14427-53-3

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 3-oxohexadecanoate is used as an intermediate in the synthesis of 3-Hydroxyhexadecanoic Acid Methyl Ester (H825380) for its potential pharmaceutical applications. This fatty acid ester, extracted from the flowers of Trollius chinensis Bunge, may have therapeutic properties that can be further explored and developed for the treatment of various medical conditions.
Used in Cosmetics Industry:
Methyl 3-oxohexadecanoate can be used as a key ingredient in the development of cosmetics and personal care products. Its unique chemical structure may provide benefits such as moisturization, skin conditioning, and emulsification properties, making it a valuable component in the formulation of creams, lotions, and other skincare products.
Used in Chemical Synthesis:
As an intermediate in the synthesis of various compounds, methyl 3-oxohexadecanoate can be utilized in the chemical industry for the production of other valuable chemicals and materials. Its versatile structure allows for further modification and functionalization, leading to the development of new compounds with potential applications in various fields.

InChI:InChI=1/C17H32O3/c1-3-4-5-6-7-8-9-10-11-12-13-14-16(18)15-17(19)20-2/h3-15H2,1-2H3

Upstream product

• 855892-23-8 2,4-dioxo-heptadecanoic acid methyl ester 
• 54665-04-2 2-acetyl-3-oxo-hexadecanoic acid ethyl ester 
• 124-41-4 sodium methylate 
• 1007476-32-5 sodium ethyl acetylacetate enolate 
• 544-63-8 n-tetradecanoic acid 
• 63125-08-6 3-Piperidino-2-hexadecensaeure-methylester 
• 67-56-1 methanol 
• 928-19-8 3-oxo-hexadecanoic acid 
• 79-20-9 acetic acid methyl ester 
• 112-64-1 tetradecanoyl chloride 
• 83728-50-1 2,2-dimethyl-5-tetradecanoyl-1,3-dioxane-4,6-dione 
• 2825-81-2 methyl hexadec-trans-2-enoate 
• 38330-80-2 monomethyl monopotassium malonate 
• 2345-28-0 pentadecan-2-one 

Downstream Products

• 16694-31-8 5-oxo-octadecanoic acid 
• 928-17-6 β-hydroxypalmitic acid 
• 51883-36-4 β-hydroxyhexadecanoic acid methyl ester 
• 51883-36-4 (R)-β-hydroxyhexadecanoic acid methyl ester 
• 928-17-6 (R)-β-hydroxypalmitic acid 
• 335263-32-6 (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-tert-butyl ester 1-[(R)-1-(2,2,2-trichloro-ethoxycarbonylmethyl)-tetradecyl] ester 
• 335263-34-8 (S)-2-Benzyloxycarbonylamino-pentanedioic acid 1-[(R)-1-(benzotriazol-1-yloxycarbonylmethyl)-tetradecyl] ester 5-tert-butyl ester 
• 929-79-3 (2E)-hexadecenoic acid 
• 10118-82-8 pahutoxin 
• 10118-82-8 choline chloride ester of (R)-3-acetoxyhexadecanoic acid 
• 32778-77-1 solenopsin B 
• 114634-29-6 Toluene-4-sulfonic acid (S)-3-hydroxy-hexadecyl ester 
• 2380-20-3 5-oxostearic acid methyl ester 
• 506-46-7 1-hexacosanoic acid 

Relevant academic research and scientific papers

Preparation of the even-numbered 3-oxo fatty acid nicotinyl esters from C6:0 to C18:0

Here, we report a systematic comparison of different methods for the transesterification of 3-oxo fatty acid alkyl esters to the corresponding nicotinyl esters. A simple method producing the target esters in high yields and purity has been developed. Nicotinyl esters are of interest for mass spectrometry analysis of fatty acids. Also, the hydrophilic head group of nicotinyl esters can be used as the basis for the preparation of liposome-building molecules.

Regiospecific oxidation of unsaturated fatty esters with palladium(II) chloride/p-benzoquinone: a sonochemical approach

Oxidation of unsaturated fatty esters to the corresponding oxo derivatives was accomplished in moderate to high yields when the substrates were treated with palladium(II) chloride and p-benzoquinone in aqueous tetrahydrofuran (THF/H2O, 4:1 v/v) under ultrasound (20 kHz).Methyl 10-undecanoate furnished methyl 10-oxoundecanoate in 92percent yield.Methyl oleate and trans-2-hexadecenoate furnished methyl 9(10)-oxostearate (65percent) and methyl 3-oxohexadecanoate (41percent) respectively.Unsaturated fatty esters with a terminal double bond were more readily oxidized than those containing an internal double bond.Methyl trans-3,12-tridecadienoate gave only methyl 12-oxo-trans-3-tridecenoate (86percent), while a cyclopentenoic fatty ester (methyl chaulmoograte) furnished a mixture of positional oxo-isomers: viz. methyl 1-oxocyclopentane-2-tridecanoate and 1-oxocyclopentane-3-tridecanoate (51.5percent total).Oxidation of methyl 12-hydroxy-, 12-azido-, 12-chloro- and 12-oxo-cis-9-octadecanoate furnished the corresponding 9-oxo-derivatives only.Methyl iso-ricinoleate (methyl 9-hydroxy-cis-12-octadecenoate) gave exclusively methyl 9-hydroxy-12-oxostearate.Without ultrasonication the same oxidation reactions at room temperature furnished low yields (30percent) of the corresponding oxo derivatives after prolonged stirring at room temperature.Aqueous THF is a superior solvent system than the commonly used aqueous N,N-dimethylformmaide (DMF). - Keywords: Aqueous THF; p-Benzoquinone; Oxidation; Oxo fatty esters; Palladium(II) chloride; Ultrasound; Unsaturated fatty esters; Wacker reaction

BETA-LACTONE COMPOUNDS

The present invention provides compounds having the general structure A, or a pharmaceutically acceptable derivatives thereof: wherein R is an alkyl group, and R1 comprises at least one moiety selected from a group consisting of an alkyl, an alkenyl, an aryl, a heterocycle, hydroxyl, ester, amido, aldehyde, and a halogen.

