505-57-7

Usage

Chemical Properties

2-Hexenal has a sweet, fragrant, almond, fruity green, leafy, apple, plum, vegetable odor.

Occurrence

Reported found in the distillation waters of several plants, such as Carpinus betulus; also identified among the constituents of tea (leaves) oil and in citronella. Also reported found in numerous foods including apple juice, apricot, banana, citrus peel oils and juices, blueberry, strawberry, guava, peach, pear, melon, cabbage, kohlrabi, cucumber, lettuce, leek, peas, tomato, thymus, butter, milk, fish, fish oil, meats, hop oil, beer, grape wines, peanut oil, pecans, potato chips, soybeans, avocado, olive, passion fruit, plum, Malay apple, star fruit, mango, cauliflower, fig, artichoke, coriander leaf, rice, radish, lovage leaf, laurel, loquat, endive, nectarines, clam, quince and tobacco.

Preparation

From interaction of butyraldehyde acetal with vinyl ether followed by hydrolysis or by any other suitable means.

Definition

ChEBI: A hexenal having the double bond at the 2-position.

Aroma threshold values

Detection: 30 ppb; aroma characteristics at 1.0%: pungent green fatty, fresh fruity aldehydic, with fresh leafy apple and watermelon nuances.

Taste threshold values

Taste characteristics at 5 ppm: fruity, fresh green, herbal and vegetative, apple and melon with a slight yeasty nuance.

Toxicity evaluation

The acute oral LD50 value in rats was reported as 0.85 g/kg (0.65-1.05 g/kg) (Moreno, 1973). The oral LD50 values for trans-2-hexenal were reported as 780-1130 and 1550-1750 mg/kg in rats and mice, respectively, and the ip LD50 values were reported as 100-200 mg/kg in both species (Gaunt, Colley, Wright, Creasey, Grasso & Gangolli, 1971). The acute dermal LD50 value in rabbits was reported as 0.60 g/kg (0.37-0.83 g/kg) (Moreno, 1973).

InChI:InChI=1/C6H10O/c1-2-3-4-5-6-7/h4-6H,2-3H2,1H3/b5-4+

Upstream product

• 2305-21-7 2-hexen-1-ol 
• 87371-83-3 hex-3-ene-1,2-diol 
• 101-33-7 1,1,3-triethoxy-hexane 
• 41818-37-5 1-methoxy-hex-1-en-3-yne 
• 34061-73-9 2-Hexenyl methyl ether 
• 92822-57-6 Carbonic acid allyl ester (E)-hex-2-enyl ester 
• 102651-78-5 hex-2-enal-N,N-dimethyl hydrazone 
• 693-02-7 hex-1-yne 
• 7642-15-1 (Z)-oct-4-ene 
• 71985-12-1 2-bromo-1-trimethylsiloxyethene 
• 123-72-8 butyraldehyde 
• 928-94-9 (Z)-2-hexen-1-ol 
• 928-95-0 (E)-2-Hexen-1-ol 
• 592-48-3 hexa-1,3-diene 

Downstream Products

• 1191-04-4 2-hexenoic acid 
• 54306-00-2 1,1-diethoxyhex-2-ene 
• 141121-07-5 tert-butyldimethyl<(1Z)-3-<(E)-2-phenylethenyl>-1-hexenyl)oxy>silane 
• 141170-85-6 tert-butyldimethyl<(1E)-3-<(E)-2-phenylethenyl>-1-hexenyl)oxy>silane 
• 2305-21-7 2-hexen-1-ol 
• 133788-00-8 6-phenyl-3a,4-dihydro-1H-cyclopenta[c]furan-5(3H)-one 
• 97250-26-5 3-Phenylhexanal 
• 5910-85-0 hepta-2,4-dienal 
• 17175-86-9 2,4-heptadienoic acid 
• 1056346-34-9 (-)-3-(4',5'-dihydro-4'-isobutyl-5'-oxo-2'-phenyloxazol-4'-yl)hexanal 

Relevant academic research and scientific papers

Chromium-Catalyzed Production of Diols From Olefins

Processes for converting an olefin reactant into a diol compound are disclosed, and these processes include the steps of contacting the olefin reactant and a supported chromium catalyst comprising chromium in a hexavalent oxidation state to reduce at least a portion of the supported chromium catalyst to form a reduced chromium catalyst, and hydrolyzing the reduced chromium catalyst to form a reaction product comprising the diol compound. While being contacted, the olefin reactant and the supported chromium catalyst can be irradiated with a light beam at a wavelength in the UV-visible spectrum. Optionally, these processes can further comprise a step of calcining at least a portion of the reduced chromium catalyst to regenerate the supported chromium catalyst.

