An aldehyde (pronounced /ˈældɨhaɪd/) is an organic compound containing a formyl group.

This functional group, with the structure R-CHO, consists of a carbonyl centre bonded
tohydrogen and an R group. [1] The group without R is called the aldehyde group or formyl
group. Aldehydes differ from ketones in that the carbonyl is placed at the end of a carbon
skeleton rather than between two carbon atoms. Aldehydes are common in organic chemistry.
Many fragrances are aldehydes.

Contents
[hide]

• 1 Structure and bonding

• 2 Nomenclature
o 2.1 IUPAC names for
aldehydes
o 2.2 Etymology

• 3 Physical properties and

characterization
• 4 Applications and occurrence
o 4.1 Naturally occurring
aldehydes
• 5 Synthesis
o 5.1 Oxidative routes
o 5.2 Specialty methods

• 6 Common reactions
o 6.1 Reduction
o 6.2 Oxidation
o 6.3 Nucleophilic addition
reactions
 6.3.1 Oxygen
nucleophiles
 6.3.2 Nitrogen
nucleophiles
 6.3.3 Carbon
 nucleophiles
o 6.4 More complex reactions

• 7 Examples of aldehydes
• 8 Related compounds
• 9 See also
• 10 External links

• 11 References

[edit]Structure and bonding

Aldehydes feature an sp2-hybridized, planar carbon center that is connected by a double bond
to oxygen and a single bond to hydrogen. The C-H bond is not acidic. Owing to resonance
stabilization of the conjugate base, an α-hydrogen in an aldehyde is far more acidic with
a pKa near 17[2], than a C-H bond in a typical alkane, with a pKa in the 30's. This acidification is
attributed to (i) the electron-withdrawing quality of the formyl center and (ii) the fact that the
conjugate base, an enolate anion, delocalizes its negative charge. Related to (i), the aldehyde
group is somewhat polar.

Aldehydes (except formaldehyde) can exist in either the keto or the enol tautomer. Keto-enol
tautomerism is catalyzed by either acid or base. Usually the enol is the minority tautomer, but it
is more reactive.

[edit]Nomenclature

[edit]IUPAC names for aldehydes

The common names for aldehydes do not strictly follow official guidelines, such as those
recommended by IUPAC but these rules are useful. IUPAC prescribes the following
nomenclature for aldehydes:[3][4][5]

1. Acyclic aliphatic aldehydes are named as derivatives of the longest carbon chain
containing the aldehyde group. Thus, HCHO is named as a derivative of methane, and
CH3CH2CH2CHO is named as a derivative of butane. The name is formed by changing
the suffix -e of the parent alkane to -al, so that HCHO is named methanal, and
CH3CH2CH2CHO is named butanal.
2. In other cases, such as when a -CHO group is attached to a ring, the suffix -
carbaldehyde may be used. Thus, C6H11CHO is known as cyclohexanecarbaldehyde. If
 the presence of another functional group demands the use of a suffix, the aldehyde
group is named with the prefix formyl-. This prefix is preferred to methanoyl-.
3. If the compound is a natural product or a carboxylic acid, the prefix oxo- may be
used to indicate which carbon atom is part of the aldehyde group; for example,
CHOCH2COOH is named 3-oxopropanoic acid.
4. If replacing the aldehyde group with a carboxyl group (-COOH) would yield a
carboxylic acid with a trivial name, the aldehyde may be named by replacing the suffix -
ic acid or -oic acid in this trivial name by -aldehyde.

[edit]Etymology

Formic acid

The word aldehyde was coined by Justus von Liebig as a contraction of the
Latin alcohol dehydrogenatus (dehydrogenated alcohol).[6] In the past, aldehydes were
sometimes named after the corresponding alcohols, for example, vinous
aldehyde for acetaldehyde. (Vinous is from Latin vinum = wine (the traditional source
of ethanol), cognate with vinyl.)

The term formyl group is derived from the Latin and/or Italian word formica = ant. This word can
be recognized in the simplest aldehyde, formaldehyde (methanal), and in the simplest
carboxylic acid, formic acid (methanoic acid, an acid, but also an aldehyde).

[edit]Physical properties and characterization

Aldehydes have properties that are diverse and that depend on the remainder of the molecule.
Smaller aldehydes are more soluble in water, formaldehyde and acetaldehyde completely so.
The volatile aldehydes have pungent odors. Aldehydes degrade in air via the process
of autoxidation.
The two aldehydes of greatest importance in industry, formaldehyde and acetaldehyde, have
complicated behavior because of their tendency to oligomerize or polymerize. They also tend to
hydrate, forming the geminal diol. The oligomers/polymers and the hydrates exist in equilibrium
with the parent aldehyde.

