Ethyl acetate

Ball-and-stick Stick Space-filling

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14 atoms, 13 bonds.

IUPAC name: ethyl acetate
Molar mass: 88.106(12) g/mol
Atoms: 14
Polarity: polar
SMILES: CCOC(=O)C
InChIKey: XEKOWRVHYACXOJ-UHFFFAOYSA-N
PubChem CID: 8857

Made of

Structural formula of ethyl acetate. Each unlabelled corner is a carbon atom, and the two hydrogens on carbon are not drawn. It shows which atoms are joined to which, not the shape. The model above shows the shape.

A ripe pineapple, a glass of wine and a bottle of nail polish remover all carry the same volatile liquid. The Hazardous Substances Data Bank (HSDB), quoted on PubChem, lists ethyl acetate among the scented constituents of fruits and flowers and describes its smell as ether-like, recalling pineapple. ChEBI, a database of small biological molecules, classes it as the ester formed between acetic acid and ethanol. It calls the compound both an ethyl ester and an acetate ester, one name for each half. Built from carbon, hydrogen and oxygen, it has a molar mass of 88.11 g/mol.

NIOSH, the US National Institute for Occupational Safety and Health, lists other names for it, among them acetic ether and ethyl ethanoate. The liquid floats on water, while its vapour is heavier than air. Moisture breaks it down slowly, and the liquid then turns acidic.

Structure and bonding

The readout counts 14 atoms and 13 bonds, with no ring. With Labels on, four C, two O and eight H symbols appear. Near one end a carbon holds one oxygen by a double bond and a second by a single bond, which leads on to CH₂ and then CH₃. With no one central atom, the molecule takes no single shape word.

PubChem’s computed 3D model sets the angles around the C=O carbon at 126.4°, 124.0° and 109.5°, a total of 359.9°. Turned edge-on, that carbon and its three neighbours lie flat. In Chem1’s account, three regions of electron density repel least at 120° apart. The chain bends at the linking oxygen, 115.5° in the model.

Stick view leaves the C=O as the one doubled line. Chem1 treats a double bond as a σ bond on the line between the atoms, plus a π bond, a cloud above and below it. The model draws it only as a second line. Space-filling wraps the chain in hydrogens, all eight on carbon; Chem1 ties hydrogen bonding to hydrogen held by a more electronegative atom. ChEBI classes ethyl acetate as a polar solvent. The neutral molecule drawn is the one in the bottle.

Where it turns up

Pineapples are only one natural source. HSDB also finds ethyl acetate in wines and brandy, and ChEBI lists it as a metabolite of the yeast Saccharomyces cerevisiae. LOTUS, a natural-products database, reports it in Angelica gigas and Lucensosergia lucens, among other organisms.

At home it sits on the bathroom shelf in nail polish remover. Ethyl acetate is an ingredient of 96 consumer products in the Consumer Product Information Database, among them car care, hobby and craft, home maintenance and personal care products. Perfumers know it too: IFRA, the fragrance industry body, lists it among fragrance ingredients.

Food and drink use it too. HSDB records it as an aroma enhancer in grape beverages. JECFA, the food-additive expert committee of the UN Food and Agriculture Organization (FAO) and the World Health Organization (WHO), lists it as a flavouring agent and a carrier solvent.

Why it matters

Ethyl acetate earns its living as a solvent. HSDB names nitrocellulose, varnishes and lacquers among what it dissolves, with shellac, vinyl resins and printing inks alongside. HSDB’s demand figures run from 325 million pounds in 1996 to 335 million in 1997 and an estimated 400 million in 2001. Coatings took 60 per cent of that, process solvents for drugs and synthesis 15, inks 15, and adhesives, cosmetics and other uses the last 10.

Industry reaches the same ester by several routes, according to HSDB. Acetic acid and ethanol can combine directly. Commercial plants also run the Tischenko condensation of acetaldehyde over an aluminium ethoxide catalyst. Ethyl acetate also comes out as a co-product when butane is oxidised to acetic acid.

Reports to the US Environmental Protection Agency (EPA) put national volume for 2023 between 100 and 250 million pounds. The agency’s Safer Choice programme gives it a green half-circle as a solvent ingredient, expected to be of low concern.

Properties

Properties of ethyl acetate Molar mass summed from IUPAC/CIAAW 2024 standard atomic weights; formula, atom and bond counts and PubChem's molecular weight from PubChem CID 8857.
Property	Value	Unit	Source
Molecular formula (Hill order)	C₄H₈O₂
Molar mass	88.106(12) g/mol	g/mol	IUPAC/CIAAW 2024
Carbon atoms	4
Hydrogen atoms	8
Oxygen atoms	2
Bonds	13
Single bonds	12
Double bonds	1
PubChem molecular weight	88.11 g/mol	g/mol	PubChem

Safety

Ethyl acetate carries the Globally Harmonized System (GHS) signal word Danger. Under the EU classification and European Chemicals Agency (ECHA) notifications, its liquid and vapour are highly flammable, seriously irritate the eyes and can bring on drowsiness or dizziness. The dense vapour can spread along the ground to a distant ignition source, and the liquid strips oils from skin. For people who handle the solvent at work, the PubChem safety summary and the NIOSH card for ethyl acetate give the full detail.

Questions

What does the ethyl acetate molecule look like in 3D?

