Acetyl

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Acetyl

In organic chemistry

Organic chemistry

Organic chemistry is a discipline within chemistry which involves the science study of the structure, properties, composition, chemical reaction, and preparation of chemical compounds that contain carbon....
, acetyl (ethanoyl), is a functional group

Functional group

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules....
, the acyl

Acyl

An acyl group is a functional group derived by the removal of one or more hydroxyl groups from an oxoacid.. In organic chemistry, the acyl group is usually derived from a carboxylic acid of the form RCarbon Oxygen hydroxyl....
of acetic acid

Acetic acid

Acetic acid, CH3COOH, also known as ethanoic acid, is an organic acid which gives vinegar its sour taste and pungent smell. Pure, water-free acetic acid is a colourless liquid that absorbs water from the environment , and freezes at 16.7 Celsius to a colourless crystalline solid....
, with chemical formula

Chemical formula

A chemical formula is a way of expressing information about the atoms that constitute a particular chemical compound, and how the relationship between those atoms changes in chemical reactions....
-C

Carbon

Carbon is a chemical element with chemical symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalence?making four electrons available to form covalent bond chemical bonds....
O

Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
C

Carbon

Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the chemical symbol H. At standard temperature and pressure, hydrogen is a colorless, odorless, nonmetallic, tasteless, highly combustion and explosive Diatomic molecule gas with the molecular formula H2....
₃. It is sometimes abbreviated as Ac (not to be confused with the element

Chemical element

A chemical element is a type of atom that is distinguished by its atomic number; that is, by the number of protons in its atomic nucleus. The term is also used to refer to a pure chemical Chemical substance composed of atoms with the same number of protons....
actinium

Actinium

Actinium is a radioactive chemical element with the symbol Ac and atomic number 89, which was discovered in 1899. It was the first Primordial element to be isolated, although polonium, radium and radon were observed before, but not isolated until 1902....
). The acetyl radical contains a methyl group single-bonded to a carbonyl

Carbonyl

In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double bond to an oxygen atom : C=O.The term carbonyl can also refer to carbon monoxide as a ligand in an inorganic or organometallic complex ; in this situation, carbon is triple-bonded to oxygen : C=O....
. The carbon

Carbon

Electron

The electron is a subatomic particle that carries a negative electric charge. It has elementary particle and is believed to be a point particle....
available, with which it forms a chemical bond

Chemical bond

A chemical bond is the physical process responsible for the attractive interactions between atoms and molecules, and that which confers stability to diatomic and polyatomic chemical compounds....
to the remainder R of the molecule.

The acetyl radical is a component of many organic compound

Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
s, including the neurotransmitter

Neurotransmitter

Neurotransmitters are chemistry which relay, amplify and modulate signals between a neuron and another cell . Neurotransmitters are packaged into vesicles that cluster beneath the membrane on the presynaptic side of a synapse, and are released into the synaptic cleft, where they bind to receptors in the membrane on the postsynaptic side of...
acetylcholine

Acetylcholine

The chemical compound acetylcholine is a neurotransmitter in both the peripheral nervous system and central nervous system in many organisms including homo sapiens....
, and acetyl-CoA

Acetyl-CoA

Acetyl-CoA is an important molecule in metabolism, used in many biochemical reactions. Its main use is to convey the carbon atoms within the acetyl group to the citric acid cycle to be oxidation for energy production....
, and the analgesic

Analgesic

An analgesic is any member of the diverse group of Medication used to relieve pain . The word analgesic derives from Greek an- and algos ....
s acetaminophen and acetylsalicylic acid (better known as aspirin

Aspirin

Aspirin , also known as acetylsalicylic acid , is a salicylate medication, often used as an analgesic to relieve minor aches and pains, as an antipyretic to reduce fever, and as an anti-inflammatory medication....
).

Acetylation
The introduction of an acetyl group into a molecule is called acetylation

Acetylation

Acetylation describes a reaction that introduces an acetyl functional group into an organic compound. Deacetylation is the removal of the acetyl group....
(or ethanoylation).

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Encyclopedia

In organic chemistry

Organic chemistry

Functional group

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules....
, the acyl

Acyl

Acetic acid

Chemical formula

Carbon

Oxygen

Carbon

Hydrogen

Chemical element

Actinium

Carbonyl

Carbon

Electron

The electron is a subatomic particle that carries a negative electric charge. It has elementary particle and is believed to be a point particle....
available, with which it forms a chemical bond

Chemical bond

Organic compound

Neurotransmitter

Acetylcholine

The chemical compound acetylcholine is a neurotransmitter in both the peripheral nervous system and central nervous system in many organisms including homo sapiens....
, and acetyl-CoA

Acetyl-CoA

Analgesic

Aspirin

Acetylation

The introduction of an acetyl group into a molecule is called acetylation

Acetylation

Acetylation describes a reaction that introduces an acetyl functional group into an organic compound. Deacetylation is the removal of the acetyl group....
(or ethanoylation). In biological organisms, acetyl groups are commonly transferred bound to Coenzyme A

Coenzyme A

Coenzyme A is a coenzyme, notable for its role in the Fatty acid metabolism#Synthesis and Fatty acid metabolism#.CE.B2-Oxidation of fatty acids, and the oxidation of pyruvic acid in the citric acid cycle....
(CoA), in the form of acetyl-CoA. Acetyl-CoA is an important intermediate both in the biological synthesis and in the breakdown of many organic molecules.

