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An acetate is a
salt Salt is a mineral In geology and mineralogy, a mineral or mineral species is, broadly speaking, a solid chemical compound with a fairly well-defined chemical composition and a specific crystal structure that occurs naturally in pure fo ...
formed by the combination of
acetic acid Acetic acid , systematically named ethanoic acid , is a colourless liquid organic compound with the chemical formula CH3COOH (also written as CH3CO2H, C2H4O2, or HC2H3O2). Vinegar is no less than 4% acetic acid by volume, making acetic acid ...

acetic acid
with a base (e.g.
alkaline In chemistry, an alkali (; from ar, القلوي ''al-qaly'' "ashes of the saltwort") is a base (chemistry), basic, ionic compound, ionic salt (chemistry), salt of an alkali metal or an alkaline earth metal. An alkali can also be defined as ...
, earthy,
metallic Metallic may be a reference to: *Metal A metal (from Ancient Greek, Greek μέταλλον ''métallon'', "mine, quarry, metal") is a material that, when freshly prepared, polished, or fractured, shows a lustrous appearance, and conducts El ...
,
nonmetal In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, properties, behavior and the changes they undergo duri ...
lic or radical
base Base or BASE may refer to: Brands and enterprises *Base (mobile telephony provider) Base (stylized as BASE) is the third largest of Belgium Belgium ( nl, België ; french: Belgique ; german: Belgien ), officially the Kingdom of Belgium, ...
). "Acetate" also describes the
conjugate base A conjugate acid, within the Brønsted–Lowry acid–base theory The Brønsted–Lowry theory (also called proton theory of acids and bases) is an acid–base reaction theory which was proposed independently by Johannes Nicolaus Brønsted ...
or
ion An ion () is an atom An atom is the smallest unit of ordinary matter In classical physics and general chemistry, matter is any substance that has mass and takes up space by having volume. All everyday objects that can be touched are ...
(specifically, the negatively charged ion called an
anion An ion () is an atom An atom is the smallest unit of ordinary matter In classical physics and general chemistry, matter is any substance that has mass and takes up space by having volume. All everyday objects that can be touched are ...
) typically found in
aqueous solution An aqueous solution is a solution Solution may refer to: * Solution (chemistry) Image:SaltInWaterSolutionLiquid.jpg, upMaking a saline water solution by dissolving Salt, table salt (sodium chloride, NaCl) in water. The salt is the solute an ...
and written with the chemical formula . The neutral molecules formed by the combination of the acetate ion and a ''positive'' ion (called a
cation An ion () is an atom An atom is the smallest unit of ordinary matter In classical physics and general chemistry, matter is any substance that has mass and takes up space by having volume. All everyday objects that can be touched are u ...
) are also commonly called "acetates" (hence, ''acetate of lead'', ''acetate of aluminum'', etc.). The simplest of these is hydrogen acetate (called
acetic acid Acetic acid , systematically named ethanoic acid , is a colourless liquid organic compound with the chemical formula CH3COOH (also written as CH3CO2H, C2H4O2, or HC2H3O2). Vinegar is no less than 4% acetic acid by volume, making acetic acid ...

acetic acid
) with corresponding salts,
ester An ester is a chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entity, molecular entities) composed of atoms from more than one chemical element, element held together by chemic ...

ester
s, and the polyatomic anion , or . 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 A polymer (; Greek ''wikt:poly-, poly-'', "many" + ''wikt:-mer, -mer'', "part") is a Chemical substance, substance or material consisting of very large molecules, or macromolecules, composed of many Repeat unit, repeating subunits. Due to thei ...

polymers
. In nature, acetate is the most common building block for
biosynthesis Biosynthesis is a multi-step, enzyme Enzymes () are proteins that act as biological catalysts (biocatalysts). Catalysts accelerate chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and ...

biosynthesis
. For example, the
fatty acid In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, properties, behavior and the changes they undergo during ...
s are produced by connecting the two carbon atoms from acetate to a growing fatty acid.


