1634-34-0

Basic information

• Product Name: 3,5-DIHYDROXY-4-ACETYLTOLUENE
• Synonyms: 3,5-DIHYDROXY-4-ACETYLTOLUENE;2,6-DIHYDROXY-4'-METHYLACETOPHENONE;ETHANONE, 1-(2,6-DIHYDROXY-4-METHYLPHENYL)-;4-acetyl-3,5-dihydroxytoluene;4-ACETYL-3,5-DIHYDROXYTOLUENE,98.5+%;1-(2,6-Dihydroxy-4-methylphenyl)ethanone;p-Orcacetophenone;1-(2,6-dihydroxy-4-Methylphenyl)ethan-1-one
• CAS NO: 1634-34-0
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.17
• EINECS: 200-589-5
• Product Categories: Alcohols and Derivatives;Carbonyl Compounds;Aromatic Acetophenones & Derivatives (substituted);Aromatics;Intermediates;Thiazines ,Thiazoles
• Mol File: 1634-34-0.mol
• Article Data: 17

Chemical Properties

• Melting Point: 142-144 °C
• Boiling Point: 288.7°Cat760mmHg
• Flash Point: 142.6°C
• Appearance: /
• Density: 1.239g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.584
• PKA: 9.76±0.15(Predicted)
• CAS DataBase Reference: 3,5-DIHYDROXY-4-ACETYLTOLUENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-DIHYDROXY-4-ACETYLTOLUENE(1634-34-0)
• EPA Substance Registry System: 3,5-DIHYDROXY-4-ACETYLTOLUENE(1634-34-0)

Safety Data

• Hazardous Substances Data: 1634-34-0(Hazardous Substances Data)

Usage

Description

3,5-DIHYDROXY-4-ACETYLTOLUENE, also known as p-Orcacetophenone, is an acetophenone derivative with a molecular structure featuring two hydroxyl groups at the 3rd and 5th positions, and an acetyl group at the 4th position. It is a synthetic compound that has gained attention for its potential applications in various industries.

Uses

Used in Pharmaceutical Industry:
3,5-DIHYDROXY-4-ACETYLTOLUENE is used as a key intermediate in the synthesis of sodium glucose co-transporter 2 (SGLT2) inhibitors. These inhibitors are crucial for the development of antidiabetic agents, which help regulate blood sugar levels in patients with diabetes. The compound plays a significant role in the pharmaceutical industry by contributing to the creation of life-saving medications for diabetes management.
Used in Chemical Synthesis:
As an acetophenone derivative, 3,5-DIHYDROXY-4-ACETYLTOLUENE can be utilized in various chemical synthesis processes. Its unique molecular structure allows it to be a versatile building block for the development of new compounds with potential applications in different industries, such as materials science, agrochemicals, and more. The compound's reactivity and functional groups make it a valuable asset in the field of organic chemistry.

Preparation

Preparation by reaction of acetic anhydride on orcinol, ? with concentrated sulfuric acid at 130° (65%) ; ? with Amberlite IR-120 or Zeokarb-225, cation exchange resins (sulfonic acid type) at 160° (20%).

InChI:InChI=1/C9H10O3/c1-5-3-7(11)9(6(2)10)8(12)4-5/h3-4,11-12H,1-2H3

Upstream product

• 13444-19-4 2,4-diacetyl-5-methyl-resorcinol 
• 504-15-4 orcinol 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 97066-60-9 2-Acetyl-3-dimethylamino-5-hydroxy-5-methyl-2-cyclohexenon 
• 20982-28-9 5-methylbenzene-1,3-diyl diacetate 
• 7446-70-0 aluminium trichloride 
• 98-95-3 nitrobenzene 
• 75-36-5 acetyl chloride 
• 889140-51-6 orcinol monoacetate 
• 1257655-53-0 2,6-bis(trimethylsilyloxy)-4-methylacetophenone 
• 141-78-6 ethyl acetate 

Downstream Products

• 27465-63-0 2-ethyl-5-methylresorcinol 
• 107057-96-5 5-hydroxy-3,4,7-trimethylcoumarin 
• 209746-55-4 2',6'-dihydroxy-4'-methylacetophenone 2'-O-(2,3,4,6-O-tetraacetyl)-β-D-glucopyranoside 
• 13444-19-4 2,4-diacetyl-5-methyl-resorcinol 
• 701936-27-8 1-(2,6-bis-benzyloxy-4-methyl-phenyl)-ethanone 
• 835885-39-7 1-[2-hydroxy-6-(methoxymethoxy)-4-methylphenyl]ethan-1-one 
• 701936-17-6 3-benzofuran-5-yl-1-(2,6-dihydroxy-4-methyl-phenyl)-propan-1-one 
• 701936-18-7 3-(2,3-dihydro-benzofuran-5-yl)-1-(2,6-dihydroxy-4-methyl-phenyl)-propan-1-one 
• 835885-26-2 1-(2,6-bis-benzyloxy-4-methyl-phenyl)-3-(2,3-dihydro-benzofuran-5-yl)-propenone 
• 1049661-85-9 (E)-3-Benzofuran-5-yl-1-[2-hydroxy-4-methyl-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-propenone 
• 209746-56-5 3-(benzo[b]furan-5-yl)-2',6'-dihydroxy-4'-methylpropiophenone 2'-O-β-D-glucopyranoside 

Relevant articles and documents

Vinylogous addition of siloxyfurans to benzopyryliums: A concise approach to the tetrahydroxanthone natural products

A concise approach to the tetrahydroxanthone natural products employing vinylogous addition of siloxyfurans to benzopyryliums and a late-stage Dieckmann cyclization has been developed. With this methodology, chiral, racemic forms of the natural products blennolides B and blennolide C have been synthesized in a maximum of four steps from a 5-hydroxychromone substrate. The regio- and diastereoselectivity of the vinylogous additions was probed using computational studies, which suggested the involvement of Diels-Alder-like transition states.

Derivatives of Natural Product Agrimophol as Disruptors of Intrabacterial pH Homeostasis in Mycobacterium tuberculosis

This article reports the rational medicinal chemistry of a natural product, agrimophol (1), as a new disruptor of intrabacterial pH (pHIB) homeostasis in Mycobacterium tuberculosis (Mtb). Through the systematic investigation of the structure-activity relationship of 1, scaffold-hopping of the diphenylmethane scaffold, pharmacophore displacement strategies, and studies of the structure-metabolism relationship, a new derivative 5a was achieved. Compound 5a showed 100-fold increased potency in the ability to reduce pHIB to pH 6.0 and similarly improved mycobactericidal activity compared with 1 against both Mycobacterium bovis-BCG and Mtb. Compound 5a possessed improved metabolic stability in human liver microsomes and hepatocytes, lower cytotoxicity, higher selectivity index, and similar pKa value to natural 1. This study introduces a novel scaffold to an old drug, resulting in improved mycobactericidal activity through decreasing pHIB, and may contribute to the critical search for new agents to overcome drug resistance and persistence in the treatment of tuberculosis.

3,5-DISUBSTITUTED PYRAZOLES USEFUL AS CHECKPOINT KINASE 1 (CHK1) INHIBITORS, AND THEIR PREPARATIONS AND APPLICATIONS

Potent inhibitors of Chk1 have the structure formula (I) below. Pharmaceutical compositions comprising the Chk1 inhibitors, uses thereof and their preparation process.