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Fucoxanthin

CAS No.:
3351-86-8
Catalog Number:
AG00C0VR
Molecular Formula:
C42H58O6
Molecular Weight:
658.9063
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
≥95%
1 week
United States
$153
- +
10mg
≥95%
1 week
United States
$229
- +
25mg
≥95%
1 week
United States
$464
- +
50mg
≥95%
1 week
United States
$823
- +
100mg
98%
1 week
United States
$1540
- +
Product Description
Catalog Number:
AG00C0VR
Chemical Name:
Fucoxanthin
CAS Number:
3351-86-8
Molecular Formula:
C42H58O6
Molecular Weight:
658.9063
MDL Number:
MFCD01745140
IUPAC Name:
[(1S,3R)-3-hydroxy-4-[(3E,5E,7E,9E,11E,13E,15E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyl-17-oxooctadeca-1,3,5,7,9,11,13,15-octaenylidene]-3,5,5-trimethylcyclohexyl] acetate
InChI:
InChI=1S/C42H58O6/c1-29(18-14-19-31(3)22-23-37-38(6,7)26-35(47-33(5)43)27-40(37,10)46)16-12-13-17-30(2)20-15-21-32(4)36(45)28-42-39(8,9)24-34(44)25-41(42,11)48-42/h12-22,34-35,44,46H,24-28H2,1-11H3/b13-12+,18-14+,20-15+,29-16+,30-17+,31-19+,32-21+/t23?,34-,35-,40+,41+,42-/m0/s1
InChI Key:
SJWWTRQNNRNTPU-ABBNZJFMSA-N
SMILES:
C/C(=C\C=C\C=C(\C=C\C=C(\C(=O)C[C@]12O[C@]2(C)C[C@H](CC1(C)C)O)/C)/C)/C=C/C=C(/C=C=C1C(C)(C)C[C@@H](C[C@@]1(C)O)OC(=O)C)\C
UNII:
06O0TC0VSM
Properties
Complexity:
1530  
Compound Is Canonicalized:
No
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Defined Bond Stereocenter Count:
7  
Exact Mass:
658.423g/mol
Formal Charge:
0
Heavy Atom Count:
48  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
658.92g/mol
Monoisotopic Mass:
658.423g/mol
Rotatable Bond Count:
12  
Topological Polar Surface Area:
96.4A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
8.1  
Literature
Title Journal
Protective and therapeutic effects of fucoxanthin against sunburn caused by UV irradiation. Journal of pharmacological sciences 20160901
Fucoxanthin Inhibits the Inflammation Response in Paw Edema Model through Suppressing MAPKs, Akt, and NFκB. Journal of biochemical and molecular toxicology 20160301
The anti-apoptotic effect of fucoxanthin on carbon tetrachloride-induced hepatotoxicity. The Journal of toxicological sciences 20130201
Capacity of fucoxanthin for scavenging peroxyl radicals and inhibition of lipid peroxidation in model systems. Free radical research 20121101
Anti-neoplastic effects of fucoxanthin and its deacetylated product, fucoxanthinol, on Burkitt's and Hodgkin's lymphoma cells. Oncology reports 20121001
Anti-inflammatory effect of fucoxanthin derivatives isolated from Sargassum siliquastrum in lipopolysaccharide-stimulated RAW 264.7 macrophage. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20120901
Biosynthesis of fucoxanthin and diadinoxanthin and function of initial pathway genes in Phaeodactylum tricornutum. Journal of experimental botany 20120901
Carotenoids reverse multidrug resistance in cancer cells by interfering with ABC-transporters. Phytomedicine : international journal of phytotherapy and phytopharmacology 20120815
Pharmacokinetics of fucoxanthinol in human plasma after the oral administration of kombu extract. The British journal of nutrition 20120601
A potential commercial source of fucoxanthin extracted from the microalga Phaeodactylum tricornutum. Applied biochemistry and biotechnology 20120401
Fucoxanthin promotes translocation and induction of glucose transporter 4 in skeletal muscles of diabetic/obese KK-A(y) mice. Phytomedicine : international journal of phytotherapy and phytopharmacology 20120315
Combination of fucoxanthin and conjugated linoleic acid attenuates body weight gain and improves lipid metabolism in high-fat diet-induced obese rats. Archives of biochemistry and biophysics 20120301
Fucoxantin: a treasure from the sea. Marine drugs 20120301
Stereocontrolled total synthesis of fucoxanthin and its polyene chain-modified derivative. Organic letters 20120203
In vitro cytotoxic effect of ethanol extract prepared from sporophyll of Undaria pinnatifida on human colorectal cancer cells. Phytotherapy research : PTR 20120201
Xanthigen suppresses preadipocyte differentiation and adipogenesis through down-regulation of PPARγ and C/EBPs and modulation of SIRT-1, AMPK, and FoxO pathways. Journal of agricultural and food chemistry 20120201
Antioxidant activity of Hawaiian marine algae. Marine drugs 20120201
Photo-excitation of carotenoids causes cytotoxicity via singlet oxygen production. Biochemical and biophysical research communications 20120106
Marine carotenoids and oxidative stress. Marine drugs 20120101
Fucoxanthin attenuates rifampin-induced cytochrome P450 3A4 (CYP3A4) and multiple drug resistance 1 (MDR1) gene expression through pregnane X receptor (PXR)-mediated pathways in human hepatoma HepG2 and colon adenocarcinoma LS174T cells. Marine drugs 20120101
Effects of dietary fucoxanthin on cholesterol metabolism in diabetic/obese KK-A(y) mice. Lipids in health and disease 20120101
