41031-87-2

Usage

Uses

Used in the Food Industry:
(Z)-4-oxo-7-decenal is used as a flavoring agent for its strong citrus-like aroma and taste, enhancing the flavor of various food products.
Used in the Agricultural Industry:
(Z)-4-oxo-7-decenal is utilized for its antimicrobial properties, potentially serving as a natural alternative for controlling pests and diseases in crops.
Used in Healthcare:
Due to its antioxidant properties, (Z)-4-oxo-7-decenal is being studied for its potential applications in healthcare, possibly contributing to the development of new treatments or therapies.
Used as a Natural Insect Repellent:
(Z)-4-oxo-7-decenal's potential as a natural insect repellent is being explored, which could offer an eco-friendly solution for pest control in both agricultural and residential settings.

InChI:InChI=1/C10H16O2/c1-2-3-4-5-7-10(12)8-6-9-11/h3-4,9H,2,5-8H2,1H3/b4-3+

Upstream product

• 7348-78-9 (Z)-1-bromo-2-pentene 
• 43160-75-4 2-ethoxy-3-vinylsulfanyl-propene 
• 61856-14-2 1-nitro-dec-7c-en-4-one 
• 71127-59-8 1-[1,3]dioxolan-2-yl-non-6c-en-3-one 
• 43125-21-9 (Z)-hex-3-en-1-ylmagnesium bromide 
• 74-88-4 methyl iodide 
• 41031-85-0 2-(2-[1,3]dioxolan-2-yl-ethyl)-4,4,6-trimethyl-5,6-dihydro-4H-[1,3]oxazine 
• 72049-83-3 (Z)-1-hydroxydec-7-en-4-one 
• 125630-63-9 2-Methyl-2-dodecen-9-yn-6-one 
• 96202-74-3 (Z)-1-(1,3-dioxolan-2-yl)-non-6-en-3-one p-toluenesulfonylhydrazone 
• 78078-51-0 cis-1,1-trimethylenedioxy-7-decen-4-one 
• 6728-31-0 (Z)-4-heptenal 
• 79837-80-2 (Z)-7-bromo-3-heptene 
• 16400-32-1 1-bromo-pent-2-yne 

Downstream Products

• 41031-88-3 (Z)-2-(2-pentenyl)-2-cyclopenten-1-one 
• 1101843-02-0 methyl jasmonate 
• 221682-41-3 (Z)-2-(2-(but-2-en-1-yl)-3-oxocyclopentyl)acetic acid 
• 1211-29-6 methyl jasmonate 

Relevant academic research and scientific papers

Syntheses of methyl jasmonate and analogues

This account corresponds to the presentation given by the main author on the occasion of the 2nd Swiss Industrial Symposium in Basel (October 19th, 2018). After a short historical introduction to methyl-jasmonate and methyl-epijasmonate, it essentially focuses on the reported more promising industrial approaches devoted to the synthesis of these naturally occurring odorants isolated from jasmine flowers. Some attempts to simplify these approaches, as well as independent unreported strategies are also presented. Several asymmetric methodologies are also discussed such as Xie hydrogenation, Corey-CBS reduction, enzymatic resolution, and 1,4-addition.

Synthesis of 2-Alkyl-2-cyclopenten-1-ones. A Versatile Kinetic Alkylation-Ozonolysis Procedure for the Preparation of γ-Ketoaldehydes

A range of 2-alkyl-2-cyclopenten-1-ones including the prostaglandin precursor 2-(6-methoxycarbonylhexyl)-2-cyclopenten-1-one and the jasmonoid precursor 2--2-cyclopenten-1-one, have been prepared by a short synthetic route which begins with 6-methyl-5-hepten-2-one and generates the key 1,4-ketoaldehyde intermediates by a kinetic alkylation-ozonolysis procedure.

