581-12-4

Basic information

• Product Name: (-)-Ngainone
• Synonyms: (-)-1-[(2R,5S)-5-(3-Furyl)-2-methyl-2,3,4,5-tetrahydrofuran-2-yl]-4-methyl-2-pentanone;(-)-Ngainone;(-)-Ngaione;(2R)-2β-(2-Oxo-4-methylpentyl)-2-methyl-5β-(3-furanyl)tetrahydrofuran;(2R,5S)-5-(3-Furyl)-2-(2-oxo-4-methylpentyl)-2-methyltetrahydrofuran;cis-Ngaione;1-(5-(3-Furyl)tetrahydro-2-methyl-2-furyl)-4-methyl-2-pentanone, (2R,5S)-(-);2-Pentanone, 1-(5-(3-furyl)-2-methyl-tetrahydro-2-furyl)-4-methyl-, (2R,5S)-(-)-
• CAS NO: 581-12-4
• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.37
• Mol File: 581-12-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 343.6°Cat760mmHg
• Flash Point: 161.6°C
• Appearance: /
• Density: 1.016g/cm³
• CAS DataBase Reference: (-)-Ngainone(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Ngainone(581-12-4)
• EPA Substance Registry System: (-)-Ngainone(581-12-4)

Safety Data

• Hazardous Substances Data: 581-12-4(Hazardous Substances Data)

Usage

Description

(-)-Ngainone is a prenylated flavonoid natural product isolated from the stem bark of the African plant, Cylicodiscus gabunensis. It exhibits significant antiplasmodial activity against the malaria parasite, Plasmodium falciparum, and possesses antioxidant and cytotoxic properties, making it a promising candidate for the development of new antimalarial drugs and a potential therapeutic agent for various diseases.

Uses

Used in Pharmaceutical Industry:
(-)-Ngainone is used as an antimalarial agent for its significant antiplasmodial activity against the malaria parasite, Plasmodium falciparum. It inhibits the growth of the parasite at the early ring and trophozoite stages, making it a promising candidate for the development of new antimalarial drugs.
Used in Antioxidant Applications:
(-)-Ngainone is used as an antioxidant agent for its antioxidant properties, which can help protect cells from damage caused by reactive oxygen species and contribute to the prevention and treatment of various diseases.
Used in Cytotoxic Applications:
(-)-Ngainone is used as a cytotoxic agent for its cytotoxic properties, which can help target and eliminate cancer cells, making it a potential therapeutic agent for cancer treatment.
Used in Drug Development:
(-)-Ngainone is used as a chemical compound for further research and drug development due to its natural origin and diverse biological activities, including its antiplasmodial, antioxidant, and cytotoxic properties.

Upstream product

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• 131317-18-5 5α-(3'-furyl)-2β-(toluenesulfonyl)methoxy-2α-methyloxolane 
• 60007-01-4 bis-1,3-propane dithioketal of 5α-(3'-furyl)-2β-((formyl)methyl)-2α-methyloxolane 
• 100059-30-1 5-Methyl-2,3,4,5-tetrahydro-[2,3']bifuranyl-5-carboxylic acid methyl ester 
• 60122-18-1 5α-(3'-furyl)-2β-(iodomethyl)-2α-methyloxolane 
• 131317-12-9 5α-(3'-furyl)-2β-hydroxymethyl-2α-methyloxolane 
• 60007-02-5 bis-1,3-propane dithioketal of trans-4-methyl-1-(2,3,4,5-tetrahydro-5-methyl<2,3'-bifuran>-5-yl)-2-pentanone 
• 131317-18-5 5α-(3'-furyl)-2α-(toluenesulfonyl)methoxy-2β-methyloxolane 
• 60007-01-4 bis-1,3-propane dithioketal of 5α-(3'-furyl)-2α-((formyl)methyl)-2β-methyloxolane 
• 60122-18-1 5α-(3'-furyl)-2α-(iodomethyl)-2β-methyloxolane 
• 131317-12-9 5α-(3'-furyl)-2α-hydroxymethyl-2β-methyloxolane 
• 60007-02-5 bis-1,3-propane dithioketal of cis-4-methyl-1-(2,3,4,5-tetrahydro-5-methyl<2,3'-bifuran>-5-yl)-2-pentanone 
• 51703-95-8 9-acetoxy-9-[3]furyl-2,6-dimethyl-non-5ξ-en-4-one 

Relevant articles and documents

Formal Total Synthesis of Ipomeamarone via the Dihydrofuran Annulation

A formal synthesis of (2R-cis)-4-methyl-1-(2,3,4,5-tetrahydro)-5-methyl--2-pentanone, or ipomeamarone (1) was accomplished from 3-furaldehyde 5 and ethyl-2-bromocrotonate 4.The key step involved the formation of the dihydrofuran ring in 2 via a vinyloxirane rearrangement of 3 in the dihydrofuran annulation.Mechanistic duality of reactions of those tetrahydrofurans possessing acidic hydrogens adjacent to the ring is addressed.