82462-67-7

Basic information

• Product Name: (+)-(4aS,8aS)-4-[2-(3-furyl)ethyl]-4a,5,6,7,8,8a-hexahydro-3,4a,8,8-tetramethylnaphthalen-2(1H)-one
• CAS NO: 82462-67-7
• Molecular Weight: 300.441
• Mol File: 82462-67-7.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (+)-(4aS,8aS)-4-[2-(3-furyl)ethyl]-4a,5,6,7,8,8a-hexahydro-3,4a,8,8-tetramethylnaphthalen-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(4aS,8aS)-4-[2-(3-furyl)ethyl]-4a,5,6,7,8,8a-hexahydro-3,4a,8,8-tetramethylnaphthalen-2(1H)-one(82462-67-7)
• EPA Substance Registry System: (+)-(4aS,8aS)-4-[2-(3-furyl)ethyl]-4a,5,6,7,8,8a-hexahydro-3,4a,8,8-tetramethylnaphthalen-2(1H)-one(82462-67-7)

Safety Data

• Hazardous Substances Data: 82462-67-7(Hazardous Substances Data)

Usage

General Description

The chemical compound "(+)-(4aS,8aS)-4-[2-(3-furyl)ethyl]-4a,5,6,7,8,8a-hexahydro-3,4a,8,8-tetramethylnaphthalen-2(1H)-one" is a synthetic organic compound with the molecular formula C19H28O. It is a ketone derivative, and its structure includes a furan ring and a naphthalene ring. The compound is a colorless to pale yellow liquid with a sweet, floral odor. Its exact uses and applications are not well-documented, and further research may be needed to fully understand its properties and potential uses.

Upstream product

• 18676-07-8 (-)-Hispanolone 
• 250127-08-3 (-)-(1S,4aS,8aS)-1-(3-furyl)ethynyl-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-1-trimethylsiloxynaphthalene 
• 250127-09-4 (-)-(1S,4aS,8aS)-1-(3-furyl)ethynyl-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphth-1-ol 
• 250127-02-7 (-)-(1R,4aS,8aS)-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-1-trimethylsilylethynylnaphth-1-ol 
• 250127-03-8 (+)-(4aS,8aS)-4a,5,6,7,8,8a-hexahydro-3,4a,8,8-tetramethyl-4-trimethylsilylethynylnaphthalen-2(1H)-one 
• 250127-07-2 (-)-(1S,4aS,8aS)-1-ethynyl-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethyl-1-trimethylsiloxynaphthalene 
• 250127-06-1 (-)-(1S,4aS,8aS)-1-ethynyl-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphth-1-ol 
• 250127-04-9 (+)-(4aS,8aS)-4-ethynyl-4a,5,6,7,8,8a-hexahydro-3,4a,8,8-tetramethyl-naphthalen-2(1H)-one 
• 250127-01-6 (4aS,8aS)-2-bromo-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalen-1(2H)-one 
• 224048-24-2 (2ζ,4aS,8aS)-2,5,5,8a-Tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1(2H)-one 
• 110654-75-6 (+)-(4aS,5S)-5-benzoyloxy-3,4,4a,5,6,7-hexahydro-1,1,4a-trimethylnaphthalen-2(1H)-one 
• 80926-09-6 (+)-(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethyl-1-trimethylsilyloxynaphthalene 
• 110715-80-5 (-)-(1S,8aS)-1,2,3,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalen-1-ol 
• 60134-39-6 (-)-(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalen-1(2H)-one 

Downstream Products

• 18676-07-8 (-)-Hispanolone 
• 170711-93-0 6β-hydroxy-15,16-epoxy-labda-8,13(16),14-trien-7-one 
• 864817-63-0 15,16-epoxy-6-hydroxylabda-5,8,13⁽¹⁶⁾,14-tetraen-7-one 
• 170711-93-0 6α-hydroxy-15,16-epoxylabda-8,13(16),14-trien-7-one 

Relevant articles and documents

Dehydrohispanolone Derivatives Attenuate the Inflammatory Response through the Modulation of Inflammasome Activation

The NLRP3 inflammasome plays a critical role in inflammation-mediated human diseases and represents a promising drug target for novel anti-inflammatory therapies. Hispanolone is a labdane diterpenoid isolated from the aerial parts of Ballota species. This diterpenoid and some derivatives have demonstrated anti-inflammatory effects in classical inflammatory pathways. In the present study, a series of dehydrohispanolone derivatives (1-19) was synthesized, and their anti-inflammatory activities toward NLRP3 inflammasome activation were evaluated. The structures of the dehydrohispanolone analogues produced were elucidated by NMR spectroscopy and mass spectrometry. Four derivatives significantly inhibited IL-1β secretion, with 15 and 18 being the most active (IC50 = 18.7 and 13.8 μM, respectively). Analysis of IL-1β and caspase-1 expression revealed that the new diterpenoids 15 and 18 are selective inhibitors of the NLRP3 inflammasome, reinforcing the previously demonstrated anti-inflammatory properties of hispanolone derivatives.

The absolute stereochemistry of a diterpene from Ballota aucheri

The semi-synthetic transformation of hispanolone, isolated from Ballota africana, into βp-hydroxy-15,16-epoxylabda-8,13(16),14-trien-7-one has established an ent-labdane absolute stereochemistry for a diterpene metabolite originally isolated from B. aucheri.

Total synthesis of (-)-hispanolone and an improved approach towards prehispanolone

On the basis of the recently reported construction of (±)-hispanolone (2), the enantiomerically pure form of (-),2, employed in our partial synthesis of the specific platelet activating factor receptor antagonist prehispanolone (3), was prepared from (S)-