Thursday, March 13, 2008

The Japanese magic bullet

The people of the Sea Shepherd claim the Japanese have a magic bullet.


starbird said...

Butyric acid
From Wikipedia, the free encyclopedia
Butyric acid

IUPAC name butanoic acid
Other names butyric acid
CAS number [107-92-6]
PubChem 264
MeSH Butyric+acid
Molecular formula C4H8O2
Molar mass 88.1051 g/mol
Density 0.96 g/mL
Melting point
-7.9 °C (265.1 K)

Boiling point
163.5 °C (436.5 K)

Solubility in water miscible
Main hazards Corrosive; Harmful to aquatic organisms
R-phrases 34
S-phrases 26 36 45
Flash point 72 °C
temperature 452 °C
RTECS number ES5425000
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references
Butyric acid, (from Greek βούτυρος = butter) IUPAC name -Butanoic acid, or normal butyric acid, is a carboxylic acid with structural formula CH3CH2CH2-COOH. It is found in rancid butter, parmesan cheese, and vomit, and has an unpleasant odor and acrid taste, with a sweetish aftertaste (similar to ether). Butyric acid can be detected by mammals with good scent detection abilities (e.g. dogs) at 10 ppb, whereas humans can detect it in concentrations above 10 ppm.
Butyric acid is a fatty acid occurring in the form of esters in animal fats and plant oils. The glyceride of butyric acid makes up 3% to 4% of butter. When butter goes rancid, butyric acid is liberated from the glyceride by hydrolysis leading to the unpleasant odor. It is an important member of the fatty acid sub-group called short chain fatty acids. Butyric acid is a weak acid with a pKa of 4.82, similar to acetic acid which has pKa 4.76.[1] The similar strength of these acids results from their common -CH2COOH terminal structure.[2] Butyric acid has density 0.96 g/cm3 and molecular mass 88.1051; thus pure butyric acid is 10.9 molar.
Normal butyric acid or fermentation butyric acid is also found as a hexyl ester (hexyl butanoate) in the oil of Heracleum giganteum (a type of cow parsnip) and as an octyl ester (octyl butanoate) in parsnip (Pastinaca sativa); it has also been noticed in the fluids of the flesh and in perspiration.
It is ordinarily prepared by the fermentation of sugar or starch, brought about by the addition of putrefying cheese, with calcium carbonate added to neutralize the acids formed in the process. The butyric fermentation of starch is aided by the direct addition of Bacillus subtilis. Salts and esters of the acid are called butanoates.
Butyric acid is used in the preparation of various butanoate esters. Low-molecular-weight esters of butyric acid, such as methyl butanoate, have mostly pleasant aromas or tastes. As a consequence, they find use as food and perfume additives. They are also used in organic laboratory courses, to teach the Fisher esterification reaction.
The acid is an oily colorless liquid that freezes at -8 °C; it boils at 164 °C. It is easily soluble in water, ethanol, and ether, and is thrown out of its aqueous solution by the addition of calcium chloride. Potassium dichromate and sulfuric acid oxidize it to carbon dioxide and acetic acid, while alkaline potassium permanganate oxidizes it to carbon dioxide. The calcium salt, Ca(C4H7O2)2·H2O, is less soluble in hot water than in cold.
There is an isomer, methylpropanoic acid, (formerly isobutyric acid) which has the same chemical formula C4H8 O2 but a different structure. It has similar chemical properties but different physical properties.
Contents [hide]
1 Butanoate fermentation
1.1 Acetone and butanol fermentation
1.2 Butyric acid function/activity
2 References
3 See also
4 External links
[edit]Butanoate fermentation

