capsanthin

(3R,3'S,5'R)-3,3'-dihydroxy-beta,kappa-caroten-6'-one

CAS: 465-42-9 C40 H56 O3 MW: 584.88392000

Identification

Namecapsanthin
IUPAC(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 Number465-42-9
EINECS207-364-1
FDA UNII420NY1J57N
Molecular FormulaC40 H56 O3
Molecular Weight584.88392000
MDL NumberMFCD03423725
Nikkaji NumberJ5.891B
Beilstein2493991

Regulatory

FDA/DG SANTE Petitions, Reviews, NoticesEU SANCO
DG SANTE Food Additivescapsanthin

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)

Cosmetic Information

CosIngcosmetic data
Cosmetic Usescosmetic colorants

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral ToxicityNot determined
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 capsanthin usage levels up tonot for fragrance use.
Recommendation for capsanthin flavor usage levels up tonot for flavor use.

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Potential Uses

cosmetic colorants

Natural Occurrence

capsicum annuum cayenne fruit paprika PMC pepper bell pepper fruit

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 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.