98309-94-5

Basic information

• Product Name: (4aS,8aR)-3,8a-dimethyl-5-methylidene-4,4a,5,6,7,8,8a,9-octahydronaphtho[2,3-b]furan
• Synonyms: Atractylon
• CAS NO: 98309-94-5
• Molecular Formula: C₁₅H₂₀O
• Molecular Weight: 216.3187
• Mol File: 98309-94-5.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 287.1°C at 760 mmHg
• Flash Point: 121.7°C
• Density: 1.02g/cm³
• Vapor Pressure: 0.00437mmHg at 25°C
• Refractive Index: 1.535
• CAS DataBase Reference: (4aS,8aR)-3,8a-dimethyl-5-methylidene-4,4a,5,6,7,8,8a,9-octahydronaphtho[2,3-b]furan(CAS DataBase Reference)
• NIST Chemistry Reference: (4aS,8aR)-3,8a-dimethyl-5-methylidene-4,4a,5,6,7,8,8a,9-octahydronaphtho[2,3-b]furan(98309-94-5)
• EPA Substance Registry System: (4aS,8aR)-3,8a-dimethyl-5-methylidene-4,4a,5,6,7,8,8a,9-octahydronaphtho[2,3-b]furan(98309-94-5)

Safety Data

• Hazardous Substances Data: 98309-94-5(Hazardous Substances Data)

Usage

General Description

The chemical compound (4aS,8aR)-3,8a-dimethyl-5-methylidene-4,4a,5,6,7,8,8a,9-octahydronaphtho[2,3-b]furan, also known as patchouli alcohol, is a naturally occurring sesquiterpene alcohol found in the essential oil of patchouli plants. It is commonly used in perfumery due to its earthy, musky, and slightly sweet odor. Patchouli oil, which contains high levels of patchouli alcohol, is also used in traditional medicine for its purported anti-inflammatory, antifungal, and antiseptic properties. Additionally, patchouli alcohol has been investigated for its potential as a mosquito repellent. Its unique chemical structure and versatile properties make it a valuable compound in various industries.

Upstream product

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• 600151-49-3 6-methoxy-4a-methyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-one 
• 162657-45-6 6-methoxy-4a-methyl-1-(trimethylsilyloxy)-2,3,4,4a,5,8-hexahydronaphthalene 
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• 105631-39-8 (4'aS,5'R,8'R,8'aR)-8'-Hydroxy-8'a-methyl-octahydro-spiro[[1,3]dioxolane-2,2'-naphthalene]-5'-carboxylic acid methyl ester 
• 98466-47-8 (1S,4S,4aS)-4-Hydroxy-4a-methyl-6-oxo-1,2,3,4,4a,5,6,7-octahydro-naphthalene-1-carboxylic acid methyl ester 

Relevant articles and documents

One-step synthesis of furan rings from α-isopropylidene ketones mediated by iodine/DMSO: An approach to potent bioactive terpenes

The system I2/dimethyl sulfoxide mediates the one-step transformation of α-isopropylidene ketones into furan rings following a biomimetic approach. This methodology has been used for the synthesis of terpene furans such as mintfurane, curzerene, atractylon, and isoatractylon, all of them possessing interesting biological activities. The synthesis of linderazulene directly from 4,5-epoxygermacrone via a cascade reaction shows the potential of this protocol. Additionally, this compound proved to show significant ixodicidal activity.

Sesquiterpene Metabolites of the Antarctic Gorgonian Dasystenella acanthina

The ethereal extract of the Antarctic gorgonian Dasystenella acanthina was found to contain three main nonpolar and relatively transient sesquiterpene metabolites (1-3), which were isolated and submitted to spectral analysis. Two of them were identified as the previously reported compounds trans-β-farnesene (1) and isofuranodiene (3), whereas the third metabolite, the furanoeudesmane 2, was unknown. The structure elucidation of this new sesquiterpene was solved mainly on the basis of its spectral properties and correlation with known compounds.

Structures of Novel Sesquiterpene Alcohols from Chloranthus japonicus (Chloranthaceae)

Tree novel sesquiterpene alcohols, shizuka-acoradienol (2), shizukafuranol (3) and shizukolidol (4), were isolated from Chloranthus japonicus Sieb. (Japanese name: Hitori-shizuka, Chloranthaceae).Their structures were elucidated on the basis of their physicochemical properties and some chemical reactions.Furanodienone (5), scopoletin (6a) and isoscopoletin (6b) were also isolated from this plant.