24703-35-3

Basic information

• Product Name: bicyclogermacrene,(+)-bicyclogermacrene
• Synonyms: bicyclogermacrene,(+)-bicyclogermacrene
• CAS NO: 24703-35-3
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.3511
• Mol File: 24703-35-3.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 267.8°Cat760mmHg
• Flash Point: 104.6°C
• Appearance: /
• Density: 0.861g/cm³
• Vapor Pressure: 0.0132mmHg at 25°C
• Refractive Index: 1.474
• CAS DataBase Reference: bicyclogermacrene,(+)-bicyclogermacrene(CAS DataBase Reference)
• NIST Chemistry Reference: bicyclogermacrene,(+)-bicyclogermacrene(24703-35-3)
• EPA Substance Registry System: bicyclogermacrene,(+)-bicyclogermacrene(24703-35-3)

Safety Data

• Hazardous Substances Data: 24703-35-3(Hazardous Substances Data)

Usage

General Description

Bicyclogermacrene is a natural bicyclic sesquiterpene found in a variety of plants such as ginger and black pepper. It is also known as (+)-bicyclogermacrene and has a spicy, woody, and herbaceous aroma. This chemical is often used in the perfume and flavor industries due to its unique scent profile. Additionally, bicyclogermacrene has been studied for its potential therapeutic properties, including its anti-inflammatory and antioxidant effects, making it of interest in the field of medicinal chemistry. Overall, bicyclogermacrene is a versatile chemical with both olfactory and potential health benefits.

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

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Relevant articles and documents

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.