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CONTENTS PAGES
1 INTRODUCTION
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10 REFERENCES

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 BUTYRIC ACID IN PHARMACEUTICAL

INTRODUCTION
Butyric acid is a saturated short – chain fatty acid with a 4-carbon backbone. Butyric acid is
commonly found in esterified form in animal fats and plant oils .Butyric acid is a colorless liquid
with a penetrating and unpleasant odor. Butyric acid also known as butanoic acid and other
names are 1- Propanecarboxylic acid. The reasons why we choose butyric acid is because it has
various application in industry and currently there is a great interest in using it as a precursor to
biofuels. Besides, butyric acid also is widely occur in pharmaceutical and chemical industry. The
general formula of this compound is C4H8O2 or CH3CH2CH2COOH. Any relevant
information that we found is industrially, butyric acid is prepared by fermentation of sugar or
starch, made more efficient by use of Clostridium tyrobutyricum in a process called catalytic
upgrading. Salts and esters of the acid are called butyrates or butanoates. Butyric acid or
fermentation butyric acid is also present as the octyl ester (octyl butyrate) in parsnip (Pastinaca
sativa) and in the fruit of the ginko tree.

Butyric acid was first observed in impure form in 1814 by the French chemist Michel Eugene
Chevreul. By 1818, he had purified it sufficiently to characterize it. However, Chevrul did not
publish his early research on butyric acid: instead, he deposited his findings in manuscript form
with the secretary of the Academy of Sciences in Paris,France. Henri Braconnot, a French
chemist,was also researching the composition of butter and was publishing his findings, and this
led to disputes about priority. As early as 1815, Chevreul claimed that he had found the
substance responsible for the smell of butter. By 1817, he published some of his findings
regarding the properties of butyric acid and named it. However, it was not until 1823 that he
presented the properties of butyric acid in detail. The name of butyric acid comes from the Latin
word for butter, butyrum (or buturum), the substance in which butyric acid was first found.

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Below is general structure of butyric acid.

(https://en.wikipedia.org/wiki/Butyric_acid)

( (https://pubchem.ncbi.nlm.nih.gov/compound/Butyric-acid#section=Absorption-Distribution-
and-Excretion))

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DISCUSSION
i. Chemical and Physical Properties
The physical properties of butyric acid are oily, colorless liquid that solidifies at -8 °C
and 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. The salts and esters of this acid are
known as butyrates. ( (http://www.newworldencyclopedia.org/entry/Butyric_acid)) The
solubility of this compound is greater than or equal to 100 mg/mL at 66° F while its water
solubility is 60000 mg/L (at 25 °C). The chemical properties of butyric acid include its
acidity is 4.82, the molar mass is 88.11 g/mol and the chemical formula is C4H8O2.
An isomer, called isobutyric acid, has the same chemical formula (C4H8 O2) but a different
structure. It has similar chemical properties but different physical properties.

ii. Function group of the compound

Butyric acid is a group of four-carbon organic compounds that have
both hydroxyland carboxylic acid functional groups. They can be viewed as derivatives
of butyric acid. The carboxylate anion and the esters of hydroxybutyric acids are known
as hydroxybutyrates. (https://en.m.wikipedia.org/wiki/Hydroxybutyric_acid, n.d.)
There are three isomers, distinguished by the distance between the two functional groups:

 alpha-Hydroxybutyric acid (2-hydroxybutyric acid)

 beta-Hydroxybutyric acid (3-hydroxybutyric acid)
 gamma-Hydroxybutyric acid (4-hydroxybutyric acid, GHB)

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iii. Importance of the compound

Butyric acid is used in the preparation of various butyrate esters. Low - molecular -
weight esters of butyric acid, such as methyl butyrate, have mostly pleasant aromas or
tastes. As a consequence, they are used as food and perfume additives. It is an approved
food flavoring. Due to its powerful odor, it has also been used as a fishing bait additive.
Many of the commercially available flavors used in carp (Cyprinus carpio) baits use
butyric acid as their ester base ; however, it is not clear whether fish are attracted by the
butyric acid itself or the substances added to it. Butyric acid was one of the few organic
acids shown to be palatable for both tench and blittering. Butyric acid, along with acetic
acid, can be reacted with cellulose to produce the organic ester cellulose acetate
butyrate (CAB), which is used in a wide variety of tools, parts, and coatings, and is
more resistant to degradation then cellulose acetate. However, CAB can degrade with
exposure to heat and moisture, releasing butyric acid.

Butyric acid has powerful anti- inflammatory effects in the body thanks to its ability
to suppress the activity of certain proteins that produce inflammation. In particular, it
helps control our inflammatory immune response by regulating inflammation –
producing T- cells.Weight loss also one of the importance butyric acid which is has a
nifty trick up its sleeve when it comes to weight loss. While many studies have only
been done on animals, human research shows that short – chain fatty acids like butyrate
have positive metabolic effects and helping improve insulin sensitivity and energy
(glucose) balance.

Some of the most famous studies done on butylic acid show its ability to fight
cancer. This is expecially true when it comes to colorectal cancer, with research finding
that butyrate actually induces “death by apoptosis in colon cancer cells”. The
combination of a high fiber diet (which equals more butyric acid produced), healthy gut
flora ( which butyrate and resistant starcg feed), and decreased inflammation that
butyrate promotes appears to be the reason researchers state, “ a high – fiber diet
protects against colorectal tumors in a microbiota – and butyrate- dependent manner.
(https://draxe.com/butyric-acid/, n.d.)

