7507-89-3

Basic information

• Product Name: 1-(2,6-DIHYDROXY-4-METHOXYPHENYL)ETHANONE
• Synonyms: 1-(2,6-Dihydroxy-4-methoxyphenyl)ethanone , Tech.;4-O-Methylphloroacetophenone;NSC 401443;4-O-Methylphloracetophenone;Acetophenone, 2',6'-dihydroxy-4'-methoxy-;Ethanone, 1-(2,6-dihydroxy-4-methoxyphenyl)-;2',6'-DIHYDROXY-4'-METHOXYACETOPHENONE;1-(2,6-DIHYDROXY-4-METHOXYPHENYL)ETHANONE
• CAS NO: 7507-89-3
• Molecular Formula: C₉H₁₀O₄
• Molecular Weight: 182.17
• Product Categories: Aromatic Acetophenones & Derivatives (substituted)
• Mol File: 7507-89-3.mol
• Article Data: 24

Chemical Properties

• Melting Point: 144 °C
• Boiling Point: 356.7 °C at 760 mmHg
• Flash Point: 146.3 °C
• Appearance: /
• Density: 1.284 g/cm³
• PKA: 9.27±0.15(Predicted)
• CAS DataBase Reference: 1-(2,6-DIHYDROXY-4-METHOXYPHENYL)ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,6-DIHYDROXY-4-METHOXYPHENYL)ETHANONE(7507-89-3)
• EPA Substance Registry System: 1-(2,6-DIHYDROXY-4-METHOXYPHENYL)ETHANONE(7507-89-3)

Safety Data

• Hazardous Substances Data: 7507-89-3(Hazardous Substances Data)

Usage

Preparation

Obtained by reaction of boiling aqueous potassium hydroxide, ? on the Methyl 3-acetyl-2,4-dihydroxy-6-methoxybenzoate (quantitative yield) ; ? on the 3-trichloroacetyl-2,6-dihydroxy-4-methoxyacetophenone.

Upstream product

• 186581-53-3 diazomethane 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 412036-13-6 3-acetyl-2,4-dihydroxy-6-methoxy-benzoic acid methyl ester 
• 412036-66-9 2-acetyl-5-methoxy-4-trichloroacetyl-resorcinol 
• 832-58-6 1-(2,4,6-trimethoxyphenyl)ethanone 
• 63013-34-3 2,6-dihydroxy-4-methoxyacetophenone 2-O-β-D-gentiobioside 
• 77-78-1 dimethyl sulfate 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 480-34-2 eugenin 
• 521-34-6 sciadopitysin 
• 481-46-9 ginkgetin 
• 10378-90-2 2,4-dihydroxy-6-methoxy-benzoic acid methyl ester 
• 720698-36-2 2,2,2-trichloro-1-(2,4-dihydroxy-6-methoxy-phenyl)-ethanone 

Downstream Products

• 24587-98-2 2',6'-dihydroxy-4'-methoxyacetophenone 2'-O-(2,3,4,6-O-tetraacetyl)-β-D-glucopyranoside 
• 136258-09-8 2'-hydroxy-4'-methoxy-6'-tetrahydropyranyloxyacetophenone 
• 136258-10-1 2',6'-dihydroxy-4'-methoxy-3'-tetrahydropyranylacetophenone 
• 77179-30-7 1-(2,6-dihydroxy-4-methoxy-3-(3-methylbut-2-en-1-yl)phenyl)ethan-1-one 
• 3818-99-3 10-acetyl-3,4,6,7-tetrahydro-5-methoxy-2,2,8,8-tetramethyl-2H,8H-benzo<1,2-b:5,4-b'>dipyran 
• 4655-89-4 8-Acetyl-7-hydroxy-5-methoxy-3,4-dihydro-2,2-dimethyl-2H-<1>benzopyran 
• 23937-88-4 1-{2-[3-(2-Acetyl-3-hydroxy-5-methoxy-phenoxy)-2-hydroxy-propoxy]-6-hydroxy-4-methoxy-phenyl}-ethanone 
• 76554-79-5 1-(2-ethoxy-6-hydroxy-4-methoxy-phenyl)-ethanone 
• 7507-87-1 2-Acetyl-3-hydroxy-5-methoxy-[1,4]benzochinon 
• 14218-44-1 <2-Acetyl-3-hydroxy-5-methoxy-phenoxy>-essigsaeure-ethylester 
• 66568-98-7 5,4'‐dihydroxy‐7,3'‐dimethoxyflavanone 
• 93012-86-3 7-methoxy-3',4',5-trihydroxyflavanone 
• 186693-85-6 1-[2-hydroxy-4-methoxy-6-(methoxymethoxy)phenyl]ethan-1-one 
• 81719-04-2 4,2',6'-trihydroxy-4'-methoxychalkone 

Relevant articles and documents

Structure of pleoside from Pleopeltis thunbergiana]

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Structural features and antioxidant activities of Chinese quince (Chaenomeles sinensis) fruits lignin during auto-catalyzed ethanol organosolv pretreatment

Chinese quince fruits (Chaenomeles sinensis) have an abundance of lignins with antioxidant activities. To facilitate the utilization of Chinese quince fruits, lignin was isolated from it by auto-catalyzed ethanol organosolv pretreatment. The effects of three processing conditions (temperature, time, and ethanol concentration) on yield, structural features and antioxidant activities of the auto-catalyzed ethanol organosolv lignin samples were assessed individually. Results showed the pretreatment temperature was the most significant factor; it affected the molecular weight, S/G ratio, number of β-O-4′ linkages, thermal stability, and antioxidant activities of lignin samples. According to the GPC analyses, the molecular weight of lignin samples had a negative correlation with pretreatment temperature. 2D-HSQC NMR and Py-GC/MS results revealed that the S/G ratios of lignin samples increased with temperature, while total phenolic hydroxyl content of lignin samples decreased. The structural characterization clearly indicated that the various pretreatment conditions affected the structures of organosolv lignin, which further resulted in differences in the antioxidant activities of the lignin samples. These results can be helpful for controlling and optimizing delignification during auto-catalyzed ethanol organosolv pretreatment, and they provide theoretical support for the potential applications of Chinese quince fruits lignin as a natural antioxidant in the food industry.

Sterubin: Enantioresolution and Configurational Stability, Enantiomeric Purity in Nature, and Neuroprotective Activity in Vitro and in Vivo

Alzheimer′s disease (AD) is a neurological disorder with still no preventive or curative treatment. Flavonoids are phytochemicals with potential therapeutic value. Previous studies described the flavanone sterubin isolated from the Californian plant Eriodictyon californicum as a potent neuroprotectant in several in vitro assays. Herein, the resolution of synthetic racemic sterubin (1) into its two enantiomers, (R)-1 and (S)-1, is described, which has been performed on a chiral chromatographic phase, and their stereochemical assignment online by HPLC-ECD coupling. (R)-1 and (S)-1 showed comparable neuroprotection in vitro with no significant differences. While the pure stereoisomers were configurationally stable in methanol, fast racemization was observed in the presence of culture medium. We also established the occurrence of extracted sterubin as its pure (S)-enantiomer. Moreover, the activity of sterubin (1) was investigated for the first time in vivo, in an AD mouse model. Sterubin (1) showed a significant positive impact on short- and long-term memory at low dosages.