128087-96-7

Usage

Uses

Used in Perfumery Industry:
Hedione is used as a key ingredient in high-end perfumes for its ability to enhance and elongate the overall scent, providing a sense of transparency and depth to fragrances. Its light and fresh jasmine-like scent makes it a popular choice for creating light and airy floral compositions.
Used in Mood Enhancement:
Hedione is used in fragrance formulations for its mood-boosting and uplifting effects, making it a sought-after ingredient in many perfumes and scented products. Its ability to positively influence mood and emotions adds to its value in the perfumery industry.

InChI:InChI=1/C13H22O3/c1-3-4-5-6-11-10(7-8-12(11)14)9-13(15)16-2/h10-11H,3-9H2,1-2H3

Upstream product

• 694528-26-2 2-(1-hydroxypentyl)cyclopent-2-en-1-one 
• 1445-45-0 Trimethyl orthoacetate 
• 25564-22-1 2-pentyl-2-cyclopenten-1-one 
• 108-59-8 malonic acid dimethyl ester 
• 146143-16-0 (1R,2S,3R)-1-hydroxy-3-methoxycarbonylmethyl-2-pentylcyclopentane 
• 155016-12-9 (1R,2S,3R)-3-hydroxymethyl-2-pentyl-1-cyclopentanol 
• 120-92-3 cyclopentanone 
• 110-62-3 pentanal 
• 16424-35-4 2-pentylidenecyclopentan-1-one 
• 186581-53-3 diazomethane 
• 98674-52-3 (-)-9,10-dihydrojasmonic acid 
• 128893-61-8 3-(2-Cyano-ethyl)-4-oxo-nonanoic acid methyl ester 
• 54562-27-5 ((1R,2S,3R)-3-Hydroxy-2-pentyl-cyclopentyl)-acetic acid methyl ester 
• 67-56-1 methanol 

Downstream Products

• 57374-49-9 methyl 2-(3-acetoxy-2-pentylcyclopent-2-en-1-yl)acetate 
• 96844-45-0 (+)-9,10-dihydro-7-iso-jasmonic acid 
• 2570-03-8 (+/-)-methyl trans-dihydrojasmonate 
• 1567-89-1 N-(2,4-dinitrophenyl)-N'-isopropylidene-hydrazine 
• 958-60-1 2-butanone 2,4-dinitrophenylhydrazone 
• 108478-44-0 6-methylheptane-2-one (2,4-dinitrophenyl)hydrazone 

Related news

The smelling of Hedione (cas 128087-96-7) results in sex-differentiated human brain activity08/23/2019

A large family of vomeronasal receptors recognizes pheromone cues in many animals including most amphibia, reptiles, rhodents, and other mammals. Humans possess five vomeronasal-type 1 receptor genes (VN1R1–VN1R5), which code for proteins that are functional in recombinant expression systems. W...detailed

Relevant academic research and scientific papers

Enantioselective synthesis of both enantiomers of methyl dihydrojasmonate using solid-liquid asymmetric phase-transfer catalysis

Both enantiomers of methyl dihydrojasmonate (-)-1 and (+)-1 were obtained by a short route using asymmetric Michael addition of dimethyl malonate onto pentyl enone 3, followed by nonracemizing demethoxycarbonylation. The key enantioselective step involves a new system of asymmetric solid - liquid phase-transfer catalysis using solvent-free conditions. Enantiomeric excess as high as 90% (91% yield) was achieved.

METABOLISM OF THE PLANT GROWTH REGULATOR DIHYDROJASMONIC ACID IN BARLEY SHOOTS

Key Word Index--Hordeum vulgare; Gramineae; barley; (+/-)-9,10-dihydrojasmonic acid metabolism; (-)-9,10-dihydro-11ξ-hydroxyjasmonic acid; (-)-9,10-dihydro-12-hydroxyjasmonic acid; (-)-9,10-dihydro-11-ξ-hydroxyjasmonic acid O(11)-β-D glucopyranoside.Abstract--The biotransformation of (+/-)-9,10-dihydrojasmonic acid (DJA) was studied in six-day-old barley seedlings.Both and DJA were fed to excised shoots and the formed metabolites analysed after 72 hr.DJA was converted into two major and some minor metabolites, purified by chromatographic methods.The major metabolites were identified mainly by spectroscopic investigations as (-)-9,10-dihidro-11ξ-hydroxyjasmonic acid and its O(11)-β-D-glucopyranoside.To a lesser extent (-)-9,10-dihydro-12-hydroxyjasmonic acid was also found.

New jasmonate analogues as potential anti-inflammatory agents

In an effort to develop new anti-inflammatory agents, methyl jasmonate analogues (2-20) were synthesized and evaluated for their inhibitory effects on the production of pro-inflammatory mediators (NO, IL-6, and TNF-α) in lipopolysaccharide (LPS)-activated RAW264.7 murine macrophage cells. The introduction of an enone functionality to the structure of a plant hormone (1) rendered the product (2) a significant anti-inflammatory activity. Analogues further derived from 2 (7, 9, 13, and 15) exhibited even more enhanced activity, and these compounds were much more potent than natural anti-inflammatory prostaglandins (PGA1, PGA2, and 15-deoxy-Δ12,14-PGJ2). Among them, compounds 9 and 15 showed the highest potency, while compounds 7 and 13 would be more desirable with respect to safety. This is the first study demonstrating the anti-inflammatory potential of jasmonate derivatives, and the present results suggest that α-haloenone jasmonates (7, 9, 13, and 15) may serve as potential anti-inflammatory leads.

