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148244-82-0,MFCD03427692
Catalog No.:AA001FGO

148244-82-0 | β-D-Glucopyranose, diglycoside with (2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-1,4-butanediol

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5mg
98%(HPLC)powder
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10mg
98%(HPLC)powder
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25mg
98%(HPLC)powder
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA001FGO
Chemical Name:
β-D-Glucopyranose, diglycoside with (2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-1,4-butanediol
CAS Number:
148244-82-0
Molecular Formula:
C26H38O12
Molecular Weight:
542.5727
MDL Number:
MFCD03427692
SMILES:
OC[C@@H]([C@@H](Cc1ccc(c(c1)OC)O)CO)Cc1ccc(c(c1)OC)O.OC[C@H]1O[C@@H](O)[C@@H]([C@H]([C@@H]1O)O)O
Properties
Computed Properties
 
Complexity:
861  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
12  
Heavy Atom Count:
48  
Hydrogen Bond Acceptor Count:
16  
Hydrogen Bond Donor Count:
10  
Rotatable Bond Count:
15  
XLogP3:
-0.7  

Literature

Title: Asbestos Induces Oxidative Stress and Activation of Nrf2 Signaling in Murine Macrophages: Chemopreventive Role of the Synthetic Lignan Secoisolariciresinol Diglucoside (LGM2605).

Journal: International journal of molecular sciences 20160301

Title: Flaxseed lignans enriched in secoisolariciresinol diglucoside prevent acute asbestos-induced peritoneal inflammation in mice.

Journal: Carcinogenesis 20160201

Title: Identification and functional characterization of a flax UDP-glycosyltransferase glucosylating secoisolariciresinol (SECO) into secoisolariciresinol monoglucoside (SMG) and diglucoside (SDG).

Journal: BMC plant biology 20140101

Title: Lignans in seeds of Linum species.

Journal: Phytochemistry 20121001

Title: Evaluation of the efficacy of flaxseed meal and flaxseed extract in reducing menopausal symptoms.

Journal: Journal of medicinal food 20120901

Title: Potential effects of lignan-enriched flaxseed powder on bodyweight, visceral fat, lipid profile, and blood pressure in rats.

Journal: Fitoterapia 20120701

Title: [Effects of secoisolariciresinol diglucoside combined with bortezomib on induction of apoptosis in lung cancer cell line A549].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20120201

Title: Comparative effects of sesame seed lignan and flaxseed lignan in reducing the growth of human breast tumors (MCF-7) at high levels of circulating estrogen in athymic mice.

Journal: Nutrition and cancer 20120101

Title: Role of bifidobacteria in the activation of the lignan secoisolariciresinol diglucoside.

Journal: Applied microbiology and biotechnology 20111001

Title: Effect of flaxseed lignans added to milk or fed to cows on oxidative degradation of dairy beverages enriched with polyunsaturated fatty acids.

Journal: The Journal of dairy research 20110201

Title: [Effects of flaxseed extract on rheological properties of blood in experimental ovariectomy].

Journal: Eksperimental'naia i klinicheskaia farmakologiia 20110101

Title: Natural products in regression and slowing of progression of atherosclerosis.

Journal: Current pharmaceutical biotechnology 20101201

Title: Cytostatic inhibition of cancer cell growth by lignan secoisolariciresinol diglucoside.

Journal: Nutrition research (New York, N.Y.) 20101101

Title: Health effects with consumption of the flax lignan secoisolariciresinol diglucoside.

Journal: The British journal of nutrition 20100401

Title: Dietary flaxseed lignan or oil combined with tamoxifen treatment affects MCF-7 tumor growth through estrogen receptor- and growth factor-signaling pathways.

Journal: Molecular nutrition & food research 20100301

Title: The effect of secoisolariciresinol diglucoside and flaxseed oil, alone and in combination, on MCF-7 tumor growth and signaling pathways.

Journal: Nutrition and cancer 20100101

Title: Further studies on a human intestinal bacterium Ruminococcus sp. END-1 for transformation of plant lignans to mammalian lignans.

Journal: Journal of agricultural and food chemistry 20090826

Title: Effects of the flaxseed lignans secoisolariciresinol diglucoside and its aglycone on serum and hepatic lipids in hyperlipidaemic rats.

Journal: The British journal of nutrition 20090801

Title: Milk concentration of the mammalian lignan enterolactone, milk production, milk fatty acid profile, and digestibility in dairy cows fed diets containing whole flaxseed or flaxseed meal.

Journal: The Journal of dairy research 20090801

Title: Determination of lignans in flaxseed using liquid chromatography with time-of-flight mass spectrometry.

Journal: Journal of chromatography. A 20090109

Title: Patented techniques for the extraction and isolation of secoisolari-ciresinol diglucoside from flaxseed.

Journal: Recent patents on food, nutrition & agriculture 20090101

Title: Regulation of zinc transporters by dietary flaxseed lignan in human breast cancer xenografts.

Journal: Molecular biology reports 20081201

Title: Hydrolysis kinetics of secoisolariciresinol diglucoside oligomers from flaxseed.

Journal: Journal of agricultural and food chemistry 20081112

Title: Validation of a reversed phase high performance thin layer chromatographic-densitometric method for secoisolariciresinol diglucoside determination in flaxseed.

Journal: Journal of chromatography. A 20081017

Title: Flaxseed lignan attenuates high-fat diet-induced fat accumulation and induces adiponectin expression in mice.

Journal: The British journal of nutrition 20080901

Title: Effect of feeding flax or linseed meal on progesterone clearance rate in ovariectomized ewes.

Journal: Domestic animal endocrinology 20080801

Title: Metabolism of the lignan macromolecule into enterolignans in the gastrointestinal lumen as determined in the simulator of the human intestinal microbial ecosystem.

