60784-31-8

Usage

Uses

Used in Food Industry:
(Z)-non-2-enal is used as a flavoring agent for its ability to enhance the aroma and taste of food products. Its natural presence in citrus fruits and its antimicrobial properties also make it a potential natural preservative, helping to extend the shelf life of food products by inhibiting the growth of certain microorganisms.
Used in Fragrance Industry:
(Z)-non-2-enal is used as a fragrance ingredient due to its strong and characteristic woody, green, and fatty odor. It can be incorporated into various scent formulations to create unique and appealing fragrances for perfumes, cosmetics, and other scented products.
Used in Insect Control:
(Z)-non-2-enal has potential applications in insect control due to its antimicrobial properties. Studies have shown that it could be effective in controlling certain insects, such as female bed bugs, by disrupting their growth and reproduction processes.
Used in Natural Preservatives:
(Z)-non-2-enal can be used as a natural preservative in food products, thanks to its inhibitory effects on the growth of certain microorganisms. This makes it a valuable alternative to synthetic preservatives, offering a more natural and eco-friendly option for maintaining the freshness and safety of food products.

InChI:InChI=1S/C9H16O/c1-2-3-4-5-6-7-8-9-10/h7-9H,2-6H2,1H3/b8-7-

Upstream product

• 99190-49-5 non-2-ynal semicarbazone 
• 5921-73-3 2-nonyn-1-ol 
• 1846-69-1 non-2-ynal 
• 41453-56-9 (Z)-2-nonen-1-ol 
• 13264-70-5 5-hexyl-dihydro-furan-2,3-dione 
• 104306-01-6 3-bromo-1,1-dichloro-nonane 
• 1071-51-8 1,1,3-tribromononane 
• 31502-14-4 2-nonenyl alcohol 
• 111-71-7 heptanal 
• 75-07-0 acetaldehyde 
• 60900-57-4 methyl 9-(R,S)-hydroperoxy-10-trans,12-cis-octadecadienoate 
• 32671-92-4 methyl 9-(R,S)-hydroperoxy-10-trans,12-trans-octadecadienoate 
• 17673-33-5 9,10,12-trihydroxyoctadecanoic acid 
• 64-19-7 acetic acid 

Downstream Products

• 1577-98-6 (Z)-non-2-enoic acid 
• 111-14-8 oenanthic acid 
• 1577-98-6 (E)-2-nonenoic acid 
• 1361412-71-6 (R)-3-(nitromethyl)nonyl 4-methylbenzoate 
• 1616858-81-1 (2R,6S)-5-benzoyl-2-hexyl-6-hydroxy-6-methyl-2H-pyran-3(6H)-one 
• 1616858-93-5 (2R,6S)-2-hexyl-6-hydroxy-6-methyl-5-(4-nitrophenyl)-2H-pyran-3(6H)-one 

Relevant academic research and scientific papers

Method for preparing olefine aldehyde through catalytic oxidation of enol ether

The invention relates to the technical field of olefine aldehyde preparation, and provides a method for preparing olefine aldehyde through catalytic oxidation of enol ether. According to the invention, a palladium catalyst, a copper salt, a solvent and enol ether are mixed and subjected to a catalytic oxidation reaction to obtain olefine aldehyde. According to the method, the copper salt is used as the oxidizing agent, the mixed solvent of water and acetonitrile is used as the reaction solvent, and the volume ratio of water to acetonitrile in the mixed solvent is controlled to be (3-7): (3-7), so that the catalytic oxidation reaction can be smoothly carried out in the mixed solvent with a specific ratio, and the generation of palladium black precipitate can be avoided. The method provided by the invention has the advantages of simple steps, low reagent cost, no need of dangerous reagents, wide substrate adaptability and small catalyst dosage. Furthermore, octadecane mercaptan is added to promote the catalytic oxidation reaction, and when the dosage of the palladium catalyst is extremely low, the olefine aldehyde yield can be greatly increased by adding octadecane mercaptan.

Method for reducing carboxylic acid compound into aldehyde

The invention discloses a method for reducing a carboxylic acid compound into aldehyde. In a nitrogen atmosphere, in an organic solvent, a ligand/Cu catalyst, the carboxylic acid compound, an anhydride compound and hydrosilane are added by a one-pot method, a reaction is performed under the condition of the temperature of 20-120 DEG C for 2-20 h, after the reaction is completed, quenching and column chromatography separation are performed to obtain the product. The carboxylic acid compound can be successfully converted into aldehyde through one-pot reaction, especially unsaturated carboxylic acid can be reduced, and the reaction yield is generally relatively high. Compared with the prior art, the method has the outstanding advantages that the cheap copper salt is used as a catalyst, so that the experiment cost is greatly reduced. Meanwhile, the used method enlarges the application range of the reaction substrate, improves the compatibility of functional groups, and provides a new synthesis way for reducing the carboxylic acid compound into aldehyde.

Enzyme-mediated enantioselective hydrolysis of 1,2-diol monotosylate derivatives bearing an unsaturated substituent

We have succeeded in the easy preparation of optically active 1,2-diol monotosylates bearing an unsaturated substituent via enzymatic hydrolysis. Lipase PS quickly catalyzes the hydrolyses of 2-acetoxybut-3-enyl tosylate, which has a double bond, and 2-acetoxybut-3-ynyl tosylate, which has a triple bond, with excellent enantioselectivity to afford the corresponding optically active compounds. The reaction is also applicable to acetates with a longer chain, which has a double bond at the terminus. To demonstrate the applicability of this method, enantiomerically pure (R)-massoialactone, a natural coconut flavor, has been synthesized from racemic 2-acetoxypent-4-enyl tosylate in several steps. Furthermore, the enzyme can recognize the stereochemistry of olefins, and the (Z)-alkenyl structure is more suitable for the enantioselective hydrolysis than the (E)-isomer.

