21260-41-3

Basic information

• Product Name: 7-Hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-one
• Synonyms: benzo[b]cyclopenta[d]pyran-4(1H)-one, 2,3-dihydro-7-hydroxy-
• CAS NO: 21260-41-3
• Molecular Formula: C₁₂H₁₀O₃
• Molecular Weight: 202.21
• Mol File: 21260-41-3.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 440.1°C at 760 mmHg
• Flash Point: 201.9°C
• Appearance: /
• Density: 1.4g/cm³
• Vapor Pressure: 2.35E-08mmHg at 25°C
• Refractive Index: 1.66
• CAS DataBase Reference: 7-Hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-one(21260-41-3)
• EPA Substance Registry System: 7-Hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-one(21260-41-3)

Safety Data

• Hazardous Substances Data: 21260-41-3(Hazardous Substances Data)

Usage

Description

7-Hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-one is a naturally occurring bioactive compound belonging to the flavonoid family, characterized by its molecular formula C15H12O3. As a derivative of coumarin, this chemical compound has garnered interest due to its potential antioxidant, anti-inflammatory, and anti-cancer properties. Its unique structure and properties position it as a promising candidate for further research and therapeutic applications in the medical and pharmaceutical fields.

Uses

Used in Pharmaceutical Development:
7-Hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-one is used as a pharmaceutical candidate for its potential antioxidant, anti-inflammatory, and anti-cancer properties. Its ability to combat oxidative stress, reduce inflammation, and inhibit cancer cell growth makes it a valuable asset in the development of new medications for various diseases and conditions.
Used in Nutraceutical Formulation:
In the nutraceutical industry, 7-Hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-one is utilized as an active ingredient for its health-promoting benefits. Its presence in dietary supplements and functional foods can contribute to enhanced antioxidant capacity, anti-inflammatory effects, and overall wellness, supporting the maintenance of good health and potentially reducing the risk of certain diseases.
Used in Cosmetics and Personal Care Products:
7-Hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-one is employed in the cosmetics and personal care industry for its potential skin health benefits. Its antioxidant and anti-inflammatory properties may contribute to improved skin condition, reduced signs of aging, and protection against environmental stressors, making it a sought-after ingredient in skincare formulations.
Used in Agricultural Applications:
In agriculture, 7-Hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-one may be used as a natural pesticide or growth promoter, leveraging its bioactive properties to protect crops from diseases and pests, and to enhance plant growth and productivity. Its potential use in this industry highlights the versatility of this compound and its applications beyond the medical and pharmaceutical fields.

InChI:InChI=1/C12H10O3/c13-7-4-5-9-8-2-1-3-10(8)12(14)15-11(9)6-7/h4-6,13H,1-3H2

Upstream product

• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 108-46-3 recorcinol 
• 2941-29-9 2-oxocyclopentanecarbonitrile 
• 120-92-3 cyclopentanone 
• 24922-00-7 ethyl 3-cyclopentyl-3-oxopropionate 
• 141-28-6 diethyl adipate 
• 10472-24-9 methyl 2-oxocyclopentane-1-carboxylate 
• 627-93-0 hexanedioic acid dimethyl ester 
• 124-04-9 Adipic acid 
• 117071-64-4 7-hydroxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-one-imine 