Iodine-catalyzed alcohol disproportionation method

The invention relates to the technical field of catalysis, in particular to an iodine-catalyzed alcohol disproportionation method which comprises the following steps: sequentially adding alcohol, iodine and a solvent into a high-temperature and high-pressure reaction kettle, introducing a certain amount of nitrogen, conducting reacting for a certain time, collecting an organic phase after the reaction is ended, and conducting fractionating to obtain corresponding alkane and aldehyde/ketone. Alcohol disproportionation is efficient and atom-economical conversion without any additional oxidizing agent and reducing agent, and hydrocarbon and aldehyde/ketone molecules which are easy to separate can be formed at the same time. Meanwhile, the method has wide functional group tolerance, various substrate samples including aryl alcohol derivatives, heterocyclic alcohol derivatives, allyl alcohol derivatives and dihydric alcohol are tested, and the result shows that most of the substrate samples show good or extremely good yield.

METHOD FOR PRODUCING CROSS ALDOL CONDENSATE USING AMINE-CARRYING CATALYST

PROBLEM TO BE SOLVED: To provide a method for producing a cross aldol condensate with improved selectivity of a cross aldol condensate, the target material. SOLUTION: A method for producing a cross aldol condensate has a step of performing a cross aldol condensation reaction of different two substrates in the presence of an amine-carrying catalyst with an amine compound immobilized to a carrier, the substrate containing two compounds selected from aldehyde and/or ketone having α hydrogen. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPO&INPIT

An Engineered Alcohol Oxidase for the Oxidation of Primary Alcohols

Structure-guided directed evolution of choline oxidase has been carried out by using the oxidation of hexan-1-ol to hexanal as the target reaction. A six-amino-acid variant was identified with a 20-fold increased kcat compared to that of the wild-type enzyme. This variant enabled the oxidation of 10 mm hexanol to hexanal in less than 24 h with 100 % conversion. Furthermore, this variant showed a marked increase in thermostability with a corresponding increase in Tm of 20 °C. Improved solvent tolerance was demonstrated with organic solvents including ethyl acetate, heptane and cyclohexane, thereby enabling improved conversions to the aldehyde by up to 30 % above conversion for the solvent-free system. Despite the evolution of choline oxidase towards hexan-1-ol, this new variant also showed increased specific activities (by up to 100-fold) for around 50 primary aliphatic, unsaturated, branched, cyclic, benzylic and halogenated alcohols.

Selective catalytic oxidation of alkenes employing homobinuclear manganese(II) catalysts with TBHP

The two novel homobinuclear compounds [Mn2(II,II) (μ1,1-4-CH3-C6H4COO)2(phen)4](ClO4)2 (1) and [Mn2(II,II) (μ1,3-4-CH3-C6H4COO)2(bipy)4](ClO4)2 (2), where bipy = 2,2-bipyridine and phen = 1,10-phenanthroline, have been synthesized and characterized by elemental analyses and spectral methods (UV–Vis, FTIR, and X-ray). A single-crystal X-ray diffraction structure analysis of the compounds revealed that the manganese atom is octahedrally coordinated. In compound 1, the binuclear(II) structure is monodentate, bridged with one oxygen atom of carboxylate ligand in μ1,1 mode, and each Mn(II) center is coordinated with two phen ligands. In compound 2, the binuclear(II) structure is syn–anti bidentate, bridged with two oxygen atoms of carboxylate ligand in μ1,3 mode, and each Mn(II) center is coordinated with two bipy ligands. The Mn–Mn separation is 3.441 (1) ? and 4.450 (1) ? for 1 and 2, respectively. The catalytic potentials of these compounds have been tested for the oxidation reaction of various olefins (i.e., styrene, cyclohexene, ethyl benzene, 1-hexene, 1-octene). The oxidation reactions were carried out in the presence of catalytic amounts of 1 and 2 with a peroxide oxygen donor (TBHP = tert-Butyl hydroperoxide) in acetonitrile at 70 °C. On comparing the catalytic activities of 1 and 2, both catalysts showed good activity (～100% conv. in 24 h) in the oxidation of studied alkenes, and excellent conversion was obtained for cyclohexene (～100% conv. in 3 h; TON = 265 and TON = 257, respectively, for 1 and 2).

