4194-71-2

Usage

Uses

Used in Pharmaceutical Industry:
(Z)-2-Decen-1-ol is used as an intermediate in the synthesis of Falcarinol, which is a covalent cannabinoid CB1 receptor antagonist. This application is significant because it induces pro-allergic effects in the skin, making it a valuable compound in the development of pharmaceutical products targeting specific skin conditions.
Used in Agricultural Industry:
As a natural pesticide, (Z)-2-Decen-1-ol is produced by carrots and red ginseng, providing protection to the host roots from various fungal diseases. This application highlights its potential as a sustainable and environmentally friendly alternative to synthetic pesticides in agriculture.
Used in Nutritional Industry:
(Z)-2-Decen-1-ol has been shown to have nutritional benefits, particularly in reducing the risk of developing specific forms of cancer. This application emphasizes its importance in the development of health supplements and functional foods that promote overall well-being and disease prevention.

Upstream product

• 4117-14-0 2-decyn-1-ol 
• 3452-09-3 1-nonyne 
• 629-04-9 1-Bromoheptane 
• 1187817-22-6 (Z)-2-(dec-2-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 680192-98-7 deutero-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 58396-45-5 (E)-1,3-decadiene 
• 2051-25-4 deca-1,3-diene 

Downstream Products

• 107033-43-2 [(2S,3R)-3-heptyloxiran-2-yl]methanol 
• 123932-68-3 (2R,3S)-3-heptyloxirane methanol 
• 135987-28-9 (Z)-2-decenyl 1-diphenylphosphate 
• 935701-42-1 (2S,3R)-2,3-epoxy-1-decanol tosylate 
• 4117-11-7 falcarinone 
• 4117-12-8 panaxynol 
• 2497-23-6 (Z)-dec-2-en-1-yl acetate 
• 1308381-98-7 (2R,3R)-2,3-epoxy decanal 
• 3913-81-3 (E)-2-decenal 

Relevant academic research and scientific papers

Comparison of the Key Aroma Compounds in Fresh, Raw Ginger (Zingiber officinale Roscoe) from China and Roasted Ginger by Application of Aroma Extract Dilution Analysis

By application of a comparative aroma extract dilution analysis on the volatile fractions isolated by solvent extraction and solvent-assisted flavor evaporation (SAFE) from fresh raw Chinese ginger (Zingiber officinale Roscoe) and roasted ginger, 21 or 33 odorants, respectively, with flavor dilution (FD) factors in the range of 32-4096 were identified. In raw ginger, the highest FD factors were found for (E)-isoeugenol, 1,8-cineol, vanillin, geranial, and linalool. After roasting, in particular, the FD factors of 3-(methylthio)propanal (cooked potato-like), 4-hydroxy-2,5-dimethyl-3(2H)-furanone (caramel-like), 3-hydroxy-4,5-dimethyl-2(5H)-furanone (seasoning-like), and geraniol were substantially increased. The application of static headspace/olfactometry (SHO) on ground raw ginger revealed a high FD factor for highly volatile acetaldehyde which clearly decreased after roasting. By contrast, the SHO application revealed high FD factors for malty smelling methylpropanal and 3-methylbutanal, which both were exclusively detected in roasted ginger. Thirteen odorants, namely, decanoic acid, (Z)-2-decenal, (Z)-4-decenal, (E)-4,5-epoxy-(E)-2-decenal, (E)-4,5-epoxy-(E)-2-undecenal, fenchol, (Z)-3-hexenal, 3-hydroxy-4,5-dimethyl-2(5H)-furanone, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, 3-methyl-2-buten-1-thiol, 2-methylpropanal, (E)-2-nonenal, and 1-nonen-3-one, were identified in ginger for the first time. Chiral analysis showed a much higher percent by weight portion for the (R)-enantiomer in citronellal, citronellol, and linalool, which was not much changed during pan-frying.

CONTROLLING BIOFILMS WITH CYCLOPROPANATED FATTY ACIDS

Compositions and methods for using cyclopropanated structural analogs of fatty acid biofilm dispersal agents are characterized by superior biofilm dispersion. When used in combination with antimicrobials, these analogs decrease the minimum inhibitory concentration of antimicrobial agents required for eradication of the biofilm and/or treatment of infection. Methods for using these analogs include direct application to a surface, blending with lipid based carriers, or covalent anchoring the molecule to a surface.

