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secoisolariciresinol diglucoside
beta-d-glucopyranose, diglycoside with 2,3-bis((4-hydroxy-3-methoxyphenyl)methyl-1,4-butanediol, (R-(R*,R*))-

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CAS Number: 148244-82-0Picture of molecule3D/inchi
FDA UNII: Search
MDL:MFCD03427692
Molecular Weight:686.70582000
Formula:C32 H46 O16
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Category:GSCCombobox
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 989.17 °C. @ 760.00 mm Hg (est)
Flash Point:1026.00 °F. TCC ( 552.00 °C. ) (est)
logP (o/w): -2.933 (est)
Soluble in:
 water, 1581 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Secoisolariciresinol Diglucoside 98%
BOC Sciences
For experimental / research use only.
Seco-isolariciresinol diglucoside
Carbosynth
For experimental / research use only.
Secoisolariciresinol Diglucoside
Changsha Organic Herb
Flax Lignans Flaxseed Hull extract SDG Secoisolariciresinol Diglucoside
Santa Cruz Biotechnology
For experimental / research use only.
Secoisolariciresinol Diglucoside
Sigma-Aldrich: Sigma
For experimental / research use only.
Secoisolariciresinol diglucoside ≥97% (HPLC)
sds
 
Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
GSCCombobox
Recommendation for secoisolariciresinol diglucoside usage levels up to:
 not for fragrance use.
 
Recommendation for secoisolariciresinol diglucoside flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
ClinicalTrials.gov:search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :56841034
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(3S)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol;(2R,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
Chemidplus:0148244820
 
References:
 (3S)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol;(2R,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):56841034
Pubchem (sid):135120183
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
 bmhb-diglc
beta-d-glucopyranose, diglycoside with 2,3-bis((4-hydroxy-3-methoxyphenyl)methyl-1,4-butanediol, (R-(R*,R*))-
(3S)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol;(2R,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
2,3-bis(3-methoxy-4-hydroxybenzyl)butane-1,4-diol 1,4-diglucoside
 

Articles:

PubMed:RNAi-mediated pinoresinol lariciresinol reductase gene silencing in flax (Linum usitatissimum L.) seed coat: Consequences on lignans and neolignans accumulation.
PubMed:Novel synthetic (S,S) and (R,R)-secoisolariciresinol diglucosides (SDGs) protect naked plasmid and genomic DNA From gamma radiation damage.
PubMed:The impact of dietary isoflavonoids on malignant brain tumors.
PubMed:Ruminal Prevotella spp. may play an important role in the conversion of plant lignans into human health beneficial antioxidants.
PubMed:Identification and functional characterization of a flax UDP-glycosyltransferase glucosylating secoisolariciresinol (SECO) into secoisolariciresinol monoglucoside (SMG) and diglucoside (SDG).
PubMed:Isolation, characterization and antihyperlipidemic activity of secoisolariciresinol diglucoside in poloxamer-407-induced experimental hyperlipidemia.
PubMed:Secoisolariciresinol Diglucoside (SDG) Isolated from Flaxseed, an Alternative to ACE Inhibitors in the Treatment of Hypertension.
PubMed:Permeability and conjugative metabolism of flaxseed lignans by Caco-2 human intestinal cells.
PubMed:Phenolic compounds in flaxseed: a review of their properties and analytical methods. An overview of the last decade.
PubMed:Bioaccessibility of lignans from flaxseed (Linum usitatissimum L.) determined by single-batch in vitro simulation of the digestive process.
PubMed:Synthesis and antioxidant evaluation of (S,S)- and (R,R)-secoisolariciresinol diglucosides (SDGs).
PubMed:Cloning, expression, and characterization of the β-glucosidase hydrolyzing secoisolariciresinol diglucoside to secoisolariciresinol from Bacteroides uniformis ZL1.
PubMed:Flaxseed (Linum usitatissimum L.) extract as well as (+)-secoisolariciresinol diglucoside and its mammalian derivatives are potent inhibitors of α-amylase activity.
PubMed:Radiation mitigating properties of the lignan component in flaxseed.
PubMed:Antidiabetic effect of secoisolariciresinol diglucoside in streptozotocin-induced diabetic rats.
PubMed:Flaxseed - a miraculous defense against some critical maladies.
PubMed:The biomedical potential of genetically modified flax seeds overexpressing the glucosyltransferase gene.
PubMed:Investigation of in vitro and in vivo antioxidant potential of secoisolariciresinol diglucoside.
PubMed:Radioprotective role in lung of the flaxseed lignan complex enriched in the phenolic secoisolariciresinol diglucoside (SDG).
PubMed:Flaxseed lignan complex administration in older human type 2 diabetics manages central obesity and prothrombosis-an invitation to further investigation into polypharmacy reduction.
PubMed:Among plant lignans, pinoresinol has the strongest antiinflammatory properties in human intestinal Caco-2 cells.
PubMed:Evaluation of the efficacy of flaxseed meal and flaxseed extract in reducing menopausal symptoms.
PubMed:Production of secoisolariciresinol from defatted flaxseed by bacterial biotransformation.
PubMed:[Nutritional value and functional properties of flaxseed].
PubMed:Lignans in seeds of Linum species.
PubMed:[Effects of secoisolariciresinol diglucoside combined with bortezomib on induction of apoptosis in lung cancer cell line A549].
PubMed:Concentration kinetics of secoisolariciresinol diglucoside and its biosynthetic precursor coniferin in developing flaxseed.
PubMed:Flaxseed bioactive compounds change milk, hormonal and biochemical parameters of dams and offspring during lactation.
PubMed:Potential effects of lignan-enriched flaxseed powder on bodyweight, visceral fat, lipid profile, and blood pressure in rats.
PubMed:A review of animal and human studies for management of benign prostatic hyperplasia with natural products: perspective of new pharmacological agents.
PubMed:Qualitative and quantitative analysis of the major phenolic compounds as antioxidants in barley and flaxseed hulls using HPLC/MS/MS.
PubMed: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.
PubMed:Lignan transformation by gut bacteria lowers tumor burden in a gnotobiotic rat model of breast cancer.
PubMed:[Effects of flaxseed extract on rheological properties of blood in experimental ovariectomy].
PubMed:Abscisic acid regulates pinoresinol-lariciresinol reductase gene expression and secoisolariciresinol accumulation in developing flax (Linum usitatissimum L.) seeds.
PubMed:Role of bifidobacteria in the activation of the lignan secoisolariciresinol diglucoside.
PubMed:Effects of flaxseed lignan and oil on bone health of breast-tumor-bearing mice treated with or without tamoxifen.
PubMed:IR and Raman studies of oil and seedcake extracts from natural and genetically modified flax seeds.
PubMed:Effect of flaxseed lignans added to milk or fed to cows on oxidative degradation of dairy beverages enriched with polyunsaturated fatty acids.
PubMed:Cytostatic inhibition of cancer cell growth by lignan secoisolariciresinol diglucoside.
PubMed:Natural products in regression and slowing of progression of atherosclerosis.
PubMed:Flaxseed lignan lowers blood cholesterol and decreases liver disease risk factors in moderately hypercholesterolemic men.
PubMed:Extraction of lignans from flaxseed and evaluation of their biological effects on breast cancer MCF-7 and MDA-MB-231 cell lines.
PubMed:The effect of secoisolariciresinol diglucoside and flaxseed oil, alone and in combination, on MCF-7 tumor growth and signaling pathways.
PubMed:Bacterial transformation of dietary lignans in gnotobiotic rats.
PubMed:Health effects with consumption of the flax lignan secoisolariciresinol diglucoside.
PubMed:Dietary flaxseed lignan or oil combined with tamoxifen treatment affects MCF-7 tumor growth through estrogen receptor- and growth factor-signaling pathways.
