6728-26-3

Basic information

• Product Name: TRANS-2-HEXENAL
• Synonyms: BETA-PROPYLACROLEIN;LEAF ALDEHYDE;FEMA 2560;HEXEN-1-AL,TRANS-2-;HEX-2(TRANS)-ENAL;T2 HEXENAL;TRANS-2-HEXENYL ALDEHYDE;TRANS-2-HEXENAL
• CAS NO: 6728-26-3
• Molecular Formula: C₆H₁₀O
• Molecular Weight: 98.14
• EINECS: 229-778-1
• Product Categories: Fatty & Aliphatic Acids, Esters, Alcohols & Derivatives;aldehyde Flavor;Aldehydes;C1 to C6;Carbonyl Compounds
• Mol File: 6728-26-3.mol

Chemical Properties

• Melting Point: -78°C (estimate)
• Boiling Point: 47 °C17 mm Hg(lit.)
• Flash Point: 101 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 0.846 g/mL at 25 °C(lit.)
• Vapor Density: 3.4 (vs air)
• Vapor Pressure: 10 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.446(lit.)
• Storage Temp.: 0-6°C
• Water Solubility: Insoluble
• BRN: 1699684
• CAS DataBase Reference: TRANS-2-HEXENAL(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-2-HEXENAL(6728-26-3)
• EPA Substance Registry System: TRANS-2-HEXENAL(6728-26-3)

Safety Data

• Hazard Codes: Xn,Xi,F
• Statements: 10-21/22-36/37/38-20/21/22-43
• Safety Statements: 16-26-36-36/37
• RIDADR: UN 1988 3/PG 3
• WGK Germany: 2
• RTECS: MP5900000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 6728-26-3(Hazardous Substances Data)

Usage

Uses

Used in Food Industry:
TRANS-2-HEXENAL is used as a flavoring agent in the food industry to enhance the taste and aroma of various food products.
Used in Quality Evaluation of Virgin Olive Oils:
TRANS-2-HEXENAL is used in the evaluation of the quality of protected designation of origin virgin olive oils. It is analyzed using headspace solid-phase microextraction-gas chromatography with flame ionization detection and multivariate analysis to determine the presence and concentration of this compound in olive oils.
Used in Determination of Low-Molecular-Weight Carbonyl Compounds:
TRANS-2-HEXENAL is used in the multicomponent method for the determination of low-molecular-weight carbonyl compounds in biological samples. This method helps in identifying and quantifying the presence of these compounds, which can be useful in various research and analytical applications.

Descriptioin

Tans-2-Hexenal is a colorless to pale yellow clear liquid. It occurs naturally in tomatoes, banana and black tea. It gives a leafy, fruity, fatty, apple banana, strawberry note.1 It is mostly used as a flavoring agent in food. It is also used in air care products, cleaning and furnishing care products, laundry and dishwashing products.

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 3468, 1949 DOI: 10.1021/ja01178a061Tetrahedron Letters, 36, p. 8513, 1995 DOI: 10.1016/0040-4039(95)01784-F

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

Upstream product

• 928-96-1 (Z)-3-Hexen-1-ol 
• 101-33-7 1,1,3-triethoxy-hexane 
• 101713-97-7 1-ethoxy-hex-3-en-2-ol 
• 123-72-8 butyraldehyde 
• 109-92-2 ethyl vinyl ether 
• 928-94-9 (Z)-2-hexen-1-ol 
• 928-95-0 (E)-2-Hexen-1-ol 
• 6789-80-6 (3Z)-hexenal 
• 69112-21-6 (E)-3-hexenal 
• 54306-00-2 1,1-diethoxyhex-2-ene 
• 67746-30-9 (E)-1,1-Diethoxy-hex-2-ene 
• 927-77-5 n-propylmagnesium bromide 
• 78906-21-5 trans-3-trimethylsiloxyacrolein 
• 18318-83-7 (E)-1,1-dimethoxy-2-hexene 

Downstream Products

• 22329-75-5 (2E,4E)-octadienoic acid 
• 67077-39-8 trans-3-hepten-2-ol 
• 102178-95-0 hex-2t-enal-[4-(4-phenylazo-phenyl)-semicarbazone] 
• 928-95-0 (E)-2-Hexen-1-ol 
• 2122-02-3 1-(hex-2-enylidene)-2-(2,4-dinitrophenyl)hydrazine 
• 80387-31-1 (3E,5E)-nona-3,5-dien-2-one 
• 61452-39-9 β-Phenylthio-hexanal 
• 61452-43-5 β-Benzylthio-hexanal 
• 112197-08-7 1-(2-methoxy-3-pyridyl)-(E)-2-hexen-1-ol 
• 137032-35-0 (1-Dimethoxymethyl-2-methoxy-pentylselanyl)-benzene 
• 97250-26-5 3-Phenylhexanal 
• 137032-64-5 3-Hydroxy-2-phenylselanyl-hexanal 
• 139080-10-7 3-Methyl-2-((E)-pent-1-enyl)-cyclohex-2-enone 
• 53963-25-0 [1-((Z)-2-Methoxy-vinyl)-butylsulfanyl]-benzene 