Butanoate is produced as end-product of a fermentation process solely performed by obligate anaerobic bacteria. Fermented Kombucha "tea" includes butyric acid as a result of the fermentation. This fermentation pathway was discovered by Louis Pasteur in 1861. Examples of butanoate-producing species of bacteria:
Clostridium acetobutylicum
Clostridium butyricum
Clostridium kluyveri
Clostridium pasteurianum
Fusobacterium nucleatum
Butyrivibrio fibrisolvens
Eubacterium limosum
The pathway starts with the glycolytic cleavage of glucose to two molecules of pyruvate, as happens in most organisms. Pyruvate is then oxidized into acetyl coenzyme A using a unique mechanism that involves an enzyme system called pyruvate-ferredoxin oxidoreductase. Two molecules of carbon dioxide (CO2) and two molecules of elemental hydrogen (H2) are formed as wastes products from the cell. Then:
Action Responsible enzyme
Acetyl coenzyme A converts into acetoacetyl coenzyme A acetyl-CoA-acetyl transferase
Acetoacetyl coenzyme A converts into β-hydroxybutyryl CoA β-hydroxybutyryl-CoA dehydrogenase
β-hydroxybutyryl CoA converts into crotonyl CoA crotonase
Crotonyl CoA converts into butyryl CoA (CH3CH2CH2C=O-CoA) butyryl CoA dehydrogenase
A phosphate group replaces CoA to form butyryl phosphate phosphobutyrylase
The phosphate group joins ADP to form ATP and butyrate butyrate kinase
ATP is produced, as can be seen, in the last step of the fermentation. Three molecules of ATP are produced for each glucose molecule, a relatively high yield. The balanced equation for this fermentation is:
C6H12O6 → C4H8O2 + 2CO2 + 2H2
[edit]Acetone and butanol fermentation
Several species form acetone and butanol in an alternative pathway, which starts as butyrate fermentation. Some of these species are:
Clostridium acetobutylicum: the most prominent acetone and butanol producer, used also in industry
Clostridium beijerinckii
Clostridium tetanomorphum
Clostridium aurantibutyricum
These bacteria begin with butanoate fermentation as described above, but, when the pH drops below 5, they switch into butanol and acetone production in order to prevent further lowering of the pH. Two molecules of butanol are formed for each molecule of acetone.
The change in the pathway occurs after acetoacetyl CoA formation. This intermediate then takes two possible pathways:
Acetoacetyl CoA → acetoacetate → acetone, or
Acetoacetyl CoA → butyryl CoA → butanal → butanol.
[edit]Butyric acid function/activity
Highly-fermentable fibers like oat bran, pectin, and guar are transformed by colonic bacteria into short-chain fatty acids including butyrate.
Butanoate has diverse and, it seems, paradoxical effects on cellular proliferation, apoptosis and differentiation that may be either pro-neoplastic or anti-neoplastic, depending upon factors such as the level of exposure, availability of other metabolic substrate, and the intracellular milieu. Butanoate is thought by some to be protective against colon cancer. However, not all studies support a chemopreventive effect, and the lack of agreement (particularly between in vivo and in vitro studies) on butyrate and colon cancer has been termed the "butyrate paradox." There are many reasons for this discrepant effect, including differences between the in vitro and in vivo environments, the timing of butanoate administration, the amount administered, the source (usually dietary fiber) as a potential confounder, and an interaction with dietary fat. Together, the studies suggest that the chemopreventive benefits of butanoate depend in part on amount, time of exposure with respect to the tumorigenic process, and the type of fat in the diet.[3] Low carbohydrate diets like the Atkins diet are known to reduce the amount of butanoate produced in the colon.
Butyric acid has been associated with the ability to inhibit the function of histone deacetylase enzymes, thereby favouring an acetylated state of histones in the cell. Acetylated histones have a lower affinity for DNA than non-acetylated histones, due to the neutralisation of electrostatic charge interections. In general, it is thought that transcription factors will be unable to access regions where histones are tightly associated with DNA (ie non-acetylated, e.g., heterochromatin). Therefore, it is thought that butyric acid enhances the transcriptional activity at promoters, which are typically silenced/downregulated due to histone deacetylase activity.
This article incorporates information from the 1911 encyclopedia.

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