PubMed:Concentration of the mammalian lignans enterolactone and enterodiol in milk of cows fed diets containing different concentrations of whole flaxseed.
PubMed:Flaxseed and pure secoisolariciresinol diglucoside, but not flaxseed hull, reduce human breast tumor growth (MCF-7) in athymic mice.
PubMed:Vitexins, nature-derived lignan compounds, induce apoptosis and suppress tumor growth.
PubMed:Weekly excretion of the mammalian lignan enterolactone in milk of dairy cows fed flaxseed meal.
PubMed:Further studies on a human intestinal bacterium Ruminococcus sp. END-1 for transformation of plant lignans to mammalian lignans.
PubMed:Flaxseed and cardiovascular health.
PubMed:Ruminal metabolism of flaxseed ( Linum usitatissimum) lignans to the mammalian lignan enterolactone and its concentration in ruminal fluid, plasma, urine and milk of dairy cows.
PubMed: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.
PubMed:Effects of the flaxseed lignans secoisolariciresinol diglucoside and its aglycone on serum and hepatic lipids in hyperlipidaemic rats.
PubMed:The chain length of lignan macromolecule from flaxseed hulls is determined by the incorporation of coumaric acid glucosides and ferulic acid glucosides.
PubMed:Patented techniques for the extraction and isolation of secoisolari-ciresinol diglucoside from flaxseed.
PubMed:Determination of lignans in flaxseed using liquid chromatography with time-of-flight mass spectrometry.
PubMed:Hydrolysis kinetics of secoisolariciresinol diglucoside oligomers from flaxseed.
PubMed:Validation of a reversed phase high performance thin layer chromatographic-densitometric method for secoisolariciresinol diglucoside determination in flaxseed.
PubMed:Effect of feeding flax or linseed meal on progesterone clearance rate in ovariectomized ewes.
PubMed:The effect of a lignan complex isolated from flaxseed on inflammation markers in healthy postmenopausal women.
PubMed:Metabolism of the lignan macromolecule into enterolignans in the gastrointestinal lumen as determined in the simulator of the human intestinal microbial ecosystem.
PubMed:Lignans are accessible to human breast cancer xenografts in athymic mice.
PubMed:Effects of dietary flaxseed lignan extract on symptoms of benign prostatic hyperplasia.
PubMed:Separation and determination of secoisolariciresinol diglucoside oligomers and their hydrolysates in the flaxseed extract by high-performance liquid chromatography.
PubMed:Flaxseed lignan attenuates high-fat diet-induced fat accumulation and induces adiponectin expression in mice.
PubMed:Hydroxycinnamic acids are ester-linked directly to glucosyl moieties within the lignan macromolecule from flaxseed hulls.
PubMed:Dietary flaxseed lignan extract lowers plasma cholesterol and glucose concentrations in hypercholesterolaemic subjects.
PubMed:Enhancing lignan biosynthesis by over-expressing pinoresinol lariciresinol reductase in transgenic wheat.
PubMed:Secoisolariciresinol diglucoside induces neovascularization-mediated cardioprotection against ischemia-reperfusion injury in hypercholesterolemic myocardium.
PubMed:Enantioselective dehydroxylation of enterodiol and enterolactone precursors by human intestinal bacteria.
PubMed:Regression of hypercholesterolemic atherosclerosis in rabbits by secoisolariciresinol diglucoside isolated from flaxseed.
PubMed:Regulation of zinc transporters by dietary flaxseed lignan in human breast cancer xenografts.
PubMed:Antioxidant activities of the flaxseed lignan secoisolariciresinol diglucoside, its aglycone secoisolariciresinol and the mammalian lignans enterodiol and enterolactone in vitro.
PubMed:Microwave-assisted extraction of the main phenolic compounds in flaxseed.
PubMed:Determination of mammalian lignans in biological samples by modified gas chromatography/mass spectrometry.
PubMed:Purification of secoisolariciresinol diglucoside with column chromatography on a sephadex LH-20.
PubMed:Isolation and characterization of a human intestinal bacterium, Eubacterium sp. ARC-2, capable of demethylating arctigenin, in the essential metabolic process to enterolactone.
PubMed:Feeding flaxseed oil but not secoisolariciresinol diglucoside results in higher bone mass in healthy rats and rats with kidney disease.
PubMed:AAPH-mediated antioxidant reactions of secoisolariciresinol and SDG.
PubMed: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.
PubMed:The flavonoid herbacetin diglucoside as a constituent of the lignan macromolecule from flaxseed hulls.
PubMed:Secoisolariciresinol diglucoside: relevance to angiogenesis and cardioprotection against ischemia-reperfusion injury.
PubMed:Effect of processing and storage on the stability of flaxseed lignan added to dairy products.
PubMed:Suppression of hypercholesterolemic atherosclerosis by pentoxifylline and its mechanism.
PubMed:Daily consumption for six weeks of a lignan complex isolated from flaxseed does not affect endothelial function in healthy postmenopausal women.
PubMed:Assessing exposure to lignans and their metabolites in humans.
PubMed:Flax lignans--analytical methods and how they influence our lunderstanding of biological activity.
PubMed:Pinoresinol-lariciresinol reductase gene expression and secoisolariciresinol diglucoside accumulation in developing flax (Linum usitatissimum) seeds.
PubMed:Occurrence and activity of human intestinal bacteria involved in the conversion of dietary lignans.
PubMed:Sesamin is one of the major precursors of mammalian lignans in sesame seed (Sesamum indicum) as observed in vitro and in rats.
