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CAS No.: | 2478-38-8 |
---|---|
Name: | Acetosyringone |
Article Data: | 37 |
Molecular Structure: | |
Formula: | C10H12O4 |
Molecular Weight: | 196.203 |
Synonyms: | Acetophenone,4'-hydroxy-3',5'-dimethoxy- (6CI,7CI,8CI);1-(4-Hydroxy-3,5-dimethoxyphenyl)ethanone;2,6-Dimethoxy-4-acetophenol;2,6-Dimethoxy-4-acetylphenol;3',5'-Dimethoxy-4'-hydroxyacetophenone;4-Acetyl-2,6-dimethoxyphenol;4'-Hydroxy-3',5'-dimethoxyacetophenone;Syringone;Syringylethanone;Acetosyringone; |
EINECS: | 219-610-5 |
Density: | 1.172 g/cm3 |
Melting Point: | 124-127 °C(lit.) |
Boiling Point: | 334.7 °C at 760 mmHg |
Flash Point: | 131.7 °C |
Solubility: | soluble in water |
Appearance: | beige to light brown crystalline powder |
Hazard Symbols: | Xi |
Risk Codes: | 36/37/38 |
Safety: | 26-36 |
PSA: | 55.76000 |
LogP: | 1.61200 |
Conditions | Yield |
---|---|
With lithium thioethoxide In N,N-dimethyl-formamide at 70℃; for 0.25h; Inert atmosphere; Microwave irradiation; regioselective reaction; | 95% |
With magnesium iodide for 0.5h; neat (no solvent); | 90% |
With zirconium(IV) chloride; methoxybenzene In dichloromethane at 40℃; for 48h; Sealed tube; | 63% |
methyl 4-O-tert-butyldimethylsilyl-3,5-dimethoxybenzoate
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride | 92% |
1-(4-Hydroxy-3,5-dimethoxyphenyl)ethanol
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
With copper diacetate; ethylene glycol at 50℃; for 8h; Green chemistry; chemoselective reaction; | 91% |
4-ethylsyringol
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
With copper diacetate; ethylene glycol at 90℃; for 12h; Green chemistry; chemoselective reaction; | 84% |
C11H16O4
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
With copper diacetate; ethylene glycol at 50℃; for 8h; Green chemistry; chemoselective reaction; | 83% |
1-(4-Hydroxy-3,5-dimethoxyphenyl)ethanol
A
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
B
2,6-dimethoxy-p-quinone
Conditions | Yield |
---|---|
With oxygen; (pyridine)cobalt In methanol under 2585.7 Torr; for 24h; Ambient temperature; Title compound not separated from byproducts; | A 4 % Spectr. B 82% |
With oxygen; (pyridine)cobalt In methanol under 2585.7 Torr; for 24h; Ambient temperature; | A 4 % Spectr. B 82% |
Conditions | Yield |
---|---|
With bismuth(lll) trifluoromethanesulfonate In toluene for 1h; Fries rearrangement; Heating; | 80% |
With aluminum (III) chloride In nitrobenzene at 0℃; Solvent; Reagent/catalyst; | 80% |
With aluminium trichloride; nitrobenzene at 2 - 3℃; dann bei Zimmertemperatur; | |
With aluminium trichloride; nitrobenzene | |
With aluminium trichloride In nitrobenzene |
3,3'-dimethoxy-4-carboxymethoxyacetophenone
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
Stage #1: 3,3'-dimethoxy-4-carboxymethoxyacetophenone With triethylamine In N,N-dimethyl-formamide; toluene for 3h; Curtius rearrangement; Heating; Stage #2: With potassium hydroxide; glycerol In ethanol; N,N-dimethyl-formamide; toluene for 2h; Heating; Further stages.; | 70% |
1-(4-hydroxy-3-iodo-5-methoxy-phenyl)ethan-1-one
sodium methylate
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
With methanol; copper at 140℃; |
1-(4-hydroxy-3,5-dimethoxyphenyl)ethanone benzyl ether
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
With hydrogen bromide; acetic acid bei gewoehnlicher Temperatur; |
The Acetosyringone, with CAS registry number 2478-38-8, belongs to the following product category: Aromatic Acetophenones & Derivatives (substituted). Its systematic name and its IUPAC name are the same, which is 1-(4-hydroxy-3,5-dimethoxyphenyl)ethanone. And this chemical is a kind of beige to light brown crystalline powder.
Physical properties of Acetosyringone are: (1)ACD/LogP: 1.699; (2)ACD/LogD (pH 5.5): 1.70; (3)ACD/LogD (pH 7.4): 1.63; (4)ACD/BCF (pH 5.5): 11.49; (5)ACD/BCF (pH 7.4): 9.92; (6)ACD/KOC (pH 5.5): 199.64; (7)ACD/KOC (pH 7.4): 172.35; (8)#H bond acceptors: 4; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 4; (11)Index of Refraction:1.528; (12)Molar Refractivity: 51.519 cm3; (13)Molar Volume: 167.398 cm3; (14)Polarizability: 20.424 10-24cm3; (15)Surface Tension: 39.9329986572266 dyne/cm; (16)Density: 1.172 g/cm3; (17)Flash Point: 131.705 °C; (18)Enthalpy of Vaporization: 60.054 kJ/mol; (19)Boiling Point: 334.653 °C at 760 mmHg
Preparation of Acetosyringone: This chemical can be prepared by 1-(3,4,5-trimethoxy-phenyl)-ethanone. This reaction will need reagent AlCl3. The yield is about 60%.
Uses of Acetosyringone: It can be used to produce 3',5'-dimethoxy-4'-isopropoxyacetophenone. This reaction will need reagent K2CO3 and solvent dimethylformamide. The reaction time is 4.5 hour(s). The yield is about 65.9%.
When you are using this chemical, please be cautious about it as the following:
The Acetosyringone irritates to eyes, respiratory system and skin. When use it, wear suitable protective clothing, gloves and eye/face protection. If contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)InChI=1S/C10H12O4/c1-6(11)7-4-8(13-2)10(12)9(5-7)14-3/h4-5,12H,1-3H3;
(2)InChIKey=OJOBTAOGJIWAGB-UHFFFAOYSA-N;
(3)Smilesc1(c(c(cc(c1)C(C)=O)OC)O)OC;
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 650mg/kg (650mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) | Journal of Medicinal Chemistry. Vol. 7, Pg. 178, 1964. |
mouse | LD50 | oral | > 10gm/kg (10000mg/kg) | Bromatologia i Chemia Toksykologiczna. Vol. 14, Pg. 301, 1981. |