19435-97-3

Basic information

• Product Name: (1R,4S,4aR,8aS)-1,6-dimethyl-4-(1-methylethyl)-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-ol
• Synonyms: (1R,4S,4aR,8aS)-1,6-dimethyl-4-(propan-2-yl)-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-ol; 1.beta.-Cadin-4-en-10-ol; 1-naphthalenol, 1,2,3,4,4a,7,8,8a-octahydro-1,6-dimethyl-4-(1-methylethyl)-, (1R,4S,4aR,8aS)-
• CAS NO: 19435-97-3
• Molecular Formula: C₁₅H₂₆O
• Molecular Weight: 222.3663
• Mol File: 19435-97-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 303.4°C at 760 mmHg
• Flash Point: 128.3°C
• Density: 0.937g/cm³
• Vapor Pressure: 8.96E-05mmHg at 25°C
• Refractive Index: 1.489
• CAS DataBase Reference: (1R,4S,4aR,8aS)-1,6-dimethyl-4-(1-methylethyl)-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4S,4aR,8aS)-1,6-dimethyl-4-(1-methylethyl)-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-ol(19435-97-3)
• EPA Substance Registry System: (1R,4S,4aR,8aS)-1,6-dimethyl-4-(1-methylethyl)-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-ol(19435-97-3)

Safety Data

• Hazardous Substances Data: 19435-97-3(Hazardous Substances Data)

Usage

Description

(1R,4S,4aR,8aS)-1,6-dimethyl-4-(1-methylethyl)-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-ol is a terpenoid compound with the molecular formula C15H26O. It is a derivative of naphthol, featuring a complex structure with multiple methyl groups and a hydroxyl group attached to a naphthalene core. This organic compound is known for its potential applications in various industries due to its unique properties and functional groups.

Uses

Used in Perfumery Industry:
(1R,4S,4aR,8aS)-1,6-dimethyl-4-(1-methylethyl)-1,3,4,4a,7,8,8a-octahydronaphthalen-1-ol is used as a fragrance ingredient for its unique scent characteristics, contributing to the creation of various perfumes and scented products.
Used in Flavor Industry:
(1R,4S,4aR,8aS)-1,6-dimethyl-4-(1-methylethyl)-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-ol is utilized as a flavoring agent, enhancing the taste profiles of food and beverage products, thanks to its distinct flavor attributes.
Used in Pharmaceutical Industry:
(1R,4S,4aR,8aS)-1,6-dimethyl-4-(1-methylethyl)-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-ol serves as an active pharmaceutical ingredient or an intermediate in the synthesis of drugs, owing to its potential medicinal properties and chemical reactivity.
Used in Medical Field:
It has potential applications in medicine, possibly due to its ability to interact with biological systems, offering therapeutic benefits that can be explored for treating various health conditions.
Used in Agricultural Field:
(1R,4S,4aR,8aS)-1,6-dimethyl-4-(1-methylethyl)-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-ol may also find use in agriculture, potentially serving as a component in pesticides, herbicides, or other agrochemicals, leveraging its chemical properties for crop protection and enhancement.

