基本情報
- CAS
22888-70-6- 標準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- 分子式
- C25H22O10
- 平均分子量
- 482.4 g/mol
- 単同位体質量
- 482.12129689
概要
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.
名称と識別子
- 優先名称
- 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
- 現地名
- シリビニン
- 英語名
- Silybin
- 分子式
- C25H22O10
- 分子量
- 482.44
名称と別名
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
名称をさらに表示
(2R,3R)-3,5,7-トリヒドロキシ-2-[(2R,3R)-3-(4-ヒドロキシ-3-メトキシフェニル)-2-(ヒドロキシメチル)-2,3-ジヒドロ-1,4-ベンゾジオキシン-6-イル]クロマン-4-オンシリビン(2R,3R)-2α-[(2R,3R)-2-(3-メトキシ-4-ヒドロキシフェニル)-3-(ヒドロキシメチル)-2,3-ジヒドロ-1,4-ベンゾジオキシン-7-イル]-3β,5,7-トリヒドロキシ-2,3-ジヒドロ-4H-1-ベンゾピラン-4-オン(+)-シリビンフラボビオン(2R)-2α-[[(2R,3R)-2,3-ジヒドロ-3β-(4-ヒドロキシ-3-メトキシフェニル)-2α-(ヒドロキシメチル)-1,4-ベンゾジオキシン]-6-イル]-2,3-ジヒドロ-3β,5,7-トリヒドロキシ-4H-1-ベンゾピラン-4-オン(2R,3R)-2-[[(2R)-2,3-ジヒドロ-3β-(4-ヒドロキシ-3-メトキシフェニル)-2α-(ヒドロキシメチル)-1,4-ベンゾジオキシン]-6-イル]-2,3-ジヒドロ-3,5,7-トリヒドロキシ-4H-1-ベンゾピラン-4-オンシリビンBシリビニン2α-[2α-(ヒドロキシメチル)-3β-(4-ヒドロキシ-3-メトキシフェニル)-2,3-ジヒドロ-1,4-ベンゾジオキシン-6-イル]-3β,5,7-トリヒドロキシ-2,3-ジヒドロ-4H-1-ベンゾピラン-4-オン
物性
構造計算による物性
- XLogP
- 2.4
- 極性表面積
- 155 Ų
- 水素結合供与体数
- 5
- 水素結合受容体数
- 10
- 回転可能結合数
- 4
- 重原子数
- 35
- 形式電荷
- 0
- 複雑度
- 750
実験および物理化学的性質
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]
物理化学的性質
- 融点
- 164 · 164-174°C
- 比旋光度
- 20 · D20 +11° (c = 0.25 in acetone + alcohol)
- 沸点
- 793 · 793.0±60.0 °C(Predicted)
- 比重(密度)
- 1.527 · 1.527±0.06 g/cm3(Predicted)
- 貯蔵温度
- -20 °C · -20°C
- 溶解性
- アセトン（控えめ）、DMSO、メタノ（控えめ）
- 外見
- 個体
- 酸解離定数(Pka)
- 6.42 · pKa 6.42±0.04 (Uncertain)
- 色
- ペールイエロー
- 水溶解度
- 54 mg/L · 54mg/L(24.99℃)
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
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.
危険有害性情報
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%)
安全データ
- wgk
- 3
- rtecs
- DJ2981770
- ridadr
- 3172
- 毒性
- LD50 intravenous in mouse: 1056mg/kg
- hs_code
- 29329990
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26-37/39-24/25-22-36
- Hazard Classifications
- Acute Tox. 4 Oral
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
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.
応用分野
説明Silybin, 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].
使用Silibinin 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
一般的な説明Silibinin, a principal component of silymarin, is a flavonolignan and an orally active flavonoid. It is isolated from the seeds of milk thistle (Sylibum marianum L).
上流・下流製品情報
上流原料
関連反応
1 件
化合物ノート
読み込み中…