CAS 27208-80-6 Polydatin (HCID 5281718)

概要

Trans-piceid is a stilbenoid that is trans-resveratrol substituted at position 3 by a beta-D-glucosyl residue. It has a role as a geroprotector, an antioxidant, a metabolite, an anti-arrhythmia drug, a potassium channel modulator, a hepatoprotective agent and a nephroprotective agent. It is a beta-D-glucoside, a polyphenol, a stilbenoid and a monosaccharide derivative. It is functionally related to a trans-resveratrol.

名称と識別子

優先名称: Polydatin
IUPAC: (2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[(E)-2-(4-hydroxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
現地名: (E)-5-β-D-グルコピラノシルオキシ-3,4'-スチルベンジオール
英語名: Polydatin
分子式: C20H22O8
分子量: 390.39

名称と別名

Piceid27208-80-6Trans-Piceid3,4,5-Trihydroxystilbene-3-beta-monoglucoside3,4,5-TsgResveratrol 3-beta-mono-D-glucosideResveratrol 3-O-beta-glucopyranosideXM261C37CQ3,4'-5-Trihydroxystilbene-3-beta-D-glucopyranosideresveratrol 3-O-beta-D-glucosidetrans-resveratrol 3-beta-glucosidetrans-resveratrol 3-beta-D-glucoside

名称をさらに表示

(E)-5-β-D-グルコピラノシルオキシ-3,4'-スチルベンジオールtrans-ピセイド3-(β-D-グルコピラノシルオキシ)-5-[(E)-2-(4-ヒドロキシフェニル)エテニル]フェノールピセイドレスベラトロール3-O-グルコシド(E)-5-(β-D-グルコピラノシルオキシ)スチルベン-3,4'-ジオール(E)-5'-(β-D-グルコピラノシルオキシ)スチルベン-3',4-ジオールポリダチンtrans-レスベラトロールグルコシド(E)-5-(β-D-グルコピラノシルオキシ)-3,4'-スチルベンジオール(E)-3-(β-D-グルコピラノシルオキシ)スチルベン-4',5-ジオール5-[(E)-2-(4-ヒドロキシフェニル)エテニル]-3-(β-D-グルコピラノシルオキシ)フェノール[3-ヒドロキシ-5-[(E)-4-ヒドロキシスチリル]フェニル]β-D-グルコピラノシドtrans-ポリダチン[3-[(E)-2-(4-ヒドロキシフェニル)エテニル]-5-ヒドロキシフェニル]β-D-グルコピラノシド(E)-3-(β-D-グルコピラノシルオキシ)-4',5-スチルベンジオール3-(β-D-グルコピラノシルオキシ)-5-[(E)-2-(4-ヒドロキシフェニル)ビニル]フェノール[(E)-3,4'-ジヒドロキシスチルベン]-5-イルβ-D-グルコピラノシド4',5-ジヒドロキシスチルベン-3-イルβ-D-グルコピラノシドレスベラトロール3-グルコシドResveratrol 3-O-β-D-glucopyranoside(2S,3R,4S,5S,6R)-2-(3-Hydroxy-5-((E)-4-hydroxystyryl)phenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triolPieceidPlydatinPiceid>(E)-Piceidrans-picei(E)-PolydatinPolydatin CRStrans-Polydatin

trans-resveratrol 3-O-beta-D-glucosideCHEBI:81983,4',5-trihydroxystilbene-3-beta-D-glucoside3-Hydroxy-5-(2-(4-hydroxyphenyl)ethenyl)phenyl-beta-D-glucosidebeta-D-Glucopyranoside, 3-hydroxy-5-(2-(4-hydroxyphenyl)ethenyl)phenylbeta-D-Glucopyranoside, 3-hydroxy-5-[2-(4-hydroxyphenyl)ethenyl]phenylPolydatin (E)-polydatin, (E)-

データベース識別子

CAS: 27208-80-6、65914-17-2
PubChem CID: 5281718
DTXSID: DTXSID001030555
ChEMBL: CHEMBL142652
ChEBI: CHEBI:8198
UNII: XM261C37CQ
EC Number: 111-790-2、683-198-7
Nikkaji: J17.288J、J9.897C

物性

構造計算による物性

XLogP: 1.7
極性表面積: 140 Å²
水素結合供与体数: 6
水素結合受容体数: 8
回転可能結合数: 5
重原子数: 28
形式電荷: 0
複雑度: 506

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15

LipidsPolyketides [PK] -> Aromatic polyketides [PK13] -> Diphenyl ethers, biphenyls, dibenzyls and stilbenes [PK1309]

Endocrine DisruptorsPotential endocrine disrupting compound

Melting Point130 - 140 °C

Physical DescriptionSolid

物理化学的性質

融点: 223 · 223-226 °C(lit.)
沸点: 707.7 · 707.7±60.0 °C(Predicted)
比旋光度: -77.5 · -77.5 º (c=0.2, EtOH)
比重(密度): 1.521 · 1.521±0.06 g/cm3(Predicted)
貯蔵温度: 2 · Sealed in dry,2-8°C
溶解性: DMSO、エタノール、メタノール
酸解離定数(Pka): 9.21 · 9.21±0.10(Predicted)
外見: 個体
色: オフホワイト
主な用途: 食品および飲料
InChI: InChI=1/C20H22O8/c21-10-16-17(24)18(25)19(26)20(28-16)27-15-8-12(7-14(23)9-15)2-1-11-3-5-13(22)6-4-11/h1-9,16-26H,10H2/b2-1+/t16-,17-,18+,19-,20-/s3
InChIKey: HSTZMXCBWJGKHG-RPHGGTSJNA-N
SMILES: O(C1C=C(O)C=C(/C=C/C2C=CC(O)=CC=2)C=1)[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O |&1:17,18,19,21,23,r|
LogP: 0.412 · 0.412 (est)
CAS データベース: 27208 · 27208-80-6(CAS DataBase Reference)

化学的性質

化学的特性Off-White Solid

安全と法規制

GHS分類

GHS Classification · 6 件

Danger

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, 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 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

危険有害性情報

Hazard Classes and Categories · 2 件

Skin Irrit. 2 (100%)

Eye Irrit. 2 (100%)

安全データ

wgk: 3
hs_code: 29389090
safety_code: 22-24/25
Hazard Classifications: Eye Irrit. 2
ストレージクラス: 11 - Combustible Solids

化学と産業

薬理情報

Cellular LocationsCytoplasm

応用分野 · 3 件

説明Polydatin is a stilbene glucoside and a precursor to trans-resveratrol (Item No. 70675) that has been found in V. vinifera and has diverse biological activities. It scavenges DPPH radicals and inhibits copper-induced lipid peroxidation (IC50s = 198 and 19.1 μM, respectively). Polydatin inhibits the proliferation of, and induces cell cycle arrest at the S phase in, Caco-2 colon cancer cells. It decreases infarct size, cardiomyocyte fibrosis, and apoptosis in a mouse model of myocardial ischemia-reperfusion injury induced by left anterior descending (LAD) coronary artery occlusion when administered at a dose of 40 mg/kg per day.

使用A Stilbenoid glucoside and is a major Resveratrol derivative.

一般的な説明This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

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補足説明

定義ChEBI: A stilbenoid that is trans-resveratrol substituted at position 3 by a beta-D-glucosyl residue.

化合物ノート

読み込み中…

(E)-5-β-D-グルコピラノシルオキシ-3,4'-スチルベンジオール

基本情報

概要