24173-71-5

Usage

Uses

Used in Fragrance and Cosmetics Industry:
Kobusone is used as a fragrance ingredient for its pleasant and versatile scent, enhancing the appeal of various cosmetic products.
Used in Medicinal and Therapeutic Applications:
Kobusone is used as a potential therapeutic agent for its anti-inflammatory and antioxidant properties, indicating its potential in treating various health conditions.
Used in Pest Control:
Kobusone is used as a natural insect repellent for its effectiveness against ticks and mosquitoes, contributing to pest control and protection against insect-borne diseases.

InChI:InChI=1/C14H22O2/c1-13(2)8-9-10(13)6-7-14(3)12(16-14)5-4-11(9)15/h9-10,12H,4-8H2,1-3H3/t9-,10+,12+,14+/m0/s1

Upstream product

• 87-44-5 β-caryophyllene 
• 1139-30-6 caryophyllene oxide 
• 10577-25-0 5,6-epoxy-2-hydroxymethyl-6,10,10-trimethyl-bicyclo[7.2.0]undecan-2-ol 
• 60594-22-1 caryophyllene oxide 
• 118-65-0 (-)-isocaryophyllene 

Downstream Products

• 87-44-5 β-caryophyllene 
• 1139-30-6 caryophyllene oxide 
• 1176003-49-8 (-)-(1S,4S,7R,8R,9S)-9-epi-presilphiperfolan-1-ol 
• 219314-01-9 (E)-15-norcaryophyll-4-en-8β-yl tosylate 
• 24173-72-6 Isokobuson 

Relevant academic research and scientific papers

Synthesis of Caryophyllane Oximes and Hydrazone and Their O- and N-Acylated Derivatives

Kobusone oxime and hydrazone were synthesized for the first time in yields of 78 and 71%, respectively, via condensation of the sesquiterpene ketone kobusone, which was prepared by oxidation of caryophyllene oxide, with hydroxylamine and hydrazine. Acylation of the caryophyllane oxime and hydrazone produced series of O- and N-derivatives in preparative yields up to 90%. The molecular structures of the acyloximes and acetylhydrazone were established by X-ray crystal structure analyses.

Four-Step Access to the Sesquiterpene Natural Product Presilphiperfolan-1β-ol and Unnatural Derivatives via Supramolecular Catalysis

Terpenes constitute one of the most structurally varied classes of natural products. A wide range of these structures are produced in nature by type I terpene cyclase enzymes from one single substrate. However, such reactivity has proven difficult to reproduce in solution with man-made systems. Herein we report the shortest synthesis of the tricyclic sesquiterpene presilphiperfolan-1β-ol to date, utilizing the supramolecular resorcinarene capsule as catalyst for the key step. This synthetic approach also allows access to unnatural derivatives of the natural product, which would not be accessible through the biosynthetic machinery. Additionally, this study provides useful insight into the biosynthesis of the presilphiperfolanol natural products, including the first experimental evidence consistent with the proposed biosynthetic connection between caryophyllene and the presilphiperfolanols.

Meroterpene-like compounds derived from β-caryophyllene as potent α-glucosidase inhibitors

Meroterpenoids isolated from guava (Psidium guajava) and Rhodomyrtus tomentosa possess special skeletons which incorporate terpenoids with phloroglucinol derivatives. Most of these meroterpenoids showed high cytotoxicity against cancer cell lines. However

Exploring sesquiterpene alkaloid-like scaffolds via Beckmann-transannular remodelling of beta-caryophyllene

High-throughput screening (HTS) is the dominant approach to identify lead compounds in drug development. However, most compound-screening collections provide little structural or stereochemical complexity, which do not offer enough diversity to merit the modulation of many drug targets. Here we describe a facile strategy for the creation of diverse compounds with high structural and stereochemical complexity using readily available natural products, β-caryophyllene, as a synthetic starting point. Our findings demonstrate that a cascaded Beckmann-transannular protocol transforms macrocyclic natural products into poly-heterocyclic unnatural skeletal types. These compounds are significantly more complex and diverse than those in standard screening collections.

Convenient synthesis of deuterium labelled sesquiterpenes

Sesquiterpenes are an important class of molecules, with roles ranging from pollination and signalling to defense mechanisms. Despite their apparent importance, the limited number of commercial standards has hindered their study and precise quantification. Herein, we report the syntheses of fourteen labelled sesquiterpenes with a high level of deuterium incorporation (>95%) for applications in MS-based studies.

