capsanthin
(3R,3'S,5'R)-3,3'-dihydroxy-beta,kappa-caroten-6'-one
Identification
| Name | capsanthin |
| 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 Number | 465-42-9 |
| EINECS | 207-364-1 |
| FDA UNII | 420NY1J57N |
| Molecular Formula | C40 H56 O3 |
| Molecular Weight | 584.88392000 |
| MDL Number | MFCD03423725 |
| Nikkaji Number | J5.891B |
| Beilstein | 2493991 |
Regulatory
| FDA/DG SANTE Petitions, Reviews, Notices | EU SANCO |
| DG SANTE Food Additives | capsanthin |
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
| CosIng | cosmetic data |
| Cosmetic Uses | cosmetic colorants |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| 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. |
Potential Uses
Natural Occurrence
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 ajà (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.