27829-72-7

Basic information

• Product Name: Ethyl (E)-hex-2-enoate
• Synonyms: 2-Hexenoic acid, ethyl ester, (E)-;2-Hexenoicacid,ethylester,(E)-;Ethyl (2E)-2-hexenoate;ethylester,(e)-2-hexenoicaci;ethylester,(E)-2-Hexenoicacid;RARECHEM AL BI 0150;(E)-ETHYL 2-HEXENOATE;FEMA 3675
• CAS NO: 27829-72-7
• Molecular Formula: C₈H₁₄O₂
• Molecular Weight: 142.2
• EINECS: 248-681-5
• Mol File: 27829-72-7.mol
• Article Data: 33

Chemical Properties

• Melting Point: −2 °C(lit.)
• Boiling Point: 123-126 °C12 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 0.95 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.32mmHg at 25°C
• Refractive Index: n20/D 1.46(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• BRN: 1701323
• CAS DataBase Reference: Ethyl (E)-hex-2-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl (E)-hex-2-enoate(27829-72-7)
• EPA Substance Registry System: Ethyl (E)-hex-2-enoate(27829-72-7)

Safety Data

• Hazard Codes: C
• Statements: 34-10
• Safety Statements: 26-27-28-36/37/39-36/39-45-35-3/9-36-15
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 2
• RTECS: MP7750000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 27829-72-7(Hazardous Substances Data)

Usage

Chemical Properties

Ethyl trans-2-hexenoate has a fruity, green, pulpy pineapple and apple odor.

Occurrence

Reported found in apple brandy, cognac, grape brandy, concord grapes, wild grapes, passion fruit, quince, strawberry, guava, pineapple, pawpaw and wood apple.

Uses

(2E)-2-Hexenoic Acid Ethyl Ester is an odor active compound found in fruits such as papaya fruit cv. Red Maradol and guava (Psidium guajava L. cv. Red Suprema).

Taste threshold values

Taste characteristics at 10 ppm: fruity, green and sweet with a juicy, fruity undernote

Synthesis Reference(s)

Tetrahedron Letters, 27, p. 2903, 1986 DOI: 10.1016/S0040-4039(00)84675-4

InChI:InChI=1/C8H14O2/c1-3-5-6-7-8(9)10-4-2/h6-7H,3-5H2,1-2H3/b7-6+

Synthetic route

butyraldehyde (123-72-8) + ethyl bromoacetate (105-36-2) → ethyl (E)-hex-2-enoate (27829-72-7)

Conditions	Yield
With tributylstibine at 100℃; for 2.5h; other aldehydes and ketones;	92%
With tributylstibine at 100℃; for 2.5h;	92%
With tributylstibine at 100℃; for 3.5h;	92%
With sodium hydrogencarbonate; triphenylphosphine In water at 20℃; for 12h;

butyraldehyde (123-72-8) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → ethyl (E)-hex-2-enoate (27829-72-7)

Conditions	Yield
In benzene at 20℃; Wittig reaction;	90%
In dichloromethane at 20℃; for 47h; Wittig Olefination; Inert atmosphere;	72%
In dichloromethane for 18h; Wittig olefination reaction;	66%
Wittig Olefination; Inert atmosphere;
In dichloromethane for 72h; Wittig Rearrangement; Inert atmosphere;	1.36 g

Upstream product

• 21188-61-4 3-acetoxy-hexanoic acid ethyl ester 
• 64277-92-5 ethyl (E)-6-iodo-2-hexenoate 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 123-72-8 butyraldehyde 
• 72258-75-4 2-<(ethoxycarbonyl)methyl>-2-oxo-4,5-dimethyl-1,3,2-dioxaphospholane 
• 250607-12-6 3-butyroyl-5,5-dimethyloxazolidin-2-one 
• 250607-11-5 3-(3'-phenylpropionyl)-5,5-dimethyloxazolidin-2-one 
• 13419-69-7 (E)-2-Hexenoic acid 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 6728-26-3 (E)-2-Hexenal 
• 64-17-5 ethanol 
• 1191-04-4 2-hexenoic acid 
• 623-73-4 diazoacetic acid ethyl ester 
• 372-31-6 ethyl 4,4,4-trifluoroacetoacetate 

Downstream Products

• 59739-10-5 ethyl 2,3-methanohexanoate 
• 18191-59-8 allylsilane 
• 607375-40-6 ethyl (Z)-3-(2-(triethoxysilyl)ethyl)hex-2-enoate 
• 6728-26-3 (E)-2-Hexenal 
• 1026405-21-9 C₁₈H₂₇NO₄S 
• 105882-02-8 N-[(2E)-hex-2-en-1-yl]-4-methylbenzene-1-sulfonamide 
• 88207-86-7 ethyl 6-propyl-5,6-dihydro-β-resorcylate 
• 61454-93-1 Ethyl trans-3-propyloxirane-2-carboxylate 
• 26553-46-8 ethyl (E)-3-hexenoate 
• 64187-83-3 ethyl (3Z)-hex-3-enoate 
• 129801-01-0 ethyl (1β,2α,3β)-4-methylene-3-(phenylsulfonyl)-2-propylcyclopentanecarboxylate 
• 75804-38-5 Ethyl (Z)-2-(phenylseleno)hexen-2-oate 
• 928-95-0 (E)-2-Hexen-1-ol 
• 123-66-0 Ethyl hexanoate 

Relevant articles and documents

A convenient synthesis of amino acid-derived precursors to the important wine aroma 3-sulfanylhexan-1-ol (3SH)

A convenient, straightforward synthesis of the important amino acid-derived aroma precursors, 3-S-cysteinylhexan-1-ol (Cys-3SH) and 3-S-glutathionylhexan-1-ol (GSH-3SH) from commercially available butan-1-ol is reported. The versatility of this approach to include deuterium labelling is also demonstrated.

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Synthesis of alkyl sulfonic acid aldehydes and alcohols, putative precursors to important wine aroma thiols

The synthesis of the low molecular weight sulfonic acids, 2-methyl-4-oxopentane-2-sulfonic acid, 1-hydroxyhexane-3-sulfonic acid, 1-oxohexane-3-sulfonic acid and 1-hydroxyhexane-1,3-disulfonic acid from trans-2-hexenal and ethyl hex-2-enoate is reported. These sulfonic acids are putative precursors to the important wine aroma thiols, 3-mercaptohexan-1-ol, 3-mercaptohexyl acetate and 4-mercapto-4-methylpentan-2-one.

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.

Oxidative esterification of aliphatic aldehydes and alcohols with ethanol over gold nanoparticle catalysts in batch and continuous flow reactors

Selective esterification of aliphatic aldehydes and alcohols with ethanol in the absence of a base is a more difficult reaction than that with methanol. Gold nanoparticles on ZnO were found to catalyze the oxidative esterification of octanal to ethyl octanoate with high selectivity. In addition, it was found that Au/ZnO was the most effective catalyst for yielding the desired ethyl ester without a base by direct esterification of 1-octanol with ethanol. As far as we know, this is the first report on oxidative esterification to give aliphatic ethyl esters from less reactive aliphatic alcohols and aldehydes without a base. The optimal size of gold NPs ranged from 2 to 6 nm and the presence of Au(0) was indispensable for this reaction. Au/ZnO exhibited the highest catalytic activity in both batch and flow reactors. The conversion was maintained for more than 20 h with 95% selectivity to the desired ethyl ester in the flow system.