Fucoxanthin enhances HO-1 and NQO1 expression in murine hepatic BNL CL.2 cells through activation of the Nrf2/ARE system partially by its pro-oxidant activity. Journal of agricultural and food chemistry 20111026
Nitrocapsanthin and nitrofucoxanthin, respective products of capsanthin and fucoxanthin reaction with peroxynitrite. Journal of agricultural and food chemistry 20111012
Protective effects of fucoxanthin against ferric nitrilotriacetate-induced oxidative stress in murine hepatic BNL CL.2 cells. Toxicology in vitro : an international journal published in association with BIBRA 20111001
Fat burners: nutrition supplements that increase fat metabolism. Obesity reviews : an official journal of the International Association for the Study of Obesity 20111001
Fucoxanthin exerts differing effects on 3T3-L1 cells according to differentiation stage and inhibits glucose uptake in mature adipocytes. Biochemical and biophysical research communications 20110617
Ultrafast excited state dynamics of fucoxanthin: excitation energy dependent intramolecular charge transfer dynamics. Physical chemistry chemical physics : PCCP 20110614
The allenic carotenoid fucoxanthin, a novel marine nutraceutical from brown seaweeds. Journal of the science of food and agriculture 20110501
Femtosecond transient absorption spectroscopic study of a carbonyl-containing carotenoid analogue, 2-(all-trans-retinylidene)-indan-1,3-dione. The journal of physical chemistry. A 20110324
Pressurized liquid method for fucoxanthin extraction from Eisenia bicyclis (Kjellman) Setchell. Journal of bioscience and bioengineering 20110201
Fucoxanthin and its deacetylated product, fucoxanthinol, induce apoptosis of primary effusion lymphomas. Cancer letters 20110128
A preparative method for isolation of fucoxanthin from Eisenia bicyclis by centrifugal partition chromatography. Phytochemical analysis : PCA 20110101
Protective effect of Fucoxanthin against UVB-induced skin photoaging in hairless mice. Bioscience, biotechnology, and biochemistry 20110101
A marine carotenoid, fucoxanthin, induces regulatory T cells and inhibits Th17 cell differentiation in vitro. Bioscience, biotechnology, and biochemistry 20110101
Fucoxanthin, a marine carotenoid present in brown seaweeds and diatoms: metabolism and bioactivities relevant to human health. Marine drugs 20110101
Fucoxanthin inhibits the inflammatory response by suppressing the activation of NF-κB and MAPKs in lipopolysaccharide-induced RAW 264.7 macrophages. European journal of pharmacology 20101215
Fucoxanthin regulates adipocytokine mRNA expression in white adipose tissue of diabetic/obese KK-Ay mice. Archives of biochemistry and biophysics 20101201
Fucoxanthin induces apoptosis in human leukemia HL-60 cells through a ROS-mediated Bcl-xL pathway. Toxicology in vitro : an international journal published in association with BIBRA 20100901
Fucoxanthin-rich seaweed extract suppresses body weight gain and improves lipid metabolism in high-fat-fed C57BL/6J mice. Biotechnology journal 20100901
Fucoxanthin supplementation improves plasma and hepatic lipid metabolism and blood glucose concentration in high-fat fed C57BL/6N mice. Chemico-biological interactions 20100805
Purified canola lutein selectively inhibits specific isoforms of mammalian DNA polymerases and reduces inflammatory response. Lipids 20100801
Suppressive effects of the marine carotenoids, fucoxanthin and fucoxanthinol on triglyceride absorption in lymph duct-cannulated rats. European journal of nutrition 20100601
Characterization of a trimeric light-harvesting complex in the diatom Phaeodactylum tricornutum built of FcpA and FcpE proteins. Journal of experimental botany 20100601
Fucoxanthin induces apoptosis in osteoclast-like cells differentiated from RAW264.7 cells. Journal of agricultural and food chemistry 20100526
Bioavailability and metabolism of fucoxanthin in rats: structural characterization of metabolites by LC-MS (APCI). Molecular and cellular biochemistry 20100101
Comparative ecophysiology and genomics of the toxic unicellular alga Fibrocapsa japonica. The New phytologist 20100101
Evaluation of anti-inflammatory effect of fucoxanthin isolated from brown algae in lipopolysaccharide-stimulated RAW 264.7 macrophages. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20100101
Inhibition of proliferation of a hepatoma cell line by fucoxanthin in relation to cell cycle arrest and enhanced gap junctional intercellular communication. Chemico-biological interactions 20091210
In vitro and in vivo evaluation of mutagenicity of fucoxanthin (FX) and its metabolite fucoxanthinol (FXOH). The Journal of toxicological sciences 20091201
Comparative effects of beta-carotene and fucoxanthin on retinol deficiency induced oxidative stress in rats. Molecular and cellular biochemistry 20091101
Single and repeated oral dose toxicity study of fucoxanthin (FX), a marine carotenoid, in mice. The Journal of toxicological sciences 20091001
