35740-18-2

Basic information

• Product Name: 9-[(3,3-Dimethyl-2-oxiranyl)methoxy]-7H-furo[3,2-g][1]benzopyran-7-one
• Synonyms: (+/-)-Prangenin;9-[(3,3-Dimethyl-2-oxiranyl)methoxy]-7H-furo[3,2-g][1]benzopyran-7-one;Imperatorin epoxide;Oxyimperatorin;oxyimperatorin(+/-)-prangenin imperatorin epoxide 9-((3,3-dimethyl-2-oxiranyl)methoxy)-7h-furo(3,2-g)(1)benzopyran-7-one
• CAS NO: 35740-18-2
• Molecular Formula: C16H14O5
• Molecular Weight: 286.27936
• Mol File: 35740-18-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 115-116 °C
• Boiling Point: 471.4°C at 760 mmHg
• Flash Point: 238.9°C
• Appearance: /
• Density: 1.320
• Vapor Pressure: 4.67E-09mmHg at 25°C
• Refractive Index: 1.606
• CAS DataBase Reference: 9-[(3,3-Dimethyl-2-oxiranyl)methoxy]-7H-furo[3,2-g][1]benzopyran-7-one(CAS DataBase Reference)
• NIST Chemistry Reference: 9-[(3,3-Dimethyl-2-oxiranyl)methoxy]-7H-furo[3,2-g][1]benzopyran-7-one(35740-18-2)
• EPA Substance Registry System: 9-[(3,3-Dimethyl-2-oxiranyl)methoxy]-7H-furo[3,2-g][1]benzopyran-7-one(35740-18-2)

Safety Data

• Hazardous Substances Data: 35740-18-2(Hazardous Substances Data)

Usage

General Description

9-[(3,3-dimethyl-2-oxiranyl)methoxy]-7H-furo[3,2-g][1]benzopyran-7-one is a complex organic compound with a long and specific chemical name. It is a furanocoumarin derivative, which is a class of compounds found in certain plants that are known for their antibacterial, antifungal, and anticancer properties. This particular chemical has a furan ring fused to a benzopyran structure and also contains a cyclic ether group. Furanocoumarins have been studied for their potential pharmaceutical applications, particularly in the field of cancer treatment and as potential treatments for HIV and fungal infections. The compound may have other potential biological activities as well, but further research is needed to fully understand its chemical properties and potential applications.

InChI:InChI=1/C16H14O5/c1-16(2)11(21-16)8-19-15-13-10(5-6-18-13)7-9-3-4-12(17)20-14(9)15/h3-7,11H,8H2,1-2H3

Upstream product

• 482-44-0 imperatorin 

Downstream Products

• 31575-93-6 heraclenol 

Relevant articles and documents

Synthesis of imperatorin analogs and their evaluation as acetylcholinesterase and butyrylcholinesterase inhibitors

In this study, we synthesized several imperatorin analogs using imperatorin and xanthotoxin as substrates. The anti-cholinesterase activities of all compounds were evaluated in in vitro experiments according to the modified Ellman's method. For each synthesized compound, IC50 values for both enzymes were established. Galantamine hydrobromide was used as a positive control in the enzymatic experiments. All active compounds showed selectivity toward butyrylcholinesterase (BuChE) rather than acetylcholinesterase. The most active ones were 8-(3-methylbutoxy)-psoralen and 8-hexoxypsoralen with IC 50 values for BuChE of around 16.5 and 16.4 μM, respectively. The results of our study may be considered as the beginning of a search for potential anti-Alzheimer's disease drugs based on the structure of natural furocoumarins. Several imperatorin analogs were synthesized using imperatorin and xanthotoxin as substrates. Their anti-cholinesterase activities were evaluated, and all active compounds showed selectivity toward butyrylcholinesterase (BuChE) rather than acetylcholinesterase. The most active compounds were 8-(3-methylbutoxy)-psoralen and 8-hexoxypsoralen with IC 50 values for BuChE of around 16.5 and 16.4 μM, respectively.

Epoxidation of some natural furocoumarins and furochromones using γ-ray

Epoxidation of imperatorin (1a) with m-chloroperbenzoic acid (mcpba) under the irradiation of γ-ray gave a mixture of epoxide 3a and dioxofuran 4a. Whereas, alloimperatorin (1b) under the same condition obtained the epoxide 3b as a sole product. On the other hand, it was successfully epoxidized xanthotoxin (1c) with mcpba under the same condition as above. In addition, visnagin (2a) was epoxidized to give a mixture of epoxides 5a, 6a. While, khellin (2b) gave the epoxide 5b, no other products were observed.

Synthesis of Furocoumarin-Type Potential Intercalative Alkylating and Oxidizing Agents of DNA Through Dimethyldioxirane Epoxidation of Imperatorin and Its Derivatives

Epoxidation of imperatorin (1a) by dimethyldioxirane (DMD) affords the natural product prangenin (2a) in excellent yield.Similarly, alloimperatorin (1b) and its methyl and acetate derivatives 1b-d are epoxidized with DMD to give the corresponding epoxides 2b-d in quantitative yields.Furthermore, the reaction of the imperatorin allylic hydroperoxide 1e with DMD, and for comparison with m-chloroperbenzoic acid (CPBA), yields the diastereomeric epoxy hydroperoxides (R*,S*)- and (R*,R*)-2e in low but of opposite diastereoselectivity.Thus, for DMD the (R*,S*)/(R*,R*)-2e ratio is 56:44 and for CPBA 40:60.Key Words: Epoxidation / Furocoumarins / Imperatorin / Alloimperatorin / Prangenin / Dioxirane, dimethyl- / Oxygen transfer