4'-Hydroxy-3',5'-dimethoxyacetophenon

Acetosyringone

HCID 17198CAS 2478-38-8
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Grundinformationen

Standard-SMILES
COc1cc(C(C)=O)cc(OC)c1O
InChIKey
OJOBTAOGJIWAGB-UHFFFAOYSA-N
Summenformel
C10H12O4
Durchschnittliche Molmasse
196,2 g/mol
Monoisotopische Masse
196,07355886

Überblick

Acetosyringone is a member of the class of acetophenones that is 1-phenylethanone substituted by a hydroxy group at position 4 and methoxy groups at positions 3 and 5. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, a peripheral nervous system drug, an anti-asthmatic drug and a plant metabolite. It is a member of acetophenones, a member of phenols and a dimethoxybenzene.

Namen und Bezeichner

Bevorzugter Name
Acetosyringone
IUPAC
1-(4-hydroxy-3,5-dimethoxyphenyl)ethanone
Lokaler Name
4'-Hydroxy-3',5'-dimethoxyacetophenon
Englischer Name
Acetosyringone
Summenformel
C10H12O4
Molmasse
196.2

Namen und Synonyme

Acetosyringone2478-38-81-(4-Hydroxy-3,5-dimethoxyphenyl)ethanone4'-HYDROXY-3',5'-DIMETHOXYACETOPHENONEAcetosyringenin1-(4-hydroxy-3,5-dimethoxyphenyl)ethan-1-one866P45Y84SCHEBI:2404DTXSID2062454RefChem:552431DTXCID1037147219-610-5
Weitere Namen anzeigen
Syringylethanone4-acetylsyringol5'SYRINGACETONE
3',5'-Dimethoxy-4'-hydroxyacetophenoneEthanone, 1-(4-hydroxy-3,5-dimethoxyphenyl)-Acetosyringon3,5-Dimethoxy-4-hydroxyacetophenoneMFCD00008748Acetophenone, 4'-hydroxy-3',5'-dimethoxy-4-hydroxy-3,5-dimethoxyacetophenone4-Hydroksy-3',5'-dwumetoksyacetofenon

Datenbank-Bezeichner

CAS
2478-38-8
PubChem CID
17198
DTXSID
DTXSID2062454
ChEMBL
CHEMBL224146
ChEBI
CHEBI:2404
UNII
866P45Y84S
EC Number
219-610-5
Nikkaji
J55.026D

Eigenschaften

Berechnete Struktureigenschaften

XLogP
0,2
Polarare Oberfläche (TPSA)
55,8 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
3
Schwere Atome
14

Experimentelle und physikochemische Eigenschaften

Chemical ClassesBiological Agents -> Plant Oils and Extracts
Flavoring AgentsEU Flavoring substances
Endocrine DisruptorsPotential endocrine disrupting compound
Physical DescriptionWhite to brown solid; [Sigma-Aldrich MSDS]
Collision Cross Section138.14 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physikochemische Eigenschaften

Schmelzpunkt
124 · 124-127 °C(lit.)
Siedepunkt
293.08 °C · 293.08°C (rough estimate)
Dichte
1.2166 · 1.2166 (rough estimate)
Brechungsindex
1.543 · 1.5430 (estimate)
storage temp.
Inert atmosphere,Room Temperature
Löslichkeit
Chloroform (Slightly), Methanol (Slightly)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H315 (100%): 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 49 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 2 Einträge

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Ethanone, 1-(4-hydroxy-3,5-dimethoxyphenyl)-: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummarySafe when used as a flavoring agent in food; [EFSA] A skin and strong eye irritant; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Sicherheitsdaten

F
10
wgk
2
hs_code
29145090
RTECS-Nr.
AM8440000
risk_code
36/37/38
hazard_code
Xi

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological Classification · 2 Einträge

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.

Drugs that are used to treat asthma.

Verwendung und Herstellung

UsesA flavoring agent that naturally occurs in pork and sherry; [EFSA]
Anwendungen · 2 Einträge

BeschreibungAcetosyringone is a phenol secreted by wounded plant tissues. It induces expression of virulence A genes and chemotaxis in A. tumefaciens strains that contain a tumor-inducing plasmid used to transfer genetic information to plant cells. Acetosyringone is widely used to increase efficacy of genetic transformation for the creation of genetically modified dicotyledonous and monocotyledonous plants.

VerwendenA buffer also known as acetosyringone that is used in the synthesis of tetramethoxychalcone and its analogues as anticancer agents in vitro.

Darstellung

synthetischePreparation by adding a solution of 4-hydroxy-3- iodo-5-methoxyacetophenone and cupric chloride in DMF to a solution of sodium methoxide in methanol and heating between 105° and 120° (86%).

Vor- und nachgelagerte Produkte

Anbieter50 Anbieter

杭州创引化工科技有限公司0571-87086220 13516718938 · [email protected]
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]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: A member of the class of acetophenones that is 1-phenylethanone substituted by a hydroxy group at position 4 and methoxy groups at positions 3 and 5.

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