Acetate

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For other uses, see Acetate (disambiguation).

Acetate

Names

IUPAC name

Acetate

Systematic IUPAC name

Ethanoate

Identifiers

CAS Number • 71-50-1

3D model (JSmol) • Interactive image

ChemSpider • 170

PubChem CID • 175

InChI[show]

SMILES[show]
 Properties

Chemical formula C

2H

3O−

Conjugate acid Acetic acid

Except where otherwise noted, data are given for materials in

their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

An acetate /ˈæsɪteɪt/ is a salt formed by the combination of acetic acid with

an alkaline, earthy, metallic or nonmetallic and other base. "Acetate" also describes the conjugate
base or ion (specifically, the negatively charged ion called an anion) typically found in aqueous
solution and written with the chemical formula C
2H

3O
−

2. The neutral molecules formed by the combination of the acetate ion and a positive ion (called

a cation) are also commonly called "acetates" (hence, acetate of lead, acetate of aluminum, etc.).
The simplest of these is hydrogen acetate (called acetic acid) with corresponding salts, esters, and
the polyatomic anion CH
3CO
−

2, or CH

3COO
−

.
Most of the approximately 5 billion kilograms of acetic acid produced annually in industry are used in
the production of acetates, which usually take the form of polymers. In nature, acetate is the most
common building block for biosynthesis. For example, the fatty acids are produced by connecting the
two carbon atoms from acetate to a growing fatty acid.[1]

Contents

• 1Nomenclature and common formula

• 2Salts
• 3Esters
• 4Acetate in biology
• 5Fermentation acetyl CoA to acetate
• 6Fermentation of acetate
• 7Structures
• 8See also
• 9References
• 10External links

Nomenclature and common formula[edit]

When part of a salt, the formula of the acetate ion is written as CH
3CO
−

2, C

2H

3O
−

2, or CH

3COO
−

. Chemists often represent acetate as OAc− or, less commonly, AcO−. Thus, HOAc is the symbol for
acetic acid, NaOAc for sodium acetate, and EtOAc for ethyl acetate[2] (as Ac is common symbol
for acetyl group CH3CO[3][4]).The pseudoelement symbol "Ac" is also sometimes encountered in
chemical formulas as indicating the entire acetate ion (CH3CO2−).[citation needed] It is not to be confused
with the symbol of actinium, the first element of the actinide series; context guides disambiguation.
For example, the formula for sodium acetate might be abbreviated as "NaOAc", rather than
"NaC2H3O2". Care should also be taken to avoid confusion with peracetic acid when using the OAc
abbreviation; for clarity and to avoid errors when translated, HOAc should be avoided in literature
mentioning both compounds.
Although its systematic name is ethanoate (/ɪˈθænoʊ.eɪt/), the common acetate remains
the preferred IUPAC name.[5]

Salts[edit]

acetate anion
The acetate anion, [CH3COO]−,(or [C2H3O2]−) is one of the carboxylate family. It is the conjugate
base of acetic acid. Above a pH of 5.5, acetic acid converts to acetate:[2]
CH3COOH ⇌ CH3COO− + H+
Many acetate salts are ionic, indicated by their tendency to dissolve well in water. A commonly
encountered acetate in the home is sodium acetate, a white solid that can be prepared by
combining vinegar and sodium bicarbonate ("bicarbonate of soda"):
CH3COOH + NaHCO3 → CH3COO−Na+ + H2O + CO2
Transition metals can be complexed by acetate. Examples of acetate complexes
include chromium(II) acetate and basic zinc acetate.
Commercially important acetate salts are aluminium acetate, used in dyeing, ammonium
acetate, a precursor to acetamide, and potassium acetate, used as a diuretic. All three salts
are colourless and highly soluble in water.[6]

Esters[edit]
 acetate ester
Acetate esters have the general formula CH3CO2R, where R is an organyl group. The esters
are the dominant forms of acetate in the marketplace. Unlike the acetate salts, acetate
esters are often liquids, lipophilic, and sometimes volatile. They are popular because they
have inoffensive, often sweet odors, they are inexpensive, and they are usually of low
toxicity.
Almost half of acetic acid production is consumed in the production of vinyl acetate,
precursor to polyvinyl alcohol, which is a component of many paints. The second largest use
of acetic acid is consumed in the production of cellulose acetate. In fact, "acetate" is jargon
for cellulose acetate, which is used in the production of fibres or diverse products, e.g.
the acetate discs used in audio record production. Cellulose acetate can be found in many
household products. Many industrial solvents are acetates, including methyl acetate, ethyl
acetate, isopropyl acetate, ethylhexyl acetate. Butyl acetate is a fragrance used in food
products.[6]