Synthesis and Biological Evaluation of Bromo- and Fluorodanicalipin A

We disclose the syntheses of (+)-bromodanicalipin A as well as (±)-fluorodanicalipin A. The relative configuration and ground-state conformation in solution of both molecules was secured by J-based configuration analysis which revealed that these are identical to natural danicalipin A. Furthermore, preliminary toxicological investigations suggest that the adverse effect of danicalipin A may be due to the lipophilicity of the halogens. Halologs: The syntheses of bromo- and fluorodanicalipin A are reported and the ground-state conformation was determined by J-based configuration analysis (see scheme, R=H). A preliminary comparative study of their toxicology suggests that the adverse effect arises from the lipophilicity of the halogens which counterbalance the polar C14 sulfate.

Biological Investigations of (+)-Danicalipin A Enabled Through Synthesis

A total synthesis of the chlorosulfolipid (+)-danicalipin A has been accomplished in 12 steps and 4.4 % overall yield. The efficient and scalable synthesis enabled in-depth investigations of the lipid's biological properties, in particular cytotoxicity towards various mammalian cell lines. Furthermore, the ability of (+)-danicalipin A to increase the uptake of fluorophores into bacteria and mammalian cells was demonstrated, indicating it may enhance membrane permeability. By comparing (+)-danicalipin A with racemic 1,14-docosane disulfate, and the diol precursor of (+)-danicalipin A, we have shown that both chlorine and sulfate functionalities are necessary for biological activity.

Highly efficient Au hollow nanosphere catalyzed chemo-selective oxidation of alcohols

Micelles of poly(styrene-b-2-vinyl pyridine-b-ethylene oxide) (PS-PVP-PEO) with core-shell-corona structures have been used as a scaffold for the fabrication of gold (Au) hollow nanospheres of particle size 26 ± 2 nm using HAuCl4 and NaBH4 as metal precursor and reducing agent, respectively. The PS core acts as a template for hollow void, the PVP shell serves as reaction sites for inorganic precursors, and PEO corona stabilizes the composite particles. Under acidic conditions, the PVP shell domain becomes positively charged pyridinum-species that electrostatically interacts with negatively charged AuCl4- ions. On reduction of these composite particles and subsequent solvent extraction leads to the formation of Au hollow nanospheres. Various analytical tools such as powder X-ray diffraction (XRD), transmission electron microscope (TEM), thermogravimetric analyses (TG/DTA), dynamic light scattering of (DLS) have been employed to characterize the polymeric micelles and hollow nanoparticles. The TEM and XRD studies confirmed the formation of highly crystalline Au hollow nanospheres. The Au hollow nanosphere/H2O2 system efficiently catalyzes the chemoselective oxidation of allylic-type unsaturated alcohols into aldehydes and ketones under mild liquid-phase conditions. The versatility of present catalytic system for the oxidation of other substrates like aliphatic-, acylic-, aromatic-, and heteroaromatic alcohols to their respective keto compounds has also been reported.

Survey of volatile oxylipins and their biosynthetic precursors in bryophytes

Oxylipins are metabolites which are derived from the oxidative fragmentation of polyunsaturated fatty acids. These metabolites play central roles in plant hormonal regulation and defense. Here we survey the production of volatile oxylipins in bryophytes and report the production of a high structural variety of C5, C6, C8 and C9 volatiles of mosses. In liverworts and hornworts oxylipin production was not as pronounced as in the 23 screened mosses. A biosynthetic investigation revealed that both, C18 and C20 fatty acids serve as precursors for the volatile oxylipins that are mainly produced after mechanical wounding of the green tissue of mosses.

Aerobic oxidation of primary aliphatic alcohols to aldehydes catalyzed by a palladium(II) polyoxometalate catalyst

A hexadecyltrimethylammonium salt of a "sandwich" type polyoxometalate has been used as a ligand to attach a palladium(II) center. This Pd-POM compound was an active catalyst for the fast aerobic oxidation of alcohols. The unique property of this catalyst is its significant preference for the oxidation of primary versus secondary aliphatic alcohols. Since no kinetic isotope effect was observed for the dehydrogenation step, this may be the result of the intrinsically higher probability for oxidation of primary alcohols attenuated by steric factors as borne out by the higher reactivity of 1-octanol versus 2-ethyl-1-hexanol. The reaction is highly selective to aldehyde with little formation of carboxylic acid; autooxidation is inhibited. No base is required to activate the alcohol. The fast reactions appear to be related to the electron-acceptor nature of the polyoxometalate ligand that may also facilitate alcohol dehydrogenation in the absence of base.

Highly regioselective terminal alkynes hydroformylation and Pauson-Khand reaction catalysed by mesoporous organised zirconium oxide based powders

Zirconia-silica mesoporous powders act as very efficient heterogeneous catalysts for both alkyne hydroformylation and Pauson-Khand reaction and yield regioselectivities opposite to those usually observed. The Royal Society of Chemistry 2006.

Synthesis and reactivity of Z and E functionalized allylic fluorides

The allylic fluorides 1 and 2 are used as models to study the effect of the allylic C-F bond on the diastereoselectivity of reactions occurring on the vicinal double bond, as well as the compatibility of this C-F bond with various reagents. The configurational stability of the Z double bonds in enals and enones 1 and 3 is noteworthy. This allowed us to perform various types of reactions (including thermal Diels-Alder cycloadditions) on derivatives 1 with full control of the Z geometry.