Aldehydes are readily identified by spectroscopic methods. Using IR spectroscopy, they display
a strong νCO band near 1700 cm−1. In their 1H NMR spectra, the formyl hydrogen center absorbs
near δ9, which is a distinctive part of the spectrum. This signal shows the characteristic coupling
to any protons on the alpha carbon.

[edit]Applications and occurrence

Important aldehydes and related compounds. The aldehyde group (or formyl group) is colored red. From the left:
(1) formaldehyde and (2) its trimer 1,3,5-trioxane, (3)acetaldehyde and (4) its enol vinyl alcohol,
(5) glucose (pyranose form as α-D-glucopyranose), (6) the flavorant cinnamaldehyde, (7) the visual pigment retinal,
and (8) the vitamin pyridoxal.

[edit]Naturally occurring aldehydes

Traces of many aldehydes are found in essential oils and often contribute to their favorable
odors, e.g. cinnamaldehyde, cilantro, and vanillin. Possibly because of the high reactivity of the
formyl group, aldehydes are not common in several of the natural building blocks - amino acids,
nucleic acids, lipids. Most sugars, however, are derivatives of aldehydes. These "aldoses" exist
as hemiacetals, a sort of masked form of the parent aldehyde. For example, in aqueous solution
only a tiny fraction of glucose exists as the aldehyde.

[edit]Synthesis

There are several methods for preparing aldehydes,[7] but the dominant technology
is hydroformylation.[8] Illustrative is the generation of butyraldehyde by hydroformylation
of propene:

H2 + CO + CH3CH=CH2 → CH3CH2CH2CHO
[edit]Oxidative routes
Aldehydes are commonly generated by alcohol oxidation. In industry, formaldehyde is
produced on a large scale by oxidation of methanol. Oxygen is the reagent of choice, being
"green" and cheap. In the laboratory, more specialized oxidizing agents are used, but
chromium(VI) reagents are popular. Oxidation can be achieved by heating the alcohol with
an acidified solution of potassium dichromate. In this case, excess dichromate will further
oxidize the aldehyde to a carboxylic acid, so either the aldehyde is distilled out as it forms
(if volatile) or milder reagents such as PCC are used.[9]

[O] + CH3(CH2)9OH → CH3(CH2)8CHO + H2O

Oxidation of primary alcohols to form aldehydes and can be achieved under milder,
chromium-free conditions by employing methods or reagents such as IBX acid, Dess-
Martin periodinane, Swern oxidation,TEMPO, or the Oppenauer oxidation.

Another oxidation route significant in industry is the Wacker process, whereby

ethylene is oxidized to acetaldehyde in the presence of copper and palladium
catalysts (acetaldehyde is also produced on a large scale by the hydration of
acetylene).

[edit]Specialty methods
Reaction name Comment
Substrate

Ozonolysis alkene ozonolysis of non-fully-substituted alkenes yield aldehydes

upon reductive work-up.
Organic Reduction of an ester with diisobutylaluminium hydride
ester
reduction (DIBAL-H) or sodium aluminium hydride
Rosenmund acid chloride or using lithium tri-t-butoxyaluminium hydride
reaction (LiAlH(OtBu)3).
Wittig reaction ketone reagent methoxymethylenetriphenylphosphine in a modified
Wittig reaction.
Formylation nucleophilic
various reactions for example the Vilsmeier-Haack reaction
reactions arenes
Nef reaction Nitro
compound
Zincke reaction pyridines Zincke aldehydes form in a variation
Stephen nitriles
aldehyde reagents tin(II) chloride and hydrochloric acid.
synthesis
Meyers oxazine
oxazine hydrolysis
synthesis
McFadyen- hydrazide is a base-catalyzed thermal decomposition of
 Stevens
acylsulfonylhydrazides
reaction
[edit]Common reactions
Aldehydes are highly reactive and participate in many reactions.[7]" From the industrial
perspective, important reactions are condensations, e.g. to prepare plasticizers and
polyols, and reduction to produce alcohols, especially "oxo-alcohols." From the
biological perspective, the key reactions involve addition of nucleophiles to the formyl
carbon in the formation of imines (oxidative deamination) and hemiacetals (structures
of aldose sugars).[7]

[edit]Reduction
Main article: Aldehyde reduction

The formyl group can be readily reduced to a primary alcohol (-CH2OH). Typically this
conversion is accomplished by catalytic hydrogenation either directly or by transfer
hydrogenation. Stoichiometric reductions are also popular, as can be effected
with sodium borohydride.