A carboxylate-bridged Mn(II) compound with 6-methylanthranilate/bipy: oxidation of alcohols/alkenes and catalase-like activity

A novel manganese compound, [Mn2(μ1,3-6-CH3-2-NH2C6H4COO)2(bipy)4](ClO4)2 (bipy?=?2,2′-bipyridine), was synthesized and used as a catalyst precursor in the oxidation of alkenes and primary alcohols to corresponding aldehydes, ketones, and acids. The six-coordinate compound has a binuclear structure in which two Mn(II) ions adopt a syn-anti μ1,3-bridging mode with two carboxylate groups and two chelated bipy ligands. The compound exhibits good activity in the oxidation of cyclohexene to 2-cyclohexene-1-one as the major product (93% conv. in 3?h, 79.3% selectivity) and of cinnamyl alcohol to cinnamaldehyde as the major product with 46% selectivity (100% conv. in 1.5?h) with tert-butyl hydroperoxide (TBHP) in acetonitrile at 70?°C. Furthermore, the catalase-like activity of the compound was studied in different solvents (acetonitrile, methanol, Tris-HCl buffer; TOF?=?29,910?h?1 in Tris-HCl buffer).

Aerobic oxidation of alcohols over Ru-Mn-Ce and Ru-Co-Ce catalysts: The effect of calcination temperature

Two ternary mixed oxides, Ru-Mn-Ce and Ru-Co-Ce, were prepared by a co-precipitation method and used in the aerobic oxidation of alcohols to corresponding aldehydes (ketones). Interestingly, different catalytic results were obtained when these compounds were calcined. The calcination temperature had an adverse effect on the catalytic performance of Ru-Mn-Ce catalysts, while being beneficial to the Ru-Co-Ce catalysts. To illustrate these effects, these materials were characterized using X-ray diffraction (XRD), Fourier transformed infrared spectroscopy (FT-IR), X-ray photoelectron spectroscopy (XPS), Temperature-programmed reduction (TPR), Electron paramagnetic resonance (EPR) and other techniques. The data showed that ruthenium oxides were uniformly dispersed in the mixed oxides, and phase transformations occur after calcination. Mn3O4was transformed to MnO2for the Ru-Mn-Ce catalyst, while CoO(OH) was transformed to Co3O4in the Ru-Co-Ce catalyst.The interactions between ruthenium oxides and Co (Mn)-Ce mixed oxides of the former strengthened while the latter weakened. Calcination decreased the content of adsorbed oxygen and restricted oxygen transfer mechanism in the manganese system, while the opposite effect was observed with the cobalt-containing catalyst. Under optimal reaction conditions, various kinds of alcohols were transformed to corresponding aldehydes (ketones) in high yields over the Ru-Mn-Ce catalyst suggesting these ternary oxides are environmental friendly and economical catalytic systems.

The synthesis of Aldehyde by oxidation of the alcohol

The present invention relates to an aldehyde synthesis method which includes a step of synthesizing aldehyde by carrying out a reaction with alcohol having an allyl group in the presence of a catalyst. By controlling pressure and types of catalysts, induction of selective oxidation of alcohol is possible, thereby ensuing excellent economic feasibility as well as favorable yields and reaction time.COPYRIGHT KIPO 2017

Synthesis method of 2-hexenal

The invention discloses a synthesis method of 2-hexenal. The method includes: adding a mixed solution of n-butanal and vinyl alkyl ether into a catalyst boron trifluoride diethyl etherate solution dropwise to carry out reaction, subjecting the obtained acetal to heating hydrolysis distillation under the catalytic action of a Lewis acid aqueous solution, and subjecting an obtained 2-hexenal crude product to continuous pressure reduction distillation, thus obtaining high purity 2-hexenal. The method provided by the invention has the characteristics of stable route and process and high yield, and the product has competitive edge.

Alpha, beta-unsaturated carbonyl compound production method

The present invention relates to an alpha, beta-unsaturated carbonyl compound production method comprising the following steps: (1) oxidizing reaction of a primary alcohol with 3-20 carbon atoms under the effect of an oxidase for selective oxidation of a terminal alcoholic hydroxyl group into an aldehyde group to obtain an aldehyde group compound; (2) Reformatsky reaction of the aldehyde group compound and a halide under the catalytic effect of a metal to produce a corresponding alpha, beta-unsaturated carbonyl compound, the alpha, beta-unsaturated carbonyl compound production method is low-cost, less in environmental pollution, moreover, by alcohol oxidizing reaction by use of the oxidase, the quantitative and high selectivity corresponding alpha, beta-unsaturated carbonyl compound can be obtained, and the after processing is convenient.