Basic information
- CAS
2478-38-8- Standard SMILES
COc1cc(C(C)=O)cc(OC)c1O- InChIKey
OJOBTAOGJIWAGB-UHFFFAOYSA-N- Molecular formula
- C10H12O4
- Average molar mass
- 196.2 g/mol
- Monoisotopic mass
- 196.07355886
Overview
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.
Names & identifiers
- Preferred name
- Acetosyringone
- IUPAC
- 1-(4-hydroxy-3,5-dimethoxyphenyl)ethanone
- English name
- Acetosyringone
- Molecular formula
- C10H12O4
- Molecular weight
- 196.2
Names & synonyms
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
Show more names
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
Database identifiers
- CAS
2478-38-8- PubChem CID
- 17198
- DTXSID
DTXSID2062454- ChEMBL
CHEMBL224146- ChEBI
CHEBI:2404- UNII
- 866P45Y84S
- EC Number
- 219-610-5
- Nikkaji
- J55.026D
Properties
Computed structural properties
- XLogP
- 0.2
- Topological polar surface area
- 55.8 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 3
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 190
Experimental & physicochemical properties
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]
Physicochemical properties
- Melting point
- 124 · 124-127 °C(lit.)
- Boiling point
- 293.08 °C · 293.08°C (rough estimate)
- Density
- 1.2166 · 1.2166 (rough estimate)
- refractive index
- 1.543 · 1.5430 (estimate)
- FLAVIS Number
- 7.164 · 07.164 | 4-Hydroxy-3,5-dimethoxyacetophenone
- storage temp.
- Inert atmosphere,Room Temperature
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- form
- Crystalline Powder
- pka
- 8.19 · 8.19±0.23(Predicted)
- color
- Beige to light brown
- Odor
- 100 % · at 100.00%. odorless
- Water Solubility
- soluble
- BRN
- 1966119 · 1966119
- Henry's Law Constant
- 5 · 5.0×105 mol/(m3Pa) at 25℃, McFall et al. (2020)
- InChI
- 1S/C10H12O4/c1-6(11)7-4-8(13-2)10(12)9(5-7)14-3/h4-5,12H,1-3H3
- InChIKey
- OJOBTAOGJIWAGB-UHFFFAOYSA-N
- SMILES
- COc1cc(cc(OC)c1O)C(C)=O
- LogP
- 1.699 · 1.699 (est)
- CAS DataBase Reference
- 2478 · 2478-38-8(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 866 P45Y84S · 866P45Y84S
- NIST Chemistry Reference
- 1 · Ethanone, 1-(4-hydroxy-3,5-dimethoxyphenyl)-(2478-38-8)
- EPA Substance Registry System
- Acetosyringone (2478-38-8)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36
- WGK Germany
- 2 · 2
- RTECS
- 8440000 · AM8440000
- F
- 10 · 10
- Hazard Note
- Irritant
- HS Code
- 29145090 · 29145090
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
Safety & regulation
GHS classification
GHS Classification
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.
Hazard information
Regulatory Information
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%)
Safety data
- F
- 10
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 2
- rtecs
- AM8440000
- hs_code
- 29145090
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
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.
Uses & manufacturing
UsesA flavoring agent that naturally occurs in pork and sherry; [EFSA]
Applications
Uses4’-Hydroxy-3’,5’-dimethoxyacetophenone used in the synthesis of tetramethoxychalcone and its analogues as anticancer agents. It is a naturally occuring compound found in plants and used in plant-pathogen recognition.
DescriptionAcetosyringone 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.
Usesinsect attractant, plant hormone
UsesA buffer also known as acetosyringone that is used in the synthesis of tetramethoxychalcone and its analogues as anticancer agents in vitro.
Uses4’-Hydroxy-3’,5’-dimethoxyacetophenone used in the synthesis of tetramethoxychalcone and its analogues as anticancer agents. It is a naturally occuring compound found in plants and used in plant-pathogen recognition.
Preparation methods
PreparationPreparation 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%).
Upstream & downstream products
Upstream raw materials
Suppliers100 total
杭州创引化工科技有限公司0571-87086220 13516718938 · [email protected]
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Additional notes
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.
Related reactions
19 records
Compound notes
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