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126-29-4,MFCD00075896
Catalog No.:AA000QLA

126-29-4 | β,β-Carotene-3,3'-diol, 5,6:5',6'-diepoxy-5,5',6,6'-tetrahydro-, (3S,3'S,5R,5'R,6S,6'S)-

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1mg
≥90%
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$2,747.00   $1,923.00
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  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA000QLA
Chemical Name:
β,β-Carotene-3,3'-diol, 5,6:5',6'-diepoxy-5,5',6,6'-tetrahydro-, (3S,3'S,5R,5'R,6S,6'S)-
CAS Number:
126-29-4
Molecular Formula:
C40H56O4
Molecular Weight:
600.8702
MDL Number:
MFCD00075896
SMILES:
C/C(=C\C=C\C=C(\C=C\C=C(\C=C\[C@]12O[C@]2(C)C[C@H](CC1(C)C)O)/C)/C)/C=C/C=C(/C=C/[C@]12O[C@]2(C)C[C@H](CC1(C)C)O)\C
Properties
Computed Properties
 
Complexity:
1270  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
6  
Defined Bond Stereocenter Count:
9  
Heavy Atom Count:
44  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
10  
XLogP3:
9.8  

Literature

Title: Enhancement of non-photochemical quenching in the Bryophyte Physcomitrella patens during acclimation to salt and osmotic stress.

Journal: Plant & cell physiology 20121001

Title: Investigating the interaction between the violaxanthin cycle enzyme zeaxanthin epoxidase and the thylakoid membrane.

Journal: Journal of photochemistry and photobiology. B, Biology 20120903

Title: Violaxanthin de-epoxidase is rate-limiting for non-photochemical quenching under subsaturating light or during chilling in Arabidopsis.

Journal: Plant physiology and biochemistry : PPB 20120901

Title: Biosynthesis of fucoxanthin and diadinoxanthin and function of initial pathway genes in Phaeodactylum tricornutum.

Journal: Journal of experimental botany 20120901

Title: Efficient heterologous transformation of Chlamydomonas reinhardtii npq2 mutant with the zeaxanthin epoxidase gene isolated and characterized from Chlorella zofingiensis.

Journal: Marine drugs 20120901

Title: Isolation and characterization of a lycopene ε-cyclase gene of Chlorella (Chromochloris) zofingiensis. Regulation of the carotenogenic pathway by nitrogen and light.

Journal: Marine drugs 20120901

Title: Insights into the region responding to ΔpH change in major light harvesting complex.

Journal: Journal of photochemistry and photobiology. B, Biology 20120604

Title: Thermal degradation kinetics of neoxanthin, violaxanthin, and antheraxanthin in virgin olive oils.

Journal: Journal of agricultural and food chemistry 20120523

Title: A theoretical investigation of xanthophyll-protein hydrogen bonding in the photosystem II antenna.

Journal: The journal of physical chemistry. B 20120412

Title: Modeling of a violaxanthin-chlorophyll b chromophore pair in its LHCII environment using CAM-B3LYP.

Journal: Journal of photochemistry and photobiology. B, Biology 20120402

Title: Role of xanthophylls in light harvesting in green plants: a spectroscopic investigation of mutant LHCII and Lhcb pigment-protein complexes.

Journal: The journal of physical chemistry. B 20120329

Title: Morphology, ultrastructure and life cycle of Vitrella brassicaformis n. sp., n. gen., a novel chromerid from the Great Barrier Reef.

Journal: Protist 20120301

Title: Seasonal changes of violaxanthin cycle pigment de-epoxidation in wintergreen and evergreen plants.

Journal: Acta biochimica Polonica 20120101

Title: Violaxanthin and diadinoxanthin de-epoxidation in various model lipid systems.

Journal: Acta biochimica Polonica 20120101

Title: Zeaxanthin epoxidation - an in vitro approach.

Journal: Acta biochimica Polonica 20120101

Title: Identification of key residues for pH dependent activation of violaxanthin de-epoxidase from Arabidopsis thaliana.