[edit]Oxidation

The formyl group readily oxidizes to the corresponding carboxylic acid (-COOH). The
preferred oxidant in industry is oxygen or air. In the laboratory, popular oxidizing
agents include potassium permanganate, nitric acid, chromium(VI) oxide, and chromic
acid. The combination of manganese dioxide, cyanide, acetic acid and methanol will
convert the aldehyde to a methyl ester.[10]

Another oxidation reaction is the basis of the silver mirror test. In this test, an
aldehyde is treated with Tollens' reagent, which is prepared by adding a drop
of sodium hydroxide solution into silver nitrate solution to give a precipitate of silver(I)
oxide, and then adding just enough dilute ammonia solution to redissolve the
precipitate in aqueous ammonia to produce [Ag(NH3)2]+ complex. This reagent will
convert aldehydes to carboxylic acids without attacking carbon-carbon double-bonds.
The name silver mirror test arises because this reaction will produce a precipitate of
silver whose presence can be used to test for the presence of an aldehyde.

If the aldehyde cannot form an enolate (e.g., benzaldehyde), addition of strong base
induces the Cannizzaro reaction. This reaction results in disproportionation, producing
a mixture of alcohol and carboxylic acid.

[edit]Nucleophilic addition reactions

 Nucleophiles add readily to the carbonyl group. In the product, the carbonyl carbon
becomes sp3 hybridized, being bonded to the nucleophile, and the oxygen center
becomes protonated:

RCHO + Nu- → RCH(Nu)O-

RCH(Nu)O- + H+ → RCH(Nu)OH

In many cases, a water molecule is removed after the addition takes place;
in this case, the reaction is classed as an addition-elimination or addition-
condensation reaction. There are many variations of nucleophilic addition
reactions.
[edit]Oxygen nucleophiles

In the acetalisation reaction, under acidic or basic conditions,

an alcohol adds to the carbonyl group and a proton is transferred to form
a hemiacetal. Under acidic conditions, the hemiacetal and the alcohol can
further react to form an acetal and water. Simple hemiacetals are usually
unstable, although cyclic ones such as glucose can be stable. Acetals are
stable, but revert to the aldehyde in the presence of acid. Aldehydes can
react with water to form hydrates, R-C(H)(OH)(OH). These diols are stable
when strong electron withdrawing groups are present, as in chloral hydrate.
The mechanism of formation is identical to hemiacetal formation.
[edit]Nitrogen nucleophiles

In alkylimino-de-oxo-bisubstitution, a primary or secondary amine adds to

the carbonyl group and a proton is transferred from the nitrogen to the
oxygen atom to create a carbinolamine. In the case of a primary amine, a
water molecule can be eliminated from the carbinolamine to yield an imine.
This reaction is catalyzed by acid. Hydroxylamine (NH2OH) can also add to
the carbonyl group. After the elimination of water, this will result in an oxime.
An ammonia derivative of the form H2NNR2 such as hydrazine (H2NNH2)
or 2,4-dinitrophenylhydrazine can also be the nucleophile and after the
elimination of water, this will result in the formation of a hydrazone. This
forms the basis of a test for aldehydes and ketones.
[edit]Carbon nucleophiles

The cyano group in HCN can add to the carbonyl group to

form cyanohydrins, R-C(H)(OH)(CN). In the Grignard reaction, a Grignard
reagent adds to the group, eventually yielding an alcohol with a substituted
group from the Grignard reagent. Related reactions are the Barbier
reaction and the Nozaki-Hiyama-Kishi reaction. In organostannane
addition tin replaces magnesium.

In the aldol reaction, the metal enolates of ketones, esters, amides,

and carboxylic acids will add to aldehydes to form β-hydroxycarbonyl
compounds (aldols). Acid or base-catalyzed dehydration will then lead to
α,β-unsaturated carbonyl compounds. The combination of these two steps
is known as the aldol condensation. The Prins reaction occurs when a
nucleophilic alkene or alkyne reacts with an aldehyde as electrophile. The
product of the Prins reaction varies with reaction conditions and substrates
employed.

[edit]More complex reactions

Product Comment
Reaction name

Wolff-Kishner alkane If an aldehyde is converted to a simple hydrazone

reduction (RCH=NHNH2) and this is heated with a base such
as KOH, the terminal carbon is fully reduced to a
methyl group. The Wolff-Kishner reaction may be
performed as a one-pot reaction, giving the overall
conversion RCH=O → RCH3.
Pinacol coupling
diol with reducing agents such as magnesium
reaction
Wittig reaction alkene reagent an ylide
Takai reaction alkene diorganochromium reagent
Corey-Fuchs alkyne
phosphine-dibromomethylene reagent
reactions
Ohira–Bestmann alkyne
reagent dimethyl (diazomethyl)phosphonate
reaction
Johnson-Corey- epoxide
Chaykovsky reagent a sulfonium ylide
reaction
Oxo Diels Alder pyran Aldehydes can, typically in the presence of suitable
reaction catalysts, serve as partners
in cycloaddition reactions. The aldehyde serves as
the dienophile component, giving a pyran or related
compound.
Hydroacylation ketone In hydroacylation an aldehyde is added over an
alkene to form a ketone.
decarbonylation alkane catalysed by transition metals
 [edit]Examples of aldehydes

