Silibinin
Grundinformationen
- CAS
22888-70-6- Standard-SMILES
COc1cc([C@H]2Oc3cc([C@H]4Oc5cc(O)cc(O)c5C(=O)[C@@H]4O)ccc3O[C@@H]2CO)ccc1O- InChIKey
SEBFKMXJBCUCAI-HKTJVKLFSA-N- Summenformel
- C25H22O10
- Durchschnittliche Molmasse
- 482,4 g/mol
- Monoisotopische Masse
- 482,12129689
Überblick
Silibinin is a flavonolignan isolated from milk thistle, Silybum marianum, that has been shown to exhibit antioxidant and antineoplastic activities. It has a role as an antioxidant, an antineoplastic agent, a hepatoprotective agent and a plant metabolite. It is a secondary alpha-hydroxy ketone, a polyphenol, an aromatic ether, a benzodioxine and a flavonolignan.
Namen und Bezeichner
- Bevorzugter Name
- Silibinin
- IUPAC
- (2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one
- Lokaler Name
- Silibinin
- Englischer Name
- Silybin
- Summenformel
- C25H22O10
- Molmasse
- 482.44
Namen und Synonyme
silibininSilymarin IFlavobinSilybineSilibininaSilibinineSilliverSilymarine ISilibininumLegalon(2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-oneCHEBI:9144
Weitere Namen anzeigen
SILYBINSILYBIN ASILYBININSilybin(Silibinin)Sylibinybin7c3mtMepasilRealsil
(2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro-4H-chromen-4-oneSilibinin a-silibinin b mixt.(2R,3R)-3,5,7-trihydroxy-2-((2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl)-2,3-dihydro-4H-chromen-4-one(2R,3R)-3,5,7-trihydroxy-2-((2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl)-2,3-dihydrochromen-4-oneRefChem:1830594RKY41TBTF245-302-5(2R,3R)-3,5,7-trihydroxy-2-(3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl)-2,3-dihydrochromen-4-one
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2,4
- Polarare Oberfläche (TPSA)
- 155 Ų
- H-Brücken-Donoren
- 5
- H-Brücken-Akzeptoren
- 10
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 35
- Formalladung
- 0
- Komplexität
- 750
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavanones [PK1214]
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section
208.16 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
213.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physikochemische Eigenschaften
- Schmelzpunkt
- 164 · 164-174°C
- Siedepunkt
- 793 · 793.0±60.0 °C(Predicted)
- Dichte
- 1.527 · 1.527±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- Löslichkeit
- Acetone (Sparingly), DMSO, Methano (Sparingly)
- Aggregatzustand
- Solid
- pka
- 6.42 · pKa 6.42±0.04 (Uncertain)
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 9.6% (5 of 52) of reports.
Warning
H315 (82.7%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 52 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory InformationChemical: 4H-1-Benzopyran-4-one, 2-[(2R,3R)-2,3-dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-1,4-benzodioxin-6-yl]-2,3-dihydro-3,5,7-trihydroxy-, (2R,3R)-
Hazard Classes and CategoriesSkin Irrit. 2 (82.7%)
Sicherheitsdaten
- wgk
- 3
- ridadr
- 3172
- hs_code
- 29329990
- RTECS-Nr.
- DJ2981770
- risk_code
- 36/37/38
- Toxizität
- LD50 intravenous in mouse: 1056mg/kg
- hazard_code
- Xi
- safety_code
- 26-37/39-24/25-22-36
- Speicherklasse
- 11 - Combustible Solids
- Hazard Classifications
- Acute Tox. 4 Oral
Chemie und Industrie
Pharmakologische Informationen
Metabolism/MetabolitesSilybin has known human metabolites that include O-demethylated-silybin.
MeSH Pharmacological Classification
Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.
Synthetic or natural substances which are given to prevent a disease or disorder or are used in the process of treating a disease or injury due to a poisonous agent.
Anwendungen
BeschreibungSilybin, also known as silibinin, is the principal biologically active constituent of the silymarin complex (about 70–80%) and is a mixture of silybin A and silybin B. Pharmacological research demonstrated that silybin has shown pleiotropic biological properties, including potent antioxidant, anti-inflammatory, anticancer, antidiabetic, hepatoprotective, neuroprotective, antiviral, antimicrobial and immunosuppressive activities. Silibinin demonstrates promising anticancer effects in vitro and in vivo[1].
VerwendenSilibinin has been used:to study its effect on gene expression levels of various proteins involved in chromatin regulations of prostate cancer, by real time polymerase chain reaction (RT-PCR)to study its effect on cell proliferation in platelet-derived growth factor (PDGF)-treated human tenon′s fibroblasts (HTFs) by investigating the expression of proliferating cell nuclear antigen (PCNA) and by water-soluble tetrazolium salt (WST-1) assayto examine its effect on gene expression levels of stromelysine 1 (STM1), acetyl hexoseamines and collagen production during skin wound healingto study its inhibitory effect on Escherichia coli ATP synthase
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