29048-54-2

Basic information

• Product Name: 1-(2,4-Dihydroxyphenyl)-2-methyl-1-propanone
• CAS NO: 29048-54-2
• Molecular Formula: C₁₀H₁₂O₃
• Molecular Weight: 180.2005
• Mol File: 29048-54-2.mol

Chemical Properties

• Refractive Index: 1.565
• CAS DataBase Reference: 1-(2,4-Dihydroxyphenyl)-2-methyl-1-propanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,4-Dihydroxyphenyl)-2-methyl-1-propanone(29048-54-2)
• EPA Substance Registry System: 1-(2,4-Dihydroxyphenyl)-2-methyl-1-propanone(29048-54-2)

Safety Data

• Hazardous Substances Data: 29048-54-2(Hazardous Substances Data)

Usage

Synonyms

2-Methyl-3-(2,4-dihydroxyphenyl)-1-propanone

Appearance

White to yellow crystalline powder

Chemical classification

Derivative of acetophenone

Uses

a. Chemical intermediate in the synthesis of pharmaceuticals, agrochemicals, and flavors
b. Manufacture of perfumes and other aromatic chemicals
c. Antioxidant properties in the food industry as a preservative

Safety precautions

a. May cause skin and eye irritation
b. Harmful if swallowed

Upstream product

• 79-31-2 isobutyric Acid 
• 108-46-3 recorcinol 
• 78-82-0 Isobutyronitrile 
• 97-72-3 2-Methylpropionic anhydride 

Downstream Products

• 251463-53-3 2,4-diacetoxyphenyl isopropyl ketone 
• 874219-62-2 acetic acid 3-(2,4-dimethoxy-phenyl)-4-isopropyl-2-oxo-2H-chromen-7-yl ester 
• 29048-55-3 1-(2-hydroxy-4-methoxyphenyl)-2-methyl-1-propanone 
• 1204737-60-9 1-(2,4-dihydroxy-3-iodo-phenyl)-2-methyl-propan-1-one 
• 1611466-21-7 C₄₅H₅₄O₈ 
• 1611466-11-5 C₂₄H₃₆O₈ 
• 1611466-03-5 O,O-dibenzyl-4-i-butylresorcinol 
• 1611466-05-7 O,O-dibenzyl-2-(benzyloxymethyl)-4-ibutylresorcinol 
• 1611465-61-2 O,O-dibenzyl-2-(benzyloxymethyl)-4-ibutyl-6-bromoresorcinol 

Relevant articles and documents

Exploring efficacy of natural-derived acetylphenol scaffold inhibitors for α-glucosidase: Synthesis, in vitro and in vivo biochemical studies

The discovery of novel α-glucosidase inhibitors and anti-diabetic candidates from natural or natural-derived products represents an attractive therapeutic option. Here, a collection of acetylphenol analogues derived from paeonol and acetophenone were synthesized and evaluated for their α-glucosidase inhibitory activity. Most of derivatives, such as 9a–9e, 9i, 9m–9n and 11d–1e, (IC50 = 0.57 ± 0.01 μM to 8.45 ± 0.57 μM), exhibited higher inhibitory activity than the parent natural products and were by far more potent than the antidiabetic drug acarbose (IC50 = 57.01 ± 0.03 μM). Among these, 9e and 11d showed the most potent activity in a non-competitive manner. The binding processes between the two most potent compounds and α-glucosidase were spontaneous. Hydrophobic interactions were the main forces for the formation and stabilization of the enzyme - acetylphenol scaffold inhibitor complex, and induced the topography image changes and aggregation of α-glucosidase. In addition, everted intestinal sleeves in vitro and the maltose loading test in vivo further demonstrated the α-glucosidase inhibition of the two compounds, and our findings proved that they have significant postprandial hypoglycemic effects.

Primulin derivative as well as synthesis method and application of primulin derivative

The invention discloses a primulin derivative with antibacterial activity shown as the structural general formula (I), wherein R is selected from C2-C20 alkyls. The primulin derivative is prepared from raw materials including m-dihydroxybenzene and a fatty acid derivative by the steps: carrying out Friedel-Crafts acylation and methylation to synthesize a paeonol derivative, and carrying out oxidization after carrying out carbonyl reduction. The primulin derivative has good antibacterial activity and can be used as a potential antibacterial agent.

Natural products as sources of new fungicides (II): antiphytopathogenic activity of 2,4-dihydroxyphenyl ethanone derivatives

A series of 17 simple 1-(2,4-dihydroxyphenyl) ethanones were synthesised, and their structures characterised by 1H, 13C NMR and ESI-MS. Their in vitro antifungal activities were evaluated against five phytopathogenic fungi including Glomerella cingulate, Botrytis cirerea, Fusarium graminearum, Curvularia lunata and Fusarium oxysporum f. sp. vasinfectum by the mycelial growth inhibition assay. Compounds 2g and 2h exhibited broad-spectrum inhibitory activity against the mycelial growth of the tested pathogens with IC50 values in the range of 16-36 g/mL, and in particular being more active to G. cingulate, with IC50 values of 16.50 and 19.25 g/mL, respectively, than the other pathogens. Preliminary SAR indicated that an α,β-unsaturated ketone unit of the alkyl chain of the compounds is the structure requirement for fungicidal action. The results suggested that 2g and 2h may be promising leads in the development of new antifungal agents.

