(E)-スチルベン-3,3',4',5-テトラオール

Piceatannol

HCID 667639
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基本情報

CAS
10083-24-6
標準SMILES
Oc1cc(O)cc(/C=C/c2ccc(O)c(O)c2)c1
InChIKey
CDRPUGZCRXZLFL-OWOJBTEDSA-N
分子式
C14H12O4
平均分子量
244.24 g/mol
単同位体質量
244.07355886

概要

Piceatannol is a stilbenol that is trans-stilbene in which one of the phenyl groups is substituted by hydroxy groups at positions 3 and 4, while the other phenyl group is substituted by hydroxy groups at positions 3 and 5. It has a role as a geroprotector, a hypoglycemic agent, an antineoplastic agent, a protein kinase inhibitor, a tyrosine kinase inhibitor, an apoptosis inducer and a plant metabolite. It is a polyphenol, a member of catechols, a member of resorcinols and a stilbenol. It derives from a hydride of a trans-stilbene.

名称と識別子

優先名称
Piceatannol
IUPAC
4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol
現地名
(E)-スチルベン-3,3',4',5-テトラオール
英語名
PICEATANNOL
分子式
C14H12O4
分子量
244.24

名称と別名

piceatannol10083-24-6trans-Piceatannol3-Hydroxyresveratol(E)-PiceatannolAstringenin3,3',4'5-Tetrahydroxystilbene4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol3,4,3',5'-tetrahydroxy-trans-stilbene4-[(E)-2-(3,5-dihydroxyphenyl)vinyl]benzene-1,2-diol3,3',4,5'-Tetrahydroxy-trans-stilbene6KS3LS0D4F
名称をさらに表示
アストリンゲニン(E)-ピセアタンノールtrans-ピセアタンノール(E)-3,3',4,5'-テトラヒドロキシスチルベンピセタンノールピセンアタンノール(E)-スチルベン-3,3',4',5-テトラオール(E)-スチルベン-3,3',4,5'-テトラオールピセアタンノール5-[(E)-2-(3,4-ジヒドロキシフェニル)ビニル]-1,3-ベンゼンジオール3,4,3′,5′-テトラヒドロキシ-TRANS-スチルベン3,3',4,5'-テトラヒドロキシ-trans-スチルベンピセタノール(E)-3,3′,4,5′-テトラヒドロキシスチルベン(E)-スチルベン-3,3′,4,5′-テトラオール5-[(1E)-2-(3,4-ジヒドロキシフェニル)エテニル]ベンゼン-1,3-ジオール(E)-スチルベン-3,3′,4′,5-テトラオールPiceatanlBeryl alcohol20MG/50MG/100GPiceatannol>
NSC-365798NSC-622471DB08399trans-3,3',4,5'-TetrahydroxystilbeneJ61.264BCHEBI:28814C059013,3',4,5'-STILBENETETROL, (E)-

データベース識別子

CAS
10083-24-6、4339-71-3
PubChem CID
667639
DTXSID
DTXSID6040587
ChEMBL
CHEMBL69863
ChEBI
CHEBI:28814
UNII
6KS3LS0D4F
EC Number
600-132-4
Nikkaji
J393.773I、J61.264B

物性

構造計算による物性

XLogP
2.9
極性表面積
80.9 Ų
水素結合供与体数
4
水素結合受容体数
4
回転可能結合数
2
重原子数
18

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]
LogP2.11
Endocrine DisruptorsPotential endocrine disrupting compound
Physical DescriptionSolid

物理化学的性質

融点
223 · 223.0-227.0 °C
沸点
108 °C/0.04mmHg · 108°C/0.04mmHg(lit.)
比重(密度)
1.1245 · 1.1245 (rough estimate)
屈折率
1.519 · 1.5190 (estimate)
貯蔵温度
2 · 2-8°C
溶解性
2 O: · H2O: 0.5 mg/mL

化学的性質

化学的特性yellow to golden or green crystalline powder

安全と法規制

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 50% (1 of 2) of reports.

Warning

H302+H312+H332 (50%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]

P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, 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.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 4 (50%)

安全データ

wgk
3
hs_code
29072990
safety_code
24/25
Hazard Classifications
Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 Oral
ストレージクラス
11 - Combustible Solids

化学と産業

薬理情報

Tissue LocationsPlacenta
Cellular LocationsMembrane
応用分野 · 2 件

使用A human metabolite of Resveratrol (R150000). Piceatannol is strong anti-oxidant.

一般的な説明A cell-permeable, substrate competitive and reversible plant metabolite that inhibits the activity of rat liver protein kinase A catalytic subunit (IC50 = 3 μM), PKC (IC50 = 8 μM), MLCK (IC50 = 12 μM). In RBL-2H3 cells, the selective inhibition of Syk by piceatannol results in inhibition of FceR1-mediated signaling. Also inhibits wheat embryo Ca2+-dependent protein kinase (CDPK) (IC50 = 19 μM), and p72syk (IC50 = 10 μM), a non-receptor tyrosine kinase, relative to Lyn in isolated enzyme preparations. Also possesses anti-leukemic properties. Reported to activate sirtuins and promote the survival of eukaryotic cells.

上流・下流製品情報

サプライヤー100 社

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
Syntechem Co.,Ltd[email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
上海波以尔化工有限公司[email protected]

補足説明

定義ChEBI: A stilbenol that is trans-stilbene in which one of the phenyl groups is substituted by hydroxy groups at positions 3 and 4, while the other phenyl group is substituted by hydroxy groups at positions 3 and 5.

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