38142-58-4

Basic information

• Product Name: ar-turmerone
• Synonyms: ar-turmerone;(R)-(-)-ar-Turmerone;(R)-2-Methyl-6-(4-methylphenyl)-2-heptene-4-one;[R,(-)]-2-Methyl-6-p-tolyl-2-hepten-4-one;DL-ar-Turmerone;rac-(6R*)-6-(4-Methylphenyl)-2-methyl-2-heptene-4-one
• CAS NO: 38142-58-4
• Molecular Formula: C₁₅H₂₀O
• Molecular Weight: 0
• Mol File: 38142-58-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ar-turmerone(CAS DataBase Reference)
• NIST Chemistry Reference: ar-turmerone(38142-58-4)
• EPA Substance Registry System: ar-turmerone(38142-58-4)

Safety Data

• Hazardous Substances Data: 38142-58-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
ar-Turmerone is used as an antimicrobial agent for its ability to inhibit the growth of harmful microorganisms, which can be beneficial in the development of new drugs and treatments.
Used in Food Industry:
ar-Turmerone is used as a natural preservative for its antimicrobial properties, helping to extend the shelf life of perishable food products and maintain their quality.
Used in Cosmetics Industry:
ar-Turmerone is used as an antioxidant agent for its ability to neutralize free radicals, which can contribute to the aging process and other skin conditions. This makes it a valuable ingredient in anti-aging and skin care products.
Used in Agriculture:
ar-Turmerone is used as a natural pesticide for its antimicrobial properties, offering an alternative to synthetic chemicals in protecting crops from harmful microorganisms and pests.

Upstream product

• 6651-46-3 4-methyl-2-(trimethylsiloxy)-1,3-pentadiene 
• 127866-71-1 1-Phenyl-5-(1-p-tolyl-ethylsulfanyl)-1H-tetrazole 
• 33324-92-4 (2-methylallyl)magnesium bromide 
• 95502-91-3 (E)-N-phenyl butene-2 imidothioate de methyle 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 98442-10-5 3,4-epoxy-2-methyl-6-p-tolyl-1-heptene 
• 98711-79-6 2-methyl-6-(p-tolyl)-3-phenylsulphinylheptan-4-one 
• 144782-33-2 2,2-Dimethyl-4-oxo-6-p-tolyl-heptanoic acid 
• 15795-51-4 2,2-dimethyl-5-(4-methylbenzylidene)-1,3-dioxane-4,6-dione 
• 32207-07-1 (Z)-α-atlantone 
• 26294-59-7 (E)-α-atlantone 
• 18383-55-6 6-(p-Tolyl)-2-methyl-hepten-⁽³⁾-ol-⁽²⁾ 
• 644-30-4 ar-curcumene 
• 92631-26-0 Acetic acid 2-benzenesulfinyl-1,1-dimethyl-5-p-tolyl-hexyl ester 

Downstream Products

• 19419-67-1 (S)-1,1,5,8-tetramethyl-1,2,3,4,5-pentahydrobenzo[a][7]annulene 
• 125346-98-7 1-((E)-1,5-Dimethyl-hex-3-enyl)-4-methyl-benzene 
• 644-30-4 ar-curcumene 
• 109650-88-6 (+/-)-ar-turmerone semicarbazone 

Relevant articles and documents

Linear Selective Hydroformylation of 2-Arylpropenes Using Water-Soluble Rh-PNP Complex: Straightforward Access to 3-Aryl-Butyraldehydes

Straightforward access to 3-aryl-butyraldehydes was developed through the aqueous biphasic Rh-catalyzed hydroformylation of 2-arylpropenes using a water-soluble PNP ligand. This protocol accommodates broad substrate scope with high yields (up to 95 %) and excellent linear selectivity (>99 : 1 b/l ratio). The synthesis of rac-ar-turmerone and the gram-scale hydroformylation further demonstrated the practical nature of this method.

Directed Markovnikov hydroarylation and hydroalkenylation of alkenes under nickel catalysis

We report a full account of our research on nickel-catalyzed Markovnikov-selective hydroarylation and hydroalkenylation of non-conjugated alkenes, which has yielded a toolkit of methods that proceed under mild conditions with alkenyl sulfonamide, ketone, and amide substrates. Regioselectivity is controlled through catalyst coordination to the native Lewis basic functional groups contained within these substrates. To maximize product yield, reaction conditions were fine-tuned for each substrate class, reflecting the different coordination properties of the directing functionality. Detailed kinetic and computational studies shed light on the mechanism of this family of transformations, pointing to transmetalation as the turnover-limiting step.

Aromatization of (Z) and (E)-α-atlantones isolated from Cedrus atlantica essential oil followed by condensation with thiosemicarbazide: Synthesis of new thiadiazolines derivatives

Aromatization, using Pd/C (10%) of (Z) and (E)-α-atlantones isolated from Cedrus atlantica essential oil, followed by condensation with thiosemicarbazide gave novel 1,3,4-thiadiazolic derivatives by the introduction of new functional groups on the terpeni

Application of Meldrum's acid in natural product synthesis. Synthesis of ar-turmerone and α-curcumene

Meldrum's acid (1) is employed in the synthesis of ar-turmerone (6) and α-curcumene (12). 1-(p-Tolyl)ethyl Meldrum's acid (3), synthesised by three different routes, was the key intermediate in these syntheses.

Tandem Michael-Wittig-Horner reaction: Application to the synthesis of bisabolanes

Bisabolane derivatives have been synthesized from para-substituted cinnamaldehydes according to a tandem Michael - Wittig - Horner reaction. This sequence was applied to a short access to (+/-)-ar-turmerone.

2,2-Dimethylsuccinic acid derivatives in isoprenoid synthesis: a 2,2-dimethylvinyl anion equivalent in the synthesis of ar-atlantone, ar-turmerone, and prenylated aromatic compounds

The anion of methyl 2,2-dimethylsuccinate was alkylated with benzylic bromides to give the corresponding 3-substituted-2,2-dimethylsuccinates.Hydrolysis to the dicarboxylic acids, followed by bisdecarboxylation with lead tetraacetate, afforded 1-aryl-3-methyl-2-butenes, which are model prenylated aromatic compounds.Acylation of methyl-2,2-dimethylsuccinate with E-3-(4'-methylphenyl)crotonyl chloride gave the substituted succinate 9.Hydrolysis of the ester groups and acid-catalyzed decarboxylation of the resulting β-ketoacid produced the keto acid 10, which was decarboxylated by the Kochi method, furnishing ar-atlantone.Hydrogenatio n of 10 yielded 12, which on similar decarboxylation afforded ar-turmerone.

Benzylation of ketones by a novel decarboxylative coupling reaction of benzylic chloroformate and silyl enol ether

In the presence of silver triflate, benzylic chloroformates react with silyl enol ethers to afford benzylated ketones by the decarboxylative coupling in good yields, whereas in the presence of various Lewis acids, yields of the product were poor under the same reaction conditions.

SILVER TRIFLATE-PROMOTED COUPLING REACTIONS OF BENZYLIC AND ALLYLIC SULFIDES WITH O-SILYLATED ENOLATES OF KETONES AND ESTERS, A SYNTHESIS OF (+/-)-AR-TURMERONE

Reactions of benzylic and allylic sulfides 1 having 5-mercapto-1-phenyl-1H-tetrazolyl group with O-silylated ketone and ester enolates 2 in the presence of silver triflate gave coupling products 3 in good yield. (+/-)-ar-turmerone was synthesized by this