Butyl Decanoate (Butyle Caprate)
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3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C14H28O2 | |
| Molar mass | 228.376 g·mol−1 |
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Related compounds
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Ethyl caprate |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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Butyl decanoate, also known as butyl caprate, is an organic compound belonging to the ester class of chemicals. It is the ester formed by the reaction of butan-1-ol (n-butanol) and decanoic acid (capric acid). The compound is a colorless to pale yellow liquid with a pleasant fruity, woody, waxy odor and is used primarily in flavorings, fragrances, whisky, cosmetics, and specialty industrial formulations.
| Property | |
|---|---|
| IUPAC name | Butyl decanoate |
| Other names | Butyl caprate; n-Butyl decanoate |
| Chemical formula | C₁₄H₂₈O₂ |
| Molar mass | 228.37 g/mol |
| Chemical class | Carboxylic acid ester |
| Appearance | Colorless to pale yellow liquid |
| Odor | Fruity, sweet, woody, waxy |
| Solubility in water | practically insoluble |
| Solubility in organic solvents | Soluble in ethanol, diethyl ether,
and many nonpolar organic solvents |
| Boiling point | 280-290°c |
Structure
Butyl decanoate consists of a decanoate (caprate) group esterified with a straight-chain butyl group. Like other fatty acid esters, it contains a polar ester functional group attached to two hydrophobic hydrocarbon chains, giving it amphiphilic characteristics while remaining predominantly lipophilic.
Condensed structural formula:
CH₃(CH₂)₈COO(CH₂)₃CH₃
Production
Butyl decanoate is commonly synthesised through Fischer esterification, in which decanoic acid reacts with n-butanol in the presence of an acid catalyst, typically sulfuric acid.
Reaction:
CH₃(CH₂)₈COOH + CH₃(CH₂)₃OH → CH₃(CH₂)₈COO(CH₂)₃CH₃ + H₂O
The reaction equilibrium is shifted toward ester formation by removing the water produced or by using an excess of one of the reactants.
Properties
Butyl decanoate exhibits the characteristic properties of medium-chain fatty acid esters. It has low volatility relative to short-chain esters, a relatively high boiling point, and low water solubility. The compound is chemically stable under normal storage conditions but may undergo hydrolysis in strongly acidic or alkaline environments, producing decanoic acid and butanol.
Uses
Flavoring agent
Butyl decanoate is used in flavour formulations to provide fruity, creamy, woody, and fatty notes in food products where permitted by regulatory authorities. It also gives whisky its scent and taste.
Fragrance ingredient
The compound is incorporated into perfumes, personal care products, soaps, and air fresheners because of its pleasant, long-lasting odor profile.
Cosmetics
In cosmetic formulations, butyl decanoate functions as an emollient and fragrance component, contributing to product spreadability and skin feel.
Industrial applications
The ester is employed as a speciality solvent, lubricant component, and chemical intermediate in the manufacture of various formulated products.
Safety
Butyl decanoate is generally regarded as having low acute toxicity. Contact with the liquid may cause mild irritation to the skin or eyes. Standard laboratory and industrial safety practices, including the use of appropriate personal protective equipment and adequate ventilation, are recommended during handling. It should be stored in tightly sealed containers away from strong oxidizing agents.
See also
References
- PubChem. Butyl Decanoate. National Center for Biotechnology Information.
- NIST Chemistry WebBook. Thermophysical and Spectroscopic Data for Organic Compounds.
- OECD eChemPortal. Chemical Safety Information.
- European Chemicals Agency (ECHA). Registration Dossier for Butyl Decanoate.
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