Citrate

Citrate
Identifiers
PubChem	31348
ChemSpider	29081 Y
Jmol-3D images	Image 1
SMILES C(C(=O)[O-])C(CC(=O)[O-])(C(=O)[O-])O
InChI InChI=1S/C6H8O7/c7-3(8)1-6(13,5(11)12)2-4(9)10/h13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/p-3 Y Key: KRKNYBCHXYNGOX-UHFFFAOYSA-K Y
Properties
Molecular formula	C 6H 5O3− 7
Molar mass	189 g mol-1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

A citrate is a derivative of citric acid; that is, the salts, esters, and the polyatomic anion found in solution. An example of the former, a salt is trisodium citrate; an ester is triethyl citrate. When part of a salt, the formula of the citrate ion is written as C₆H₅O₇^3- or C₃H₅O(COO)₃³⁻.

Other citric acid ions

Since citric acid is a multifunctional acid, intermediate ions exist, hydrogen citrate ion, HC₆H₅O₇²⁻ and dihydrogen citrate ion, H₂C₆H₅O₇⁻. These may form salts as well, called acid salts.

Acidity

Salts of the hydrogen citrate ions are weakly acidic, while salts of the citrate ion itself (with an inert cation such as sodium ion) are weakly basic.

Buffering

As a weak acid, citrate can be used as a component in buffer solutions, including the commonly used SSC 20X hybridization buffer. This buffer uses sodium citrate and sodium chloride to maintain a neutral 7.0 pH. Other buffers may use a mixture of sodium citrate and citric acid – canonical buffer tables compiled for biochemical studies describe solutions of citrate and acid for buffer pHs of between 3.0 and 6.2.

Chelating

Citric acid can act as a mild chelating agent; citrate, usually in the form of trisodium citrate, may be given as an anticoagulant, because it chelates calcium ions, and therefore inhibits coagulation. Another application is in the form of iron(II) citrate as a nutritional supplement. Here, the benefit is the solubility as a chelate of the otherwise mostly insoluble iron.

Metabolism

Main article: TCA cycle

Citrate is an intermediate in the TCA (Krebs) cycle. After the pyruvate dehydrogenase complex forms acetyl-CoA, from pyruvate and five cofactors (thiamine pyrophosphate, lipoamide, FAD, NAD⁺, and CoA), citrate synthase catalyzes the condensation of oxaloacetate with acetyl CoA to form citrate. Citrate continues in the TCA cycle via aconitase with the eventual regeneration of oxaloacetate, which can combine with another molecule of acetyl CoA and continue cycling.

Interactive pathway map

Click on genes, proteins and metabolites below to link to respective articles.

[[File:

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

[[

]]

|{{{bSize}}}px]]

TCA Cycle edit

Fatty acid synthesis

Citrate can also be transported out of the mitochondria and into the cytoplasm, then broken down into acetyl-CoA for fatty acid synthesis and into oxaloacetate. Citrate is a positive modulator of this conversion, and allosterically regulates the enzyme acetyl-CoA carboxylase, which is the regulating enzyme in the conversion of acetyl-CoA into malonyl-CoA (the commitment step in fatty acid synthesis). In short, citrate is transported to the cytoplasm, converted to acetyl CoA, which is converted into malonyl CoA by the acetyl CoA carboxylase, which is allosterically modulated by citrate.

See also TCA cycle

Role in glycolysis

High concentrations of cytosolic citrate can inhibit phosphofructokinase, catalyst of one of the rate-limiting steps of glycolysis.

Oxaolacetate Benefits

"A patented substance can mimic caloric restriction and thus increase the lifespan and delay the onset of age-related diseases. '

To prolong the life of unicellular and multicellular animals, many attempts have been made over the past 70 years: nutritional compounds, antioxidants or vitamin supplements, exercise, hormones ...

Although these attempts sometimes lead to better health, only the activation of certain genes could allow increasing the lifespan.

Examples of effective methods to extend the average life span and maximum, it can be the activation of certain genes by caloric restriction, that is to say, limiting total calories from carbohydrates, lipids or protein at a level of 25% to 60% below the normal.

Oxaloacetate mimics and reproduces the known effects and benefits of caloric restriction without the need to use them.

The oxaloacetic acid, or oxaloacetate which is the ionic form, is found naturally in oranges and apples freshly picked. However, this molecule is highly unstable and will not keep more than one day at room temperature.

In the body, the oxaloacetate is present in every cell, and its metabolites are directly involved in the production of mitochondrial energy appears as an intermediate in the Krebs cycle.

Through a complex process, oxaloacetate can now be stabilized and made perfectly bioavailable.

This substance has also received a first all-patents in the lengthening of life, mimicking the effects of caloric restriction.

In this sense, the oxaloacetate is close to the properties of resveratrol but acts by different mechanisms.

This is one of the few products whose ability to increase the lifespan has been verified on male mice, which have a life expectancy shorter than female mice.

When the average mortality rate of 50% was reached, it was found that oxaloacetate supplement (supplementation) caused an increase in the average lifespan of about 25% compared with control mice.

In addition to these impressive results, the researchers found that mice subjected to only supply oxaloacetate had minimal symptoms of inflammation and less tendency to the phenomenon of "bone curvature" associated with age.

In addition, bone density was higher compared to control animals, indicating effective against osteoporosis.

Subsequent studies have shown that the activity of oxaloacetate is not limited to the mouse. It was thus possible to verify in Drosophila melanogaster increased lifespan by 20% on average after adding oxaloacetate food. Similar results were also obtained on the worm C. elegans nematode.

Prolong life and protect the body from aging diseases (renal disease, autoimmune diseases, diabetes) According to all recent research oxaloacetate would own other exceptional properties, not only in mice but also in humans:

- It improves the results of all tests of endurance in mice - It significantly strengthens the antioxidant status, - It regulates blood sugar, - He opposes the denaturation of nucleic acids into the mitochondria, - It protects pancreatic cells, brain tissue and organs of vision by limiting the development of cataracts and AMD,

- It has a positive effect on arthritis and joint stiffness, - It blocks the production of fats by the body, - It repairs DNA in the cells of the skin or other tissues damaged by UV rays, - It reduces symptoms caused by chronic alcoholism (weight loss, nausea, diarrhea, tremors ...) or simply those of a hangover following a timely consumption of alcohol,

- It reduces apoptosis - It delays the onset of complications associated with most age-related diseases, - It reduces the incidence or treatment of primary or metastatic cancer. It may be administered before, during or after chemotherapy, - And most importantly regulates the expression of certain genes that are activated beneficial during caloric restriction. Oxaloacetate thus mimics the cellular conditions obtained with caloric restriction but without the need to reduce food intake.

References

Oxaloacetate Benefits