(Z)-7-NITRO-3-HEPTENE AS CENTRAL INTERMEDIATE FOR THE SYNTHESIS OF JASMONE, METHYL JASMONATE, AND γ-JASMONOLACTONE

(Z)-7-Nitro-3-heptene is used as central intermediate in the synthesis of jasmone (13), methyl jasmonate (15), and γ-jasmonolactone (16), three jasmin constituents.Conjugate addition of the title compound, by heterogeneous catalysis, to methyl vinyl ketone, or acrolein, or methyl acrylate, followed by Nef reaction, affords (Z)-undec-8-ene-2,5-dione, (Z)-1,4-dioxo-dec-7-ene, and (Z)-4-oxo-dec-7-enoic acid methyl ester respectively, which are easily converted into jasmone, methyl jasmonate and γ-jasmonolactone.

2-(2-NITROETHYL)-1,3-DIOXOLANE AS REAGENT FOR 3-OXOPROPYL ANION SYNTHON: A NEW ROUTE TO JASMONOID AND PROSTAGLANDIN INTERMEDIATES

2-(2-Nitroethyl)-1,3-dioxolane is a versatile reagent for 3-oxopropyl anion synthon.New methodology, based on nitroaldol condensation, oxidation and direct or indirect denitration sequence is developed for the conversion of 2-(2-nitroethyl)-1,3-dioxolane into (Z)-1,4-dioxodec-7-ene, (Z)-2-(2-pentenyl)-2-cyclopenten-1-one, methyl 9,12-dioxododecanoate and methyl 7-(5-oxocyclopentenyl)heptanoate, which are popular intermediates for syntheses of (Z)-jasmonoids and prostaglandins.

1-Bromo-2-ethoxycyclolithium: A Synthetic Equivalent of 2-Lithio or 3-Lithiopropenal. Application to the Synthesis of Juvenile Hormone (JH-II), β-Sinensal, and Jasmonoids.

The ethyl vinyl ether-dibromocarbene adduct was lithiated with butyllithium at -95 deg C in tetrahydrofuran.The resulting lithium carbenoid 3 was allowed to react with various electrophiles to give 1-substituted trans-1-bromo-2-ethoxycyclopropanes (1) in good yields.The trans relationship of Br and OEt groups was found particularly pertinent to the ethanolysis of 1 producing 2-substituted propenal diethyl acetal derivatives.The reaction has been applied to 1-methoxycyclohexene-dibromocarbene adducts, giving rise hereby 2-substituted 2-cyclohepten-1-one dimethyl acetals under ring enlargement.T he transformation has been utilized in the synthesis of a homoterpenoid (JH-II) or a terpenoid (β-sinensal) structure by SN2' substitution of allylic acetates with lithium dimethylcuprate(I) or iron pentacarbonyl respectively.The reaction products of 3 with aldehydes are oxidized with dimethyl sulfoxide to give cyclopropyl ketones whose ethanolysis in the presence of boron trifluoride ether complex gives β-bromo γ-keto aldehyde acetals.Debromination followed by acidic hydrolysis produces γ-keto aldehydes serving as precursors of dihydrojasmone and cis-jasmone.

Jasmonoid Synthesis from cis-4-Heptenoic Acid

Jesmonoids with cis-2-pentenyl side-chain such as cis-jasmone, methyl jasmonate, and jasmolone were easily synthesized from cis-4-heptenoic acid obtained by the ring opening reaction of β-propiolactone with di-cis-butenylcuprate.

Convenient Synthesis of Jasmonoid Compounds from γ-(Trimethylsiloxy)butyronitrile

1,4-Dioxygenated compounds 4 are constructed by the addition of a Grignard reagent to γ-(trimethylsiloxy)nitriles 1,2, and 3 and subsequent hydrolysis.Oxidation of 4 with pyridinium chlorochromate or Jones reagent yields compounds 5 which are used to produce cyclopentenones 6.Methyl jasmonate and methyl dihydrojasmonate are made by the conjugate addition of silylated ketene acetal 9 to 6a and 6b, respectively, and subsequent protodesilylation. γ-Jasmolactone is also derived from 4a by oxidation with pyridinium dichromate in DMF followed by reduction with NaBH4 in ethanol.