Stereoselective Synthesis of the Isomers of Notoincisol A: Assigment of the Absolute Configuration of this Natural Product and Biological Evaluation

The total syntheses of all stereoisomers of notoincisol A, a recently isolated natural product with potential anti-inflammatory activity, are reported. The asymmetric synthesis was conducted employing a lipase-mediated kinetic resolution, which enables easy access to all required chiral building blocks with the aim of establishing the absolute configuration of the naturally occurring isomer. This was achieved by comparison of optical properties of the isolated compound with the synthetic derivatives obtained. Moreover, an assessment of the biological activity on PPARγ (peroxisome proliferator-activated receptor gamma) as a prominent receptor related to inflammation is reported. Only the natural isomer was found to activate the PPARγ receptor, and this phenomenon could be explained based on molecular docking studies. In addition, the pharmacological profiles of the isomers were determined using the GABAA (gamma-aminobutyric acid A) ion channel receptor as a representative target for allosteric modulation related to diverse CNS activities. These compounds were found to be weak allosteric modulators of the α1β3 and α1β2γ2 receptor subtypes.

An Unsaturated Quinolone N-Oxide of Pseudomonas aeruginosa Modulates Growth and Virulence of Staphylococcus aureus

The pathogen Pseudomonas aeruginosa produces over 50 different quinolones, 16 of which belong to the class of 2-alkyl-4-quinolone N-oxides (AQNOs) with various chain lengths and degrees of saturation. We present the first synthesis of a previously proposed unsaturated compound that is confirmed to be present in culture extracts of P. aeruginosa, and its structure is shown to be trans-Δ1-2-(non-1-enyl)-4-quinolone N-oxide. This compound is the most active agent against S. aureus, including MRSA strains, by more than one order of magnitude whereas its cis isomer is inactive. At lower concentrations, the compound induces small-colony variants of S. aureus, reduces the virulence by inhibiting hemolysis, and inhibits nitrate reductase activity under anaerobic conditions. These studies suggest that this unsaturated AQNO is one of the major agents that are used by P. aeruginosa to modulate competing bacterial species.

Total syntheses of 9-epoxyfalcarindiol and its diastereomer

The first total syntheses of 9-epoxyfalcarindiol 1a and its diastereomer 1b have been achieved. Central to our approach were the Zn-cyclopropane-based amino alcohol catalyzed enantioselective alkynylation of acrolein, the diastereoselective addition of a diynic ester to an epoxy aldehyde, and the asymmetric Sharpless epoxidation of allylic alcohol catalyzed with L-(+)-diethyl tartrate and Ti(OiPr)4.

Total synthesis of panaxydol and its stereoisomers as potential anticancer agents

An efficient total synthesis of natural panaxydol 1a and its seven stereoisomers 1b-h was accomplished; four diastereomers of the natural form were prepared for the first time. Our strategy involves the Cadiot-Chodkiewicz cross-coupling reaction of chiral terminal alkynes with bromoalkynes, the asymmetric alkynylation of aldehydes, and the enantioselective Sharpless epoxidation of allylic alcohols. Preliminary in vitro cytotoxicity evaluation indicated that some synthetic panaxydols possess anticancer activities, and (3S,9R,10S)-panaxydol 1e showed a particularly promising cytotoxic effect.

Ni- and pd-catalyzed synthesis of substituted and functionalized allylic boronates

Two highly efficient and convenient methods for the synthesis of functionalized and substituted allylic boronates are described. In one procedure, readily available allylic acetates are converted to allylic boronates catalyzed by Ni/PCy3 or Ni/PPh3 complexes with high levels of stereoselectivity and in good yields. Alternatively, the borylation can be accomplished with commercially available Pd catalysts [e.g., Pd 2(dba)3, PdCl2, Pd/C], starting with easily accessed allylic halides.

Establishment of absolute stereostructure of falcarindiol, algicidal principle against Heterocapsa circularisquama from Notopterygii Rhizoma

Falcarindiol (1) was isolated as an algicidal principle against the harmful red tide dinoflagellate, Heterocapsa circularisquama, from Notopterygii Rhizoma through bioassay-guided separation. In order to determine the ambiguous absolute structure of this