19435-97-3

Usage

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

• 74799-64-7 α-cadinol formate 
• 74841-87-5 (-)-germacra-1(10),5(E)-dien-4β-ol 
• 372-97-4 farnesyl pyrophosphate 
• 372-97-4 farnesyl pyrophosphate 
• 74799-64-7 T-cadinol formate 
• 94853-23-3 C₂₂H₃₄N₂O₃S 
• 94853-13-1 rac-(1R,2S,5R,6S,7R)-7-Isopropenyl-5-isopropyl-2-methyl-bicyclo<4.4.0>decan-2-ol 
• 2543-74-0 rac-(1R,2S,5R,6R,8R)-2-Hydroxy-5-isopropyl-2,8-dimethyl-bicyclo<4.4.0>decan-7-on 
• 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 
• 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 
• 75-16-1 methylmagnesium bromide 
• 94853-17-5 rac-(1R,2S,5R,6R,7R)-5-Isopropyl-2-methyl-bicyclo<4.4.0>decan-2,7-diol 
• 94853-16-4 rac-(1R,2S,5R,6R,7R)-5-Isopropyl-2-methyl-2-(1,3,6-trioxaheptyl)-bicyclo<4.4.0>dec-7-yl-acetat 
• 94853-09-5 1-(2-Diethylaminoethoxy)-4-isopropyl-6-(5-methyl-4-hexenyl)-cyclohexadien-1,4 

Downstream Products

• 65648-26-2 α-cadinol p-nitrobenzoate 
• 101106-71-2 5,6-Epoxy-4-isopropyl-1,6-dimethyl-decahydro-[1]naphthol 
• 483-78-3 cadalene 
• 20085-91-0 (1R,6R,7S,10R)-10-hydroxy-4⁽⁵⁾-cadinen-3-one 
• 398147-34-7 15-hydroxy-α-cadinol 
• 24268-39-1 γ-muurolene 
• 35124-30-2 Amorphan-4α.9β-diol 
• 29259-92-5 (1S,4aS,5S,8R,8aR)-8-Isopropyl-2,5-dimethyl-decahydro-naphthalene-1,2,5-triol 
• 483-74-9 (-)-γ-cadinene 
• 35124-32-4 Cadinan-4-on-9β-ol 
• 35124-31-3 Amorphan-4-on-9β-ol 

Relevant academic research and scientific papers

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.

Improved selectivity of an engineered multi-product terpene synthase

Mutation of the sesquiterpene synthase Cop2 was conducted with a high-throughput screen for the cyclization activity using a non-natural substrate. A mutant of Cop2 was identified that contained three amino acid substitutions. This mutant, 17H2, converted the natural substrate FPP into germacrene D-4-ol with 77% selectivity. This selectivity is in contrast to that of the parent enzyme in which germacrene D-4-ol is produced as 29% and α-cadinol is produced as 46% of the product mixture. The mutations were shown to each contribute to this selectivity, and a homology model suggested that the mutations lie near to the active site though would be unlikely to be targeted for mutation by rational methods. Kinetic comparisons show that 17H2 maintains a kcat/KM of 0.62 mM-1 s -1, which is nearly identical to that of the parent Cop2, which had a kcat/KM of 0.58 mM-1 s-1. This journal is the Partner Organisations 2014.

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.

Stereochemistry of 1,6-germacradien-5-ol, a constituent of the needles of Scots pine (Pinus sylvestris) and of the defence secretion from larvae of the pine sawfly Neodiprion sertifer

(-)-1,6-Germacradien-5-ol [(E,E)-1,5-dimethyl-8-isopropylcyclodeca-1,6-dien-5-ol, 1] has been isolated from the defence secretion from larvae of the pine sawfly Neodiprion sertifer and from needles of Scots pine (Pinus sylvestris). It was characterized by means of spectroscopic methods and by its optical rotation. Acid-promoted transannular cyclisation isomerised 1 to the known (-)-α-cadinol (4), whereby the configuration at position 8 was established as S. The configuration at the second stereocentre, position 5, carrying the alcohol group is discussed on the basis of molecular mechanics calculations (MM2), NMR shift values, coupling constants and NOESY experiments. 1-endo-Bourbonanol (7a) and (-)-5-methoxy-1,6-germacradiene (8) were prepared from 1 and investigated by NMR spectroscopy. The evidence collected indicated that the stereoisomer isolated was (5S,8S)-1,6-germacradien-5-ol.

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.

STEREOSELEKTIVE TOTALSYNTHESE VON (+/-)-TORREYOL

Enones of formulae Ia-d undergo cyclization to give stereoselectively the enol esters IIa-d, respectively.IIa-d are suitable synthones for some sesquiterpene syntheses.-In this paper the synthesis of torreyol (1) is described by an all step strereocontrolled reaction sequence: cyclization educt 10 (Ic) was prepared by alkylation of 8 with 5 and enol ether cleavage of 9.The reaction sequence 11a (IIc)14a 1518 (ester hydrolysis, formation of the tert. alcohol, degradation of the isopropenyl group) followed by oxidation resulted in the formation of ketone 19 whose relative configuration was determined by the 2D J-resolved 400 MHz (1)H NMR spectrum.After methylation at C-8 (2223) the tosylhydrazone 25 underwent Bamford-Stevens reaction to yield (+/-)-1.

5S,8S-GERMACRA-1E,6E-DIEN-5-OL FROM THE OLEORESIN OF Picea ajanensis AND ITS BIOMIMETIC CYCLIZATION

From the oleoresin of the Yeddo spruce we have isolated a new sesquiterpene alcohol for which, on the basis of spectral and chemical chracteristics, the structure of 5S,8S-germacra-1E,6E-dien-5-ol (I) is suggested.The photocyclization of the alcohol isolated has given bourbonol, and its reaction with formic acid has yielded γ- and δ-cadinenes, the formates of T-muurolol and of T- and α-cadinols, and free T-muurolol and T- and α-cadinols