Ethyl octanoate

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Ethyl octanoate
Ethyl octanoate structure.svg
Names
Preferred IUPAC name
Ethyl octanoate
Other names
Ethyl caprylate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.078 OOjs UI icon edit-ltr-progressive.svg
EC Number
PubChem CID
RTECS number
  • RH0680000
UNII
  • InChI=1S/C10H20O2/c1-3-5-6-7-8-9-10(11)12-4-2/h3-9H2,1-2H3
    Key: YYZUSRORWSJGET-UHFFFAOYSA-N
  • O=C(OCC)CCCCCCC
Properties
C10H20O2
Molar mass 172.268 g·mol−1
Density 0.86215 g/cm3 [1]
Melting point −48 °C (−54 °F; 225 K) [2]
Boiling point 208 °C (406 °F; 481 K) [2]
70.1 mg/L [3] [4]
Vapor pressure 0.2 mbar at 20 °C; 3.18 mbar at 60 °C [2]
Viscosity 1.411 mPa·s [1]
Hazards
Flash point 79 °C (174 °F; 352 K) [2]
325 °C (617 °F; 598 K) [2]
Explosive limits 0.7 - Vol.% [2]
Lethal dose or concentration (LD, LC):
25.96 g/kg (rat, oral) [3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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. It is used in the creation of synthetic fruity scents. [5]

Contents

Synthesis

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

CH3(CH2)6COOH + CH3CH2OH ⇌ CH3(CH2)6COOCH2CH3 + H2O

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. [6]

Ethyl octanoate also sees incidental use. It is found in some wines, where overall ester concentration and composition is considered important to the flavor and aroma profile. [7]

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. Ethyl octanoate is combustible.

Related Research Articles

<span class="mw-page-title-main">Ester</span> Compound derived from an acid

In chemistry, an ester is a compound derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. These compounds contain a distinctive functional group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.

<span class="mw-page-title-main">Isobutyric acid</span> Carboxylic acid with chemical formula (CH3)2CHCO2H

Isobutyric acid, also known as 2-methylpropanoic acid or isobutanoic acid, is a carboxylic acid with structural formula (CH3)2CHCOOH. It is an isomer of butyric acid. It is classified as a short-chain fatty acid. Deprotonation or esterification gives derivatives called isobutyrates.

<span class="mw-page-title-main">Ethyl oleate</span> Chemical compound

Ethyl oleate is a fatty acid ester formed by the condensation of oleic acid and ethanol. It is a colorless oil although degraded samples can appear yellow.

<span class="mw-page-title-main">Ethyl acetate</span> Organic compound (CH₃CO₂CH₂CH₃)

Ethyl acetate is the organic compound with the formula CH3CO2CH2CH3, simplified to C4H8O2. This flammable, colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and the decaffeination process of tea and coffee. Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent.

<span class="mw-page-title-main">Valeric acid</span> Carboxylic acid – CH3(CH2)3COOH

Valeric acid or pentanoic acid is a straight-chain alkyl carboxylic acid with the chemical formula CH3(CH2)3COOH. Like other low-molecular-weight carboxylic acids, it has an unpleasant odor. It is found in the perennial flowering plant Valeriana officinalis, from which it gets its name. Its primary use is in the synthesis of its esters. Salts and esters of valeric acid are known as valerates or pentanoates. Volatile esters of valeric acid tend to have pleasant odors and are used in perfumes and cosmetics. Several, including ethyl valerate and pentyl valerate are used as food additives because of their fruity flavors.

Dodecanol, or lauryl alcohol, is an organic compound produced industrially from palm kernel oil or coconut oil. It is a fatty alcohol. Sulfate esters of lauryl alcohol, especially sodium lauryl sulfate, are very widely used as surfactants. Sodium lauryl sulfate and the related dodecanol derivatives ammonium lauryl sulfate and sodium laureth sulfate are all used in shampoos. Dodecanol is tasteless, colorless, and has a floral odor.

<span class="mw-page-title-main">Caproic acid</span> Chemical compound

Caproic acid, also known as hexanoic acid, is the carboxylic acid derived from hexane with the chemical formula CH3(CH2)4COOH. It is a colorless oily liquid with an odor that is fatty, cheesy, waxy, and like that of goats or other barnyard animals. It is a fatty acid found naturally in various animal fats and oils, and is one of the chemicals that gives the decomposing fleshy seed coat of the ginkgo its characteristic unpleasant odor. It is also one of the components of vanilla and cheese. The primary use of caproic acid is in the manufacture of its esters for use as artificial flavors, and in the manufacture of hexyl derivatives, such as hexylphenols. Salts and esters of caproic acid are known as caproates or hexanoates. Several progestin medications are caproate esters, such as hydroxyprogesterone caproate and gestonorone caproate.