Non-volatile floral oils of Diascia spp. (Scrophulariaceae)

The floral oils of Diascia purpurea, Diascia vigilis, Diascia cordata, Diascia megathura, Diascia integerrima and Diascia barberae (Scrophulariaceae) were selectively collected from trichome elaiophores. The derivatized floral oils were analyzed by gas chromatography-mass spectrometry (GC-MS), whilst the underivatized samples were analysed by electrospray ionization mass spectrometry (ESI-MS) and Fourier-transform ion cyclotron resonance mass spectrometry (FTICR-MS). The most common constituents of the floral oils investigated are partially acetylated acylglycerols of (3R)-acetoxy fatty acids (C14, C16, and C18), as was proven with non-racemic synthetic reference samples. The importance of these oils for Rediviva bees is discussed in a co-evolutionary context.

General enantioselective synthesis of butyrolactone natural products via ruthenium-SYNPHOS-catalyzed hydrogenation reactions

Enantioselective syntheses of several paraconic acids have been achieved using catalyzed asymmetric hydrogenation of β-keto esters with SYNPHOS as a ligand. This strategy allowed the short synthesis of biologically active (-)-methylenolactocin 1, (-)-protolichesterinic acid 2, (-)-phaseolinic acid 3 and (+)-roccellaric acid 4.

Enantioselective Hydrogenation of β-Keto Esters using Chiral Diphosphine-Ruthenium Complexes: Optimization for Academic and Industrial Purposes and Synthetic Applications

Enantioselective hydrogenation using chiral complexes between atropisomeric diphosphines and ruthenium is a powerful tool for producing chiral compounds. Using a simple and straightforward in situ catalyst preparation, the conditions were optimized using molecular hydrogen for both academic and industrial purposes. This led to the best conditions and the lowest catalytic ratio required for the pressure used. Hydrogenation of various β-keto esters was efficiently performed at atmospheric and higher pressures, leading to the use of very low catalyst-substrate ratios up to 1/20,000. Asymmetric hydrogenations were used in key-steps towards the total synthesis of corynomycolic acid, Duloxetine and Fluoxetine.

New potential immunoenhancing compounds. Synthesis and pharmacological evaluation of new long-chain 2-amido-2-deoxy-D-glucose derivatives

A series of long-chain fatty acids and the corresponding 2-hydroxy, 2-oxo, 3-hydroxy acid glucosamides were evaluated as immunomodulating compounds. In a preliminary screening, 2-[(2-ethoxycarbonyloxy)tetradecanoyl-amino]-2-deoxy-D-glucose (2b) and 2-(3-hydroxydodecanoyl-amino)-2-deoxy-D-glucose (5a) resulted to be the most effective in enhancing the glucosamine activity. The findings of in vitro-ex vivo tests (unidirectional mixed lymphocyte culture reaction and primary antibody production) and in vivo tests (delayed type hypersensitivity, protection against bacterial or fungal infection and against Sarcoma 180 or Lewis lung carcinoma transplants) were very encouraging and allowed to assume for the two substances a protective activity, presumably through the ability of activating phagocytic and NK cells.

Enantioselective Construction of Heterocycles: Synthesis of (R,R)-Solenopsin B

An enantioselective route to solenopsin B (1) , the major saturated component of the alkaloid mixture isolated from the venom of the fire ant, Solenopsis invicta, is reported.The key transformation in this synthesis is the smooth thermolytic cyclization of alkenyl azide 3.The precursor to 3, alcohol 4, is prepared by stereoselective reduction of an enantiomerically pure β-keto ester.

The Preparation of Optically Pure 3-Hydroxyalkanoic Acid. The Enantioface-differentiating Hydrogenation of the C=O Double Bond with Modified Raney Nickel. XXXVII

The enantioface-differentiating hydrogenation of methyl 3-oxoalkanoate (CH3(CH2)nCOCH2COOCH3, n=0, 6, 8, 10, 12) over the (R,R)-tartaric acid-NaBr-modified Raney nickel catalyst ((R,R)-TA-NaBr-MRNi) gave methyl (R)-3-hydroxyalkanoate (CH3(CH2)nCH(OH)CH2COOCH3, n=0, 6, 8, 10, 12) in an average optical yield of 85percent.After the methyl ester had been converted to dicyclohexylammonium salt of 3-hydroxyalkanoic acid, the salt was recrystallized three times from acetonitrile and then treated with acid to give optically pure (R)-3-hydroxyalkanoic acid (CH3(CH2)nCH(OH)CH2COOH, n=0, 6, 8, 10, 12) in a reasonable yield.From the hydrogenation product with (S,S)-TA-NaBr-MRNi, optically pure (S)-3-hydroxyalkanoic acid was obtained by the same process as above.