(E)-3',5'-ジメトキシスチルベン-4-オール

Pterostilbene

HCID 5281727
ノート反応
部分構造検索類似構造を探す

基本情報

CAS
18259-15-9
標準SMILES
COc1cc(/C=C/c2ccc(O)cc2)cc(OC)c1
InChIKey
VLEUZFDZJKSGMX-ONEGZZNKSA-N
分子式
C16H16O3
平均分子量
256.3 g/mol
単同位体質量
256.10994437

概要

Pterostilbene is a stilbenol that consists of trans-stilbene bearing a hydroxy group at position 4 as well as two methoxy substituents at positions 3' and 5'. It has a role as an antioxidant, a neurotransmitter, a hypoglycemic agent, an antineoplastic agent, a radical scavenger, a neuroprotective agent, an anti-inflammatory agent, an apoptosis inducer and a plant metabolite. It is a stilbenol, a diether and a member of methoxybenzenes. It derives from a hydride of a trans-stilbene.

名称と識別子

優先名称
Pterostilbene
IUPAC
4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenol
現地名
(E)-3',5'-ジメトキシスチルベン-4-オール
英語名
Pterostilbene
分子式
C16H16O3
分子量
256.3

名称と別名

Pterostilbene537-42-8trans-pterostilbene4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenolpterostilbene, (E)-3',5'-Dimethoxy-4-stilbenol3,5-Dimethoxy-4'-hydroxy-trans-stilbenePhenol, 4-[(1E)-2-(3,5-dimethoxyphenyl)ethenyl]-3',5'-dimethoxy-resveratroltrans-3,5-dimethoxy-4'-hydroxystilbene3,5-Dimethoxy-4'-hydroxystilbene26R60S6A5I
名称をさらに表示
trans-プテロスチルベン4-[(E)-2-(3,5-ジメトキシフェニル)ビニル]フェノール(E)-3,5-ジメトキシ-4'-ヒドロキシスチルベン(E)-3',5'-ジメトキシスチルベン-4-オールプテロスチルベン4-[(E)-3,5-ジメトキシスチリル]フェノール4'-ヒドロキシ-3,5-ジメトキシ-trans-スチルベンtrans-1-(3,5-ジメトキシフェニル)-2-(4-ヒドロキシフェニル)エチレンTRANS‐プテロスチルベン4-[2-(3,5-ジメトキシフェニル)エテニル]フェノール4-(3,5-ジメトキシスチリル)フェノール3,5-ジメトキシ-4′-ヒドロキシ-trans-スチルベン3,5-ジメトキシ-4′-ヒドロキシスチルベン3,5-ジ-O-メチルレスベラトロールレスベラトロールジメチルエーテルpterostibenehydroxystilbenePTEROCARPUS MARSUPIUMnootropic blueberry extract PterostilbeneAKOS 236-80(Z)-3,4’-aminostilbene(E/Z)-3,4’POVIDONE USP(RG)
4-((E)-2-(3,5-dimethoxyphenyl)ethenyl)phenolCHEBI:8630DTXSID9041106phenol, 4-((1E)-2-(3,5-dimethoxyphenyl)ethenyl)-EH-301 COMPONENT PTEROSTILBENEPhenol, 4-(2-(3,5-dimethoxyphenyl)ethenyl)-, (E)-3',5'-dimethoxy-4E-stilbenol3',5'-dimethoxy-4trans-stilbenol

データベース識別子

CAS
18259-15-9、537-42-8
PubChem CID
5281727
DTXSID
DTXSID9041106
ChEMBL
CHEMBL83527
ChEBI
CHEBI:8630
UNII
26R60S6A5I
EC Number
611-041-4
Nikkaji
J11.562B、J2.032.037K

物性

構造計算による物性

XLogP
3.8
極性表面積
38.7 Ų
水素結合供与体数
1
水素結合受容体数
3
回転可能結合数
4
重原子数
19

実験および物理化学的性質

LipidsPolyketides [PK] -> Aromatic polyketides [PK13] -> Diphenyl ethers, biphenyls, dibenzyls and stilbenes [PK1309]
Endocrine DisruptorsPotential endocrine disrupting compound

物理化学的性質

融点
89 · 89-92 ºC
沸点
420.4 · 420.4±35.0 °C(Predicted)
比重(密度)
1.169 · 1.169±0.06 g/cm3(Predicted)
貯蔵温度
2 · 2-8°C
溶解性
20 mg/mL · DMSO：>20mg/mL
酸解離定数(Pka)
9.96 · 9.96±0.26(Predicted)

化学的性質

化学的特性Pterostilbene is a white crystalline powder, sensitive to air, soluble in hot methanol, DMSO, insoluble in water. It is a stilbenoid chemically similar to resveratrol and from the leguminous plant Pterocarpus indicus.

安全と法規制

GHS分類

GHS Classification · 4 件

Danger

H318 (100%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

P264+P265, P273, P280, P305+P354+P338, P317, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 1 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 CategoriesEye Dam. 1 (100%)

安全データ

wgk
3
ridadr
3077
hs_code
29095000
risk_code
41-51/53
hazard_code
Xi,N
safety_code
26-39-61

化学と産業

薬理情報

Metabolism/MetabolitesPterostilbene has known human metabolites that include (2S,3S,4S,5R)-6-[4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid.
応用分野 · 3 件

説明Pterostilbene (PTS) is a fragrant-smelling hydrocarbon called "styrene", which is a derivative of resveratrol. It is found in blueberries and Pterocarpus marsupium (PM) heartwood. Similar to resveratrol, PTS has anti-inflammatory, anti-thrombotic, anti-cancer, anti-cancer, anti-hyperlipidemia and antibacterial effects.

天然物の起源Pterostilbene is a natural molecule found in fruits, vegetables and nuts. Blueberries are often quoted as one of the richest sources of pterostilbene. It is also found in almonds,various Vaccinium berries (including blueberries), grape leaves and vines,and Pterocarpus marsupium heartwood.

使用Substantial studies demonstrate that pterostilbene has diverse pharmacological activities for the prevention and treatment of diseases including inflammation, cancer, diabetes, and dyslipidemia.Pterostilbene has been used:to investigate its anti-oxidative stress activities and the involvement of the nuclear factor (erythroid-derived 2)-like 2 (Nrf2)-antioxidant response element (ARE) signaling pathwayto determine its effects on transcriptional activation of estrogen receptor-α (ERα) in hormone resistant breast cancer cells)

調製方法

製造方法Pterostilbene was synthesized from 3,5-dimethoxybenzyl bromide and p-nitrobenzaldehyde by Witting-Hornor reaction, reduction, diazotization and hydrolysis, with a total yield of 53.9%.

上流・下流製品情報

サプライヤー100 社

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
苏州道澜生物医药科技有限公司15952404857 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
山西玉宁生物科技有限公司13623677056
補足説明 · 1 件

定義ChEBI: Pterostilbene is a stilbenol that consists of trans-stilbene bearing a hydroxy group at position 4 as well as two methoxy substituents at positions 3' and 5'. It has a role as an antioxidant, an antineoplastic agent, a neurotransmitter, a plant metabolite, an apoptosis inducer, a neuroprotective agent, an anti-inflammatory agent, a radical scavenger and a hypoglycemic agent. It is a stilbenol, a member of methoxybenzenes and a diether. It derives from a hydride of a trans-stilbene.

関連反応

5 件
反応記録を作成

化合物ノート

読み込み中…