 Methanal (Formaldehyde)
 Ethanal (Acetaldehyde)
 Propanal (Propionaldehyde)
 Butanal (butyraldehyde)
 Benzaldehyde
 Cinnamaldehyde
 Tolualdehyde

[edit]Related compounds
Other kinds of organic compounds containing carbonyl groups include

 Dialdehydes
 Ketones
 Carboxylic acids
 Amides

Ketone
From Wikipedia, the free encyclopedia

Ketone group
Acetone

In organic chemistry, a ketone (pronounced /ˈkiːtoʊn/) is a compound with the structure

RC(=O)R', where R and R' can be a variety of atoms and groups of atoms. It features acarbonyl
group (C=O) bonded to two other carbon atoms.[1] Acetone is the simplest example of a ketone,
and in fact the word ketone derives its name from Aketon, an old German word for acetone.[2]

Ketones differ from aldehydes in that the carbonyl is placed between two carbons rather than at
the end of a carbon skeleton. They are also distinct from other functional groups, such
as carboxylic acids, esters and amides, which have a carbonyl group bonded to a hetero atom.

A ketone that has an α-hydrogen participates in a so-called keto-enol tautomerism. The reaction
with a strong base gives the corresponding enolate, often by deprotonation of the enol.

Contents
[hide]

• 1 Nomenclature
• 2 Structure and properties
o 2.1 Classes of ketones
 2.1.1 Diketones
 2.1.2 Unsaturated
ketones
 2.1.3 Cyclic ketones
o 2.2 Keto-enol
tautomerization
o 2.3 Acidity of ketones
• 3 Characterization
 o 3.1 Spectroscopy
o 3.2 Qualitative organic
tests
• 4 Synthesis
• 5 Reactions
• 6 Biochemistry
• 7 Applications
• 8 Toxicity
• 9 See also

• 10 References

[edit]Nomenclature

According to the rules of IUPAC nomenclature, ketones are named by changing the suffix -e of
the parent alkane to -one. For the most important ketones, however, traditional nonsystematic
names are still generally used, for example acetone and benzophenone. These nonsystematic
names are considered retained IUPAC names,[3] although some introductory chemistry
textbooks use names such as 2-propanone or propan-2-one instead of acetone, the simplest
ketone (CH3-CO-CH3). The position of the carbonyl group is usually denoted by a number.

Oxo is the IUPAC nomenclature for a ketone functional group. Other prefixes, however, are also
used. For some common chemicals (mainly in biochemistry), "keto" or "oxo" is the term used to
describe the ketonefunctional group. The term "oxo" is used widely through chemistry. For
example, it also refers to a single oxygen atom coordinated to a transition metal (a metal oxo).

[edit]Structure and properties

Representative ketones, from the left: acetone, a common solvent; oxaloacetate, an intermediate in the metabolism
of sugars; acetylacetone in its (mono) enol form (the enol highlighted in blue); cyclohexanone, precursor to
Nylon; muscone, an animal scent; and tetracycline, an antibiotic.
The ketone carbon is often described as "sp2 hybridized," terminology that describes both their
electronic and molecular structure. Ketones are trigonal planar about the ketonic carbon, with C-
C-O and C-C-C bond angles of approximately 120°.

The carbonyl group is polar as a consequence of the fact that the electronegativity of the
oxygen center is greater than that for carbonyl carbon. Thus, ketones are nucleophilic at oxygen
and electrophilic at carbon. Because the carbonyl group interacts with water by hydrogen
bonding, ketones are typically more soluble in water than the related methylene compounds.
Ketones are hydrogen-bond acceptors. Ketones are not usually hydrogen-bond donors and
cannot hydrogen-bond to itself. Because of their inability to serve both as hydrogen-bond
donors and acceptors, ketones tend not to "self-associate" and are more volatile
thanalcohols and carboxylic acids of comparable molecular weights. These factors relate to
pervasiveness of ketones in perfumery and as solvents.

[edit]Classes of ketones
Ketones are classified on the basis of their substituents. One broad classification subdivides
ketones into symmetrical and unsymmetrical derivatives, depending on the equivalency of the
two organic substituents attached to the carbonyl center. Acetone and benzophenone are
symmetrical ketones. Acetophenone (C6H5C(O)CH3) is an unsymmetrical ketone. In the area
of stereochemistry, unsymmetrical ketones are known for being prochiral.

[edit]Diketones
Main article: diketone

Many kinds of diketones are known, some with unusual properties. The simplest
is biacetyl (CH3C(O)C(O)CH3), once used as butter-flavoring in
popcorn. Acetylacetone (pentane-2,4-dione) is virtually a misnomer (inappropriate name)
because this species exists mainly as the monoenol CH3C(O)CH=C(OH)CH3. Its enolate is a
common ligand in coordination chemistry.

