Ethyl Hexanoate Chemical Properties

Melting point:

-67°C

Boiling point:

168 °C (lit.)

Density 

0.869 g/mL at 25 °C (lit.)

vapor density 

5 (vs air)

vapor pressure 

4hPa at 25℃

refractive index 

n20/D 1.407

FEMA 

2439 | ETHYL HEXANOATE

Flash point:

121 °F

storage temp. 

Flammables area

solubility 

0.63g/l

form 

Liquid

color 

Clear colorless

Odor

at 1.00 % in dipropylene glycol. sweet fruity pineapple waxy green banana

Odor Type

fruity

explosive limit

0.9%(V)

Water Solubility 

INSOLUBLE

Merck 

14,3777

JECFA Number

31

BRN 

1701293

Dielectric constant

4.5700000000000003

InChIKey

SHZIWNPUGXLXDT-UHFFFAOYSA-N

LogP

2.96 at 22.4℃

CAS DataBase Reference

123-66-0(CAS DataBase Reference)

NIST Chemistry Reference

Hexanoic acid, ethyl ester(123-66-0)

EPA Substance Registry System

Ethyl hexanoate (123-66-0)

Safety Information

Hazard Codes 

Xi

Risk Statements 

10-36/37/38-R36/37/38-R10

Safety Statements 

16-26-36-S36-S26-S16

RIDADR 

UN 3272 3/PG 3

WGK Germany 

1

RTECS 

MO7735000

TSCA 

Yes

HazardClass 

3

PackingGroup 

III

HS Code 

29159000

Toxicity

Both the acute oral LD₅₀ value in rats and the acute dermal LD₅₀ value in rabbits exceeded 5 g/kg (Moreno, 1975).

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Ethyl Hexanoate Usage And Synthesis

Description

Ethyl caproate (also ethyl hexanoate) is naturally found in the fruits of Ananas sativus. It can be synthesized by the direct esterification of caproic acid with ethyl alcohol. It has strong, sweet-ethereal like pineapple odor, with nuances of banana and strawberry.
Ethyl caproate is approved by the FDA for food use (as a flavoring agent in desserts and beverages) without hazard to public health. Ethyl Caproate is used to synthesize novel EP2/EP4 dual agonist of γ-lactam prostaglandin E1 analogs. It is also used as a chemical reagent in the synthesis of PPARα antagonists in the treatment of metabolic diseases.

References

[1] D. L. J. Opdyke (1974) Monographs on Fragrance Raw Materials
[2] https://www.trc-canada.com

Chemical Properties

Ethyl Hexanoate is a colorless liquid with a strong fruity odor, reminiscent of pineapples. It occurs in many fruits and is used in small amounts for floral, fruity notes in perfume compositions and in larger quantities in fruit flavors.

Chemical Properties

Ethyl hexanoate has a powerful, fruity odor with a pineapple–banana note. It has been also reported to have a winy odor.

Chemical Properties

CLEAR COLOURLESS LIQUID

Occurrence

Reported found in strawberry, rum, bourbon, cocoa, kiwi fruit, black currant, apple, orange and grapefruit juice, guava, Vitis vinifera, pineapple, strawberry jam, clove bud, cheeses, cognac, whiskies, grape wines, passion fruit juice, mango, fruit brandies, figs, corn oil, mountain papaya, pawpaw and mastic gum leaf oil.

Uses

Ethyl Caproate is used in the synthesis of novel EP2/EP4 dual agonist of γ-lactam prostaglandin E1 analogs. Also used as a chemical reagent in the synthesis of PPARα antagonists in the treatment of metabolic diseases.

Uses

Ethyl hexanoate may be used as an analytical reference standard for the determination of the analyte in wine and beer samples by chromatography based techniques.

Uses

manufacture of artificial fruit flavors.

Definition

ChEBI: A fatty acid ethyl ester obtained by the formal condensation of hexanoic acid with ethanol.

Preparation

By esterification of caproic acid with ethyl alcohol in the presence of concentrated H2SO4 or HCl

Aroma threshold values

Detection: 0.3 to 5 ppb

Taste threshold values

Taste characteristics at 10 ppm: fruity and waxy with a tropical nuance.

Synthesis Reference(s)

Journal of the American Chemical Society, 90, p. 818, 1968 DOI: 10.1021/ja01005a064
Synthetic Communications, 14, p. 77, 1984 DOI: 10.1080/00397918408060867
Synthesis, p. 929, 1978 DOI: 10.1055/s-1978-24945

General Description

Ethyl hexanoate is one of the odorants contributing to the typical guava aroma. It also contributes to the fresh strawberry aroma.

Safety Profile

A skin irritant. Flammable liquid when exposed to heat or flame; can react with oxidzing materials. When heated to decomposition it emits acrid smoke and irritating fumes. To fight fire, use CO2, foam, dry chemical. See also ESTERS.

Carcinogenicity

Not listed by ACGIH, California Proposition 65, IARC, NTP, or OSHA.

Metabolism

Aliphatic esters, including ethyl caproate, are thought to be readily hydrolysed to the corresponding alcohol and acid, which are then further metabolized (Fassett, 1963). Ethyl caproate administered orally to rats produced a uniform ketonuria and it was considered probable that caproic acid was broken down chiefly by ?-oxidation (Deuel, Hallman, Butts & Murray, 1936). When 2 g ethyl caproate dissolved in aqueous ethanol was fed directly into the rumen of a cow, 0.003°/ was transferred to the milk, reaching a maximum level of 60 /fg/litre after 2-4 hr (Honkanen, Karvonen & Virtanen, 1964). The energy from ethyl caproate was 52% available when the ester was fed to four chicks at a level of 5% in the diet (Yoshida et al. 1970).

Solubility in organics

Soluble in oils and alcohol. Poorly soluble in Ropylene glycol, insoluble in Glycerin.

Ethyl Hexanoate(123-66-0)Related Product Information

• Tris(trimethylsilyl)phosphate
• 2-Ethoxyethanol
• Dimethyl succinate
• Cholesteryl hexanoate
• Allyl hexanoate
• Ethanol
• Ethyl acetate
• Ethyl formate
• Ethyl propionate
• Hexanoic acid
• Trinexapac-ethyl
• ISOXADIFEN-ETHYL
• 6-Aminocaproic acid
• Ethylparaben
• N-HEXADECYLPHOSPHONIC ACID
• DIETHYL SEC-BUTYLMALONATE
• N-DODECYLPHOSPHONIC ACID
• Hexane
• Ethyl Caproate