Relevant articles and documents

Efficient Aerobic Oxidation of trans-2-Hexen-1-ol using the Aryl Alcohol Oxidase from Pleurotus eryngii

The selective oxidation of trans-2-hexen-1-ol to the corresponding aldehyde using a recombinant aryl alcohol oxidase from Pleurotus eryngii (PeAAOx) is reported. Especially using the two liquid phase system to overcome solubility and product inhibition issues enabled to achieve more than 2.200.000 catalytic turnovers for the production enzyme as well as molar product concentrations, pointing towards an economic feasible reaction. (Figure presented.).

EFFICIENT INDIRECT ELECTROCHEMICAL IN SITU REGENERATION OF NAD+ AND NADP+ FOR ENZYMATIC OXIDATIONS USING IRON BIPYRIDINE AND PHENANTHROLINE COMPLEXES AS REDOX CATALYSTS

Using iron bipyridine or phenanthroline complexes 1 as redox catalysts it was possible to electrochemically generate NAD(P)+ from NAD(P)H very efficiently.Electrochemically driven enzymatic oxidations of the test systems 2-hexen-1-ol and 2-butanol could be performed with 1e as redox catalyst in presence of yeast alcohol dehydogenase (YADH) or the alcohol dehydrogenase of thermoanaerobium brockii (TADH) with turnover numbers of about 40/h.

Biocatalytic synthesis of the Green Note trans-2-hexenal in a continuous-flow microreactor

The biocatalytic preparation of trans-hex-2-enal from trans-hex-2-enol using a novel aryl alcohol oxidase from Pleurotus eryngii (PeAAOx) is reported. As O2-dependent enzyme PeAAOx-dependent reactions are generally plagued by the poor solubility of O2 in aqueous media and mass transfer limitations resulting in poor reaction rates. These limitations were efficiently overcome by conducting the reaction in a flow-reactor setup reaching unpreceded catalytic activities for the enzyme in terms of turnover frequency (up to 38 s-1) and turnover numbers (more than 300000) pointing towards preparative usefulness of the proposed reaction scheme.

Characterization of a new (Z)-3:(E)-2-hexenal isomerase from tea (Camellia sinensis) involved in the conversion of (Z)-3-hexenal to (E)-2-hexenal

Two major green leaf volatiles (GLVs) in tea that contribute greatly to tea aroma, particularly the green odor, are (E)-2-hexenal and (Z)-3-hexenal. Until now, their formation and related mechanisms during tea manufacture have remained unclear. Our data showed that the contents of (E)-2-hexenal and (Z)-3-hexenal increased more than 1000-fold after live tea leaves were torn. Subsequently, a new (Z)-3:(E)-2-hexenal isomerase (CsHI) was identified in Camellia sinensis. CsHI irreversibly catalyzed the conversion of (Z)-3-hexenal to (E)-2-hexenal. Abiotic stresses including low temperature, dehydration, and mechanical wounding, did not influence the (E)-2-hexenal content in intact tea leaves during withering, but regulated the proportions of (Z)-3-hexenal and (E)-2-hexenal in torn leaves by modulating CsHI at the transcript level. For the first time, this work reveals the formation of (E)-2-hexenal during tea processing and suggests that CsHI may play a pivotal role in tea flavor development as well as in plant defense against abiotic stresses.

Synthesis and Biological Evaluation of Hoshionolactam-Based Compounds

In search of novel antitrypanosomal agents based on hoshinolactam (IC50=3.9 nM), we disclose the synthesis and biological evaluations of 14 different analogues of the natural product using combinations of different acids and lactams. Antitrypanosomal activity assays revealed that the synthesized analogues were less potent than the parent natural product.

Biosynthesis of Mycotoxin Fusaric Acid and Application of a PLP-Dependent Enzyme for Chemoenzymatic Synthesis of Substituted l -Pipecolic Acids

Fusaric acid (FA) is a well-known mycotoxin that plays an important role in plant pathology. The biosynthetic gene cluster for FA has been identified, but the biosynthetic pathway remains unclarified. Here, we elucidated the biosynthesis of FA, which features a two-enzyme catalytic cascade, a pyridoxal 5′-phosphate (PLP)-dependent enzyme (Fub7), and a flavin mononucleotide (FMN)-dependent oxidase (Fub9) in synthesizing the picolinic acid scaffold. FA biosynthesis also involves an off-line collaboration between a highly reducing polyketide synthase (HRPKS, Fub1) and a nonribosomal peptide synthetase (NRPS)-like carboxylic acid reductase (Fub8) in making an aliphatic α,β-unsaturated aldehyde. By harnessing the stereoselective C-C bond-forming activity of Fub7, we established a chemoenzymatic route for stereoconvergent synthesis of a series of 5-alkyl-, 5,5-dialkyl-, and 5,5,6-trialkyl-l-pipecolic acids of high diastereomeric ratio.

