional theory study of the structure and vibrational spectra of beta-carotene, capsanthin, and capsorubin. |
| PubMed:Qualitative and quantitative analysis of genetically modified pepper. |
| PubMed:Antioxidant activities of different colored sweet bell peppers (Capsicum annuum L.). |
| PubMed:Total synthesis of capsanthin and capsorubin using Lewis acid-promoted regio- and stereoselective rearrangement of tetrasubsutituted epoxides. |
| PubMed:A comparison of the carotenoid accumulation in Capsicum varieties that show different ripening colours: deletion of the capsanthin-capsorubin synthase gene is not a prerequisite for the formation of a yellow pepper. |
| PubMed:Proteome analysis of bell pepper (Capsicum annuum L.) chromoplasts. |
| PubMed:Identification of carotenoids in ovarian tissue in women. |
| PubMed:Biological activity of carotenoids in red paprika, Valencia orange and Golden delicious apple. |
| PubMed:Characterization of carotenoids and carotenoid esters in red pepper pods (Capsicum annuum L.) by high-performance liquid chromatography/atmospheric pressure chemical ionization mass spectrometry. |
| PubMed:Changes in carotenoid content and distribution in living plant tissue can be observed and mapped in situ using NIR-FT-Raman spectroscopy. |
| PubMed:Thermal degradation products formed from carotenoids during a heat-induced degradation process of paprika oleoresins (Capsicum annuum L.). |
| PubMed:[Effects of the dietary incorporation of carotenoid pigments on gonad development and oocyte maturity in females of rainbow trout (Oncorhynchus mykiss, Walbaum, 1972)]. |
| PubMed:Modulation of multidrug resistance and apoptosis of cancer cells by selected carotenoids. |
| PubMed:[Inhibition of oxidation of human blood low density lipoproteins by carotenoids from paprika]. |
| PubMed:Influences of gamma-irradiation and storage on the carotenoids of sun-dried and dehydrated paprika. |
| PubMed:Incorporation of carotenoids from paprika oleoresin into human chylomicrons. |
| PubMed:Quantification of carotenoids in chicken plasma after feeding free or esterified lutein and capsanthin using high-performance liquid chromatography and liquid chromatography-mass spectrometry analysis. |
| PubMed:Carotenoids in cancer chemoprevention. |
| PubMed:[Molecular cloning of full length capsanthin/capsorubin synthase homologous gene from orange (Citrus sinensis)]. |
| PubMed:Effect of ascorbic acid on the stability of beta-carotene and capsanthin in paprika (Capsicum annuum) powder. |
| PubMed:Carotenol fatty acid esters: easy substrates for digestive enzymes? |
| PubMed:The supramolecular structure of self-assembly formed by capsanthin derivatives. |
| PubMed:Growth inhibitory effect of paradicsompaprika in cancer cell lines. |
| PubMed:Degradation of non-esterified and esterified xanthophylls by free radicals. |
| PubMed:Total synthesis of capsanthin using lewis acid-promoted regio- and stereoselective rearrangement of tetrasubstituted epoxide. |
| PubMed:Supramolecular assemblies of carotenoids. |
| PubMed:Structure-reactivity relationship in the oxidation of carotenoid pigments of the pepper (Capsicum annuum L.). |
| PubMed:(9Z)-capsanthin-5,6-epoxide, a new carotenoid from the fruits of Asparagus falcatus. |
| PubMed:Cancer chemopreventive activity of carotenoids in the fruits of red paprika Capsicum annuum L. |
| PubMed:Capsanthone 3,6-epoxide, a new carotenoid from the fruits of the red paprika Capsicum annuum L. |
| PubMed:Isolation of a series of apocarotenoids from the fruits of the red paprika Capsicum annuum L. |
| PubMed:Carotenoid composition in the fruits of red paprika (Capsicum annuum var. lycopersiciforme rubrum) during ripening; biosynthesis of carotenoids in red paprika. |
| PubMed:Enzymatic hydrolysis of carotenoid fatty acid esters of red pepper (Capsicum annuum L.) by a lipase from Candida rugosa. |
| PubMed:Molecular evolution of lycopene cyclases involved in the formation of carotenoids with ionone end groups. |
| PubMed:Identification of a novel gene coding for neoxanthin synthase from Solanum tuberosum. |
| PubMed:Carotenoid composition in the fruits of Asparagus officinalis. |
