Pterostilbene

HCID 5281727CAS 18259-15-9

Grundinformationen

Standard-SMILES
COc1cc(/C=C/c2ccc(O)cc2)cc(OC)c1
InChIKey
VLEUZFDZJKSGMX-ONEGZZNKSA-N
Summenformel
C16H16O3
Durchschnittliche Molmasse
256,3 g/mol
Monoisotopische Masse
256,10994437

Überblick

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.

Namen und Bezeichner

Bevorzugter Name
Pterostilbene
IUPAC
4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenol
Englischer Name
Pterostilbene
Summenformel
C16H16O3
Molmasse
256.3

Namen und Synonyme

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
Weitere Namen anzeigen
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

Datenbank-Bezeichner

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

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,8
Polarare Oberfläche (TPSA)
38,7 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
4
Schwere Atome
19

Experimentelle und physikochemische Eigenschaften

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

Physikochemische Eigenschaften

Schmelzpunkt
89 · 89-92 ºC
Siedepunkt
420.4 · 420.4±35.0 °C(Predicted)
Dichte
1.169 · 1.169±0.06 g/cm3(Predicted)
storage temp.
2 · 2-8°C
Löslichkeit
20 mg/mL · DMSO: >20mg/mL
pka
9.96 · 9.96±0.26(Predicted)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

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.

Gefahrenhinweise

Hazard Classes and CategoriesEye Dam. 1 (100%)

Sicherheitsdaten

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

Chemie und Industrie

Pharmakologische Informationen

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.
Anwendungen · 3 Einträge

BeschreibungPterostilbene (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.

OccurrencePterostilbene 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.

VerwendenSubstantial 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)

Darstellung

synthetischePterostilbene 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%.

Vor- und nachgelagerte Produkte

Anbieter50 Anbieter

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
Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: 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.

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