[edit]Unsaturated ketones

Ketones containing alkene and alkyne units are often called unsaturated ketones. The most
widely used member of this class of compounds is methyl vinyl ketone, CH3C(O)CH=CH2, which
is useful in Robinson annulation reaction. Lest there be confusion, a ketone itself is a site of
unsaturation; that is, it can be hydrogenated.

[edit]Cyclic ketones
Many ketones are cyclic. The simplest class have the formula (CH2)nCO, where n varies from 3
for cyclopropanone to the teens. Larger derivatives exist. Cyclohexanone, a symmetrical cyclic
ketone, is an important intermediate in the production of nylon. Isophorone, derived from
acetone, is an unsaturated, unsymmetrical ketone that is the precursor to other
polymers. Muscone, 3-methylpentadecanone, is an animalpheromone.

[edit]Keto-enol tautomerization
Main article: Enol

Keto-enol tautomerism. 1 is the keto form; 2 is the enol.

Ketones that have at least one alpha-hydrogen, undergo keto-enol tautomerization; the
tautomer is an enol. Tautomerization may be catalyzed by both acids and bases. Usually, the
keto form is more stable than the enol. This equilibrium allows ketones to be prepared via the
hydration of alkynes.

[edit]Acidity of ketones
Ketones are far more acidic (pKa ≈ 20) than a regular alkane (pKa ≈ 50). This difference reflects
resonance stabilization of the enolate ion that is formed through dissociation. The relative acidity
of the α-hydrogen is important in the enolization reactions of ketones and other carbonyl
compounds. The acidity of the α-hydrogen also allows ketones and other carbonyl compounds
to undergo nucleophilic reactions at that position, with either stoichiometric and catalytic base.

[edit]Characterization

[edit]Spectroscopy

Ketones and aldehydes absorb strongly in infra-red spectrum near 1700 cm−1. The exact
position of the peak depends on the substituents.

Whereas 1H NMR spectroscopy is, in general, not useful for establishing the presence of a
ketone, 13C NMR spectra exhibit signals somewhat downfield of 200 ppm depending on
structure. Such signals are typically weak due to the absence of nuclear Overhauser effects.
Since aldehydes resonate at similar chemical shifts, multiple resonance experiments are
employed to definitively distinguish aldehydes and ketones.

[edit]Qualitative organic tests

Ketones give positive results in Brady's test, the reaction with 2,4-dinitrophenylhydrazine to give
the corresponding hydrazone. Ketones may be distinguished from aldehydes by giving a
negative result with Tollens' reagent. Methyl ketones give positive results for the iodoform test.

[edit]Synthesis

Many methods exist for the preparation of ketones in industrial scale, biology, and in academic
laboratories. In industry, the most important method probably involves oxidation of
hydrocarbons, often with air. For example, billion kilograms of cyclohexanone are produced
annually by aerobic oxidation of cyclohexane. Acetone is prepared by air-oxidation of cumene.

For specialized or small scale organic synthetic applications, ketones are often prepared
by oxidation of secondary alcohols:

R2CH(OH) + O → R2C=O + H2O

Typical strong oxidants (source of "O" in the above reaction) include potassium
permanganate or a Cr(VI) compound. Milder conditions make use of the Dess-Martin
periodinane or the Moffatt-Swern methods.

Many other methods have been developed including:

 By geminal halide hydrolysis.

 By hydration of alkynes. Such processes occur via enols and require the
presence of an acid and HgSO4. Subsequent enol-keto tautomerization gives a ketone.
This reaction always produces a ketone, even with a terminal alkyne.
 From Weinreb Amides using stoichiometric organometallic reagents.
 Aromatic ketones can be prepared in the Friedel-Crafts acylation, the
related Houben-Hoesch reaction and the Fries rearrangement.
 Ozonolysis, and related dihydroxylation/oxidative sequences, cleave alkenes to
give aldehydes and/or ketones, depending on alkene substitution pattern.
 In the Kornblum–DeLaMare rearrangement ketones are prepared from peroxides
and base.
 In the Ruzicka cyclization, cyclic ketones are prepared from dicarboxylic acids.
  In the Nef reaction, ketones form by hydrolysis of salts of secondary nitro
compounds.
 In the Fukuyama coupling, ketones form from a thioester and an organozinc
compound.
 By the reaction of an acid chloride with organocadmium
compounds or organocopper compounds.
 The Dakin-West reaction provides an efficient method for preparation of certain
methyl ketones from carboxylic acids.
 Ketones can also be prepared by the reaction of Grignard reagents with nitriles,
followed by hydrolysis.
 By decarboxylation of carboxylic anhydride.
 Ketones can be prepared from haloketones in reductive dehalogenation of halo
ketones.

