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
• Article Data: 26

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

Description

trans-2-Hexen-l-yl acetate has a pleasant, fruity odor and corresponding taste. This substance may be synthesized by heating at the boil l-bromohexen-2 -ol with sodium acetate and acetic acid.

Chemical Properties

Different sources of media describe the Chemical Properties of 2497-18-9 differently. You can refer to the following data:
1. 2-Hexen-1-yl acetate has a pleasant, fruity odor and corresponding taste.
2. clear colorless to slightly yellow liquid
3. (E)-2-Hexenyl Acetate occurs in many fruits and in some essential oils, for example, peppermint. It is a fresh, fruity, slightly green-smelling liquid and is used in fruit flavors.

Occurrence

Reported found in Fragaria vesca and other fruits; only the trans-form is known. Also reported in apple, apple juice, apricot, bilberry, guava, peach, blackberry, strawberry fruit and jam, tomato, corn mint oil, spearmint oil, white and red wine, tea, plum, plumcot, mushroom, starfruit, mango, banana and passion fruit.

Preparation

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

Taste threshold values

Taste characteristics at 10 ppm: sweet, green, fresh and fruity with a waxy apple background.

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

• 592-41-6 1-hexene 
• 64-19-7 acetic acid 
• 3375-31-3 palladium diacetate 
• 928-95-0 (E)-2-Hexen-1-ol 
• 75-36-5 acetyl chloride 
• 35926-04-6 3-acetoxy-1-hexene 
• 56922-75-9 (Z)-Hex-2-en-1-yl acetate 
• 19689-92-0 cyclohexanone O-acetyl oxime 
• 4798-44-1 1-hexene-3-ol 
• 14850-23-8 trans-4-Octene 
• 1576-98-3 trans-1,4-diacetoxy-2-butene 
• 111-55-7 ethylene glycol diacetate 
• 72-89-9 acetylcoenzyme A 
• 27829-72-7 ethyl (E)-hex-2-enoate 

Downstream Products

• 131543-46-9 Glyoxal 
• 4417-81-6 ethylglyoxal 
• 5371-49-3 acetoxyacetaldehyde 
• 75-07-0 acetaldehyde 
• 123-38-6 propionaldehyde 
• 123-72-8 butyraldehyde 
• 35926-04-6 3-acetoxy-1-hexene 

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.

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.

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.