Journal: Journal of agricultural and food chemistry 20080625

Title: Dietary flaxseed lignan extract lowers plasma cholesterol and glucose concentrations in hypercholesterolaemic subjects.

Journal: The British journal of nutrition 20080601

Title: Effects of dietary flaxseed lignan extract on symptoms of benign prostatic hyperplasia.

Journal: Journal of medicinal food 20080601

Title: Separation and determination of secoisolariciresinol diglucoside oligomers and their hydrolysates in the flaxseed extract by high-performance liquid chromatography.

Journal: Journal of chromatography. A 20080328

Title: Regression of hypercholesterolemic atherosclerosis in rabbits by secoisolariciresinol diglucoside isolated from flaxseed.

Journal: Atherosclerosis 20080301

Title: Secoisolariciresinol diglucoside induces neovascularization-mediated cardioprotection against ischemia-reperfusion injury in hypercholesterolemic myocardium.

Journal: Journal of molecular and cellular cardiology 20080101

Title: Antioxidant activities of the flaxseed lignan secoisolariciresinol diglucoside, its aglycone secoisolariciresinol and the mammalian lignans enterodiol and enterolactone in vitro.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20071101

Title: Enantioselective dehydroxylation of enterodiol and enterolactone precursors by human intestinal bacteria.

Journal: Biological & pharmaceutical bulletin 20071101

Title: Suppression of hypercholesterolemic atherosclerosis by pentoxifylline and its mechanism.

Journal: Atherosclerosis 20070601

Title: Feeding flaxseed oil but not secoisolariciresinol diglucoside results in higher bone mass in healthy rats and rats with kidney disease.

Journal: Prostaglandins, leukotrienes, and essential fatty acids 20070501

Title: Purification of secoisolariciresinol diglucoside with column chromatography on a sephadex LH-20.

Journal: Journal of chromatographic science 20070401

Title: AAPH-mediated antioxidant reactions of secoisolariciresinol and SDG.

Journal: Organic & biomolecular chemistry 20070221

Title: Secoisolariciresinol diglucoside: relevance to angiogenesis and cardioprotection against ischemia-reperfusion injury.

Journal: The Journal of pharmacology and experimental therapeutics 20070201

Title: Clostridium saccharogumia sp. nov. and Lactonifactor longoviformis gen. nov., sp. nov., two novel human faecal bacteria involved in the conversion of the dietary phytoestrogen secoisolariciresinol diglucoside.

Journal: Systematic and applied microbiology 20070101

Title: Microwave-assisted extraction of the main phenolic compounds in flaxseed.

Journal: Phytochemical analysis : PCA 20070101

Title: Effect of processing and storage on the stability of flaxseed lignan added to dairy products.

Journal: Journal of agricultural and food chemistry 20061115

Title: Contribution of linseed intake to urine and serum enterolignan levels in German females: a randomised controlled intervention trial.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20060701

Title: Occurrence and activity of human intestinal bacteria involved in the conversion of dietary lignans.

Journal: Anaerobe 20060601

Title: Flaxseed and its components reduce metastasis after surgical excision of solid human breast tumor in nude mice.

Journal: Cancer letters 20060328

Title: Phylogeny of human intestinal bacteria that activate the dietary lignan secoisolariciresinol diglucoside.

Journal: FEMS microbiology ecology 20060301

Title: Effect of processing and storage on the stability of flaxseed lignan added to bakery products.

Journal: Journal of agricultural and food chemistry 20060111

Title: Assessing exposure to lignans and their metabolites in humans.

Journal: Journal of AOAC International 20060101

Title: Dietary secoisolariciresinol diglucoside and its oligomers with 3-hydroxy-3-methyl glutaric acid decrease vitamin E levels in rats.

Journal: The British journal of nutrition 20040701

Title: The effects of dietary flaxseed on the Fischer 344 rat: II. Liver gamma-glutamyltranspeptidase activity.

Journal: Cell biochemistry and function 20040101

Title: Antithrombic and anti-atherogenic effects of partially defatted flaxseed meal using a laser-induced thrombosis test in apolipoprotein E and low-density lipoprotein receptor deficient mice.

Journal: Blood coagulation & fibrinolysis : an international journal in haemostasis and thrombosis 20031201

Title: Exposure to flaxseed or its purified lignan during suckling inhibits chemically induced rat mammary tumorigenesis.

Journal: Experimental biology and medicine (Maywood, N.J.) 20030901

Title: On-line liquid-chromatography-nuclear magnetic resonance spectroscopy-mass spectrometry coupling for the separation and characterization of secoisolariciresinol diglucoside isomers in flaxseed.

Journal: Journal of chromatography. A 20021004

Title: Isolation of the lignan secoisolariciresinol diglucoside from flaxseed (Linum usitatissimum L.) by high-speed counter-current chromatography.

Journal: Journal of chromatography. A 20020118

Title: Biosynthetic pathway to the cancer chemopreventive secoisolariciresinol diglucoside-hydroxymethyl glutaryl ester-linked lignan oligomers in flax (Linum usitatissimum) seed.

Journal: Journal of natural products 20011101

Title: An oligomer from flaxseed composed of secoisolariciresinoldiglucoside and 3-hydroxy-3-methyl glutaric acid residues.

Journal: Phytochemistry 20011001

Title: Secoisolariciresinol diglucoside from flaxseed delays the development of type 2 diabetes in Zucker rat.

Journal: The Journal of laboratory and clinical medicine 20010701

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Tags:148244-82-0 Molecular Formula|148244-82-0 MDL|148244-82-0 SMILES|148244-82-0 β-D-Glucopyranose, diglycoside with (2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]-1,4-butanediol