[edit]Reactions

Ketones engage in many organic reactions. The most important reactions follow from the
susceptibility of the carbonyl carbon toward nucleophilic addition and the tendency for the
enolates to add to electrophiles. Nucleophilic additions include in approximate order of their
generality:

 With water (hydration) gives geminal diols, which are usually not formed in
appreciable (or observable) amounts
 With an acetylide to give the α-hydroxyalkyne
 With ammonia or a primary amine gives an imine
 With secondary amine gives an enamine
 With Grignard and organolithium reagents to give, after aqueous workup,
a tertiary alcohol
 With an alcohols or alkoxides to gives the hemiketal or its conjugate base. With
a diol to the ketal. This reaction is employed to protect ketones.
 With sodium amide resulting in C-C bond cleavage with formation of the amide
RCONH2 and the alkane R'H, a reaction called the Haller-Bauer reaction.[4]
 Electrophilic addition, reaction with an electrophile gives a resonance stabilized
cation
 With phosphonium ylides in the Wittig reaction to give the alkenes
  With thiols to give the thioacetal
 With hydrazine or 1-disubstituted derivatives of hydrazine to give hydrazones.
 With a metal hydride gives a metal alkoxide salt, hydrolysis of which gives
the alcohol, an example of ketone reduction
 With halogens to form α-haloketone, a reaction that proceeds via
an enol (see Haloform reaction)
 With heavy water to give a α-deuterated ketone
 Fragmentation in photochemical Norrish reaction
 Reaction of 1,4-aminodiketones to oxazoles by dehydration in the Robinson-
Gabriel synthesis
 In the case of aryl-alkyl ketones, with sulfur and an amine give amides in
the Willgerodt reaction
 With hydroxylamine to produce oximes

[edit]Biochemistry

Acetone, acetoacetate, and beta-hydroxybutyrate are ketones (or ketone bodies)

generated from carbohydrates, fatty acids, and amino acids in humans and
most vertebrates. Ketones are elevated in blood after fasting including a night of sleep, and
in both blood and urine in starvation, hypoglycemia due to causes other
than hyperinsulinism, various inborn errors of metabolism, and ketoacidosis (usually due
to diabetes mellitus). Although ketoacidosis is characteristic of decompensated or
untreated type 1 diabetes, ketosis or even ketoacidosis can occur in type 2 diabetes in
some circumstances as well. Acetoacetate and beta-hydroxybutyrate are an important fuel
for many tissues, especially during fasting and starvation. The brain, in particular, relies
heavily on ketone bodies as a substrate for lipid synthesis and for energy during times of
reduced food intake. Ketones have been described as "magic" in their ability to increase
metabolic efficiency, while decreasing production of free radicals, the damaging byproducts
of normal metabolism. Ketone bodies are relevant to neurological diseases such as
Alzheimer's and Parkinson's disease,[5] and the heart and brain operate 25% more
efficiently using ketones as a source of energy.[6] Research has also shown ketones play a
role in reducing epileptic seizures with the high-fat, near-zero carbohydrate Ketogenic
Diet. [1]

[edit]Applications
 Ketones are produced on massive scales in industry as solvents, polymer precursors, and
pharmaceuticals. In terms of scale, the most important ketones are acetone, methylethyl
ketone, and cyclohexanone. They are also common in biochemistry, but less so than in
organic chemistry in general. The combustion of hydrocarbons is an uncontrolled oxidation
process that gives ketones as well as many other types of compounds.

[edit]Toxicity

Although it is difficult to generalize on the toxicity of such a broad class of compounds,

simple ketones are, in general, not highly toxic (for instance, the sugar fructose is a
ketone). This characteristic is one reason for their popularity as solvents. Exceptions to this
rule are the unsaturated ketones such as methyl vinyl ketone with LD50 of 7 mg/kg (oral).

Ketone bodies
From Wikipedia, the free encyclopedia

Chemical structures of the three ketone bodies: acetone (top),acetoacetic acid(middle), and beta-hydroxybutyric
acid(bottom).

Ketone bodies are three water-soluble compounds that are produced as by-
products when fatty acids are broken down for energy in the liver and kidney. They are used as
a source of energy in the heart and brain. In the brain, they are a vital source of energy
during fasting.[1] Although termed "bodies", they are dissolved substances, not particles.
The three endogenous ketone bodies are acetone, acetoacetic acid, and beta-hydroxybutyric
acid,[2] although beta-hydroxybutyric acid is not technically a ketone but a carboxylic acid. Other
ketone bodies such as beta-ketopentanoate and beta-hydroxypentanoate may be created as a
result of the metabolism of synthetic triglycerides such as triheptanoin.

