89019-84-1

Basic information

• Product Name: Ethanone, 1-(2,4-dihydroxyphenyl)-2-(3-hydroxyphenyl)-
• CAS NO: 89019-84-1
• Molecular Formula: C14H12O4
• Molecular Weight: 244.247
• Mol File: 89019-84-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Ethanone, 1-(2,4-dihydroxyphenyl)-2-(3-hydroxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 1-(2,4-dihydroxyphenyl)-2-(3-hydroxyphenyl)-(89019-84-1)
• EPA Substance Registry System: Ethanone, 1-(2,4-dihydroxyphenyl)-2-(3-hydroxyphenyl)-(89019-84-1)

Safety Data

• Hazardous Substances Data: 89019-84-1(Hazardous Substances Data)

Usage

General Description

Ethanone, 1-(2,4-dihydroxyphenyl)-2-(3-hydroxyphenyl)- is a chemical compound with a complex structure containing two aromatic rings and hydroxyl groups. Ethanone, 1-(2,4-dihydroxyphenyl)-2-(3-hydroxyphenyl)- is often used in the field of pharmaceuticals and is known for its antioxidant properties. The presence of hydroxyl groups in the molecule allows it to scavenge free radicals and protect cells from oxidative damage. Additionally, the combination of aromatic rings in its structure suggests potential applications in the development of drugs targeting conditions related to inflammation and oxidative stress. Overall, Ethanone, 1-(2,4-dihydroxyphenyl)-2-(3-hydroxyphenyl)- is a promising compound with potential therapeutic benefits in various medical applications.

Upstream product

• 621-37-4 m-hydroxyphenylacetic acid 
• 108-46-3 recorcinol 

Downstream Products

• 1352307-37-9 3-(3-hydroxyphenyl)-4-methyl-2-(4-((S)-2-((R)-3-methylpyrrolidin-1-yl)propoxy)phenyl)-2H-chromen-7-ol trifluoroacetate 
• 1352306-17-2 2-(4-iodophenyl)-4-methyl-7-((tetrahydro-2H-pyran-2-yl)oxy)-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)-2H-chromene 
• 89019-85-2 7-hydroxy-3-(3-hydroxyphenyl)-4H-chromen-4-one 

Relevant articles and documents

Identification of an Orally Bioavailable Chromene-Based Selective Estrogen Receptor Degrader (SERD) That Demonstrates Robust Activity in a Model of Tamoxifen-Resistant Breast Cancer

About 75% of breast cancers are estrogen receptor alpha (ER-α) positive, and women typically initially respond well to antihormonal therapies such as tamoxifen and aromatase inhibitors, but resistance often emerges. Fulvestrant is a steroid-based, selective estrogen receptor degrader (SERD) that both antagonizes and degrades ER-α and shows some activity in patients who have progressed on antihormonal agents. However, fulvestrant must be administered by intramuscular injections that limit its efficacy. We describe the optimization of ER-α degradation efficacy of a chromene series of ER modulators resulting in highly potent and efficacious SERDs such as 14n. When examined in a xenograft model of tamoxifen-resistant breast cancer, 14n (ER-α degradation efficacy = 91%) demonstrated robust activity, while, despite superior oral exposure, 15g (ER-α degradation efficacy = 82%) was essentially inactive. This result suggests that optimizing ER-α degradation efficacy in the MCF-7 cell line leads to compounds with robust effects in models of tamoxifen-resistant breast cancer derived from an MCF-7 background.

Free-radical-scavenging, antityrosinase, and cellular melanogenesis inhibitory activities of synthetic isoflavones

In this study, we examined the potential of synthetic isoflavones for application in cosmeceuticals. Twenty-five isoflavones were synthesized and their capacities of free-radical-scavenging and mushroom tyrosinase inhibition, as well as their impact on cell viability of B16F10 murine melanoma cells and HaCaT human keratinocytes were evaluated. Isoflavones that showed significant mushroom tyrosinase inhibitory activities were further studied on reduction of cellular melanin formation and antityrosinase activities in B16F10 melanocytes in vitro. Among the isoflavones tested, 6-hydroxydaidzein (2) was the strongest scavenger of both ABTS.+ and DPPH. radicals with SC50 values of 11.3±0.3 and 9.4±0.1 μM, respectively. Texasin (20) exhibited the most potent inhibition of mushroom tyrosinase (IC50 14.9±4.5 μM), whereas retusin (17) showed the most efficient inhibition both of cellular melanin formation and antityrosinase activity in B16F10 melanocytes, respectively. In summary, both retusin (17) and texasin (20) exhibited potent free-radical-scavenging capacities as well as efficient inhibition of cellular melanogenesis, suggesting that they are valuable hit compounds with potential for advanced cosmeceutical development.

Expedient Synthesis of Polyhydroxyisoflavones

A general and direct synthesis of polyhydroxy isoflavones (3-phenyl-4H-1-benzopyran-4-ones) starting from the corresponding unprotected phenols and arylacetic acids is described.The aryl rings may carry additional alkyl, methoxy and/or halogeno groups.Intermediate polyhydroxydeoxybenzoins (1,2-diphenylethanones) can also be isolated in good yields.