Journal: PloS one 20120101

Title: Anti-inflammatory effects of violaxanthin isolated from microalga Chlorella ellipsoidea in RAW 264.7 macrophages.

Journal: Biological & pharmaceutical bulletin 20120101

Title: The xanthophyll cycle and antioxidative defense system are enhanced in the wheat hybrid subjected to high light stress.

Journal: Journal of plant physiology 20111015

Title: Changes in thylakoid membrane thickness associated with the reorganization of photosystem II light harvesting complexes during photoprotective energy dissipation.

Journal: Plant signaling & behavior 20110901

Title: Non-photochemical fluorescence quenching in Chromera velia is enabled by fast violaxanthin de-epoxidation.

Journal: FEBS letters 20110623

Title: Acclimation- and mutation-induced enhancement of PsbS levels affects the kinetics of non-photochemical quenching in Arabidopsis thaliana.

Journal: Planta 20110601

Title: Behavior of flavonols and carotenoids of minimally processed kale leaves during storage in passive modified atmosphere packaging.

Journal: Journal of food science 20110301

Title: Origin of absorption changes associated with photoprotective energy dissipation in the absence of zeaxanthin.

Journal: The Journal of biological chemistry 20110107

Title: Analysis of LhcSR3, a protein essential for feedback de-excitation in the green alga Chlamydomonas reinhardtii.

Journal: PLoS biology 20110101

Title: Photosystem II fluorescence lifetime imaging in avocado leaves: contributions of the lutein-epoxide and violaxanthin cycles to fluorescence quenching.

Journal: Journal of photochemistry and photobiology. B, Biology 20110101

Title: Utilizing the effective xanthophyll cycle for blooming of Ochromonas smithii and O. itoi (Chrysophyceae) on the snow surface.

Journal: PloS one 20110101

Title: Antiproliferative activity of violaxanthin isolated from bioguided fractionation of Dunaliella tertiolecta extracts.

Journal: Marine drugs 20110101

Title: Activation of violaxanthin cycle in darkness is a common response to different abiotic stresses: a case study in Pelvetia canaliculata.

Journal: BMC plant biology 20110101

Title: Dynamics of zeaxanthin binding to the photosystem II monomeric antenna protein Lhcb6 (CP24) and modulation of its photoprotection properties.

Journal: Archives of biochemistry and biophysics 20101201

Title: A theoretical investigation of the photophysical consequences of major plant light-harvesting complex aggregation within the photosynthetic membrane.

Journal: The journal of physical chemistry. B 20101125

Title: Regulation and function of xanthophyll cycle-dependent photoprotection in algae.

Journal: Photosynthesis research 20101101

Title: The photoprotective mechanisms in Secale cereale leaves under Cu and high light stress condition.

Journal: Journal of photochemistry and photobiology. B, Biology 20101005

Title: Carotenoid composition and vitamin A value in ají (Capsicum baccatum L.) and rocoto (C. pubescens R. & P.), 2 pepper species from the Andean region.

Journal: Journal of food science 20101001

Title: Insights into carotenoid dynamics in non-foliar photosynthetic tissues of avocado.

Journal: Physiologia plantarum 20100901

Title: Molecular factors controlling photosynthetic light harvesting by carotenoids.

Journal: Accounts of chemical research 20100817

Title: The main thylakoid membrane lipid monogalactosyldiacylglycerol (MGDG) promotes the de-epoxidation of violaxanthin associated with the light-harvesting complex of photosystem II (LHCII).

Journal: Biochimica et biophysica acta 20100301

Title: Low-light-induced violaxanthin de-epoxidation in shortly preheated leaves: uncoupling from Delta pH-dependent nonphotochemical quenching.

Journal: Photochemistry and photobiology 20100101

Title: Olefin metathesis in carotenoid synthesis.

Journal: Organic & biomolecular chemistry 20091121

Title: Adaptation of the obligate CAM plant Clusia alata to light stress: Metabolic responses.

