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Category: natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00 %
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| Food Chemicals Codex Listed: | No |
| Soluble in: |
| | water, 77.36 mg/L @ 25 °C (est) |
Organoleptic Properties:
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| Odor and/or flavor descriptions from others (if found). |
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Cosmetic Information:
Suppliers:
Safety Information:
| Preferred SDS: View |
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| Hazards identification |
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| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
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| Pictogram | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
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Not determined
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | natural substances and extractives |
| Recommendation for isosilybin usage levels up to: | | | not for fragrance use.
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| Recommendation for isosilybin flavor usage levels up to: |
| | not for flavor use.
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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:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
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]. |
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