The distribution and accumulation of fucoxanthin and its metabolites after oral administration in mice. The British journal of nutrition 20090701
Protective effect of fucoxanthin isolated from Sargassum siliquastrum on UV-B induced cell damage. Journal of photochemistry and photobiology. B, Biology 20090504
Function of marine carotenoids. Forum of nutrition 20090101
Anti-adult T-cell leukemia effects of brown algae fucoxanthin and its deacetylated product, fucoxanthinol. International journal of cancer 20081201
Fucoxanthin restrains oxidative stress induced by retinol deficiency through modulation of Na(+)K(+)-ATPase [corrected] and antioxidant enzyme activities in rats. European journal of nutrition 20081201
Low bioavailability of dietary epoxyxanthophylls in humans. The British journal of nutrition 20080801
Pigment alterations in the brown mussel Perna perna. Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology 20080801
Growth inhibition of human hepatic carcinoma HepG2 cells by fucoxanthin is associated with down-regulation of cyclin D. Biochimica et biophysica acta 20080401
The fluorescence yield of the trimeric fucoxanthin-chlorophyll-protein FCPa in the diatom Cyclotella meneghiniana is dependent on the amount of bound diatoxanthin. Photosynthesis research 20080101
Seaweed carotenoid, fucoxanthin, as a multi-functional nutrient. Asia Pacific journal of clinical nutrition 20080101
Microalgal mediation of ripple mobility. Geobiology 20080101
Fucoxanthin, tetraprenylated toluquinone and toluhydroquinone metabolites from Sargassum heterophyllum inhibit the in vitro growth of the malaria parasite Plasmodium falciparum. Zeitschrift fur Naturforschung. C, Journal of biosciences 20080101
Radical scavenging and singlet oxygen quenching activity of marine carotenoid fucoxanthin and its metabolites. Journal of agricultural and food chemistry 20071017
Dietary combination of fucoxanthin and fish oil attenuates the weight gain of white adipose tissue and decreases blood glucose in obese/diabetic KK-Ay mice. Journal of agricultural and food chemistry 20070919
Spectroscopic and molecular characterization of the oligomeric antenna of the diatom Phaeodactylum tricornutum. Biochemistry 20070828
Fucoxanthin and fucoxanthinol enhance the amount of docosahexaenoic acid in the liver of KKAy obese/diabetic mice. Journal of agricultural and food chemistry 20070627
Morphology and cultural behavior of Botryococcus protuberans with notes on the genus. Journal of environmental biology 20070401
Characterization of fucoxanthin and fucoxanthinol esters in the Chinese surf clam, Mactra chinensis. Journal of agricultural and food chemistry 20070221
Antiangiogenic activity of brown algae fucoxanthin and its deacetylated product, fucoxanthinol. Journal of agricultural and food chemistry 20061227
Subunit composition and pigmentation of fucoxanthin-chlorophyll proteins in diatoms: evidence for a subunit involved in diadinoxanthin and diatoxanthin binding. Biochemistry 20061031
Fucoxanthin and its metabolite, fucoxanthinol, suppress adipocyte differentiation in 3T3-L1 cells. International journal of molecular medicine 20060701
Effects of fucoxanthin on lipopolysaccharide-induced inflammation in vitro and in vivo. Experimental eye research 20051001
Tertiary endosymbiosis driven genome evolution in dinoflagellate algae. Molecular biology and evolution 20050501
Neoxanthin and fucoxanthin induce apoptosis in PC-3 human prostate cancer cells. Cancer letters 20050318
Phylogeny of nuclear-encoded plastid-targeted GAPDH gene supports separate origins for the peridinin- and the fucoxanthin derivative-containing plastids of dinoflagellates. Protist 20041201
Fucoxanthin induces apoptosis and enhances the antiproliferative effect of the PPARgamma ligand, troglitazone, on colon cancer cells. Biochimica et biophysica acta 20041118
The use of pigment 'fingerprints' in the study of harmful algal blooms. Revista de biologia tropical 20040901
Biotransformation of fucoxanthinol into amarouciaxanthin A in mice and HepG2 cells: formation and cytotoxicity of fucoxanthin metabolites. Drug metabolism and disposition: the biological fate of chemicals 20040201
Enrichment of the light-harvesting complex in diadinoxanthin and implications for the nonphotochemical fluorescence quenching in diatoms. Biochemistry 20030520
Density-dependent patterns of thiamine and pigment production in the diatom Nitzschia microcephala. Phytochemistry 20030501
Vitamin A-related compounds, all-trans retinal and retinoic acids, selectively inhibit activities of mammalian replicative DNA polymerases. Biochimica et biophysica acta 20020220
Xanthophyll synthesis in diatoms: quantification of putative intermediates and comparison of pigment conversion kinetics with rate constants derived from a model. Planta 20010201
Properties