<span class="mw-page-title-main">Caprylic acid</span> Fatty acid (CH3−(CH2)6−COOH)

Caprylic acid, also known under the systematic name octanoic acid or C8 Acid, is a saturated fatty acid, medium-chain fatty acid (MCFA). It has the structural formula H3C−(CH2)6−COOH, and is a colorless oily liquid that is minimally soluble in water with a slightly unpleasant rancid-like smell and taste. Salts and esters of octanoic acid are known as octanoates or caprylates. The name of the related acyl group is octanoyl, capryloyl, or caprylyl. It is a common industrial chemical, which is produced by oxidation of the C8 aldehyde. Its compounds are found naturally in the milk of various mammals and as a minor constituent of coconut oil and palm kernel oil.

<span class="mw-page-title-main">Isovaleric acid</span> Carboxylic acid

Isovaleric acid, also known as 3-methylbutanoic acid or β-methylbutyric acid, is a branched-chain alkyl carboxylic acid with the chemical formula (CH3)2CHCH2CO2H. It is classified as a short-chain fatty acid. Like other low-molecular-weight carboxylic acids, it has an unpleasant odor. The compound occurs naturally and can be found in many foods, such as cheese, soy milk, and apple juice.

<span class="mw-page-title-main">Octyl acetate</span> Chemical compound

Octyl acetate, or octyl ethanoate, is an organic compound with the formula CH3(CH2)7O2CCH3. It is classified as an ester that is formed from 1-octanol (octyl alcohol) and acetic acid. It is found in oranges, grapefruits, and other citrus products.

<span class="mw-page-title-main">Isoamyl acetate</span> Chemical compound with banana odor

Isoamyl acetate, also known as isopentyl acetate, is an ester formed from isoamyl alcohol and acetic acid, with the molecular formula C7H14O2. It is a colorless liquid that is only slightly soluble in water, but very soluble in most organic solvents. Isoamyl acetate has a strong odor which is described as similar to both banana and pear. Pure isoamyl acetate, or mixtures of isoamyl acetate, amyl acetate, and other flavors in ethanol may be referred to as banana oil or pear oil.

Propyl hexanoate (C9H18O2), also known as propyl caproate, is an ester formed by the reaction of propanol with hexanoic acid. Although it is a completely different ester, propyl hexanoate shares the same chemical formula with methyl octanoate, ethyl heptanoate, butyl pentanoate, etc. because they all have the same total carbon chain length. The scent of this ester can be described as that of blackberries, pineapple, cheese or wine.

<span class="mw-page-title-main">1-Octanol</span> Chemical compound

1-Octanol, also known as octan-1-ol, is the organic compound with the molecular formula CH3(CH2)7OH. It is a fatty alcohol. Many other isomers are also known generically as octanols. 1-Octanol is manufactured for the synthesis of esters for use in perfumes and flavorings. It has a pungent odor. Esters of octanol, such as octyl acetate, occur as components of essential oils. It is used to evaluate the lipophilicity of pharmaceutical products.

<span class="mw-page-title-main">Ethane-1,1-dithiol</span> Chemical compound

Ethane-1,1-dithiol is an organosulfur compound with formula CH3CH(SH)2. It is a colourless smelly liquid that is added to or found in some foods. The compound is an example of a geminal dithiol.

Decenoic acid is any mono-carboxylic acid with an unbranched chain of ten carbons connected by eight single bonds and one double bond; that is, a chemical compound with formula HO(O=)C–(CH
2)
k–CH=CH–(CH
2)
7-k–H, where k is between 0 and 7 inclusive.

Dimethylaminoethyl acrylate or DMAEA is an unsaturated carboxylic acid ester having a tertiary amino group. It is a colorless to yellowish, water-miscible liquid with a pungent, amine-like odor. DMAEA is an important acrylic monomer that gives basic properties to copolymers.

Methyl hexanoate is the fatty acid methyl ester of hexanoic acid, a colourless liquid organic compound with the chemical formula CH3−(CH2)4−COO−CH3. It is found naturally in many foods and has a role as a plant metabolite. It can also be found in the cytoplasm of cells.

Pentenoic acid is any of five mono-carboxylic acids whose molecule has an unbranched chain of five carbons connected by three single bonds and one double bond. That is, any compound with one of the formulas HO(O=)C−CH=CH−CH2−CH3 (2-pentenoic), HO(O=)C−CH2−CH=CH−CH3 (3-pentenoic), or HO(O=)C−CH2−CH2−CH=CH2 (4-pentenoic). In the IUPAC-recommended nomenclature, these acids are called pent-2-enoic, pent-3-enoic, and pent-4-enoic, respectively. All these compounds have the empirical formula C
5H
8O
2.

References

  1. 1 2 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. 1 2 3 4 5 6 Record of Ethyl octanoate in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 10 August 2010.
  3. 1 2 Ethyl octanoate from PubChem, accessed 30 December 2023
  4. ↑ Mark, James E. (2007). Physical Properties of Polymer Handbook (2nd ed.). Springer. p. 294. ISBN   978-0387690025 . Retrieved 1 March 2013.
  5. ↑ 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.
  6. ↑ "Ethyl octanoate - Substance Information - ECHA". echa.europa.eu. Retrieved 2021-07-12.
  7. ↑ 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"
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