Nomenclature and common formula

When part of a
salt Salt is a mineral In geology and mineralogy, a mineral or mineral species is, broadly speaking, a solid chemical compound with a fairly well-defined chemical composition and a specific crystal structure that occurs naturally in pure fo ...
, the formula of the acetate ion is written as , , or . Chemists often represent acetate as OAc or, less commonly, AcO. Thus, HOAc is the symbol for acetic acid, NaOAc for
sodium acetate Sodium acetate, NaCH3COO, also abbreviated Sodium, NaOxygen, OAcetyl, Ac, is the sodium Salt (chemistry), salt of acetic acid. This colorless deliquescent salt has a wide range of uses. Applications Biotechnological Sodium acetate is used as t ...
, and EtOAc for
ethyl acetate Ethyl acetate ( systematically ethyl ethanoate, commonly abbreviated EtOAc, ETAC or EA) is the organic compound In , organic compounds are generally any s that contain - . Due to carbon's ability to (form chains with other carbon s), million ...

ethyl acetate
Zumdahl, S. S. “Chemistry” Heath, 1986: Lexington, MA. . (as Ac is common symbol for
acetyl In organic chemistry Organic chemistry is a branch of that studies the structure, properties and reactions of s, which contain in .Clayden, J.; Greeves, N. and Warren, S. (2012) ''Organic Chemistry''. Oxford University Press. pp. 1–15. . ...

acetyl
group CH3CO).The pseudoelement symbol "Ac" is also sometimes encountered in chemical formulas as indicating the entire acetate ion (CH3CO2). It is not to be confused with the symbol of
actinium Actinium is a chemical element In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, properties, behav ...

actinium
, the first element of the
actinide The actinoid (IUPAC nomenclature The International Union of Pure and Applied Chemistry The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations that represents chemis ...
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 Peracetic acid (also known as peroxyacetic acid, or PAA), is an organic compound In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: thei ...

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 A systematic name is a name given in a systematic way to one unique group, organism, object or chemical substance A chemical substance is a form of matter In classical physics and general chemistry, matter is any substance that has mass and ...
is ''ethanoate'' (), the common ''acetate'' remains the
preferred IUPAC name In chemical nomenclatureA chemical nomenclature is a set of rules to generate systematic names for chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entity, molecular entities) c ...
.


Salts

The acetate
anion An ion () is an atom An atom is the smallest unit of ordinary matter In classical physics and general chemistry, matter is any substance that has mass and takes up space by having volume. All everyday objects that can be touched are ...
, H3COOsup>−,(or 2H3O2sup>−) is one of the
carboxylate A carboxylate is the conjugate base A conjugate acid, within the Brønsted–Lowry acid–base theory The Brønsted–Lowry theory (also called proton theory of acids and bases) is an acid–base reaction An acid–base reaction is a ...

carboxylate
family. It is the
conjugate base A conjugate acid, within the Brønsted–Lowry acid–base theory The Brønsted–Lowry theory (also called proton theory of acids and bases) is an acid–base reaction theory which was proposed independently by Johannes Nicolaus Brønsted ...
of
acetic acid Acetic acid , systematically named ethanoic acid , is a colourless liquid organic compound with the chemical formula CH3COOH (also written as CH3CO2H, C2H4O2, or HC2H3O2). Vinegar is no less than 4% acetic acid by volume, making acetic acid ...

acetic acid
. Above a pH of 5.5, acetic acid converts to acetate: :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 Sodium acetate, NaCH3COO, also abbreviated Sodium, NaOxygen, OAcetyl, Ac, is the sodium Salt (chemistry), salt of acetic acid. This colorless deliquescent salt has a wide range of uses. Applications Biotechnological Sodium acetate is used as t ...
, a white solid that can be prepared by combining vinegar and
sodium bicarbonate Sodium bicarbonate ( IUPAC name: sodium hydrogen carbonate), commonly known as baking soda or bicarbonate of soda, is a chemical compound with the formula NaHCO3. It is a salt composed of a sodium cation (Na+) and a bicarbonate anion ( HCO3 ...

sodium bicarbonate
("bicarbonate of soda"): :CH3COOH + NaHCO3 → CH3COONa+ + H2O + CO2
Transition metal In chemistry, the term transition metal (or transition element) has three possible definitions: * The IUPAC The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations tha ...
s can be complexed by acetate. Examples of acetate complexes include
chromium(II) acetate Chromium(II) acetate hydrate, also known as chromous acetate, is the coordination compound A coordination complex consists of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of ...

