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10-Methyldodec-2-en-4-olide Sale

目录号 : GC46402

A bacterial volatile lactone

10-Methyldodec-2-en-4-olide Chemical Structure

Cas No.:874359-15-6

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1 mg
¥10,022.00
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产品描述

10-Methyldodec-2-en-4-olide is a volatile lactone that has been found in Streptomyces.1,2 It is active against the plant pathogenic fungus B. cinerea, the yeast S. cerevisiae, and the bacteria S. aureus, M. luteus, and M. phlei in an agar diffusion inhibition assay when used at a concentration of 140 μg per disc.3 10-Methyldodec-2-en-4-olide also inhibits induction of a GFP-based reporter by the quorum sensing molecule N-dodecanoylhomoserine lactone in an N-acylhomoserine lactone (AHL) P. putida biosensor strain.

1.Dickschat, J.S., Martens, T., Brinkhoff, T., et al.Volatiles released by a Streptomyces species isolated from the North SeaChem. Biodivers.2(7)837-865(2005) 2.Citron, C.A., Barra, L., Wink, J., et al.Volatiles from nineteen recently genome sequenced actinomycetesOrg. Biomol. Chem.13(9)2673-2683(2015) 3.Schulz, S., Dickschat, J.S., Kunze, B., et al.Biological activity of volatiles from marine and terrestrial bacteriaMar. Drugs8(12)2976-2987(2010)

Chemical Properties

Cas No. 874359-15-6 SDF
Canonical SMILES CCC(C)CCCCCC(O1)C=CC1=O
分子式 C13H22O2 分子量 210.3
溶解度 DMSO: soluble,Ethanol: soluble,Methanol: soluble 储存条件 Store at -20°C
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1 mg 5 mg 10 mg
1 mM 4.7551 mL 23.7756 mL 47.5511 mL
5 mM 0.951 mL 4.7551 mL 9.5102 mL
10 mM 0.4755 mL 2.3776 mL 4.7551 mL
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Research Update

Volatiles released by a Streptomyces species isolated from the North Sea

Chem Biodivers 2005 Jul;2(7):837-65.PMID:17193176DOI:10.1002/cbdv.200590062

The North Sea Streptomyces strain GWS-BW-H5 was investigated by analyzing headspace extracts of agar-plate cultures (HE) or liquid cultures (LCE), obtained with a closed-loop stripping apparatus (CLSA), by GC/MS (Table 1). The volatile profile of the HE is dominated by the known volatiles (-)-geosmin (4) and 2-methyisoborneol (1). Small amounts of sesquiterpenes occur, which are present in a more-diverse structural variety and in higher quantities in the LCE. The different structures can be rationalized by few cationic intermediates along their biosynthetic pathway. The most-prominent difference between the two culture methods were the presence of the Me-branched gamma- and delta-lactones 31-38, not previously reported from nature, in the LCE. Major components were 10-methyldodecan-5-olide (34), 10-Methyldodec-2-en-4-olide (36), and 10-methyldodec-3-en-4-olide (38). The structures of all new lactones were verified by synthesis. Furthermore, more volatiles in higher amounts were produced by the liquid culture than by to the agar plate culture. Since 36 showed inhibitory growth effects against strain GWS-BW-H5, growth inhibition against twelve other strains isolated from the same habitat was tested. Antagonistic activity against four of the strains was observed, with a slightly higher threshold level than found for penicillin G, which was used in control experiments (Table 2).