CYCLOPENTANE FATTY ACIDS FROM GIBBERELLA FUJIKUROI

Several mutants of the fungus Gibberella fujikuroi were shown to produce cyclopentane fatty acids of the jasmonic acid type.Detailed investigation of the culture filtrate of one mutant resulted in the isolation and structural elucidation of (+)-7-iso-jasmonic acid and (-)-jasmonic acid as well as their (S)-isoleucine conjugates and 4,5-didehydro-9,10-dihydrojasmonic acid.Out of nine further mutants studied, all of them produced the two isoleucine conjugates but in only four of them could free jasmonic acid be detected (max amount of 2.5 mg l-1). Key Word Index: Gibberella fujikuroi; Fusarium moniliforme; (+)-7-iso-jasmonic acid; (-)-jasmonic acid; 4,5-didehydro-9,10-dihydrojasmonic acid; N--(S)-isoleucine.

Preparation method of 3-(3-oxo-2-pentyl) cyclopentyl dimethyl malonate

The invention relates to a preparation method of 3-(3-oxo-2-pentyl) cyclopentyl dimethyl malonate. The preparation method of the 3-(3-oxo-2-pentyl) cyclopentyl dimethyl malonate comprises the following step: in the presence of a transition metal complex and a catalytic additive, reacting 2-pentyl-2-cyclopentenone with dimethyl malonate in a reaction solvent to obtain the 3-(3-oxo-2-pentyl) cyclopentyl dimethyl malonate. According to the preparation method provided by the invention, a sodium methoxide strong base catalyst is not needed, the generation of salt-containing wastewater is avoided, the method is environment-friendly and high in yield, and meanwhile, the recycling of the catalyst is realized.

Preparation method of methyl dihydrojasmonate

The invention discloses an efficient synthesis method of methyl dihydrojasmonate. Under catalysis of homogeneous rhodium and organic nitric oxide, 1-heptyne and ethylene have Pauson-Khand reaction, 2-amyl-2-cyclopentenone is rapidly and efficiently obtained, and an intermediate is subjected to addition and decarboxylation by dimethyl malonate to obtain the methyl dihydrojasmonate. The efficient synthesis method mainly has the advantages that 1-heptyne and ethylene Pauson-Khand reaction yield is effectively improved by the aid of the organic nitric oxide, and usage of rhodium catalysts is reduced. Compared with a traditional methyl dihydrojasmonate production method, the method has the advantages that route steps are short, atom economy is high, the cost is low, and the method is suitable for scale production of the methyl dihydrojasmonate.

Method for synthesizing (1R,2S)-methyl dihydrojasmonate

The invention discloses a novel method for synthesizing (1R,2S)-methyl dihydrojasmonate by using an asymmetric Michael addition reaction. The method comprises the steps: firstly, subjecting cyclopentanone, which serves as a starting raw material, to an aldol reaction with n-valeraldehyde under alkaline conditions to produce 2-pentylidene cyclopentanone 2, and then, carrying out double-bond transposition under acidic conditions, so as to obtain 2-n-pentyl-2-cyclopentenone 3; then, carrying out a Michael addition reaction with dimethyl malonate in the presence of a chiral amino-acid lithium salt, and carrying out silicagel-column chromatographic separation twice, so as to obtain (1S,2S)-2-n-pentyl-3-dimethyl malonate cyclopentanone 4; and finally, carrying out a hydrolyzed decarboxylation reaction, thereby obtaining (1R,2S)-methyl dihydrojasmonate. According to the method, the synthesis route is simple and direct, the reaction conditions are mild, and the target compound can be prepared by only four-step reactions.

Method of manufacturing methylcyclopentanone deriv. (by machine translation)

PROBLEM TO BE SOLVED: To provide an efficient method for producing a cyclopentanone derivative usable as an intermediate for a methyl (3-oxocyclopentyl)acetate derivative useful as a perfumery material.SOLUTION: The method for producing the cyclopentanone derivative expressed by general formula (III) comprises Michael addition reaction of a 2-cyclopenten-1-one derivative and an ester compound in the presence of a solid base catalyst containing a phosphazene base or a guanidine base. In the formula, Ris a 1-10C hydrocarbon group; Ris 1-4C alkyl; and Ris 1-4C alkyl or alkoxyl.

Further explorations into the synthesis of Dehydro-Hedione

Dehydrohedione (DHH) 1 may be obtained in 20% overall yield by a Reformatsky reaction with enone methyl ether 3b, followed by acidic workup of the crude reaction mixture. Alternatively, epoxidation (3-chloroperbenzoic acid, CH2Cl2, 84% yield) of the tertiary allyl alcohol derivative 4 affords a 1: 2 mixture of 8a and 8b. The latter epoxy ester 8b may also be obtained stereoselectively either from 4 (tBuO2H, [Mo(CO)6], 1,2-dichloroethane, 70°, 62% yield; or tBuO2H, [VO(acac)2], decane, 20°, 92% yield), or from 5 (AcOMe, LiN(SiMe3)2, THF, -78°, 84-87%). BF3×Et2O-Catalyzed cascade rearrangement and OH elimination of 8a afford selectively DHH 1 in 88% yield. The cis disposition of the side chains of the weakly odoriferous hedione-like analogues 2b and 2c was maintained by means of either an epoxy or a cyclopropane moiety. Copyright

Metal-ligand core-shell nanocomposite catalysts for the selective semihydrogenation of alkynes

Catalysts with a sheltered upbringing: Novel core-shell nanocomposite catalysts consisting of active metal nanoparticles encapsulated by macroligands have been prepared. They have Pd nanoparticles (PdNPs) as an active core and shell ligands having sulfoxide moieties coordinated to the PdNPs. The shell protects the catalyst from coordination by alkenes and allows the lead-free selective semihydrogenation of a wide range of alkynes without any additives (see scheme). Copyright