| PubMed:Identification of neoxanthin synthase as a carotenoid cyclase paralog. |
| PubMed:Candidate gene analysis of organ pigmentation loci in the Solanaceae. |
| PubMed:An alternative pathway to beta -carotene formation in plant chromoplasts discovered by map-based cloning of beta and old-gold color mutations in tomato. |
| PubMed:Carotenoid biosynthesis changes in five red pepper (Capsicum annuum L.) cultivars during ripening. Cultivar selection for breeding. |
| PubMed:Carotenoids in human blood plasma after ingesting paprika juice. |
| PubMed:Xanthophyll esterification accompanying carotenoid overaccumulation in chromoplast of Capsicum annuum ripening fruits is a constitutive process and useful for ripeness index. |
| PubMed:Prevention of N-methylnitrosourea-induced colon carcinogenesis in rats by oxygenated carotenoid capsanthin and capsanthin-rich paprika juice. |
| PubMed:Paprika (Capsicum annuum) oleoresin extraction with supercritical carbon dioxide. |
| PubMed:Amelioratory effect of dietary ingestion with red bell pepper on learning impairment in senescence-accelerated mice (SAMP8). |
| PubMed:Induction and control of chromoplast-specific carotenoid genes by oxidative stress. |
| PubMed:Functional integration of non-native carotenoids into chloroplasts by viral-derived expression of capsanthin-capsorubin synthase in Nicotiana benthamiana. |
| PubMed:The capsanthin-capsorubin synthase gene: a candidate gene for the y locus controlling the red fruit colour in pepper. |
| PubMed:Molecular analysis of carotenoid cyclase inhibition. |
| PubMed:Accumulation and clearance of capsanthin in blood plasma after the ingestion of paprika juice in men. |
| PubMed:Isocratic non-aqueous reversed-phase high-performance liquid chromatographic separation of capsanthin and capsorubin in red peppers (Capsicum annuum L.), paprika and oleoresin. |
| PubMed:Chemoprevention of lung and skin cancer by Beta vulgaris (beet) root extract. |
| PubMed:Metabolism of cyclic carotenoids: a model for the alteration of this biosynthetic pathway in Capsicum annuum chromoplasts. |
| PubMed:Identification of a plastid protein involved in vesicle fusion and/or membrane protein translocation. |
| PubMed:Structure of a functional geranylgeranyl pyrophosphate synthase gene from Capsicum annuum. |
| PubMed:A chromoplast-specific protein in Capsicum annuum: characterization and expression of the corresponding gene. |
| PubMed:Xanthophyll biosynthesis in chromoplasts: isolation and molecular cloning of an enzyme catalyzing the conversion of 5,6-epoxycarotenoid into ketocarotenoid. |
| PubMed:Structure and expression of two plant genes encoding chromoplast-specific proteins: occurrence of partially spliced transcripts. |
| PubMed:Separation and quantitative analysis of some carotenoid fatty acid esters of fruits by liquid chromatography. |
| PubMed:Capsicum--production, technology, chemistry, and quality. Part III. Chemistry of the color, aroma, and pungency stimuli. |
| PubMed:Gastric cytoprotective effects of vitamin A and other carotenoids. |
| PubMed:Carotenoid biosynthesis. In vitro conversion of antheraxanthin to capsanthin by a chromoplast enriched fraction of capsicum fruits. |
| PubMed:Carotenoid metabolism during chloroplast to chromoplast transformation in Capsicum annuum fruit. |
| PubMed:A study on the toxicity of natural food dyes--toxicity and enzyme inhibition in Paramecium caudatum. |
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carotenoid pigment with cyclopentane rings instead of cyclohexenes; isolated form paprika & pimientos; biosynthesized from violaxanthin. Constit. of paprika (Capsicum annuum) and asparagus (Asparagus officinalis). Potential nutriceutical
Paprika oleoresin (also known as paprika extract) is an oil soluble extract from the fruits of Capsicum Annum Linn or Capsicum Frutescens(Indian red chillies), and is primarily used as a colouring and/or flavouring in food products. It is composed of capsaicin, the main flavouring compound giving pungency in higher concentrations, and capsanthin and capsorubin, the main colouring compounds (among other carotenoids).
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