106-68-3

Usage

Uses

Used in Perfumery:
3-Octanone is used as an ingredient in perfumes due to its strong, fruity odor reminiscent of lavender. It adds a pleasant fragrance to various perfume products.
Used in Cosmetics:
3-Octanone is used as an ingredient in soaps, lotions, and creams, contributing to their scent and enhancing the overall sensory experience for the user.
Used as a Flavoring Agent:
3-Octanone is used in the food industry as a flavoring agent, providing a mushroom, ketonic, cheesy, and moldy taste with a fruity nuance at 10 ppm.
Used in Solvent Applications:
3-Octanone serves as a solvent for nitrocellulose and vinyl resins, which are used in various industrial applications.
Used in Research:
3-Octanone is used in scientific studies, such as investigating the effect of TiO2 photocatalyst on the rate and ratio of products generated in photocatalytic oxidation.
Occurrence:
3-Octanone has been identified in the low-boiling fraction of the essential oil of lavender and is also found in the essential oils of Lavandula vera (10%) and French lavender. Additionally, it is present in various fruits, vegetables, and other natural sources such as banana, bilberry, currants, guava, melon, blueberry, blackberry, strawberry jam, peas, fried potato, ginger, Mentha oils, thyme, cheeses, butter, fish, cooked meats, cognac, coffee, tea, roasted peanuts, pecan, soybean, olive, plum, beans, mushroom, wild marjoram, trassi, rice bran, litchi, calamus, buckwheat, rosemary, lemon balm, clary sage, rosemary, truffle, nectarine, anise hyssop, and maté.

Preparation

By heating propionic and caproic acids over thorium oxide or by oxidation of ethyl amyl carbinol (3-octanol) (Arctander, 1969).

Synthesis Reference(s)

Journal of the American Chemical Society, 97, p. 6863, 1975 DOI: 10.1021/ja00856a044The Journal of Organic Chemistry, 32, p. 2356, 1967 DOI: 10.1021/jo01282a605

Air & Water Reactions

Flammable. Insoluble in water.

Reactivity Profile

Ketones, such as 3-Octanone, are reactive with many acids and bases liberating heat and flammable gases (e.g., H2). The amount of heat may be sufficient to start a fire in the unreacted portion of the ketone. Ketones react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Ketones are incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. They react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4.

Hazard

Narcotic in high concentration. Moderate fire risk.

Health Hazard

May be harmful by inhalation, ingestion or skin absorption. Vapor or mist is irritating to eyes, mucous membrane and upper respiratory tract. Causes skin irritation.

Fire Hazard

Special Hazards of Combustion Products: Vapor may travel considerable distance to a source of ignition and flash back.

Biochem/physiol Actions

Taste at 10 ppm

Safety Profile

Poison by intraperitoneal route. Moderately irritating to skin, eyes, and mucous membranes by inhalation. Narcotic in high concentration. Flammable liquid when exposed to heat, sparks, flame, or oxidizers. To fight fire, use foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke. See also KETONES.

Synthesis

It can be prepared by passing a mixture of vapors of caprioc acid and acetic acid over ThO2 at 400°C, or by oxidation of d-ethyl n-amyl carbinol with chromates; another synthetic route is reported.

InChI:InChI=1/C8H16O/c1-3-5-6-7-8(9)4-2/h3-7H2,1-2H3

Upstream product

• 2809-67-8 oct-2-yne 
• 137-40-6 sodium proprionate 
• 10051-44-2 sodium caproate 
• 802294-64-0 propionic acid 
• 142-62-1 hexanoic acid 
• 557-20-0 diethylzinc 
• 111-64-8 n-octanoic acid chloride 
• 693-25-4 n-pentylmagnesium bromide 
• 107-12-0 propiononitrile 
• 421-20-5 Methyl fluorosulfonate 
• 1883-38-1 tripentylborane 
• 75144-28-4 1-bromo-1,2-dimethoxy-ethene 
• 111-65-9 octane 
• 821-06-7 (E)-1,4-dibromobutene 