Novel rearrangements of sesquiterpenoid panasinsane derivatives under acidic conditions

The sesquiterpenoid panasinsane derivatives 11 and 14-16 have been prepared from caryophyllene oxide (7). The novel rearrangement reactions of compounds 11 and 14 under TCNE-catalyzed solvolysis conditions and the reactions of compounds 15 and 16 under superacid conditions (HSO3F/Et2O, -63 °C) have been investigated. The ginsenol derivative 17 is obtained from compounds 11 and 14 under TCNE-catalyzed conditions. The rearrangement of compounds 15 and 16 under superacid conditions leads to the novel sesquiterpene derivatives (1S,4S,7S,10S,11S)-3,3,10,11-tetramethyltricyclo [5.3.1.04,10]undecan-1,11-yl sulfate (19) and (1S,4S,5S,8S)-2,2,4,8-tetramethyl tricyclo[3.3.2.14,8]undecan-11-one (20). The influence of the secondary hydroxyl group at C-5 of the panasinsane derivatives on the course of these rearrangements is discussed.

Oxidative bromination of tricyclic sesquiterpenoids (1S,3S,5R,6S,9S)-5-hydroxy-6,10,10-trimethyl-tricyclo[7.2.0.0 1,6]udecan-2-one and clovane-2β,9α-diol with the HBr-DMSO system

Oxidation of tricyclic sesquiterpenoids of the caryophyllene type with the HBr-DMSO system afforded α,β-unsaturated a-bromoketones. Since tricyclic derivatives, unlike simple alicyclic ketones, cannot undergo aromatization, all intermediate oxidation prod

Biotransformation of caryophyllene oxide by Botrytis cinerea

Biotransformation of caryophyllene oxide (1) with B. cinerea afforded 15 products (2-16). Ten of these (3-5, 7, 9-11, and 14-16) are reported here for the first time. The main reaction paths involved stereoselective epoxidation at C-8/C-13 and hydroxylation at C-7. A rearranged compound was found, which was a cyclization product 16 possessing the caryolane skeleton.

Solvolysis of caryophyllen-8β-yl derivatives: Biomimetic rearrangement- cyclization to 12-nor-8α-presilphiperfolan-9β-ol

The solvolyses of caryophyllen-8β-yl p-nitrobenzoate (14-OpNB) and 15- norcaryophyllen-8β-yl tosylate (15-OTs) were investigated as potential model reactions for the biogenesis of the tricyclic presilphiperfolanol sesquiterpenes. Buffered solvolysis of 14-OpNB in 60% aqueous acetone at 125 °C afforded caryophyllene (3) as major product, accompanied by small amounts of caryophyllen-8β-ol (14-OH) and 5,8-cyclocaryophyllen-4α-ol (16). In contrast, 15-OTs underwent a stereospecific rearrangement-cyclization to 12- nor-8α-presilphiperfolan-9β-ol (17) upon solvolysis in 60% aqueous acetone at 75 °C. The structure and stereochemistry of this trans,cis,trans- tricyclo[6.2.1.05,11]-undecane derivative were established by NMR correlation spectroscopy and X-ray crystallography. Two different mechanisms (paths A and B) for the conversion of 15-OTs to 17 by initial 1,2-migration of either the external or internal cyclobutane ring bonds (C10 and C1) followed by π-σ cyclization onto the trans double bond are discussed.

Synthesis of oxygenated compounds derived from caryophyllene.

Studies of the chemical composition of clove oil indicate caryophyllene epoxide and the presence of some other oxidation derivatives.To elucidate these oxygenated compound structures, we have undertaken the synthesis of some caryophyllene oxide derivatives using 3-chloroperbenzoic acid and caryophyllene.Caryophyllene epoxide, two diepoxides, a ketoepoxide and an aldehyde were isolated.Optimization of the procedure allowed us to selectively orient the reaction towards monoepoxides (100percent), ketoepoxides (99percent) or diepoxides (84percent).The reduction of diepoxides using lithium aluminium hydride led to two cyclic ether alcohols with tetrahydrofuranic and tetrahydropyranic rings, which were obtained in high yield and good regioselectivity.The structures of these compounds have been determined from concerted application of two-dimensional NMR techniques. - Key words: oxidation; reduction; caryophyllene; epoxide; diepoxide; ether alcohol; intramolecular cyclization