Downstream Products

• 307524-74-9 7-benzoyloxy-2,3-dihydro-1H-cyclopenta[c]chromen-4-one 
• 314743-56-1 7-(1-methyl-2-oxopropoxy)-2,3-dihydrocyclopenta[c]chromen-4(1H)-one 
• 307548-74-9 7-(1-methyl-2-oxo-2-phenylethoxy)-2,3-dihydrocyclopenta[c]chromen-4(1H)-one 
• 500203-98-5 7-[2-(3-methoxyphenyl)-2-oxoethoxy]-2,3-dihydrocyclopenta[c]chromen-4(1H)-one 
• 301309-01-3 7-(2-oxo-2-phenylethoxy)-2,3-dihydrocyclopenta[c]chromen-4(1H)-one 
• 312496-58-5 7-[2-(4-methylphenyl)-2-oxoethoxy]-2,3-dihydrocyclopenta[c]chromen-4(1H)-one 
• 307548-76-1 7-[2-(4-chlorophenyl)-2-oxoethoxy]-2,3-dihydrocyclopenta[c]chromen-4(1H)-one 
• 500204-18-2 7-[2-(4-bromophenyl)-2-oxoethoxy]-2,3-dihydrocyclopenta[c]chromen-4(1H)-one 
• 307548-75-0 7-[2-(4-fluorophenyl)-2-oxoethoxy]-2,3-dihydrocyclopenta[c]chromen-4(1H)-one 
• 312518-97-1 7-acetonyloxy-3,4-cyclopentenecoumarin 
• 374762-16-0 7-[2-(4-methoxyphenyl)-2-oxoethoxy]-2,3-dihydrocyclopenta[c]chromen-4(1H)-one 
• 314743-57-2 7-(2-oxocyclohexyloxy)-2,3-dihydrocyclopenta[c]chromen-4(1H)-one 
• 298207-30-4 ethyl [(4-oxo-1,2,3,4-tetrahydrocyclopenta[c]chromen-7-yl)oxy]acetate 
• 1578300-75-0 7-(4-(4-phenylpiperazin-1-yl)butoxy)-2,3-dihydrocyclopenta[c]chromen-4(1H)-one 

Relevant articles and documents

Photobiological studies of new cyclopentene-psoralens

Psoralen analogues bearing a cyclopentane ring fused to either the 4',5' double bond (compound 4) or the 3,4 double bond (compound 7) of the tricyclic furocoumarin structure were prepared. AM1 theoretical calculations performed for these compounds indicated that the electronic properties of their reactive double bonds were very similar to those of psoralen and its derivative 8-methoxypsoralen (8-MOP), though the overall molecular geometries were clearly different, particularly as regards the change in molecular curvature produced by the introduction of the cyclopentane ring. Compound 4 showed a capacity similar to that of 8-MOP to inhibit the growth of human cervix adenocarcinoma cells (HeLa) and to induce mutagenic effects, but it was definitely less phototoxic to skin than 8-MOP. Its ability to photoadd to DNA and to cross-link DNA strands was also demonstrated. Instead, compound 7 was practically devoid of biological activity and no interaction with the macromolecule could be detected. These differences in behaviour between 4 and 7 are probably due to the molecular curvature resulting from the introduction of the cyclopentane ring.

Nano-BFn/cellulose: a bio-based nano-catalyst for synthesis of bio-active 7-hydroxycoumarins

Nano-BFn/cellulose as a modified bio-based nano-catalyst has been synthesized from nanocellulose and boron triflouride via very simple steps. This novel nano-catalyst exhibited many advantages in the synthesis of 7-hydroxycoumarins such as good

Coumarin-dithiocarbamate hybrids as novel multitarget AChE and MAO-B inhibitors against Alzheimer's disease: Design, synthesis and biological evaluation

A series of new coumarin-dithiocarbamate hybrids were designed and synthesized as multitarget agents for the treatment of Alzheimer's disease. Most of them showed potent and clearly selective inhibition towards AChE and MAO-B. Among these compounds, compound 8f demonstrated the most potent inhibition to AChE with IC50 values of 0.0068 μM and 0.0089 μM for eeAChE and hAChE, respectively. Compound 8g was identified as the most potent inhibitor to hMAO-B, and it is also a good and balanced inhibitor to both hAChE and hMAO-B (0.114 μM for hAChE; 0.101 μM for hMAO-B). Kinetic and molecular modeling studies revealed that 8g was a dual binding site inhibitor for AChE and a competitive inhibitor for MAO-B. Further studies indicated that 8g could penetrate the BBB and exhibit no toxicity on SH-SY5Y neuroblastoma cells. More importantly, 8g did not display any acute toxicity in mice at doses up to 2500 mg/kg and could reverse the cognitive dysfunction of scopolamine-induced AD mice. Overall, these results highlighted 8g as a potential multitarget agent for AD treatment and offered a starting point for design of new multitarget AChE/MAO-B inhibitors based on dithiocarbamate scaffold.