Acetyl groups are also frequently added to histone

Histone

In biology, histones are the chief protein components of chromatin. They act as spools around which DNA winds, and they play a role in gene regulation....
s and other protein

Protein

Proteins are organic compounds made of amino acids arranged in a linear chain and joined together by peptide bonds between the carboxyl and amino groups of adjacent amino acid Residue ....
s modifying their properties. For example, on the DNA level, histone acetylation by acetyltransferase

Acetyltransferase

Acetyltransferase is a type of transferase enzyme which transfers an acetyl group.Examples include:* Histone acetyltransferases including CBP histone acetyltransferase...
s (HATs) causes an expansion of chromatin architecture allowing for genetic transcription

Transcription (genetics)

Transcription is the synthesis of RNA under the direction of DNA. RNA synthesis, or transcription, is the process of transcribing DNA nucleotide sequence information into RNA sequence information....
to take place. Conversely, removal of the acetyl group by histone deacetylase

Histone deacetylase

Histone deacetylases are a class of enzymes that remove acetyl groups from an e-N-acetyl lysine amino acid on a histone. Its action is opposite to that of histone acetyltransferase....
s (HDACs) condenses DNA structure, thereby preventing transcription.

Chemical acetylation

Acetylation

Acetylation describes a reaction that introduces an acetyl functional group into an organic compound. Deacetylation is the removal of the acetyl group....
can be achieved using a variety of methods, most commonly by the use of acetic anhydride

Acetic anhydride

Acetic anhydride is the chemical compound with the chemical formula 2O. Commonly abbreviated Acetyl2O, it is one of the simplest acid anhydrides and is a widely used reagent in organic synthesis....
or acetyl chloride

Acetyl chloride

Acetyl chloride is an acid chloride derived from acetic acid. It has the formula CH3COCl and it belongs to the class of organic compounds called acyl halides....
in the presence of a tertiary or aromatic amine

Amine

Amines are organic compounds and functional groups that contain a base nitrogen atom with a lone pair. Amines are derivative s of ammonia, wherein one or more hydrogen atoms are replaced by organic substituents such as alkyl and aryl groups....
base

Base (chemistry)

In chemistry, a base is most commonly thought of as an aqueous substance that can accept protons. A base is also often referred to as an alkali if OH- ions are involved....
.

Pharmacology

When acetyl groups are bound to certain other organic molecules, they impart an increased ability to cross the blood-brain barrier

Blood-brain barrier

The blood-brain barrier is a metabolic or cellular structure in the central nervous system that restricts the passage of various chemical substances and microscopic objects between the bloodstream and the neural tissue itself, while still allowing the passage of substances essential to metabolism function ....
. This makes the drug reach the brain more quickly, making the drug's effects more intense and increasing the effectiveness of a given dose. Acetyl groups are used to make the natural anti-inflammatant salicylic acid

Salicylic acid

Salicylic acid is a beta hydroxy acid with the chemical formula C6H4COOH, where the OH group is adjacent to the carboxylic acid....
into the more effective acetylsalicylic acid, or aspirin

Aspirin

Aspirin , also known as acetylsalicylic acid , is a salicylate medication, often used as an analgesic to relieve minor aches and pains, as an antipyretic to reduce fever, and as an anti-inflammatory medication....
. Similarly, they make the natural painkiller morphine

Morphine

Morphine is a highly potent opiate analgesic Medication, is the principal active agent in opium, and is considered to be the prototypical opioid....
into diacetylmorphine, or heroin

Heroin

Heroin is a opioid synthesized from morphine, a derivative of the opium poppy. It is the 3,6-acetate ester of morphine . The white crystalline form is commonly the hydrochloride salt diacetylmorphine hydrochloride, however heroin Freebase may also appear as a white powder....
.

Most recently, the supplement industry touts acetyl-L-carnitine as being more effective than other preparations of carnitine

Carnitine

Carnitine is a Quaternary ammonium cation biosynthesized from the amino acids lysine and methionine. In living cells, it is required for the transport of fatty acids from the cytosol into the mitochondria during the breakdown of lipids for the generation of metabolic energy....
. Also, research on irradiated rodents shows resveratrol

Resveratrol

Resveratrol is a phytoalexin produced naturally by several plants when under attack by pathogens such as bacteria or fungi. Resveratrol has also been produced by chemical synthesis and is sold as a nutritional supplement derived primarily from Japanese knotweed....
attached to acetyl as holding promise as one of the first anti-radiation medicines for human populations. For citation, see the webpage article of http://www.sciencedaily.com/releases/2008/09/080923181110.htm.

Acetyl

Acetylation

Pharmacology

See also