123408-96-8

Basic information

• Product Name: (4S,4aR,6S)-4,4a-dimethyl-6-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene
• Synonyms: (4S,4aR,6S)-6-Isopropenyl-4,4a-dimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene; naphthalene, 1,2,3,4,6,7,8,8a-octahydro-1,8a-dimethyl-7-(1-methylethenyl)-, (1S,7S,8aR)-
• CAS NO: 123408-96-8
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.3511
• Mol File: 123408-96-8.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 274.248°C at 760 mmHg
• Flash Point: 107.811°C
• Density: 0.894g/cm³
• Vapor Pressure: 0.009mmHg at 25°C
• Refractive Index: 1.495
• CAS DataBase Reference: (4S,4aR,6S)-4,4a-dimethyl-6-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,4aR,6S)-4,4a-dimethyl-6-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene(123408-96-8)
• EPA Substance Registry System: (4S,4aR,6S)-4,4a-dimethyl-6-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene(123408-96-8)

Safety Data

• Hazardous Substances Data: 123408-96-8(Hazardous Substances Data)

Usage

General Description

"(4S,4aR,6S)-4,4a-dimethyl-6-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene" is a chemical compound with a specific molecular structure and composition. It is classified as an organic compound and is commonly referred to as a terpene. (4S,4aR,6S)-4,4a-dimethyl-6-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene is formed by the combination of different carbon and hydrogen atoms to form a complex ring structure. It is often used in the production of perfumes, flavors, and pharmaceuticals due to its unique aromatic properties. Additionally, it is known for its potential medicinal properties and has been studied for its potential use in various therapeutic applications.

Upstream product

• 372-97-4 farnesyl pyrophosphate 
• 6784-45-8 1-chloro-3,7,11-trimethyldodeca-2,6,10-triene 
• 4602-84-0 farnesol 

Relevant articles and documents

Stabilisation of transition states prior to and following eudesmane cation in aristolochene synthase

The mechanistic details of the cyclisation of farnesylpyrophosphate (FPP) by aristolochene synthase (AS) from Penicillium roqueforti have only recently begun to emerge, mainly through the analysis of the reaction products generated by AS-mutants. The reaction proceeds through several intermediates including germacrene A and eudesmane cation. Previous work suggested that the side chain of phenylalanine 178 promoted the conversion of eudesmane cation to aristolochene. We now report that the catalytic function of this residue during the conversion of eudesmane cation to aristolochene is mainly due to the large size of its side chain, which facilitates the hydride shift from C2 to C3, rather than its aromatic character. In addition, F178 appears to control the regioselectivity of the final deprotonation step and, together with F112, helps stabilise the developing positive charge on C1 after the expulsion of pyrophosphate from the substrate. These results complete a screen of likely active-site aromatic residues and establish their respective roles in the conversion of FPP to aristolochene. The Royal Society of Chemistry 2006.

Accelerating Biphasic Biocatalysis through New Process Windows

Process intensification through continuous flow reactions has increased the production rates of fine chemicals and pharmaceuticals. Catalytic reactions are accelerated through an unconventional and unprecedented use of a high-performance liquid/liquid counter current chromatography system. Product generation is significantly faster than in traditional batch reactors or in segmented flow systems, which is exemplified through stereoselective phase-transfer catalyzed reactions. This methodology also enables the intensification of biocatalysis as demonstrated in high yield esterifications and in the sesquiterpene cyclase-catalyzed synthesis of sesquiterpenes from farnesyl diphosphate as high-value natural products with applications in medicine, agriculture and the fragrance industry. Product release in sesquiterpene synthases is rate limiting due to the hydrophobic nature of sesquiterpenes, but a biphasic system exposed to centrifugal forces allows for highly efficient reactions.

Stereochemistry of eudesmane cation formation during catalysis by aristolochene synthase from Penicillium roqueforti

The aristolochene synthase catalysed cyclisation of farnesyl diphosphate (1) has been postulated to proceed through (S)-germacrene A (3). However, the active site acid that reprotonates this neutral intermediate has so far proved difficult to identify and, based on high level ab initio molecular orbital and density functional theory calculations, a proton transfer mechanism has recently been proposed, in which proton transfer from C12 of germacryl cation to the C6,C7-double bond of germacryl cation (2) proceeds either directly or via a tightly bound water molecule. In this work, the stereochemistry of the elimination and protonation reactions was investigated by the analysis of the reaction products from incubation of 1 and of [12,12,12,13,13,13- 2H6]-farnesyl diphosphate (15) with aristolochene synthase from Penicillium roqueforti (PR-AS) in H2O and D2O. The results reveal proton loss from C12 during the reaction and incorporation of another proton from the solvent. Incubation of 1 with PR-AS in D2O led to the production of (6R)-[6-2H] aristolochene, indicating that protonation occurs from the face of the 10-membered germacrene ring opposite the isopropylidene group. Hence these results firmly exclude proton transfer from C12 to C6 of germacryl cation. We propose here Lys 206 as the general acid/base during PR-AS catalysis. This residue is part of a conserved network of hydrogen bonds, along which protons could be delivered from the solvent to the active site.