Upstream product

• 75-16-1 methylmagnesium bromide 
• 105986-39-8 (1R,4R,4aS,8aS)-6-Bromomethyl-4-isopropyl-1-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ol 
• 105986-39-8 (1S,4R,4aS,8aS)-6-Bromomethyl-4-isopropyl-1-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-ol 
• 94853-09-5 1-(2-Diethylaminoethoxy)-4-isopropyl-6-(5-methyl-4-hexenyl)-cyclohexadien-1,4 
• 94853-22-2 rac-(1R,2S,5R,6R,8R)-5-Isopropyl-2,8-dimethyl-2-(1,3,6-trioxa-heptyl)-bicyclo<4.4.0>decan-7-on 
• 94853-20-0 rac-(1R,2S,5R,6R)-5-Isopropyl-2-methyl-2-(1,3,6-trioxaheptyl)-bicyclo<4.4.0>decan-7-on 
• 94853-11-9 rac-(5R,6S,7R)-7-Isopropenyl-5-isopropyl-bicyclo<4.4.0>dec-1-en-2-yl-acetat 
• 94853-15-3 rac-(1R,2R,5R,6R,7R)-2-Hydroxy-5-isopropyl-2-methyl-bicyclo<4.4.0>dec-7-yl-acetat 
• 94853-12-0 rac-(1R,5R,6S,7R)-7-Isopropenyl-5-isopropyl-bicyclo<4.4.0>decan-2-on 
• 94853-21-1 rac-(1R,2S,5R,6R,7R)-5-Isopropyl-2-methyl-2-(1,3,6-trioxaheptyl)-bicyclo<4.4.0>decan-7-ol 
• 94853-14-2 rac-(1R,2S,5R,6R,7R)-(2-Hydroxy-5-isopropyl-2-methyl-bicyclo<4.4.0>dec-7-yl)-methyl keton 
• 2543-74-0 rac-(1R,2S,5R,6R,8R)-2-Hydroxy-5-isopropyl-2,8-dimethyl-bicyclo<4.4.0>decan-7-on 
• 94853-13-1 rac-(1R,2S,5R,6S,7R)-7-Isopropenyl-5-isopropyl-2-methyl-bicyclo<4.4.0>decan-2-ol 
• 94853-18-6 rac-(1R,2S,5R,6R)-2-Hydroxy-5-isopropyl-2-methyl-bicyclo<4.4.0>decan-7-on 

Downstream Products

• 65648-26-2 α-cadinol p-nitrobenzoate 
• 35124-30-2 Amorphan-4α.9β-diol 
• 101106-71-2 5,6-Epoxy-4-isopropyl-1,6-dimethyl-decahydro-[1]naphthol 
• 35124-32-4 Cadinan-4-on-9β-ol 
• 35124-31-3 Amorphan-4-on-9β-ol 
• 35049-27-5 (+/-)-Oplopanone 
• 20085-91-0 (1R,6R,7S,10R)-10-hydroxy-4⁽⁵⁾-cadinen-3-one 
• 398147-34-7 15-hydroxy-α-cadinol 
• 483-78-3 cadalene 
• 483-74-9 (-)-γ-cadinene 

Relevant articles and documents

Antimalarial Properties of Simplified Kalihinol Analogues

Several kalihinol natural products, members of the broader isocyanoterpene family of antimalarial agents, are potent inhibitors of Plasmodium falciparum, the agent of the most severe form of human malaria. Our previous total synthesis of kalihinol B provided a blueprint to generate many analogues within this family, some as complex as the natural product and some much simplified and easier to access. Each analogue was tested for blood-stage antimalarial activity using both drug-sensitive and -resistant P. falciparum strains. Many considerably simpler analogues of the kalihinols retained potent activity, as did a compound with a different decalin scaffold made in only three steps from sclareolide. Finally, one representative compound showed reasonable stability toward microsomal metabolism, suggesting that the isonitrile functional group that is critical for activity is not an inherent liability in these compounds.

A multiproduct terpene synthase from medicago truncatula generates cadalane sesquiterpenes via two different mechanisms

Terpene synthases are responsible for a large diversity of terpene carbon skeletons found in nature. The multiproduct sesquiterpene synthase MtTPS5 isolated from Medicago truncatula produces 27 products from farnesyl diphosphate (1, FDP). In this paper, we report the reaction steps involved in the formation of these products using incubation experiments with deuterium-containing substrates; we determined the absolute configuration of individual products to establish the stereochemical course of the reaction cascade and the initial conformation of the cycling substrate. Additional labeling experiments conducted with deuterium oxide showed that cadalane sesquiterpenes are mainly produced via the protonation of the neutral intermediate germacrene D (5). These findings provide an alternative route to the general accepted pathway via nerolidyl diphosphate (2, NDP) en route to sesquiterpenes with a cadalane skeleton. Mutational analysis of the enzyme demonstrated that a tyrosine residue is important for the protonation process.

BIOMIMETIC SYNTHESES OF OPPOSITOL, OPLOPANONE, AND APHANAMOL II FROM GERMACRENE-D

Biomimetic reaction of germacrene-D induced with bromonium ion has been carried out to give several bromo compounds, from which (+/-)-oppositol and (+/-)-oplopanone have been synthesized. (+/-)-Aphanamol II has also been synthesized from epoxygermacrene-D.