Contents
[hide]

• 1 Uses in the heart and

brain
• 2 Production
• 3 Ketosis and
ketoacidosis
• 4 Impact upon pH
• 5 See also
• 6 References

• 7 External links

Uses in the heart and brain

Ketone bodies can be used for energy. Ketone bodies are transported from the liver to other
tissues, where acetoacetate and beta-hydroxybutyrate can be reconverted to acetyl-CoA to
produce energy, via the citric acid cycle.

The heart gets little energy from ketone bodies except under special circumstances; it uses
mainly fatty acids.[3][4]

The brain gets its energy from ketone bodies when glucose is less available (e.g., when fasting).
In the event of low blood glucose, most other tissues have additional energy sources besides
ketone bodies (such as fatty acids), but the brain does not. After the diet has been changed to
lower blood glucose for 3 days, the brain gets 30% of its energy from ketone bodies.[5] After
about 40 days, this goes up to 70% (during the initial stages the brain does not burn ketones,
since they are an important substrate for lipid synthesis in the brain). In time the brain reduces
its glucose requirements from 120g to 40g per day.[6][unreliable source?]

Production
Acetyl-CoA

Ketone bodies are produced from acetyl-CoA (see ketogenesis) mainly in

the mitochondrial matrix of hepatocytes when carbohydrates are so scarce that energy must be
obtained from breaking down fatty acids. Because of the high level of acetyl CoA present in the
cell, the pyruvate dehydrogenase complex is inhibited, whereas pyruvate carboxylase becomes
activated. Thus, the oxaloacetate produced will enter gluconeogenesis rather than the citric acid
cycle, as the latter is also inhibited by the elevated level of NADH resulting from ß-oxidation of
fatty acids. The excess acetyl-CoA is therefore rerouted to ketogenesis. Such a state in humans
is referred to as the fasted state.

Acetone is produced by spontaneous decarboxylation of acetoacetate, yielding levels of

acetone much lower than those of other ketone bodies. Acetone cannot be converted back to
acetyl-CoA; it is instead metabolized (e.g., converted to glucose via pyruvate[7]), excreted in
the urine, or (as a consequence of its high vapor pressure) exhaled. Acetone is responsible for
the characteristic "fruity" odor of the breath of persons in ketoacidosis.[8]

Ketosis and ketoacidosis

Any production of these compounds is called ketogenesis, and this is necessary in small
amounts.

However, when excess ketone bodies accumulate, this abnormal (but not necessarily harmful)
state is called ketosis. Ketosis can be quantified by sampling the patient's exhaled air, and
testing for acetone by gas chromatography.[9] Many diabetics self test for the presence of
ketones using blood or urine testing kits.

When even larger amounts of ketone bodies accumulate such that the blood's pH is lowered to
dangerously acidic levels, this state is called ketoacidosis.

Impact upon pH
Both acetoacetic acid and beta-hydroxybutyric acid are acidic, and, if levels of these ketone
bodies are too high, the pH of the blood drops, resulting in ketoacidosis.
This happens in untreated Type I diabetes (see diabetic ketoacidosis), and also
in alcoholics after binge drinking, subsequent to starvation, and as a result of the alcohol-
induced impairment of the liver's ability to generate glucose by the process
of gluconeogenesis (see alcoholic ketoacidosis).

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Ketones are an ordinary and proficient cause of stimulation and powerful energy for the human
body. They are formed by the liver as of the fat as it is given out from fat cells in retort to the
nonexistence of glucose or the so called sugar in the diet. Our body functions all the time unlike
the human. So obviously it needs more energy which is produced by the liver. When the human
body is producing ketones, and using them for producing energy, it is termed as “ketosis”.
Ketosis is usual and not hazardous. The body produces ketones to use as energy at the time when
there is absence of sugar. The major fact to remember is that, ketones can be created by fat we
consume, so it is necessary to minimize the fat intake and also the sugar as when the sugar level
raises it causes ketone problem. As a consequence the resulting factor in the human body is
required to generate and utilize ketones for all the body activities.
Ketones are to take care in a proper way as taking proper medication for the disease would be
life saving. They are very important as they are responsible for the energy generation for our
body to enhance the metabolism .If it fails the metabolic activities are in trouble which leads
gradually to death. Proper medication has to be given to any diabetic patient as it would start to
affect the body parts one by one causing dehydration.
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The most common induce of ketosis is constantly dieting. Individuals who go on sudden low-carb dieting
often complain of weight loss, accompanied along ketosis symptoms. One of the main symptoms of
ketosis is while a person shifts from highly glycemic dieting to a dieting which doesn’t provide enough
glycogen stores. This happens when the body gets into a level of ketosis. In the starting stage, the brain
doesn’t burn ketones, just even after 2 days also if carbohydrates aren’t included in your diet, then the
brain begins burning ketones hence it directly uses the vitality from its adipose tissue stores, hence,
preserving glucose just for dreadful conditions, and precluding collapse of the body’s muscle and protein.