chromium(II) acetate
and basic zinc acetate. Commercially important acetate salts are
aluminium acetate Aluminium acetate or aluminium ethanoate (also "aluminum ~"), sometimes abbreviated AlAc in geochemistry, can refer to a number of different salts of aluminum with acetic acid. In the solid state, three salts exist under this name: basic aluminium m ...
, used in
dyeing Dyeing is the application of dyes A dye is a color Color (American English American English (AmE, AE, AmEng, USEng, en-US), sometimes called United States English or U.S. English, is the set of varieties of the English la ...

dyeing
,
ammonium acetate Ammonium acetate, also known as spirit of Mindererus in aqueous An aqueous solution is a solution Solution may refer to: * Solution (chemistry) Image:SaltInWaterSolutionLiquid.jpg, upMaking a saline water solution by dissolving Salt, tabl ...
, a precursor to
acetamide Acetamide (systematic name: ethanamide) is an organic compound In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, str ...

acetamide
, and
potassium acetate Potassium acetate (CH3COOK) is the potassium Potassium is a chemical element In chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and ...

potassium acetate
, used as a
diuretic A diuretic () is any substance that promotes diuresis Diuresis () is increased urination Urination is the release of urine from the urinary bladder through the urethra to the outside of the body. It is the urinary system's form of excreti ...
. All three salts are colourless and highly soluble in water.Hosea Cheung, Robin S. Tanke, G. Paul Torrence "Acetic acid" in ''Ullmann's Encyclopedia of Industrial Chemistry'' Weinheim, Germany: Wiley-VCH, 2005.


Esters

Acetate esters have the general formula CH3CO2R, where R is an
organyl group In organic Organic may refer to: * Organic, of or relating to an organism, a living entity * Organic, of or relating to an anatomical organ (anatomy), organ Chemistry * Organic matter, matter that has come from a once-living organism, is capable ...
. 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 Vinyl acetate is an organic compound with the Chemical formula, formula CH3CO2CH=CH2. This colorless liquid is the precursor to polyvinyl acetate and ethylene-vinyl acetate, ethene-vinyl acetate copolymers, important industrial polymers. Producti ...

vinyl acetate
, precursor to
polyvinyl alcohol Poly(vinyl alcohol) (PVOH, PVA, or PVAl) is a water Water (chemical formula H2O) is an Inorganic compound, inorganic, transparent, tasteless, odorless, and Color of water, nearly colorless chemical substance, which is the main constituen ...

polyvinyl alcohol
, which is a component of many
paint Paint is any pigmented liquid A liquid is a nearly incompressible In fluid mechanics Fluid mechanics is the branch of physics concerned with the mechanics Mechanics (Ancient Greek, Greek: ) is the area of physics concerned wi ...

paint
s. The second largest use of acetic acid is consumed in the production of
cellulose acetate Cellulose acetate refers to any acetate An acetate is a salt formed by the combination of acetic acid with a base (e.g. alkaline, earthy, metallic, nonmetal image:Simple Periodic Table Chart-en.svg, upright=1.75, Nonmetals (and metalloids ...

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 disc Acetates of 12", 10", 7" sizes An acetate disc (also known as a ''lacquer'', ''test acetate'', '' dubplate'', or '' transcription disc'') is a type of gramophone record A phonograph disc record (also known as a gramophone disc record, especiall ...
s used in audio record production. Cellulose acetate can be found in many household products. Many industrial
solvent A solvent (from the Latin Latin (, or , ) is a classical language belonging to the Italic languages, Italic branch of the Indo-European languages. Latin was originally spoken in the area around Rome, known as Latium. Through the power of the ...

solvent
s are acetates, including
methyl acetate Methyl acetate, also known as MeOAc, acetic acid methyl ester or methyl ethanoate, is a carboxylate ester An ester is a chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entit ...

methyl acetate
, ethyl acetate,
isopropyl acetate Isopropyl acetate is an ester An ester is a chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entity, molecular entities) composed of atoms from more than one chemical element, ...

isopropyl acetate
, ethylhexyl acetate. Butyl acetate is a fragrance used in food products.


