2497-18-9

Basic information

• Product Name: TRANS-2-HEXENYL ACETATE
• Synonyms: FEMA 2564;(E)-1-ACETOXY-2-HEXENE;ACETIC ACID TRANS-2-HEXEN-1-YL ESTER;ACETIC ACID TRANS-2-HEXENYL ESTER;(2E)-HEXENYL ACETATE;TRANS-2-HEXEN-1-OL ACETATE;TRANS-2-HEXEN-1-YL ACETATE;TRANS-2-HEXENOL ACETATE
• CAS NO: 2497-18-9
• Molecular Formula: C₈H₁₄O₂
• Molecular Weight: 142.2
• EINECS: 219-680-7
• Product Categories: Alphabetical Listings;Flavors and Fragrances;G-H;C8 to C9;Carbonyl Compounds;Esters
• Mol File: 2497-18-9.mol

Chemical Properties

• Melting Point: -65.52°C (estimate)
• Boiling Point: 165-166 °C(lit.)
• Flash Point: 137 °F
• Appearance: clear colorless to slightly yellow liquid
• Density: 0.898 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.87mmHg at 25°C
• Refractive Index: n20/D 1.427(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Stability: Stable. Combustible. Incompatible with strong bases, strong oxidizing agents.
• BRN: 1721851
• CAS DataBase Reference: TRANS-2-HEXENYL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-2-HEXENYL ACETATE(2497-18-9)
• EPA Substance Registry System: TRANS-2-HEXENYL ACETATE(2497-18-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• RIDADR: UN 3272 3/PG 3
• WGK Germany: 2
• RTECS: MP8425000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 2497-18-9(Hazardous Substances Data)

Usage

Uses

Used in Flavor Industry:
TRANS-2-HEXENYL ACETATE is used as a flavor compound for its fresh, fruity, and slightly green smell, which adds a pleasant taste to various food products.
Used in Fragrance Industry:
TRANS-2-HEXENYL ACETATE is used as a fragrance ingredient for its pleasant, fruity odor, which can be incorporated into perfumes, cosmetics, and other scented products.
Used in Essential Oils:
TRANS-2-HEXENYL ACETATE is used in essential oils, such as peppermint oil, to enhance their fruity and fresh scent, making them more appealing for various applications.
Used in the Food Industry:
TRANS-2-HEXENYL ACETATE is used as an additive in the food industry to provide a sweet, green, fresh, and fruity taste with a waxy apple background, enhancing the flavor of various fruits, jams, and beverages.
Used in the Beverage Industry:
TRANS-2-HEXENYL ACETATE is used as a flavor enhancer in the beverage industry, particularly in fruit-flavored drinks, teas, and wines, to impart a fresh and fruity taste.

Preparation

By heating at the boil, 1-bromohexen-2-ol with sodium acetate and acetic acid.

InChI:InChI=1/C8H14O2/c1-3-4-5-6-7-10-8(2)9/h5-6H,3-4,7H2,1-2H3/b6-5-

Upstream product

• 34686-76-5 1-bromo-2-hexene 
• 127-09-3 sodium acetate 
• 592-41-6 1-hexene 
• 64-19-7 acetic acid 
• 101366-45-4 1,5-diacetoxy-3-propyl-2-oxapentane 
• 3375-31-3 palladium diacetate 
• 108-24-7 acetic anhydride 
• 1185-59-7 tetraethylammonium acetate 
• 2305-21-7 2-hexen-1-ol 
• 928-95-0 (E)-2-Hexen-1-ol 
• 75-36-5 acetyl chloride 
• 35926-04-6 3-acetoxy-1-hexene 
• 118653-96-6 1-iodo-hex-2-ene 
• 92315-15-6 trans-1-methylcarbonyloxy-2-hexene oxide 