Journal: Journal of plant physiology 20091115

Title: Antioxidant defences and oxidative damage in salt-treated olive plants under contrasting sunlight irradiance.

Journal: Tree physiology 20090901

Title: New transgenic line of Arabidopsis thaliana with partly disabled zeaxanthin epoxidase activity displays changed carotenoid composition, xanthophyll cycle activity and non-photochemical quenching kinetics.

Journal: Journal of plant physiology 20090701

Title: A structural basis for the pH-dependent xanthophyll cycle in Arabidopsis thaliana.

Journal: The Plant cell 20090701

Title: Properties of zeaxanthin and its radical cation bound to the minor light-harvesting complexes CP24, CP26 and CP29.

Journal: Biochimica et biophysica acta 20090601

Title: Excitation energy transfer and carotenoid radical cation formation in light harvesting complexes - a theoretical perspective.

Journal: Biochimica et biophysica acta 20090601

Title: Carotenoid composition of jackfruit (Artocarpus heterophyllus), determined by HPLC-PDA-MS/MS.

Journal: Plant foods for human nutrition (Dordrecht, Netherlands) 20090601

Title: Highly sensitive and accurate profiling of carotenoids by supercritical fluid chromatography coupled with mass spectrometry.

Journal: Journal of separation science 20090501

Title: Effects of zinc toxicity on sugar beet (Beta vulgaris L.) plants grown in hydroponics.

Journal: Plant biology (Stuttgart, Germany) 20090501

Title: Distribution and evolutionary trends of photoprotective isoprenoids (xanthophylls and tocopherols) within the plant kingdom.

Journal: Physiologia plantarum 20090401

Title: Light-induced change of configuration of the LHCII-bound xanthophyll (tentatively assigned to violaxanthin): a resonance Raman study.

Journal: The journal of physical chemistry. B 20090226

Title: De novo synthesis and degradation of Lx and V cycle pigments during shade and sun acclimation in avocado leaves.

Journal: Plant physiology 20090201

Title: Mechanism and regulation of the violaxanthin cycle: the role of antenna proteins and membrane lipids.

Journal: Biochimica et biophysica acta 20090101

Title: Antiproliferative effects of carotenoids extracted from Chlorella ellipsoidea and Chlorella vulgaris on human colon cancer cells.

Journal: Journal of agricultural and food chemistry 20081126

Title: Kinetic modeling of charge-transfer quenching in the CP29 minor complex.

Journal: The journal of physical chemistry. B 20081023

Title: A pronounced light-induced zeaxanthin formation accompanied by an unusually slight increase in non-photochemical quenching: a study with barley leaves treated with methyl viologen at moderate light.

Journal: Journal of plant physiology 20081009

Title: The role of lutein in the acclimation of higher plant chloroplast membranes to suboptimal conditions.

Journal: Physiologia plantarum 20080901

Title: Enhancing the carotenoid content of Brassica napus seeds by downregulating lycopene epsilon cyclase.

Journal: Transgenic research 20080801

Title: Architecture of a charge-transfer state regulating light harvesting in a plant antenna protein.

Journal: Science (New York, N.Y.) 20080509

Title: Short-term down-regulation of zeaxanthin epoxidation in Arabidopsis thaliana in response to photo-oxidative stress conditions.

Journal: Biochimica et biophysica acta 20080501

Title: Short- and long-term modulation of the lutein epoxide and violaxanthin cycles in two species of the Lauraceae: sweet bay laurel (Laurus nobilis L.) and avocado (Persea americana Mill.).

Journal: Plant biology (Stuttgart, Germany) 20080501

Title: The Lhcb protein and xanthophyll composition of the light harvesting antenna controls the DeltapH-dependency of non-photochemical quenching in Arabidopsis thaliana.

Journal: FEBS letters 20080430

Title: Dynamics of the xanthophyll cycle and non-radiative dissipation of absorbed light energy during exposure of Norway spruce to high irradiance.