First synthesis of 3-S-glutathionylhexanal-d8 and its bisulfite adduct

3-Sulfanylhexan-1-ol (3SH) is an impact odorant of white wines, imparting tropical fruit aromas. A reliable synthetic pathway to 3-S-glutathionylhexanal (glut-3SH-al), a precursor to 3SH that has not been intensively studied, was developed starting from 1-butanol. Application of this synthesis to 1-butanol-d10, conserved eight deuteriums, producing glut-3SH-al-d8, which can be used as an internal standard for future work on the occurrence and evolution of glut-3SH-al in wine systems. Additionally, both glut-3SH-SO3 and glut-3SH-SO3-d8 were synthesised from the corresponding aldehyde, enabling further study of the role of these bisulfite adducts in 3SH biogenesis.

Catalytic performance of bulk and colloidal Co/Al layered double hydroxide with Au nanoparticles in aerobic olefin oxidation

A Co/Al layered double hydroxide material was synthesized in both bulk and exfoliated (colloidal) forms. Anion exchange with methionine allowed immobilization of Au nanoparticles previously prepared by a biomimetic method using an anti-oxidant tea aqueous extract to reduce the Au salt solution. The catalytic performance of bulk and exfoliated clays Au-hybrid materials was assessed in aerobic olefin epoxidation. Both catalysts were very active towards the epoxide products and with very interesting substrate conversion levels after 80 h reaction time. The Au-exfoliated material, where the nanosheets work as large ligands, yielded higher product stereoselectivity in the case of limonene epoxidation. This arises from a confined environment around the Au nanoparticles wrapped by the clay nanosheets modulating access to the catalytic active centres by reagents. Mechanistic assessment was also accomplished for styrene oxidation by DFT methods.

Method for continuously synthesizing trans -2 - hexenal by micro-channel reactor (by machine translation)

The invention belongs to the field, organic synthesis. The invention relates to a trans -2 - hexenal method. The method for preparing trans 4 - hexenal by continuous hydrolysis of -2 ethoxy 6 -1 dipropyl 3 -2 - dioxane (for short cyclization intermediate) through a micro-channel reactor is mainly solved by the preparation method. In the prior art, under the 10% presence of dilute acid (Unified), reflux distillation hydrolysis, oil-water layering, oil extraction, and a water layer backwater reactor are continuously distilled to the oil-free layer, and the water is undissolved. There is a long hydrolysis time, for example. Energy consumption is high, aftertreatment is tedious, serialization, hydrolysis yield and the like cannot be realized. By adopting the microchannel reactor, the 20 - 30% dilute acid concentration can be improved, the residence time is shortened, and continuous hydrolysis. The hydrolyzate is simple oil-water layering to obtain the crude product, and the hydrolyzed water layer can be recycled. The defects in the traditional hydrolytic distillation process, hydrolysis, long distillation time, complex process, and high energy consumption are overcome. , The process risk, and is suitable for industrial production. (by machine translation)

Method for synthesizing trans-2-hexenal

The invention discloses a method for synthesizing trans-2-hexenal. The method includes steps of (1), adding acidic ionic liquid into reaction flasks, completely dropwise adding vinyl ethyl ether and butyraldehyde mixed liquid into the reaction flasks at the temperatures of 0-25 DEG C, then heating systems until the temperatures of the systems reach 20-45 DEG C, carrying out stirring reaction for 1-6 hours, and carrying out reduced pressure distillation after the reaction is completely carried out so as to obtain cyclization intermediates A; adding dilute sulfuric acid aqueous solution and theintermediates A into reaction flasks, erecting reflux oil and water layering devices, carrying out heating normal-pressure distillation for 4-48 hours, and extracting upper oil layers into oil layer receiving flasks; (3), rectifying and purifying hexenal crude products, carrying out normal-pressure rectification to obtain substances with low boiling points and then carrying out reduced pressure rectification to obtain the trans-2-hexenal. A molar ratio of butyraldehyde to vinyl ethyl ether is 2:1-5:1, and the usage of the acidic ionic liquid accounts for 0.1-5% of the total weight of the vinylethyl ether; the acidic ionic liquid is [(CH2)3SO3HMIM][HSO4] or [(CH2)3SO3HMIM][CF3SO3]. The oil layers are the hexenal crude products; the mass concentration of the dilute sulfuric acid aqueous solution is 0.5-25%, and a weight ratio of the dilute sulfuric acid aqueous solution to the intermediates A is 0.2:1-2:1. The method has the advantages of environmental protection, low cost and high yield.