92691-35-5

Basic information

• Product Name: GerMacrone 4,5-epoxide
• Synonyms: (1S,6E,10S)-6,10-Dimethyl-3-(1-methylethylidene)-11-oxabicyclo[8.1.0]undec-6-en-4-one;(4S,5S)-(+)-Germacrone 4,5-epoxide
• CAS NO: 92691-35-5
• Molecular Formula: C15H22O2
• Molecular Weight: 234.33398
• Mol File: 92691-35-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 340.8±41.0 °C(Predicted)
• Appearance: /
• Density: 1.011±0.06 g/cm3(Predicted)
• CAS DataBase Reference: GerMacrone 4,5-epoxide(CAS DataBase Reference)
• NIST Chemistry Reference: GerMacrone 4,5-epoxide(92691-35-5)
• EPA Substance Registry System: GerMacrone 4,5-epoxide(92691-35-5)

Safety Data

• Hazardous Substances Data: 92691-35-5(Hazardous Substances Data)

Usage

General Description

GerMacrone 4,5-epoxide belongs to the class of chemicals known as macrolides, which are a type of antibiotics. They are derived from a group of microorganisms and are known for their powerful antimicrobial activity. GerMacrone 4,5-epoxide is specifically a derivative of gerimacrol, a macrolide compound obtained from a species of Streptomyces bacteria. It exhibits potent antibacterial and antifungal properties and has been studied for its potential use in treating various infections. Research on GerMacrone 4,5-epoxide continues to explore its pharmacological properties and potential applications in medicine.

Upstream product

• 6902-91-6 germacrone 
• 32179-17-2 (4S,5S)-epoxy-(+)-4,5-dihydrogermacrone 

Downstream Products

• 68984-97-4 isozedoarondiol 
• 116425-34-4 isozedoarondiol 
• 102130-91-6 neoprocurcumenol 
• 62754-56-7 isoprocurcumenol 
• 69010-39-5 Procurcumenol 
• 32179-17-2 (+/-)-Germacron-5,6-epoxid 
• 32179-18-3 (1S,10S),(4S,5S)-germacrone-1(10),4-diepoxide 
• 1443277-20-0 C₁₅H₂₀O 
• 1443277-21-1 C₁₅H₂₂O₂ 
• 1443277-27-7 C₁₅H₂₂O₂ 
• 68984-96-3 curcumadione 
• 1443277-30-2 C₁₅H₂₂O₂ 
• 68984-95-2 curcumenone 
• 21698-40-8 procurcumenol 

Relevant articles and documents

Germacrone derivatives as new insecticidal and acaricidal compounds: A structure-activity relationship

Currently, the use of synthetic pesticides is the main method of plant protection applied in agri- and horticulture. However, its excessive use leads to the development of pesticide resistance, a contamination of the environment, toxicity to non-target organisms, and risks for human health. With the ultimate aim of contributing to the develop of a more sustainable pest management, we used the natural product germacrone (compound 1), reported to possess significant insecticidal activity, as starting material for the generation of molecular diversity (2-24). Some of the generated derivatives are natural compounds, such as 1,10-epoxygermacrone (2), 4,5-epoxygermacrone (3), gajutsulactone A (7), germacrol (11), isogermacrone (14), 9-hydroxyeudesma-3,7(11)dien-6-one (19), eudesma-4,7(11),dien-8-one (20), eudesma-3,7(11)-dien-8-one (21) and eudesma-4(15),7(11)-dien-8-one (22). Compounds, 7,11-9,10-diepoxigermacr-4,5-en-8-ol (17), 7,11-epoxieudesma-4,7(11)-dien-8-one (23) and 7,11-epoxieudesma-3,7(11)-dien-8-one (24) are described for the first time. The biocidal activity of most of these compounds was assayed against the tick Hyalomma lusitanicum. The acaricidal effects of compound 24 were four times higher than that of germacrone (1). Compound 2 is an insect antifeedant a thousand times more potent than germacrone against Rhopalosiphum padi, which makes this substance a promising selective antifeedant against this cereal pest.

Biotransformation of germacrane epoxides by Cichorium intybus

The biotransformation of germacrone-4,5-epoxide (2), germacrone-1,10-epoxide (3), isogermacrone-4,5-epoxide (5), germacrene B-4,5-epoxide (6) and germacrene B-1,10-epoxide (7) by a suspension of fresh chicory root (Cichorium intybus) was investigated. Enz

BIOTRANSFORMATION OF SESQUITERPENES BY CULTURED CELLS OF CURCUMA ZEDOARIA

The transformation of a 10-membered ring sesquiterpene, germacrone, into guaiane-type sesquiterpenes by suspension cultured cells of Curcuma zedoaria was investigated.Germacrone was converted into several sesquiterpenes, some of which were isolated from the Curcuma spp. plants through the key intermediate, (4R,5R)-germacrone 4,5-epoxide, and their structures were determined by spectral and chemical evidence.The configurations of some of the derivatives were opposite to those of the sesquiterpenes isolated from the Curcuma sp plants, C. aromatica, C. longa and C. zedoaria.An eudesmane-type product was also isolated and its structur e was determined.From the structure, the transformation of germacrone through the intermediate, (1S,10S)-germacrone 1,10-epoxide, was supposed and further confirmed by the transformation of germacrone 1,10-epoxide into the same product by acid treatment.The structures of two new products were also determined and their transformation mechanism through curcumenone and dihydrocurcumenone was deduced. Key Word Index - Curcuma zedoaria; Zingiberaceae; cell suspension culture; biotransformation; sesquiterpene; germacrone; guaiane; eudesmane.