Downstream Products

• 91635-39-1 5-Aethyl-5-hydroxy-decan 
• 7207-50-3 oxime of 3-octanone 
• 589-98-0 rac-3-octanol 
• 585-25-1 octane-2,3-dione 
• 142-62-1 hexanoic acid 
• 5754-25-6 (2-ethyl-2-pentyl-[1,3]dioxolan-4-yl)-methanol 
• 38204-77-2 4-(4-Isopropyl-cyclohex-1-enylmethyl)-octan-3-one 
• 38325-10-9 1-(4-Isopropyl-cyclohex-1-enyl)-nonan-4-one 
• 38211-80-2 5-(4-Isopropyl-cyclohex-1-enylmethyl)-octan-3-one 
• 38204-76-1 1-(4-Isopropyl-cyclohex-1-enyl)-2-methyl-octan-3-one 
• 5413-12-7 3-ethyl-oct-1-yn-3-ol 
• 589-98-0 (R)-octan-3-ol 
• 589-98-0 (S)-octan-3-ol 
• 124-38-9 carbon dioxide 

Relevant academic research and scientific papers

Ruthenium complexes with dendritic ferrocenyl phosphanes: Synthesis, characterization, and application in the catalytic redox isomerization of allylic alcohols

An efficient system for the catalytic redox isomerization of the allylic alcohol 1-octen-3-ol to 3-octanone is presented. The homogeneous ruthenium(II) catalyst contains a monodentate phosphane ligand with a ferrocene moiety in the backbone and provides 3-octanone in quantitative yields. The activity is increased by nearly 90 % with respect to the corresponding triphenyl phosphane ruthenium(II) complex. By grafting the catalyst at the surface of a dendrimer, the catalytic activity is further increased. By introducing different spacers between ferrocene and phosphorus, the influence on the electronic properties of the complexes is shown by evaluating the electrochemical behavior of the compounds.

A tandem allylic alcohol isomerization-aldol condensation catalyzed by Rh and Ru complexes

Allylic alcohols react with aldehydes, in an atom economy aldol-type reaction, in the presence of catalytic amounts of various rhodium and ruthenium complexes. This reaction occurs with total regiocontrol under mild conditions, but varying amounts of ketone derived from the competing isomerization reaction are also observed.

Symmetric triazolylidene Ni(II) complexes applied as oxidation catalysts

A set of related Ni(II) complexes of N-heterocyclic carbene ligands (NHC) [trans-X2Ni(NHC)2] (X = Cl, I) bearing linear straight chain alkyl wingtip substituents have been synthesised and fully characterised. Single crystal XRD data revealed symmetrically aligned Ni(II) centres within square planar coordination of trans halide, trans NHC ligands. The complexes were used for the catalytic oxidation of alkanes under mild conditions in conjunction with tert-butyl hydroperoxide as an oxidant. Under optimised reaction conditions, the catalytic results pointed to good activities of circa 15% and 19% for cyclohexane and n-octane respectively. Furthermore, the catalytic systems are shown to be very efficient for the oxidation of linear alcohols to corresponding ketones.

Enzymatic hydrogenation of trans-2-nonenal in barley

Conversion of undesirable, taste-active compounds is crucial for using barley as a suitable raw material for beer production. Here, ALH1, a barley alkenal hydrogenase enzyme that reduced the α,β-unsaturated double bond of aldehydes and ketones, was found to convert trans-2-nonenal (T2N), a major contributor to the cardboard-like flavor of aged beer. Although the physiological function of ALH1 in barley development remains elusive, it exhibited high specificity with NADPH as a cofactor in the conversion of several oxylipins-including T2N, trans-2-hexenal, traumatin, and 1-octen-3-one. ALH1 action represents a previously unknown mechanism for T2N conversion in barley. Additional experimental results resolved the genomic sequence for barley ALH1, as well as the identification of a paralog gene encoding ALH2. Interestingly, T2N was not converted by purified, recombinant ALH2. The possibility to enhance ALH1 activity in planta is discussed-not only with respect to the physiological consequences thereof-but also in relation to improved beer quality.

Selective Synthesis of Alkynes by Catalytic Dehydrogenation of Alkenes over Polymer-supported Palladium Acetate in the Liquid Phase

A heterogenized palladium acetate catalyst, in the presence of oxygen and perchloric acid in ethanol-water caused the direct conversion of terminal and internal monoalkenes into the corresponding alkynes, under mild conditions and in high yields; Wacker-type ketonization occurs with the same reagents in dioxane-water.