The model is a short chain of 14 atoms and 13 bonds, with no ring: four carbons and one oxygen form the chain, a second oxygen hangs off it, and eight hydrogens coat it. Only the C=O near one end is double. The carbon carrying it lies flat with its three neighbours, while the two end carbons spread their bonds at angles near 109°.

Why does nail polish remover smell like fruit?

The Hazardous Substances Data Bank (HSDB) describes ethyl acetate as a typical ingredient of nail polish remover, and likens its smell to ether and pineapple. The same compound occurs naturally among the volatile substances of fruits and flowers, pineapples included, and in wine and brandy. NIOSH calls the odour of the pure liquid fruity.

Does ethyl acetate dissolve in water?

Some of it does. HSDB gives 64 g and, in another entry, 80 g per litre of water at 25 °C; the International Chemical Safety Cards give 8.7 g per 100 mL at 20 °C. More dissolves in cold water than in warm, according to HSDB. Moisture slowly decomposes it into an acidic mixture. With water it forms an azeotrope, a mixture boiling at a fixed 70.4 °C.

What happens to ethyl acetate in the body?

Esterases, abundant unselective enzymes that split esters, were expected to turn it into ethyl alcohol, and HSDB reports that rat blood did so. In rats the breakdown to acetic acid and ethanol was rapid. Part of the compound leaves in exhaled air and urine and the rest is metabolised, HSDB records. Breathing the vapour is the main route by which its toxic effects arise.

Made of the same elements

C₃H₇COOH Butyric acid 14 atoms, 13 bonds.
C₄H₈O Butanone 13 atoms, 12 bonds.
C₃H₈O₂ Propylene glycol 13 atoms, 12 single bonds.
C₃H₇OH 1-Propanol 12 atoms, 11 single bonds.
C₃H₈O₃ Glycerol 14 atoms, 13 single bonds.
C₃H₈O Isopropyl alcohol 12 atoms, 11 single bonds.
C₄H₉OH 1-Butanol 15 atoms, 14 single bonds.
C₂H₅OC₂H₅ Diethyl ether 15 atoms, 14 single bonds.

All 51 compounds made of carbon, hydrogen and oxygen

C₂H₅COOH Propionic acid 11 atoms, 10 bonds.
C₃H₆O Acetone 10 atoms, 9 bonds.
C₂H₆O₂ Ethylene glycol 10 atoms, 9 single bonds.
C₃H₆O₃ Lactic acid 12 atoms, 11 bonds.
C₆H₅COOH Benzoic acid 15 atoms, 15 bonds.
CH₃OCH₃ Dimethyl ether 9 atoms, 8 single bonds.
C₂H₅OH Ethanol 9 atoms, 8 single bonds.
C₄H₆O₅ Malic acid 15 atoms, 14 bonds.
C₈H₈O₃ Methyl salicylate 19 atoms, 19 bonds.
C₆H₅OH Phenol 13 atoms, 13 bonds.
C₈H₈O₃ Vanillin 19 atoms, 19 bonds.
CH₃COOH Acetic acid 8 atoms, 7 bonds.
C₆H₈O₆ Ascorbic acid 20 atoms, 20 bonds.
C₆H₅CHO Benzaldehyde 14 atoms, 14 bonds.
C₇H₆O₃ Salicylic acid 16 atoms, 16 bonds.
C₄H₆O₆ Tartaric acid 16 atoms, 15 bonds.
CH₃CHO Acetaldehyde 7 atoms, 6 bonds.
C₉H₈O₄ Aspirin 21 atoms, 21 bonds.
C₆H₈O₇ Citric acid 21 atoms, 20 bonds.
C₂H₄O Ethylene oxide 7 atoms, 7 single bonds.
C₂H₄O₃ Glycolic acid 9 atoms, 8 bonds.
CH₃OH Methanol 6 atoms, 5 single bonds.
HCOOH Formic acid 5 atoms, 4 bonds.
H₂CO₃ Carbonic acid 6 atoms, 5 bonds.
CH₂O Formaldehyde 4 atoms, 3 bonds.
C₆H₁₂O₆ Fructose 24 atoms, 24 single bonds.
C₆H₁₂O₆ Glucose 24 atoms, 24 single bonds.
H₂C₂O₄ Oxalic acid 8 atoms, 7 bonds.
C₁₄H₁₄O₃ Naproxen 31 atoms, 32 bonds.
C₁₅H₁₆O₂ Bisphenol A 33 atoms, 34 bonds.
C₁₃H₁₈O₂ Ibuprofen 33 atoms, 33 bonds.
C₁₀H₂₀O Menthol 31 atoms, 31 single bonds.
C₂₀H₁₄O₄ Phenolphthalein 38 atoms, 41 bonds.
C₁₈H₂₄O₂ Estradiol 44 atoms, 47 bonds.
C₁₂H₂₂O₁₁ Lactose 45 atoms, 46 single bonds.
C₁₂H₂₂O₁₁ Sucrose 45 atoms, 46 single bonds.
C₁₉H₂₈O₂ Testosterone 49 atoms, 52 bonds.
C₁₆H₃₂O₂ Palmitic acid 50 atoms, 49 bonds.
C₂₁H₃₀O₂ Progesterone 53 atoms, 56 bonds.
C₁₈H₃₄O₂ Oleic acid 54 atoms, 53 bonds.
C₂₁H₃₀O₅ Cortisol 56 atoms, 59 bonds.
C₂₇H₄₄O Cholecalciferol 72 atoms, 74 bonds.
C₂₇H₄₆O Cholesterol 74 atoms, 77 bonds.