Journal: Journal of plant physiology 20080418

Title: The influence of phase transitions in phosphatidylethanolamine models on the activity of violaxanthin de-epoxidase.

Journal: Biochimica et biophysica acta 20080401

Title: Simple replacement of violaxanthin by zeaxanthin in LHC-II does not cause chlorophyll fluorescence quenching.

Journal: Journal of inorganic biochemistry 20080301

Title: Pulsed EPR and DFT characterization of radicals produced by photo-oxidation of zeaxanthin and violaxanthin on silica-alumina.

Journal: The journal of physical chemistry. B 20080214

Title: The xanthophyll cycle pigments in Secale cereale leaves under combined Cd and high light stress conditions.

Journal: Journal of photochemistry and photobiology. B, Biology 20080130

Title: Laurdan fluorescence spectroscopy in the thylakoid bilayer: the effect of violaxanthin to zeaxanthin conversion on the galactolipid dominated lipid environment.

Journal: Biochimica et biophysica acta 20080101

Title: Occurrence of neoxanthin and lutein epoxide cycle in parasitic Cuscuta species.

Journal: Acta biochimica Polonica 20080101

Title: Dietary carotenoids in normal and pathological tissues of corpus uteri.

Journal: Folia histochemica et cytobiologica 20080101

Title: The importance of grana stacking for xanthophyll cycle-dependent NPQ in the thylakoid membranes of higher plants.

Journal: Physiologia plantarum 20071101

Title: Dynamics of violaxanthin and lutein epoxide xanthophyll cycles in Lauraceae tree species under field conditions.

Journal: Tree physiology 20071001

Title: Membrane curvature stress controls the maximal conversion of violaxanthin to zeaxanthin in the violaxanthin cycle--influence of alpha-tocopherol, cetylethers, linolenic acid, and temperature.

Journal: Biochimica et biophysica acta 20070901

Title: Elevated zeaxanthin bound to oligomeric LHCII enhances the resistance of Arabidopsis to photooxidative stress by a lipid-protective, antioxidant mechanism.

Journal: The Journal of biological chemistry 20070803

Title: Characterization of a beta-carotene hydroxylase of Adonis aestivalis and its expression in Arabidopsis thaliana.

Journal: Planta 20070601

Title: Fluorescence lifetime imaging microscopy of Chlamydomonas reinhardtii: non-photochemical quenching mutants and the effect of photosynthetic inhibitors on the slow chlorophyll fluorescence transient.

Journal: Journal of microscopy 20070501

Title: Carotenoid radical cations as a probe for the molecular mechanism of nonphotochemical quenching in oxygenic photosynthesis.

Journal: The journal of physical chemistry. B 20070405

Title: Amino sugars: new inhibitors of zeaxanthin epoxidase, a violaxanthin cycle enzyme.

Journal: Journal of plant physiology 20070301

Title: The Arabidopsis aba4-1 mutant reveals a specific function for neoxanthin in protection against photooxidative stress.

Journal: The Plant cell 20070301

Title: The roles of specific xanthophylls in light utilization.

Journal: Planta 20070101

Title: Femtosecond time-resolved transient absorption spectroscopy of xanthophylls.

Journal: The journal of physical chemistry. B 20061116

Title: Xanthophyll-induced aggregation of LHCII as a switch between light-harvesting and energy dissipation systems.

Journal: Biochimica et biophysica acta 20061101

Title: A two-photon excitation study on the role of carotenoid dark states in the regulation of plant photosynthesis.

Journal: Photosynthesis research 20061101

Title: De-epoxidation of violaxanthin in the minor antenna proteins of photosystem II, LHCB4, LHCB5, and LHCB6.

Journal: The Journal of biological chemistry 20060804

Title: Functional roles of the major chloroplast lipids in the violaxanthin cycle.

Journal: Planta 20060801

Title: Preferential inhibition of the lycopene epsilon-cyclase by the substituted triethylamine compound MPTA in higher plants.