Acetate in biology

Acetate is a common anion in biology. It is mainly utilized by organisms in the form of
acetyl coenzyme A Acetyl-CoA (acetyl coenzyme A) is a molecule that participates in many biochemical reaction Biochemistry or biological chemistry, is the study of chemical processes within and relating to living organism In biology, an organism (from A ...

acetyl coenzyme A
.
Intraperitoneal injection Intraperitoneal injection or IP injection is the injection of a substance into the peritoneum The peritoneum is the serous membrane In anatomy Anatomy (Greek ''anatomē'', 'dissection') is the branch of biology Biology is the natu ...
of sodium acetate (20 or 60 mg per kg body mass) was found to induce headache in sensitized rats, and it has been proposed that acetate resulting from oxidation of
ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic Organic may refer to: * Organic, of or relating to an organism, a living entity * Organic, of or relating to an anatomical organ (anatomy), ...

ethanol
is a major factor in causing
hangover A hangover is the experience of various unpleasant physiological Physiology (; ) is the scientific Science () is a systematic enterprise that builds and organizes knowledge Knowledge is a familiarity or awareness, of someone or som ...
s. Increased serum acetate levels lead to accumulation of
adenosine Adenosine is an organic compound , CH4; is among the simplest organic compounds. In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen chemical bond, bonds. Due to carbon's ability to Catenation, cate ...

adenosine
in many tissues including the brain, and administration of the
adenosine Adenosine is an organic compound , CH4; is among the simplest organic compounds. In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen chemical bond, bonds. Due to carbon's ability to Catenation, cate ...

adenosine
receptor antagonist
caffeine Caffeine is a central nervous system The central nervous system (CNS) is the part of the nervous system In biology Biology is the natural science that studies life and living organisms, including their anatomy, physical structu ...

caffeine
to rats after ethanol was found to decrease
nociceptive Nociception (also nocioception, from Latin ''nocere'' 'to harm or hurt') is the Somatosensory system, sensory nervous system's process of encoding noxious stimuli. It deals with a series of events and processes required for an organism to receive a ...
behavior.


Fermentation acetyl CoA to acetate

Pyruvate is converted into by the enzyme
pyruvate dehydrogenase Pyruvic acid (CH3COCOOH) is the simplest of the alpha-keto acids, with a carboxylic acid and a ketone functional group. Pyruvate, the conjugate acid, conjugate base, CH3COCOO−, is an intermediate in several metabolic pathways throughout the ce ...

pyruvate dehydrogenase
. This acetyl-CoA is then converted into acetate in ''E. coli'', whilst producing ATP by
substrate-level phosphorylation Substrate-level phosphorylation is a metabolism reaction that results in the production of ATP ATP may refer to: Companies and organizations * Association of Tennis Professionals * American Technical Publishers * ', a Danish pension * Armeni ...
. Acetate formation requires two enzymes: phosphate acetyltransferase and acetate kinase.       acetyl-CoA + phosphate → acetyl-phosphate + CoA       acetyl-phosphate + ADP → acetate + ATP


Fermentation of acetate

Acetic acid can also undergo a
dismutation In chemistry, disproportionation, sometimes called dismutation, is a redox reaction in which one compound of intermediate oxidation state converts to two compounds, one of higher and one of lower oxidation states. More generally, the term can be ap ...
reaction to produce
methane Methane (, ) is a chemical compound with the chemical formula A chemical formula is a way of presenting information about the chemical proportions of s that constitute a particular or molecule, using symbols, numbers, and sometimes a ...
and
carbon dioxide Carbon dioxide (chemical formula A chemical formula is a way of presenting information about the chemical proportions of s that constitute a particular or molecule, using symbols, numbers, and sometimes also other symbols, such as pare ...

carbon dioxide
: :CH3COO + H+ → CH4 + CO2 Δ''G''° = −36 kJ/mol This
disproportionation In chemistry Chemistry is the science, scientific study of the properties and behavior of matter. It is a natural science that covers the Chemical element, elements that make up matter to the chemical compound, compounds composed of atoms, mo ...

disproportionation
reaction is catalysed by
methanogen Methanogens are microorganisms that produce methane Methane (, ) is a chemical compound with the chemical formula A chemical formula is a way of presenting information about the chemical proportions of s that constitute a particular ...
archaea Archaea ( ; singular archaeon ) constitute a domain Domain may refer to: Mathematics *Domain of a function, the set of input values for which the (total) function is defined **Domain of definition of a partial function **Natural domain of a pa ...