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iv) Application of the compound
One of the most intriguing possible application of butyric acid is the ability to prevent or even
treat colorectal cancer. Currently, the clinical evidence in primarily anecdotal, but when it comes
down to the biochemistry, the results are clear: butyric acid can inhibit the growth and
proliferation of colon cancer cells. That’s largely because of the well-known “Warburg effect,”
which describes the tendency of cancer cells to generate energy almost entirely through
anaerobic processes like fermentation even in the presence of oxygen. Normal cells do not do
this because anaerobic metabolism is less energy efficient. Using fermentation as a primary
energy generation method leads to the production of unusually high levels of butyric acid. In
turn, high levels of butyric acid increase its gene regulatory in the cell, which causes a colon
cancer cell to undergo apoptosis that is, controlled cell death.

Similarly, there is evidence suggesting that butyric acid can promote the expression of a
GCPR that induces cancer cell apoptosis. Normally, the GCPR is not active in colon cancer cells,
but evidence indicates that when butyric acid is introduced, it can cause the GCPR to activate,
which can cause the cancer cell to undergo apoptosis. This cell communication pathway is
entirely separate from the HDAC-mediated pathway, which makes butyric acid an even more
exciting treatment possibility for researchers to explore in the future, since it may combat
colorectal cancer through multiple pathways which would make the treatment more effective by
coming at the cancer from multiple directions.

Butyric acid also contribute to weight loss and the efforts is still in the early stages, animal
studies suggest that there may be benefits of butyric acid for patients with diabetes, metabolic
syndrome, and obesity. For instance, in one study, a supplement of butyric acid significantly
reduced obesity and insulin resistance in mice that were fed a high-fat diet. There is also some
evidence suggesting that butyric acid may promote the release of hormones that suppress
appetite. While it is clear that human studies will be needed before any strong conclusions can be
drawn, butyric acid supplementation presents an exciting avenue for researchers and clinicians
who are looking for innovative ways to help patients confront issues related to energy intake and
metabolism.

v) Synthesis
Oxidation of primary alcohol
 Carboxylic acids can be prepared from aldehydes (which can be prepared from primary
alcohols)
 Oxidizing agents : K2Cr2O7 (potassium dichromate), CrO3 ( chromium trioxide) – used
alongside H2SO4 and H2O
 During the reaction, the potassium dichromate(VI) solution turns from orange to green

CH3CH2CH2CH2OH + CrO3 → CH3CH2CH2COOH

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vi) Reaction
Hydration of carboxylic acids

 When carboxylic acids are placed in water , they undergo deprotonation.

 Deprotonation : removal/transfer of proton (H+) from a Bronsted-Lowry acid in an acid
base reaction. The reaction yield conjugate base of the acid

CH3CH2CH2COOH + H2O → CH3CH2CH2COO¯+ H3O+

Addition of strong base

 Yield salt :used in drugs and medicine due to the solubility

 The salt are more water soluble than the carboxylic acid itself.
 The salt can be converted back to carboxylic acid bye the additional of strong acid

CH3CH2CH2COO¯Na+ + HCl → CH3CH2CH2COOH + NaCl

vii) Any relevant information

As we know, butyric acid is generally weak acid so they are not completely dissolved in
water (aqueous solution). One of the analytical equipment that can detect butyric acid is HPLC.
This is because HPLC has the refinement of packing material up to 3 to 10µm. HPLC also has
high separation capacity that enable it to analysis multiple components, thus superior quantitative
capability and reproducibility of results.

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CONCLUSION

Butyric acid (CH3CH2CH2COOH) also has many uses in the pharmaceutical industry as it is
becoming one of the important components for of nutrition for human health. Butyric acid is now
been tested to give nutrition for human colon for its short chain fatty acids that play a significant
maintenance of mucusal health. Butyric acid also is the preferred energy substrate for the cells in
the colon thus is very important to the well being of human colon. (Cheng, 2013)

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 APPENDIX
Some pictures that related to butyric acid in pharmaceutical :

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REFERENCES

Bibliography
1. (n.d.). Retrieved from https://pubchem.ncbi.nlm.nih.gov/compound/Butyric-
acid#section=Absorption-Distribution-and-Excretion

2. (http://www.newworldencyclopedia.org/entry/Butyric_acid). (n.d.).

3. (https://pubchem.ncbi.nlm.nih.gov/compound/Butyric-acid#section=Absorption-
Distribution-and-Excretion). (n.d.).

4. http://www.newworldencyclopedia.org/entry/Butyric_acid. (n.d.).

5. https://draxe.com/butyric-acid/. (n.d.).

6. https://en.m.wikipedia.org/wiki/Hydroxybutyric_acid. (n.d.).

7. https://en.wikipedia.org/wiki/Butyric_acid. (n.d.).

8. htt (Cheng, 2013)

9. ps://pubchem.ncbi.nlm.nih.gov/compound/Butyric-acid#section=Heat-of-Combustion.
(n.d.).

10. Ahmed. (1995). Toxicological effects of ethanol on human health. PubMed.

11. Bon. (2015). Citric acid. Science Daily.
12. Denniston, K. J. (2004). General, Organic, and Biochemistry. McGraw HILL
International.
13. Nutr, E. J. (2015). The role of acetic acid on glucose uptake and blood flow rates in the
skeletal muscle in humans with impaired glucose tolerance. PubMed.
14. Radu, G. I. (March 12th 2018). Introductory Chapter: Carboxylic Acids - Key Role in
Life Sciences. IntechOpen

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