Ethyl octanoate

Names
Preferred IUPAC name

Ethyl octanoate

Other names

Ethyl caprylate

Identifiers

CAS Number

* 106-32-1 Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 7511

EC Number |

* 203-385-5

PubChem CID

* 7799

RTECS number |

* RH0680000

UNII |

* 81C5MOP582 Y

InChI

* InChI=1S/C10H20O2/c1-3-5-6-7-8-9-10(11)12-4-2/h3-9H2,1-2H3

Key: YYZUSRORWSJGET-UHFFFAOYSA-N

SMILES

* O=C(OCC)CCCCCCC

Properties

Chemical formula

| C10H20O2
Molar mass | 172.268 g·mol−1
Density | 0.86215 g/cm3[1]
Melting point |  −48 °C (−54 °F; 225 K)[4]
Boiling point |  208 °C (406 °F; 481 K)[4]

Solubility in water

| 70.1 mg/L [2][3]
Vapor pressure | 0.2 mbar at 20 °C; 3.18 mbar at 60 °C[4]
Viscosity | 1.411 mPa·s[1]
Hazards
Flash point |  79 °C (174 °F; 352 K)[4]

Autoignition
temperature

|  325 °C (617 °F; 598 K)[4]
Explosive limits | 0.7 - Vol.%[4]
Lethal dose or concentration (LD, LC):

LD50 (median dose)

| 25.96 g/kg (rat, oral)[2]

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Tracking categories (test):

* SizeSet

Ethyl octanoate, also known as ethyl caprylate, is a fatty acid ester formed from caprylic acid and ethanol. A colorless liquid at room temperature, it has the semi-developed formula of CH3(CH2)6COOCH2CH3, and is used in food industries as a flavoring and in the perfume industry as a scent additive. It is present in many fruits and alcoholic beverages, and has a strong odor of fruit and flowers.

## Contents

* 1 Synthesis
* 2 Uses
* 3 Safety
* 4 References

## Synthesis

Ethyl octanoate can be synthesized from caprylic acid and ethanol via a classic Fischer–Speier esterification.

3(CH

6COOH + CH
3CH
2OH ⇌ CH
3(CH

6COOCH
2CH
3 \+ H

Equilibrium can be shifted towards the right side of the equation through removal of water.

## Uses

Ethyl octanoate does not see widespread use due to the greater availability of reasonably similar esters such as ethyl acetate. However, there are certain applications where it fills a niche. Ethyl octanoate has a strong odor of fruit and flowers and a taste of apricot, and as such it can be used as a flavoring or to create scents. It sees some use as a cleaning agent.[5] ==Uses and occurrence== Ethyl octanoate is used in the creation of synthetic fruity scents.[6] It occurs above the odor threshold in young red wines.[7] In some wines, overall ester concentration and composition is considered important to the flavor and aroma profile.[8]

## Safety

Like many esters, ethyl octanoate is not considered to be toxic. LD50 in rats is 25.96 g/kg. Though it has a low explosive limit of only 0.67 vol%, it is also weakly volatile, with a vapor pressure of only 0.2 mbar at room temperature and therefore unable to create an explosive atmosphere at room temperature. Ethyl octanoate is combustible.

## References

1. ↑ 1.0 1.1 Sheu, Yaw-Wen; Tu, Chein-Hsiun (2006). "Densities and Viscosities of Binary Mixtures of Isoamyl Acetate, Ethyl Caproate, Ethyl Benzoate, Isoamyl Butyrate, Ethyl Phenylacetate, and Ethyl Caprylate with Ethanol at T = (288.15, 298.15, 308.15, and 318.15) K". Journal of Chemical and Engineering Data 51 (2): 496–503. doi:10.1021/je050389b.
2. ↑ 2.0 2.1 Ethyl octanoate from PubChem, accessed 30 December 2023
3. ↑ Mark, James E. (2007). Physical Properties of Polymer Handbook (2nd ed.). Springer. p. 294. ISBN 978-0387690025. https://books.google.com/books?id=fZl7q7UgEXkC&q=hildebrand+parameters+of+representative+polymers&pg=PA289. Retrieved 1 March 2013.
4. ↑ 4.0 4.1 4.2 4.3 4.4 4.5 Record of Ethyl octanoate in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 10 August 2010.
5. ↑ "Ethyl octanoate - Substance Information - ECHA" (in en-GB). https://echa.europa.eu/substance-information/-/substanceinfo/100.003.078.
6. ↑ Fahlbusch, Karl-Georg; Hammerschmidt, Franz-Josef; Panten, Johannes; Pickenhagen, Wilhelm; Schatkowski, Dietmar; Bauer, Kurt; Garbe, Dorothea; Surburg, Horst (15 January 2003). "Flavors and Fragrances". Flavors and Flagrances. Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH Verlag GmbH & Co. doi:10.1002/14356007.a11_141. ISBN 3527306730. http://www.mrw.interscience.wiley.com/emrw/9783527306732/ueic/article/a11_141/current/abstract. Retrieved 9 August 2019.
7. ↑ Ferreira, Vicente; lPez, Ricardo; Cacho, Juan F. (2000). "Quantitative determination of the odorants of young red wines from different grape varieties". Journal of the Science of Food and Agriculture 80 (11): 1659–1667. doi:10.1002/1097-0010(20000901)80:11<1659::aid-jsfa693>3.0.co;2-6. Bibcode: 2000JSFA...80.1659F.
8. ↑ Marais, J. et al. (2003) http://www.sawislibrary.co.za/dbtextimages/MaraisJ10.pdf "Effect of Different Wine-Making Techniques on the Composition and Quality of Pinotage Wine. I. Low-Temperature Skin Contact Prior to Fermentation"

* v
* t
* e

Esters

Methyl Esters|

* Methyl formate
* Methyl acetate
* Methyl propionate
* Methyl butyrate
* Methyl pentanoate

Ethyl Esters|

* Ethyl formate
* Ethyl acetate
* Ethyl propionate
* Ethyl butyrate
* Ethyl pentanoate
* Ethyl hexanoate
* Ethyl heptanoate
* Ethyl octanoate
* Ethyl decanoate

Propyl Esters|

* Propyl acetate
* Propyl propanoate
* Isopropyl acetate
* Isopropyl palmitate

Butyl Esters|

* Butyl acetate
* Butyl butyrate

Amyl Esters|

* Amyl acetate
* Isoamyl acetate
* Sec-Amyl acetate
* Pentyl propanoate
* Pentyl butyrate
* Pentyl pentanoate
* Pentyl hexanoate

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