PubMed:High accumulation of dehydrodiconiferyl alcohol-4-beta-D: -glucoside in free and immobilized Linum usitatissimum cell cultures.
PubMed:Contribution of linseed intake to urine and serum enterolignan levels in German females: a randomised controlled intervention trial.
PubMed:Analysis of enterolignan glucuronides in serum and urine by HPLC-ESI-MS.
PubMed:Phylogeny of human intestinal bacteria that activate the dietary lignan secoisolariciresinol diglucoside.
PubMed:Effect of processing and storage on the stability of flaxseed lignan added to bakery products.
PubMed:A lignan complex isolated from flaxseed does not affect plasma lipid concentrations or antioxidant capacity in healthy postmenopausal women.
PubMed:Intestinal bacterial communities that produce active estrogen-like compounds enterodiol and enterolactone in humans.
PubMed:Flaxseed and its components reduce metastasis after surgical excision of solid human breast tumor in nude mice.
PubMed:Pharmacokinetics of enterolignans in healthy men and women consuming a single dose of secoisolariciresinol diglucoside.
PubMed:Hypocholesterolemic and antiatherosclerotic effect of flax lignan complex isolated from flaxseed.
PubMed:High-performance thin-layer chromatographic-densitometric determination of secoisolariciresinol diglucoside in flaxseed.
PubMed:The effects of dietary flaxseed on the Fischer 344 rat: II. Liver gamma-glutamyltranspeptidase activity.
PubMed:Dietary secoisolariciresinol diglucoside and its oligomers with 3-hydroxy-3-methyl glutaric acid decrease vitamin E levels in rats.
PubMed:Mammary gland morphogenesis is enhanced by exposure to flaxseed or its major lignan during suckling in rats.
PubMed:The effect of flax seed cultivars with differing content of alpha-linolenic acid and lignans on responses to mental stress.
PubMed: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.
PubMed:High-performance liquid chromatographic analysis of secoisolariciresinol diglucoside and hydroxycinnamic acid glucosides in flaxseed by alkaline extraction.
PubMed:Exposure to flaxseed or its purified lignan during suckling inhibits chemically induced rat mammary tumorigenesis.
PubMed:Flaxseed: a source of hypocholesterolemic and antiatherogenic agents.
PubMed:Transformation of arctiin to estrogenic and antiestrogenic substances by human intestinal bacteria.
PubMed:On-line liquid-chromatography-nuclear magnetic resonance spectroscopy-mass spectrometry coupling for the separation and characterization of secoisolariciresinol diglucoside isomers in flaxseed.
PubMed:Isolation of the lignan secoisolariciresinol diglucoside from flaxseed (Linum usitatissimum L.) by high-speed counter-current chromatography.
PubMed:Biosynthetic pathway to the cancer chemopreventive secoisolariciresinol diglucoside-hydroxymethyl glutaryl ester-linked lignan oligomers in flax (Linum usitatissimum) seed.
PubMed:An oligomer from flaxseed composed of secoisolariciresinoldiglucoside and 3-hydroxy-3-methyl glutaric acid residues.
PubMed:Secoisolariciresinol diglucoside from flaxseed delays the development of type 2 diabetes in Zucker rat.
PubMed:Exposure to flaxseed or purified lignan during lactation influences rat mammary gland structures.
PubMed:HPLC method for analysis of secoisolariciresinol diglucoside in flaxseeds.
PubMed:Human intestinal bacteria capable of transforming secoisolariciresinol diglucoside to mammalian lignans, enterodiol and enterolactone.
PubMed:Plasma insulin-like growth factor I levels in rats are reduced by dietary supplementation of flaxseed or its lignan secoisolariciresinol diglycoside.
PubMed:Antioxidant Activity of Secoisolariciresinol Diglucoside-derived Metabolites, Secoisolariciresinol, Enterodiol, and Enterolactone.
PubMed:Quantitation of the lignan secoisolariciresinol diglucoside in baked goods containing flax seed or flax meal.
PubMed:Urinary composition and postprandial blood changes in H-secoisolariciresinol diglycoside (SDG) metabolites in rats do not differ between acute and chronic SDG treatments.
PubMed:Oxidative stress as a mechanism of diabetes in diabetic BB prone rats: effect of secoisolariciresinol diglucoside (SDG).
PubMed:Protective effect of secoisolariciresinol diglucoside against streptozotocin-induced diabetes and its mechanism.
PubMed:Antioxidant activity of the flaxseed lignan secoisolariciresinol diglycoside and its mammalian lignan metabolites enterodiol and enterolactone.
PubMed:Dose effects of flaxseed and its lignan on N-methyl-N-nitrosourea-induced mammary tumorigenesis in rats.
PubMed:Dietary supplementation with secoisolariciresinol diglycoside (SDG) reduces experimental metastasis of melanoma cells in mice.
PubMed:Reduction of serum cholesterol and hypercholesterolemic atherosclerosis in rabbits by secoisolariciresinol diglucoside isolated from flaxseed.
PubMed:Chronic exposure to secoisolariciresinol diglycoside alters lignan disposition in rats.
PubMed:Hydroxyl radical-scavenging property of secoisolariciresinol diglucoside (SDG) isolated from flax-seed.
PubMed:Flaxseed and its lignan and oil components reduce mammary tumor growth at a late stage of carcinogenesis.
PubMed:The influence of flaxseed and lignans on colon carcinogenesis and beta-glucuronidase activity.
PubMed:Investigation of mammalian lignan precursors in flax seed: first evidence of secoisolariciresinol diglucoside in two isomeric forms by liquid chromatograph/mass spectrometry.
PubMed:Revealing the mammalian lignan precursor secoisolariciresinol diglucoside in flax seed by ionspray mass spectrometry.
 
Notes:
major precursor of mammalian lignans.
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