Downstream Products

• 1433269-73-8 (E)-1-(hex-2-en-1-yl)-4-methoxybenzene 
• 1433269-75-0 (E)-methyl 4-(hex-2-en-1-yl)benzoate 
• 1609955-08-9 (S,E)-methyl 2-(N-ethyl-N-(4-methoxyphenyl)amino)-2-phenyloct-4-enoate 
• 78633-31-5 (2E)-hex-2-en-1-ylbenzene 
• 67590-77-6 (hex-2-enyl)benzene 
• 64275-32-7 (1-vinylbutyl)benzene 
• 90036-65-0 trans-Hex-2-enyl phenyl selenide 
• 90633-60-6 1-[((E)-Hex-2-ene)-1-sulfonyl]-4-methyl-benzene 
• 89268-72-4 (R)-1-(hex-1-en-3-ylsulfonyl)-4-methylbenzene 
• 109756-11-8 ethyl 3-propylpent-4-enoate 
• 138234-61-4 ethyl 4-octenoate 

Relevant articles and documents

On the role of triflic acid in the metal triflate-catalysed acylation of alcohols

The acylation of alcohols by anhydrides, catalysed by a wide range of metal triflates, is a powerful and mild method for the preparation of a variety of esters. Mechanistic insights demonstrate that triflic acid is generated under these reaction conditions and that, at least, two competing catalytic cycles are operating at the same time: a rapid one involving triflic acid and a slower one involving the metal triflate.

Scalable green approach toward fragrant acetates

The advantageous properties of ethylene glycol diacetate (EGDA) qualify it as a useful substitute for glycerol triacetate (GTA) for various green applications. We scrutinised the lipase-mediated acetylation of structurally diverse alcohols in neat EGDA furnishing the range of naturally occurring fragrant acetates. We found that such enzymatic system exhibits high reactivity and selectivity towards activated (homo) allylic and non-activated primary/secondary alcohols. This feature was utilised in the scalable multigram synthesis of fragrant (Z)-hex-3-en-1-yl acetate in 70percent yield. In addition, the Lipozyme 435/EGDA system was also found to be applicable for the chemo-selective acetylation of (hydroxyalkyl) phenols as well as for the kinetic resolution of chiral secondary alcohols. Lastly, its discrimination power was demonstrated in competitive experiments of equimolar mixtures of two isomeric alcohols. This enabled the practical synthesis of 1-pentyl acetate isolated as a single product in 68percent yield from the equimolar mixture of 1-pentanol and 3-pentanol.

OLEFIN METATHESIS CATALYSTS

This invention relates generally to metathesis catalysts and the use of such catalysts in the metathesis of olefins and olefin compounds, more particularly, in the use of such catalysts in Z and E selective olefin metathesis reactions. The invention has utility in the fields of organometallics and organic synthesis.

Fast-initiating, ruthenium-based catalysts for improved activity in highly E-selective cross metathesis

Ruthenium-based olefin metathesis catalysts bearing dithiolate ligands have been recently employed to generate olefins with high E-selectivity (>99% E) but have been limited by low to moderate yields. In this report, 1H NMR studies reveal that a major contributing factor to this low activity is the extremely low initiation rates of these catalysts with trans olefins. Introducing a 2-isopropoxy-3-phenylbenzylidene ligand in place of the conventional 2-isopropoxybenzylidene ligand resulted in catalysts that initiate rapidly under reaction conditions. As a result, reactions were completed in significantly less time and delivered higher yields than those in previous reports while maintaining high stereoselectivity (>99% E).

Identification of (Z)-3:(E)-2-Hexenal isomerases essential to the production of the leaf aldehyde in plants