Although still problematical, this level of ketosis is regarded as relatively safe. In fact, in some cases
ketosis is deliberately caused in the ketogenic dieting, which is utilized to treat epilepsy. Still, prolonged
ketosis is capable of causing the body and also it is highly discouraged. Sustained ketosis symptoms are
much seen in individuals that move to fad dieting for weight loss.

You should learn to point the symptoms of ketosis before it grows into DKA. As there is excessively little
insulin, the level of blood sugar will normally be high. You may also be experiencing either one or more
like urinating more frequently, being sick or feeling sick, finding it difficult to breathe, breathe that odor of
pear drops, feeling thirsty for all the time, flushed skin or having dry, feeling tired or confused, pain in your
abdomen.

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Ketones formation:
Ketones are formed when our human body gets power by flouting down fat as an alternative of sugar. The
major reason for this alternative breaking is that there is no enough insulin in the blood and not enough
sugar is available.

Ketones in severe stage:

Ketones become a difficulty when the patient does not have an adequate amount of insulin to organize
ketone creation correctly or they are ravenous because of lack of food. When more amounts of ketones
are formed too swiftly they disturb the fragile equilibrium of the body’s metabolism and can direct to a
crisis called diabetic ketoacidosis.

Who is vulnerable to Ketones?

Populace, who make use of insulin at the time of sickness, and now and then anxiety, can make ketone
levels increase. Children who suffer with diabetes every so often can face the trouble to let know the
symptoms of growing ketones as of additional early day’s sickness. Pregnant women with diabetes may
have far above the ground ketone levels can have an effect on the baby inside, so expectant women with
diabetes required to take additional concern.

How to identify the signs of ketones:

• Because there is too small insulin, blood sugar levels will typically be elevated. There are many
symptoms experienced by the patients.

• Urinating more recurrently

• Having dehydrated skin

• sensation unwell or being unwell

• Feeling weary and perplexed

• Finding tough to respire

• Chronic pain in stomach

• Prevailing of thirsty always.

Some of these symptoms occur because as ketone stage rises, blood becomes further acidic. This
causes the Acidic blood, joint with lack of moisture resulting in dehydration, cause diabetic ketoacidosis

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Ketone bodies are 3 water-soluble compounds which are developed as by-products while fatty acids are
collapsed for energy in the kidney and liver. They are utilized as a source of vitality in the brain and heart.
Brain, is the vital source of energy during fasting. Though it is termed as “bodies”, they are broke up
substances, not particles. The 3 endogenous ketone bodies are acetoacetic acid, acetone, and beta-
hydroxybutyric acid, though beta-hydroxybutyric acid isn’t actually a ketone simply a carboxylic acid.
Remaining ketone bodies like beta-hydroxypentanoate and beta-ketopentanoate may be developed as
an outcome of metabolism of celluloid triglycerides like triheptanoin.
Ketone bodies can also be utilized for vitality. Ketone bodies are carried from liver to other tissues, at
which beta-hydroxybutyrate and acetoacetate can be again converted to acetyl-CoA to acquire energy,
through citric acid cycle. The heart acquires little vitality from ketone bodies excluding under peculiar
circumstances; it utilizes mainly fatty acids.
The brain acquires its vitality from ketone bodies while glucose is available in less number. e.g.,
when fasting. In the case when the blood glucose level is low, most other tissues induce additional vitality
sources as well ketone bodies like fatty acids, only the brain doesn’t. After the diet the level of blood
glucose will be lowered and it will be for 3 days, the brain acquires 30% of its vitality from ketone
bodies. Later on about forty days, this rises up to 70% i.e. during the starting stages the brain doesn’t
burn ketones, as for lipid deductions in the brain they are considered as an important substrate.

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Ketone (ketone body): in the liver, fatty acid oxidation and decomposition of the intermediate product
acetoacetate, β-hydroxybutyric acid and acetone, the three collectively known as ketone bodies.

Liver synthesis of ketone bodies with strong enzymes, but the lack of the enzyme by ketone bodies.
Ketone is a product of lipolysis, rather than a product of high blood sugar. Eating carbohydrates will not
lead to an increase in ketone bodies.

During starvation Ketone bodies provide a source of power for many parts of the body, including the
brain, and therefore have important physiological significance.

The importance of ketone bodies is that, due to the presence of blood-brain barrier, in addition to glucose
and ketone body substances outside the brain cannot enter the brain to provide energy.

During starvation ketone provides 25% -75% enegry to our brain. However, too much ketones cause
poisoning. Avoid excessive ketone body production, the must be a good supply of sugar.

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