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isosilybin
4H-1-benzopyran-4-one, 2-(2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-1,4-benzodioxin-6-yl)-2,3-dihydro-3,5,7-trihydroxy-

Supplier Sponsors

Name:3,5,7-trihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one
CAS Number: 72581-71-6Picture of molecule3D/inchi
FDA UNII: Search
Nikkaji Web:J458.501A
MDL:MFCD09842608
XlogP3-AA:2.40 (est)
Molecular Weight:482.44234000
Formula:C25 H22 O10
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
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Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Soluble in:
 water, 77.36 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.
Isosilybin 98%
BOC Sciences
For experimental / research use only.
Isosilybin >98%
Odor: characteristic
Use: Useful in the treatment of liver disease.
Carbosynth
For experimental / research use only.
Isosilybin
Santa Cruz Biotechnology
For experimental / research use only.
isoSilybin
Sigma-Aldrich: Sigma
For experimental / research use only.
Isosilybin ≥98% (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:
natural substances and extractives
Recommendation for isosilybin usage levels up to:
 not for fragrance use.
 
Recommendation for isosilybin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :3085830
National Institute of Allergy and Infectious Diseases:Data
3,5,7-trihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one
Chemidplus:0072581716
 
References:
 3,5,7-trihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:72581-71-6
Pubchem (cid):3085830
Pubchem (sid):135233928
 
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
KEGG (GenomeNet):C16808
HMDB (The Human Metabolome Database):HMDB33322
FooDB:FDB011349
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 milk thistle
Search Trop Picture
 
Synonyms:
4H-1-benzopyran-4-one, 2-(2,3-dihydro-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-1,4-benzodioxin-6-yl)-2,3-dihydro-3,5,7-trihydroxy-
3,5,7-trihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one
 

Articles:

PubMed:Chemoenzymatic Synthesis, Characterization, and Scale-up of Milk Thistle Flavonolignan Glucuronides.
PubMed:Synchronous microencapsulation of multiple components in silymarin into PLGA nanoparticles by an emulsification/solvent evaporation method.
PubMed:Pyranone natural products as inspirations for catalytic reaction discovery and development.
PubMed:Accumulation of silymarin in milk thistle seeds under drought stress.
PubMed:A biomimetic strategy to access the silybins: total synthesis of (-)-isosilybin A.
PubMed:The effects of milk thistle (Silybum marianum) on human cytochrome P450 activity.
PubMed:Isolation and purification of diastereoisomeric flavonolignans from silymarin by binary-column recycling preparative high-performance liquid chromatography.
PubMed:Simplified procedure of silymarin extraction from Silybum marianum L. Gaertner.
PubMed:Identification of isosilybin a from milk thistle seeds as an agonist of peroxisome proliferator-activated receptor gamma.
PubMed:Flavonolignans from Aspergillus iizukae, a fungal endophyte of milk thistle (Silybum marianum).
PubMed:Biotransformation on the flavonolignan constituents of Silybi Fructus by an intestinal bacterial strain Eubacterium limosum ZL-II.
PubMed:Mechanistic study of the biomimetic synthesis of flavonolignan diastereoisomers in milk thistle.
PubMed:An assessment of pharmacokinetics and antioxidant activity of free silymarin flavonolignans in healthy volunteers: a dose escalation study.
PubMed:A systematic approach to evaluate herb-drug interaction mechanisms: investigation of milk thistle extracts and eight isolated constituents as CYP3A inhibitors.
PubMed:Milk thistle's active components silybin and isosilybin: novel inhibitors of PXR-mediated CYP3A4 induction.
PubMed:HiFSA fingerprinting applied to isomers with near-identical NMR spectra: the silybin/isosilybin case.
PubMed:Synchronized and controlled release of multiple components in silymarin achieved by the osmotic release strategy.
PubMed:Absolute configuration of isosilybin A by X-ray crystallography of the heavy atom analogue 7-(4-Bromobenzoyl)isosilybin A.
PubMed:Absorption and metabolism of milk thistle flavanolignans in humans.
PubMed:A sensitive LC-MS/MS assay for the simultaneous analysis of the major active components of silymarin in human plasma.
PubMed:Angiopreventive efficacy of pure flavonolignans from milk thistle extract against prostate cancer: targeting VEGF-VEGFR signaling.
PubMed:Pyrazinecarboxamides as potential elicitors of flavonolignan and flavonoid production in Silybum marianum and Ononis arvensis cultures in vitro.
PubMed:Electrochemical investigation of flavonolignans and study of their interactions with DNA in the presence of Cu(II).
PubMed:Effects of silymarin nanoemulsion against carbon tetrachloride-induced hepatic damage.
PubMed:Isosilybin A induces apoptosis in human prostate cancer cells via targeting Akt, NF-κB, and androgen receptor signaling.
PubMed:Enhanced production of silymarin by Ag+ elicitor in cell suspension cultures of Silybum marianum.
PubMed:Identification of hepatoprotective flavonolignans from silymarin.
PubMed:Large-scale isolation of flavonolignans from Silybum marianum extract affords new minor constituents and preliminary structure-activity relationships.
PubMed:Two flavonolignans from milk thistle (Silybum marianum) inhibit CYP2C9-mediated warfarin metabolism at clinically achievable concentrations.
PubMed:Influence of exogenous salicylic acid on flavonolignans and lipoxygenase activity in the hairy root cultures of Silybum marianum.
PubMed:[Silymarin in the treatment of chronic liver diseases: past and future].
PubMed:Isosilibinin inhibits advanced human prostate cancer growth in athymic nude mice: comparison with silymarin and silibinin.
PubMed:Hepatic metabolism and biliary excretion of silymarin flavonolignans in isolated perfused rat livers: role of multidrug resistance-associated protein 2 (Abcc2).
PubMed:Identifying the differential effects of silymarin constituents on cell growth and cell cycle regulatory molecules in human prostate cancer cells.
PubMed:New insight into the biosynthesis of flavanolignans in the white-flowered variant of Silybum marianum.
PubMed:Isosilybin B causes androgen receptor degradation in human prostate carcinoma cells via PI3K-Akt-Mdm2-mediated pathway.
PubMed:Gram-scale purification of flavonolignan diastereoisomers from Silybum marianum (Milk Thistle) extract in support of preclinical in vivo studies for prostate cancer chemoprevention.
PubMed:Pharmacokinetics and metabolic profile of free, conjugated, and total silymarin flavonolignans in human plasma after oral administration of milk thistle extract.
PubMed:Inhibition of T-cell inflammatory cytokines, hepatocyte NF-kappaB signaling, and HCV infection by standardized Silymarin.
PubMed:Isosilybin B and isosilybin A inhibit growth, induce G1 arrest and cause apoptosis in human prostate cancer LNCaP and 22Rv1 cells.
PubMed:Hepatoprotective herbal drug, silymarin from experimental pharmacology to clinical medicine.
PubMed:Anticancer potential of silymarin: from bench to bed side.
PubMed:Synchronized and sustained release of multiple components in silymarin from erodible glyceryl monostearate matrix system.
PubMed:Structure elucidation and antioxidant activity of (-)-isosilandrin isolated from Silybum marianum L.
PubMed:Analysis and comparison of active constituents in commercial standardized silymarin extracts by liquid chromatography-electrospray ionization mass spectrometry.
PubMed:Separation and characterization of silybin, isosilybin, silydianin and silychristin in milk thistle extract by liquid chromatography-electrospray tandem mass spectrometry.
PubMed:Silymarin and silibinin cause G1 and G2-M cell cycle arrest via distinct circuitries in human prostate cancer PC3 cells: a comparison of flavanone silibinin with flavanolignan mixture silymarin.
PubMed:Milk thistle and prostate cancer: differential effects of pure flavonolignans from Silybum marianum on antiproliferative end points in human prostate carcinoma cells.
PubMed:Molecular structure and stereochemistry of silybin A, silybin B, isosilybin A, and isosilybin B, Isolated from Silybum marianum (milk thistle).
PubMed:Analysis of the active components of silymarin.
PubMed:Primary cultures of human hepatocytes as a tool in cytotoxicity studies: cell protection against model toxins by flavonolignans obtained from Silybum marianum.
PubMed:[Determination of the active flavonoids in silymarine].
PubMed:Inhibition of the superoxide anion release and hydrogen peroxide formation in PMNLs by flavonolignans.
PubMed:Determination of active component in silymarin by RP-LC and LC/MS.
PubMed:[Separation and determination of effective components in silymarin and preparations of silymarin by MECC].
PubMed:Flavonolignan production from Silybum marianum transformed and untransformed root cultures.
PubMed:Comparative pharmacokinetics of silipide and silymarin in rats.
PubMed:Pharmacokinetics of silybin in bile following administration of silipide and silymarin in cholecystectomy patients.
PubMed:Effect of the flavanolignans of Silybum marianum L. on lipid peroxidation in rat liver microsomes and freshly isolated hepatocytes.
PubMed:[Structure of silandrin and silymonin, two new flavanolignans from a white blooming Silybum marianum variety].
 
Notes:
flavanolignan from silybum marianum. Constit. of Silybum marianum (milk thistle)
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