Journal: Journal of plant physiology 20060301

Title: Evidence for a rebinding of antheraxanthin to the light-harvesting complex during the epoxidation reaction of the violaxanthin cycle.

Journal: Journal of plant physiology 20060301

Title: [Determination of carotenoids in flue-cured tobacco leaves during its growth by reversed-phase high performance liquid chromatography].

Journal: Se pu = Chinese journal of chromatography 20060301

Title: Characterization of a nonphotochemical quenching-deficient Arabidopsis mutant possessing an intact PsbS protein, xanthophyll cycle and lumen acidification.

Journal: Planta 20060201

Title: Metabolic responses to water deficit in two Eucalyptus globulus clones with contrasting drought sensitivity.

Journal: Tree physiology 20060201

Title: Quantitative variations of individual carotenoids in relationship with the leaflet development of six species of the genus Ceratozamia (Cycads).

Journal: Journal of plant physiology 20060201

Title: The role of carotenoid cleavage dioxygenases in the regulation of carotenoid profiles during maturation in citrus fruit.

Journal: Journal of experimental botany 20060101

Title: Balance of xanthophylls molecular and protonated molecular ions in electrospray ionization.

Journal: Journal of mass spectrometry : JMS 20050701

Title: Herbicidal and antioxidant responses of transgenic rice overexpressing Myxococcus xanthus protoporphyrinogen oxidase.

Journal: Plant physiology and biochemistry : PPB 20050501

Title: Role of hexagonal structure-forming lipids in diadinoxanthin and violaxanthin solubilization and de-epoxidation.

Journal: Biochemistry 20050315

Title: Temperature-induced isomerization of violaxanthin in organic solvents and in light-harvesting complex II.

Journal: Journal of photochemistry and photobiology. B, Biology 20050201

Title: De-epoxidation of violaxanthin in light-harvesting complex I proteins.

Journal: The Journal of biological chemistry 20040625

Title: Violaxanthin de-epoxidase, the xanthophyll cycle enzyme, requires lipid inverted hexagonal structures for its activity.

Journal: Biochemistry 20040420

Title: Detection of unusual carotenoid esters in fresh mango (Mangifera indica L. cv. 'Kent').

Journal: Phytochemistry 20031001

Title: Functional analysis of beta- and epsilon-ring carotenoid hydroxylases in Arabidopsis.

Journal: The Plant cell 20030601

Title: Thermotropic phase behaviour of alpha-dipalmitoylphosphatidylcholine multibilayers is influenced to various extents by carotenoids containing different structural features--evidence from differential scanning calorimetry.

Journal: Biochimica et biophysica acta 20030131

Title: [Photosynthetic pigments of tomato under conditions of biotic stress and effects of furostanol glycosides].

Journal: Prikladnaia biokhimiia i mikrobiologiia 20030101

Title: Alternative pathways of carotenoid biosynthesis in prokaryotes and eukaryotes.

Journal: Doklady. Biochemistry and biophysics 20030101

Title: Comparison of violaxanthin de-epoxidation from the stroma and lumen sides of isolated thylakoid membranes from Arabidopsis: implications for the mechanism of de-epoxidation.

Journal: Planta 20021201

Title: Carotenoids and carotenoid esters in potatoes (Solanum tuberosum L.): new insights into an ancient vegetable.

Journal: Journal of agricultural and food chemistry 20021120

Title: Molecular configuration of xanthophyll cycle carotenoids in photosystem II antenna complexes.

Journal: The Journal of biological chemistry 20021108

Title: Pigment binding of photosystem I light-harvesting proteins.

Journal: The Journal of biological chemistry 20021004

Title: Dynamics of chromophore binding to Lhc proteins in vivo and in vitro during operation of the xanthophyll cycle.

Journal: The Journal of biological chemistry 20021004

Title: Genetic engineering of a zeaxanthin-rich potato by antisense inactivation and co-suppression of carotenoid epoxidation.