The green odor of plants is characterized by green leaf volatiles (GLVs) composed of C6 compounds. GLVs are biosynthesized from polyunsaturated fatty acids in thylakoid membranes by a series of enzymes. A representative member of GLVs (E)-2-hexenal, known as the leaf aldehyde, has been assumed to be produced by isomerization from (Z)-3-hexenal in the biosynthesis pathway; however, the enzyme has not yet been identified. In this study, we purified the (Z)-3:(E)-2-hexenal isomerase (HI) from paprika fruits and showed that various plant species have homologous HIs. Purified HI is a homotrimeric protein of 110 kDa composed of 35-kDa subunits and shows high activity at acidic and neutral pH values. Phylogenetic analysis showed that HIs belong to the cupin superfamily, and at least three catalytic amino acids (His, Lys, Tyr) are conserved in HIs of various plant species. Enzymatic isomerization of (Z)-3-hexenal in the presence of deuterium oxide resulted in the introduction of deuterium at the C4 position of (E)-2-hexenal, and a suicide substrate 3-hexyn-1-al inhibited HI irreversibly, suggesting that the catalytic mode of HI is a keto-enol tautomerism reaction mode mediated by a catalytic His residue. The gene expression of HIs in Solanaceae plants was enhanced in specific developmental stages and by wounding treatment. Transgenic tomato plants overexpressing paprika HI accumulated (E)-2-hexenal in contrast to wild-type tomato plants mainly accumulating (Z)-3-hexenal, suggesting that HI plays a key role in the production of (E)-2-hexenal in planta.

High Trans Kinetic Selectivity in Ruthenium-Based Olefin Cross-Metathesis through Stereoretention

The first kinetically controlled, highly trans-selective (>98%) olefin cross-metathesis reaction is demonstrated using Ru-based catalysts. Reactions with either trans or cis olefins afford products with highly trans or cis stereochemistry, respectively. This E-selective olefin cross-metathesis is shown to occur between two trans olefins and between a trans olefin and a terminal olefin. Additionally, new stereoretentive catalysts have been synthesized for improved reactivity. (Chemical Equation Presented).

Practical Stannylation of Allyl Acetates Catalyzed by Nickel with Bu3SnOMe

A practical and scalable nickel-catalyzed allylic stannylation of allyl acetates with Bu3SnOMe is described. A variety of acyclic and cyclic allyl acetates, even with base-sensitive moieties, undergoes the stannylation by using NiBr2/4,4′-di-tert-butylbipyridine (dtbpy)/Mn catalyst system to afford highly functionalized allyl stannanes with excellent regioselectivity and yields. Furthermore, the scope of protocol is also extended by the reaction of propargyl acetates, giving rise to propargyl or allenyl stannanes. Additionally, a unique diastereoselectivity using the nickel catalyst different from the palladium was demonstrated for the stannylation of cyclic allyl acetates. In the reaction, inexpensive and stable nickel complexes, abundant reductant (Mn), and atom-economical stannyl source were used.

Selenium-catalyzed C(sp3)-H acyloxylation: Application in the expedient synthesis of isobenzofuranones

Oxidative Se-catalyzed C(sp3)-H bond acyloxylation has been used to construct a diverse array of isobenzofuranones from simple ortho-allyl benzoic acid derivatives. The synthetic procedure employs mild reaction conditions and gives high chemoselectivity enabled by an inexpensive organodiselane catalyst. The presented approach offers a new synthetic pathway toward the core structures of phthalide natural products.

Titanium carbenoid-mediated cyclopropanation of allylic alcohols: Selectivity and mechanism

A new method for the chemo- and stereoselective conversion of allylic alcohols into the corresponding cyclopropane derivatives has been developed. The cyclopropanation reaction was carried out with an unprecedented titanium carbenoid generated in situ from Nugent's reagent, manganese and methylene diiodide. The reaction involving the participation of an allylic hydroxyl group, proceeded with conservation of the alkene geometry and in a high diastereomeric excess. The scope, limitations and mechanism of this metal-catalysed reaction are discussed. This journal is

Achieving control over the branched/linear selectivity in palladium-catalyzed allylic amination

Palladium-catalyzed reaction of unsymmetrical allylic electrophiles with amines gives rise to regioisomeric allylic amines. We have found that linear products result from the thermodynamically controlled isomerization of the initially formed branched products. The isomerization is promoted by protic acid and active palladium catalyst. The use of base shuts down the isomerization pathway and allows for the preparation and isolation of branched allylic amines. Solvent plays a key role in achieving high kinetic regioselectivity and in controlling the rate of isomerization. The isomerization can be combined with ring-closing metathesis to afford the synthesis of exocyclic allylic amines from their endocyclic precursors.