13383-63-6

Basic information

• Product Name: 1-(2,4,6-trihydroxy-3,5-dimethylphenyl)ethan-1-one
• Synonyms: 1-(2,4,6-trihydroxy-3,5-dimethylphenyl)ethan-1-one;1-(2,4,6-Trihydroxy-3,5-dimethylphenyl)ethanone;2,4,6-Trihydroxy-3,5-dimethylacetophenone;Einecs 236-459-0;2,4,6-Trihydroxy-3,5-Dimethylacetiphenone
• CAS NO: 13383-63-6
• Molecular Formula: C₁₀H₁₂O₄
• Molecular Weight: 196.19988
• EINECS: 236-459-0
• Mol File: 13383-63-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 220-222 °C
• Boiling Point: 355.5°Cat760mmHg
• Flash Point: 183°C
• Appearance: /
• Density: 1.318g/cm³
• Vapor Pressure: 1.52E-05mmHg at 25°C
• Refractive Index: 1.609
• PKA: 8.47±0.33(Predicted)
• CAS DataBase Reference: 1-(2,4,6-trihydroxy-3,5-dimethylphenyl)ethan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,4,6-trihydroxy-3,5-dimethylphenyl)ethan-1-one(13383-63-6)
• EPA Substance Registry System: 1-(2,4,6-trihydroxy-3,5-dimethylphenyl)ethan-1-one(13383-63-6)

Safety Data

• Hazardous Substances Data: 13383-63-6(Hazardous Substances Data)

Usage

Preparation

Preparation by reaction of acetonitrile on 1,3-dimethyl-phloroglucinol (Hoesch reaction), (66%).

InChI:InChI=1/C10H12O4/c1-4-8(12)5(2)10(14)7(6(3)11)9(4)13/h12-14H,1-3H3

Upstream product

• 480-66-0 2,4,6-trihydroxyacetophenone 
• 74-88-4 methyl iodide 
• 4463-02-9 2,4-dimethylbenzene-1,3,5-triol 
• 108-24-7 acetic anhydride 
• 4396-13-8 2,4-diformyl 2,4,6-trihydroxybenzene 
• 108-73-6 3,5-dihydroxyphenol 
• 58818-99-8 2,4,6-Triacetoxy-1,3-dimethylbenzene 
• 75-05-8 acetonitrile 

Downstream Products

• 13197-10-9 5,6-Dihydroxy-1,3-dioxo-2,6-dimethyl-4-acetyl-cyclohexen-⁽⁴⁾ 
• 93290-61-0 5,7-Dihydroxy-2-(3,4-dimethoxyphenyl)-6,8-dimethyl-4H-1-benzopyran-4-one 
• 95272-99-4 2-(3,4-dihydroxy-phenyl)-5,7-dihydroxy-6,8-dimethyl-chroman-4-one 
• 1204194-91-1 C₁₇H₁₅NO₆ 
• 1204194-98-8 C₁₉H₂₀O₆ 
• 1204194-96-6 C₁₈H₁₈O₅ 
• 1252795-97-3 C₁₇H₁₆O₅ 
• 1204194-83-1 C₁₇H₁₆O₅ 
• 95273-01-1 2,3-dihydro-5,7-dihydroxy-2-(4-methoxyphenyl)-6,8-dimethylchromen-4-one 
• 95403-16-0 Farrerol 
• 27593-80-2 5,7-dihydroxy-6,8-dimethylflavanone 
• 1204194-89-7 C₁₇H₁₅NO₆ 
• 1204194-87-5 C₁₇H₁₅ClO₄ 
• 1204194-85-3 C₁₇H₁₅ClO₄ 

Relevant articles and documents

Discovery of Anti-TNBC Agents Targeting PTP1B: Total Synthesis, Structure-Activity Relationship, in Vitro and in Vivo Investigations of Jamunones

Twenty-three natural jamunone analogues along with a series of jamunone-based derivatives were synthesized and evaluated for their inhibitory effects against breast cancer (BC) MDA-MB-231 and MCF-7 cells. The preliminary structure-activity relationship revealed that the length of aliphatic side chain and free phenolic hydroxyl group at the scaffold played a vital role in anti-BC activities and the methyl group on chromanone affected the selectivity of molecules against MDA-MB-231 and MCF-7 cells. Among them, jamunone M (JM) was screened as the most effective anti-triple-negative breast cancer (anti-TNBC) candidate with a high selectivity against BC cells over normal human cells. Mechanistic investigations indicated that JM could induce mitochondria-mediated apoptosis and cause G0/G1 phase arrest in BC cells. Furthermore, JM significantly restrained tumor growth in MDA-MB-231 xenograft mice without apparent toxicity. Interestingly, JM could downregulate phosphatidylinositide 3-kinase (PI3K)/Akt pathway by suppressing protein-tyrosine phosphatase 1B (PTP1B) expression. These findings revealed the potential of JM as an appealing therapeutic drug candidate for TNBC.

A Novel Synthesis of 1-(2,4,6-Trihydroxy-3,5-dimethylphenyl)ethanone (Di-C-methylphloracetophenone) and Two New Non-Aromatic C-Benzylated Derivatives

The synthesis of the title compound 1e was achieved by an easy three-step procedure from 1,3,5-benzenetriol (1a, phloroglucinol).Compound 1a was C-methylated using MeI.The crude mixture obtained was acetylated to give 1d which was converted into 1e using BF3*AcOH complex.Benzylation of the latter with benzyl chloride afforded the new non-aromatic compound 2.Reaction of 2 with NaOH and benzoyl chloride (Scheme 1) gave the new compound 4.Its structure was established by X-ray analysis. - Keywords: Acetophenone / Di-C-methylphloracetopheneone