archaea
in their fermentative metabolism. One electron is transferred from the
carbonyl In organic chemistry Organic chemistry is a branch of chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: their composition, structure, pro ...

carbonyl
function ( e donor) of the
carboxylic A carboxylic acid is an organic acid that contains a carboxyl group (C(=O)OH) attached to an R-group. The general formula of a carboxylic acid is R−COOH or R−CO2H, with substituent, R referring to the alkyl, alkenyl, aryl, or other group. ...
group to the
methyl A methyl group is an alkyl In organic chemistry Organic chemistry is a branch of chemistry Chemistry is the study of the properties and behavior of . It is a that covers the that make up matter to the composed of s, s and s: t ...

methyl
group ( e acceptor) of acetic acid to respectively produce CO2 and methane gas.


Structures

Image:Acetate-anion-3D-vdW.png,
Space-filling model Space filling or spacefilling may refer to: *Space-filling curve 400px, Three iterations of the Peano curve construction, whose limit is a space-filling curve. In mathematical analysis, a space-filling curve is a curve In mathematics, a curve ...
of the acetate anion
Image:Acetate-anion-resonance-hybrid-2D-skeletal.png,
resonance hybrid In chemistry, resonance, also called mesomerism, is a way of describing bonding in certain molecules or ions by the combination of several contributing structures (or ''forms'', also variously known as ''resonance structures'' or ''canonical str ...
of the acetate anion
Image:Acetate-resonance-2D-skeletal.png,
canonical forms of the acetate anion


See also

*
Acetylation Acetylation (or in IUPAC nomenclature The International Union of Pure and Applied Chemistry The International Union of Pure and Applied Chemistry (IUPAC ) is an international federation of National Adhering Organizations that represents che ...

Acetylation
*
Cellulose acetate Cellulose acetate refers to any acetate An acetate is a salt formed by the combination of acetic acid with a base (e.g. alkaline, earthy, metallic, nonmetal image:Simple Periodic Table Chart-en.svg, upright=1.75, Nonmetals (and metalloids ...

Cellulose acetate
*
Copper(II) acetate Copper(II) acetate, also referred to as cupric acetate, is the chemical compound with the chemical formula, formula Copper, Cu(OAc)2 where AcO− is acetate (). The hydrated derivative, Cu2(OAc)4(H2O)2, which contains one molecule of water for eac ...

Copper(II) acetate
*
Fermentation (biochemistry) Fermentation is a metabolic Metabolism (, from el, μεταβολή ''metabolē'', "change") is the set of life Life is a characteristic that distinguishes physical entities that have biological processes, such as Cell signalin ...
*
Sodium acetate Sodium acetate, NaCH3COO, also abbreviated Sodium, NaOxygen, OAcetyl, Ac, is the sodium Salt (chemistry), salt of acetic acid. This colorless deliquescent salt has a wide range of uses. Applications Biotechnological Sodium acetate is used as t ...
*
Mixed acid fermentation Mixed acid fermentation is the biological process by which a six-carbon sugar e.g. glucose is converted into a complex and variable mixture of acids. It is an wikt:anaerobic, anaerobic fermentation reaction that is common in bacteria. It is charac ...
*
Acetic acid Acetic acid , systematically named ethanoic acid , is a colourless liquid organic compound with the chemical formula CH3COOH (also written as CH3CO2H, C2H4O2, or HC2H3O2). Vinegar is no less than 4% acetic acid by volume, making acetic acid ...

Acetic acid
*
Acetyl chloride Acetyl chloride (CH3COCl) is an acyl chloride In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group -Carbonyl, COChlorine, Cl. Their formula is usually written RCOCl, where R is a side chain. ...

Acetyl chloride
*
Zinc acetate Zinc acetate is a salt Salt is a mineral In geology and mineralogy, a mineral or mineral species is, broadly speaking, a solid chemical compound with a fairly well-defined chemical composition and a specific crystal structure that oc ...

Zinc acetate


References


External links

{{Authority control Carboxylate anions Leaving groups