18676-07-8

Basic information

• Product Name: Hispanolone
• Synonyms: Hispanolone;(3S)-4-[2-(3-Furyl)ethyl]-3,4,4a,5,6,7,8,8aβ-octahydro-4β-hydroxy-3β,4aα,8,8-tetramethylnaphthalen-2(1H)-one;LC-5505
• CAS NO: 18676-07-8
• Molecular Formula: C20H30O3
• Molecular Weight: 318.4504
• Mol File: 18676-07-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 417.2°Cat760mmHg
• Flash Point: 206.1°C
• Appearance: /
• Density: 1.045g/cm³
• Vapor Pressure: 1.05E-07mmHg at 25°C
• Refractive Index: 1.506
• CAS DataBase Reference: Hispanolone(CAS DataBase Reference)
• NIST Chemistry Reference: Hispanolone(18676-07-8)
• EPA Substance Registry System: Hispanolone(18676-07-8)

Safety Data

• Hazardous Substances Data: 18676-07-8(Hazardous Substances Data)

Usage

General Description

Hispanolone is a chemical compound primarily found in the bark of the Pygeum africanum tree. It is a natural steroid and has been shown to have anti-inflammatory, anti-androgenic, and anti-estrogenic properties. Hispanolone is commonly used in traditional medicine to treat symptoms of benign prostatic hyperplasia (BPH) and related conditions. Its anti-inflammatory effects may help reduce swelling and discomfort in the prostate, while its anti-androgenic properties may help to inhibit the production of hormones that contribute to BPH. Additionally, its anti-estrogenic properties may help to balance hormone levels in the body. Hispanolone has also been researched for potential applications in addressing acne, baldness, and other hormonal disorders.

InChI:InChI=1/C20H30O3/c1-14-16(21)12-17-18(2,3)8-5-9-19(17,4)20(14,22)10-6-15-7-11-23-13-15/h7,11,13-14,17,22H,5-6,8-10,12H2,1-4H3/t14-,17+,19+,20-/m1/s1

Upstream product

• 132922-55-5 (-)-Prehispanolone 
• 82509-26-0 (+)-(2S,3R,4S,4aS,8aS)-3,4-epoxy-4-[2-(3-furyl)ethyl]-1,2,3,4,4a,5,6,7,8,8a-decahydro-3,4a,8,8-tetramethylnaphth-2-ol 
• 80926-09-6 (+)-(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethyl-1-trimethylsilyloxynaphthalene 
• 224048-24-2 (2ζ,4aS,8aS)-2,5,5,8a-Tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1(2H)-one 
• 250127-12-9 (+)-(2S,3R,4S,4aS,8aS)-2-tert-butyldimethylsiloxy-3,4-epoxy-4-[2-(3-furyl)ethyl]-1,2,3,4,4a,5,6,7,8,8a-decahydro-3,4a,8,8-tetramethylnaphthalene 
• 250127-11-8 (+)-(2S,4aS,8aS)-2-tert-butyldimethylsiloxy-4-[2-(3-furyl)ethyl]-1,2,4a,5,6,7,8,8a-octahydro-3,4a,8,8-tetramethylnaphthalene 
• 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 
• 250127-10-7 (+)-(2S,4aS,8aS)-4-[2-(3-furyl)ethyl]-1,2,4a,5,6,7,8,8a-octahydro-3,4a,8,8-tetramethylnaphth-2-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 
• 110654-75-6 (+)-(4aS,5S)-5-benzoyloxy-3,4,4a,5,6,7-hexahydro-1,1,4a-trimethylnaphthalen-2(1H)-one 
• 25487-94-9 (-)-(4aS,8aS)-4,4a,5,6,7,8-hexahydro-2,5,5,8a-tetramethylnaphthalen-1(8aH)-one 
• 110715-80-5 (-)-(1S,8aS)-1,2,3,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalen-1-ol 

Downstream Products

• 170711-93-0 6β-hydroxy-15,16-epoxy-labda-8,13(16),14-trien-7-one 
• 170711-93-0 6α-hydroxy-15,16-epoxylabda-8,13(16),14-trien-7-one 
• 82462-67-7 (+)-(4aS,8aS)-4-[2-(3-furyl)ethyl]-4a,5,6,7,8,8a-hexahydro-3,4a,8,8-tetramethylnaphthalen-2(1H)-one 

Relevant articles and documents

PREHISPANOLONE, A LABDANE DITERPENE FROM LEONURUS HETEROPHYLLUS

A new labdane diterpene, prehispanolone, has been isolated from Leonurus heterophyllus.Its structure, 9α,13R;15,16-diepoxylabdan-14-en-7-one, was established by spectroscopic means as well as by examination of its derivatives.

Total syntheses of naturally occurring molecules possessing 1,7- dioxaspiro[4.4]nonane skeletons

The syntheses of several naturally occurring molecules, namely prehispanolone, sphydrofuran, secosyrins, and syringolides are reviewed. Interestingly, these compounds are all structurally related, possessing a 1,7-dioxaspiro[4.4]nonane framework. The pivotal step in these synthetic endeavors involves the peracid oxidation of substituted 2- trimethylsilylfurans to but-2-en-4-olides. A subsequent intramolecular Michael addition procedure was also essential in the construction of the spiro skeleton. Two significant issues concerning regioselectivity and stereoselectivity are also addressed.