Stereocontrol by quaternary centres: A stereoselective synthesis of (-)-luminacin D

Very high diastereoselectivity can be achieved by 1,3-chelation-controlled allylation of aldehydes that possess a non-chelating α-ether substituent, even if the α-position is a quaternary centre and/or a spiro-epoxide. This reaction was used as a key step in an enantioselective synthesis of the angiogenesis inhibitor luminacin D.

Discovery and SAR study of hydroxyacetophenone derivatives as potent, non-steroidal farnesoid X receptor (FXR) antagonists

Compound 1 (IC50 = 35.2 ± 7.2 μM), a moderate FXR antagonist was discovered via high-throughput screening. Structure-activity relationship studies indicated that the shape and the lipophilicity of the substituents of the aromatic ring affect the activity dramatically, increasing the shape and the lipophilicity of the substituents of the aromatic ring enhances the potency of FXR antagonists. Especially, when the OH at C2 position of the aromatic ring was replaced by the OBn substituent (analog 2b), its activity could be improved to IC50 = 1.1 ± 0.1 μM. Besides, the length of the linker and the tetrazole structure are essential for retaining the activity.

2, 4 Dihydroxy-5-bromo[2'-methyl] propiophenone oxime as an analytical reagent: Studies on Cu(II) chelate

Cu(II) was determined spectrophotometrically after co-precipitation with 2, 4 Dihydroxy-5-bromo[2'-methyl] propiophenone oxime (DHBMPO) at room temperature. Obeyance of Beer's law was found and from that Molar absorptivity and Sandell's sensitivity were c

IMIDAZOLE CARBOXAMIDES

The present invention provides certain imidazole carboxamide derivatives, pharmaceutical compositions thereof, methods of using the same and processes for preparing the same.

BENZOFURAN AND BENZOTHIOPHENE-2-CARBOXYLIC ACID AMIDE DERIVATIVES

The present invention relates to compounds of formula I wherein X, A and R1 to R4 are as defined in the description and claims, and pharmaceutically acceptable salts thereof. The compounds are useful for the treatment and/or prevention of diseases which are associated with the modulation of H3 receptors.

4,5-Diarylisoxazole Hsp90 chaperone inhibitors: Potential therapeutic agents for the treatment of cancer

Inhibitors of the Hsp90 molecular chaperone are showing considerable promise as potential chemotherapeutic agents for cancer. Here, we describe the structure-based design, synthesis, structure - activity relationships and pharmacokinetics of potent small-molecule inhibitors of Hsp90 based on the 4,5-diarylisoxazole scaffold. Analogues from this series have high affinity for Hsp90, as measured in a fluorescence polarization (FP) competitive binding assay, and are active in cancer cell lines where they inhibit proliferation and exhibit a characteristic profile of depletion of oncogenic proteins and concomitant elevation of Hsp72. Compound 40f (VER-52296/NVP-AUY922) is potent in the Hsp90 FP binding assay (IC50 = 21 nM) and inhibits proliferation of various human cancer cell lines in vitro, with GI50 averaging 9 nM. Compound 40f is retained in tumors in vivo when administered i.p., as evaluated by cassette dosing in tumor-bearing mice. In a human colon cancer xenograft model, 40f inhibits tumor growth by ～50%.

ISOXAZOLE COMPOUNDS AS INHIBITORS OF HEAT SHOCK PROTEINS

Isoxazoles of formula (A) or (B) are inhibitors of HSP90 activity, and useful for treatment of, for example cancers: (A), (B) wherein R1, is a group of formula (IA): -Ar1-(Alk1)p-(Z)r-(Alk2)S-Q, wherein in any compatible combination Ar1 is an optionally substituted aryl or heteroaryl radical, Alk1and Alk2 are optionally substituted divalent Cl-C6 alkylene or C2-C6 alkenylene radicals, p, r and s are independently 0 or 1, Z is -0-, -S-, -(C=O)-, -(C=S)-, -SO2-, -C(=O)O-, -C(=O)NRA-, -C(=S)NRA-, - SO2NRA-, -NRAC(=O)-, -NRASO2- or -NRA- wherein RA is hydrogen or Cl-C6 alkyl, and Q is hydrogen or an optionally substituted carbocyclic or heterocyclic radical; R2 is (i) a group of formula (IA) above or (ii) a carboxamide radical; or (iii) a non aromatic carbocyclic or heterocyclic ring wherein a ring carbon is optionally substituted, and/or a ring nitrogen is optionally substituted by a group of formula -(Alk1)p-(Z)r-(Alk2)s-Q wherein Q, Alk1, Alk2, Z, p, r and s are as defined above in relation to group (IA); and R3 is hydrogen, optionally substituted cycloalkyl, cycloalkenyl, C1-C6 alkyl, C1-C6 alkenyl, or C1-C6 alkynyl; or a carboxyl, carboxamide, or carboxyl ester group.