Journal: Metabolic engineering 20021001

Title: Kinetics of violaxanthin de-epoxidation by violaxanthin de-epoxidase, a xanthophyll cycle enzyme, is regulated by membrane fluidity in model lipid bilayers.

Journal: European journal of biochemistry 20020901

Title: A major light-harvesting polypeptide of photosystem II functions in thermal dissipation.

Journal: The Plant cell 20020801

Title: Single and double knockouts of the genes for photosystem I subunits G, K, and H of Arabidopsis. Effects on photosystem I composition, photosynthetic electron flow, and state transitions.

Journal: Plant physiology 20020601

Title: Phytochrome and blue light-mediated stomatal opening in the orchid, paphiopedilum.

Journal: Plant & cell physiology 20020601

Title: Ascorbate deficiency can limit violaxanthin de-epoxidase activity in vivo.

Journal: Plant physiology 20020301

Title: Carotenoid S(1) state in a recombinant light-harvesting complex of Photosystem II.

Journal: Biochemistry 20020115

Title: Overexpression of violaxanthin de-epoxidase: properties of C-terminal deletions on activity and pH-dependent lipid binding.

Journal: Planta 20020101

Title: Comparative X-ray studies on the interaction of carotenoids with a model phosphatidylcholine membrane.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20020101

Title: Specific effects of gamma-radiation on the fine structure of the photosynthetic apparatus: evaluation of the character of disturbances in vivo using high-order derivative spectrophotometry.

Journal: Doklady. Biochemistry and biophysics 20020101

Title: Physiology and xanthophyll cycle activity of Nannochloropsis gaditana.

Journal: Biotechnology and bioengineering 20011005

Title: Structure-reactivity relationship in the oxidation of carotenoid pigments of the pepper (Capsicum annuum L.).

Journal: Journal of agricultural and food chemistry 20011001

Title: The major antenna complex of photosystem II has a xanthophyll binding site not involved in light harvesting.

Journal: The Journal of biological chemistry 20010921

Title: Configuration and dynamics of xanthophylls in light-harvesting antennae of higher plants. Spectroscopic analysis of isolated light-harvesting complex of photosystem II and thylakoid membranes.

Journal: The Journal of biological chemistry 20010706

Title: The de-epoxidase and epoxidase reactions of Mantoniella squamata (Prasinophyceae) exhibit different substrate-specific reaction kinetics compared to spinach.

Journal: Planta 20010701

Title: De-epoxidation of violaxanthin after reconstitution into different carotenoid binding sites of light-harvesting complex II.

Journal: The Journal of biological chemistry 20010622

Title: Absence of lutein, violaxanthin and neoxanthin affects the functional chlorophyll antenna size of photosystem-II but not that of photosystem-I in the green alga Chlamydomonas reinhardtii.

Journal: Plant & cell physiology 20010501

Title: Photochemical behavior of xanthophylls in the recombinant photosystem II antenna complex, CP26.

Journal: Biochemistry 20010206

Title: Xanthophyll synthesis in diatoms: quantification of putative intermediates and comparison of pigment conversion kinetics with rate constants derived from a model.

Journal: Planta 20010201

Title: Effect of 13-cis violaxanthin on organization of light harvesting complex II in monomolecular layers.

Journal: Biochimica et biophysica acta 20010119

Title: Time-resolved fluorescence analysis of the recombinant photosystem II antenna complex CP29. Effects of zeaxanthin, pH and phosphorylation.

Journal: European journal of biochemistry 20010101

Title: Biochemical basis of color as an aesthetic quality in Citrus sinensis.

Journal: Journal of agricultural and food chemistry 20010101

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SDS
Tags:126-29-4 Molecular Formula|126-29-4 MDL|126-29-4 SMILES|126-29-4 β,β-Carotene-3,3'-diol, 5,6:5',6'-diepoxy-5,5',6,6'-tetrahydro-, (3S,3'S,5R,5'R,6S,6'S)-