Defect-Engineered Ruthenium MOFs as Versatile Heterogeneous Hydrogenation Catalysts

Ruthenium MOF [Ru3(BTC)2Yy] ? Gg (BTC=benzene-1,3,5-tricarboxylate; Y=counter ions=Cl?, OH?, OAc?; G=guest molecules=HOAc, H2O) is modified via a mixed-linker approach, using mixtures of BTC and pyridine-3,5-dicarboxylate (PYDC) linkers, triggering structural defects at the distinct Ru2 paddlewheel (PW) nodes. This defect-engineering leads to enhanced catalytic properties due to the formation of partially reduced Ru2-nodes. Application of a hydrogen pre-treatment protocol to the Ru?MOFs, leads to a further boost in catalytic activity. We study the benefits of (1) defect engineering and (2) hydrogen pre-treatment on the catalytic activity of Ru?MOFs in the Meerwein-Ponndorf-Verley reaction and the isomerization of allylic alcohols to saturated ketones. Simple solvent washing could not avoid catalyst deactivation during recycling for the latter reaction, while hydrogen treatment prior to each catalytic run proved to facilitate materials recyclability with constant activity over five runs.

Arachidonic acid-dependent carbon-eight volatile synthesis from wounded liverwort (Marchantia polymorpha)

Eight-carbon (C8) volatiles, such as 1-octen-3-ol, octan-3-one, and octan-3-ol, are ubiquitously found among fungi and bryophytes. In this study, it was found that the thalli of the common liverwort Marchantia polymorpha, a model plant species, emitted high amounts of C8 volatiles mainly consisting of (R)-1-octen-3-ol and octan-3-one upon mechanical wounding. The induction of emission took place within 40 min. In intact thalli, 1-octen-3-yl acetate was the predominant C8 volatile while tissue disruption resulted in conversion of the acetate to 1-octen-3-ol. This conversion was carried out by an esterase showing stereospecificity to (R)-1-octen-3-yl acetate. From the transgenic line of M. polymorpha (des6KO) lacking arachidonic acid and eicosapentaenoic acid, formation of C8 volatiles was only minimally observed, which indicated that arachidonic and/or eicosapentaenoic acids were essential to form C8 volatiles in M. polymorpha. When des6KO thalli were exposed to the vapor of 1-octen-3-ol, they absorbed the alcohol and converted it into 1-octen-3-yl acetate and octan-3-one. Therefore, this implied that 1-octen-3-ol was the primary C8 product formed from arachidonic acid, and further metabolism involving acetylation and oxidoreduction occurred to diversify the C8 products. Octan-3-one was only minimally formed from completely disrupted thalli, while it was formed as the most abundant product in partially disrupted thalli. Therefore, it is assumed that the remaining intact tissues were involved in the conversion of 1-octen-3-ol to octan-3-one in the partially disrupted thalli. The conversion was partly promoted by addition of NAD(P)H into the completely disrupted tissues, suggesting an NAD(P)H-dependent oxidoreductase was involved in the conversion.

Base free transfer hydrogenation using a covalent triazine framework based catalyst

Isomerisation of allylic alcohols to saturated ketones can be efficiently catalysed by a heterogeneous molecular system resulting from IrIIICp? anchoring to a covalent triazine framework. The obtained catalysts are active, selective, and fully recyclable.

Biocatalytic oxidative kinetic resolution of sec-alcohols: Stereocontrol through substrate-modification

Whole lyophilised cells of Rhodococcus ruber DSM 44541 were employed for the oxidative kinetic resolution of sec-alcohols using acetone as hydrogen acceptor. The enantioselectivity of this process could be controlled effectively by introducing C-C multiple bonds into substrates, which were inefficiently recognised, in particular short-chain (ω-1)-alcohols and (ω-2)-analogs. Thus, the enantioselectivities of rac-2-pentanol (E=16.8) and rac-3-octanol (E=13.3) were significantly improved by introducing a C=C bond adjacent to the alcohol moiety to give racemic (E)-pent-3-en-2-ol and 4-(E)-octen-3-ol, which were resolved with excellent selectivities (E >100 and 50, respectively). In addition, it was found that high stereodifferentiation between the E- and Z-configured double bonds occurred, as the corresponding (Z)-isomers were not converted. Similar selectivity-enhancing effects were observed with acetylenic analogs.

Development of new iron catalysts for the tandem isomerization-aldol condensation of allylic alcohols

(bda)Fe(CO)3 and (COT)Fe(CO)3 are shown to be excellent catalysts for the tandem isomerization-aldol reaction of allylic alcohols with aldehydes and to significantly increase the scope of this aldolization process, especially, in the