capsorubin
(3S,3'S,5R,5'R)-3,3'-dihydroxy-kappa,kappa-carotene-6,6'-dione
Identification
| Name | capsorubin |
| IUPAC | (2E,4E,6E,8E,10E,12E,14E,16E,18E)-1,20-bis[(1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl]-4,8,13,17-tetramethylicosa-2,4,6,8,10,12,14,16,18-nonaene-1,20-dione |
| CAS Number | 470-38-2 |
| EINECS | 207-425-2 |
| FDA UNII | 805VAB3L0H |
| Molecular Formula | C40 H56 O4 |
| Molecular Weight | 600.88312000 |
| Nikkaji Number | J646.999J |
| Beilstein | 2494276 |
Regulatory
| FDA/DG SANTE Petitions, Reviews, Notices | EU SANCO |
| DG SANTE Food Additives | capsorubin |
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 741.80 °C. @ 760.00 mm Hg (est) |
| Flash Point | 782.00 °F. TCC ( 416.40 °C. ) (est) |
| logP (o/w) | 7.970 (est) |
| Soluble in | water, 2.839e-008 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| 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 | natural substances and extractives |
| Recommendation for capsorubin usage levels up to | not for fragrance use. |
| Recommendation for capsorubin flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
(3S,5R,3'S,5'R)-3,3'-
dihydroxy-?,?-carotene-6,6'-dione
(3S,3'S,5R,5'R)-3,3'-
dihydroxy-kappa,kappa-carotene-6,6'-dione
(2E,4E,6E,8E,10E,12E,14E,16E,18E)-1,20-bis[(1R,4S)-4-
hydroxy-1,2,2-trimethylcyclopentyl]-4,8,13,17-tetramethylicosa-2,4,6,8,10,12,14,16,18-nonaene-1,20-dione
PubMed:
Effect of model dissolved organic matter coating on sorption of phenanthrene by TiO2 nanoparticles.
PubMed:
Alteration of flower color in Iris germanica L. 'Fire Bride' through ectopic expression of phytoene synthase gene (crtB) from Pantoea agglomerans.
PubMed:
De novo transcriptome analysis of Liriodendron chinense petals and leaves by Illumina sequencing.
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:
Simultaneous determination of free capsorubin and capsanthin in red pepper powder using u-HPLC.
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:
Cloning and functional characterization of a gene for capsanthin-capsorubin synthase from tiger lily (Lilium lancifolium Thunb. 'Splendens').
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:
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:
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:
Qualitative and quantitative differences in the carotenoid composition of yellow and red peppers determined by HPLC-DAD-MS.
PubMed:
Carotenoid synthesis: retrospect and recent progress.
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:
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:
Thermal degradation products formed from carotenoids during a heat-induced degradation process of paprika oleoresins (Capsicum annuum L.).
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:
[Molecular cloning of full length capsanthin/capsorubin synthase homologous gene from orange (Citrus sinensis)].
PubMed:
Degradation of non-esterified and esterified xanthophylls by free radicals.
PubMed:
Structure-reactivity relationship in the oxidation of carotenoid pigments of the pepper (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:
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:
Xanthophyll esterification accompanying carotenoid overaccumulation in chromoplast of Capsicum annuum ripening fruits is a constitutive process and useful for ripeness index.
PubMed:
Paprika (Capsicum annuum) oleoresin extraction with supercritical carbon dioxide.
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:
Isocratic non-aqueous reversed-phase high-performance liquid chromatographic separation of capsanthin and capsorubin in red peppers (Capsicum annuum L.), paprika and oleoresin.
PubMed:
Developmental and stress regulation of gene expression for plastid and cytosolic isoprenoid pathways in pepper fruits.
PubMed:
Metabolism of cyclic carotenoids: a model for the alteration of this biosynthetic pathway in Capsicum annuum chromoplasts.
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:
Synthetic carotenoids, novel polyene polyketones and new capsorubin isomers as efficient quenchers of singlet molecular oxygen.
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 violaxanthin to capsorubin by a chromoplast enriched fraction of Capsicum fruits.
PubMed:
[Remarks on the structure of capsorubin].
PubMed:
[Presence of stereoisomers of capsorubin in the pepper].