24703-35-3

Usage

Uses

Used in Perfume Industry:
Bicyclogermacrene, (+)-bicyclogermacrene is used as a fragrance ingredient for its unique spicy, woody, and herbaceous aroma, contributing to the complexity and depth of perfume compositions.
Used in Flavor Industry:
In the flavor industry, bicyclogermacrene, (+)-bicyclogermacrene is utilized as a flavoring agent to impart its distinctive scent profile to food products, enhancing the sensory experience of consumers.
Used in Medicinal Chemistry:
Bicyclogermacrene, (+)-bicyclogermacrene is studied for its potential therapeutic applications, particularly for its anti-inflammatory and antioxidant effects, making it a compound of interest in the development of new medications and health products.

InChI:InChI=1/C15H24/c1-11-5-6-14-12(2)7-8-15(3,4)10-13(14)9-11/h5,7,13-14H,6,8-10H2,1-4H3

Upstream product

• 372-97-4 farnesyl pyrophosphate 

Downstream Products

• 1254173-25-5 psiguadial A 
• 6750-60-3 spathulenol 
• 74409-93-1 [1aR-(1aα,7α,7aβ,7bα)]-1a,2,3,5,6,7,7a,7b-octahydro-1,1,4,7-tetramethyl-1H-cycloprop[e]azulene 

Relevant academic research and scientific papers

Enantioselective microbial synthesis of the indigenous natural product (-)-α-bisabolol by a sesquiterpene synthase from chamomile (Matricaria recutita)

(-)-α-Bisabolol, a sesquiterpene alcohol, is a major ingredient in the essential oil of chamomile (Matricaria recutita) and is used in many health products. The current supply of (-)-α-bisabolol is mainly dependent on the Brazilian candeia tree (Eremanthus erythropappus) by distillation or by chemical synthesis. However, the distillation method using the candeia tree is not sustainable, and chemical synthesis suffers from impurities arising from undesirable α-bisabolol isomers. Therefore enzymatic synthesis of (-)-α-bisabolol is a viable alternative. In the present study, a cDNA encoding (-)-α-bisabolol synthase (MrBBS) was identified from chamomile and used for enantioselective (-)-α-bisabolol synthesis in yeast. Chamomile MrBBS was identified by Illumina and 454 sequencing, followed by activity screening in yeast. When MrBBS was expressed in yeast, 8mg of α-bisabolol was synthesized de novo per litre of culture. The structure of purified α-bisabolol was elucidated as (S,S)- α-bisabolol [or (-)-α-bisabolol]. Although MrBBS possesses a putative chloroplast-targeting peptide, it was localized in the cytosol, and a deletion of its N-terminal 23 amino acids significantly reduced its stability and activity. Recombinant MrBBS showed kinetic properties comparable with those of other sesquiterpene synthases. These data provide compelling evidence that chamomile MrBBS synthesizes enantiopure (-)-α-bisabolol as a single sesquiterpene product, opening a biotechnological opportunity to produce (-)-α-bisabolol.

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.