BUTYRIC ACID
BUTYRIC ACID
Butyric Acid = Butanoic acid
CAS Number: 107-92-6
EC Number: 203-532-3
Linear Formula: CH3CH2CH2COOH
Molecular Weight: 88.11
Butyric acid is a volatile fatty acid that can be used as a flavoring agent.
Butyric acid has fruity or cheesy flavor and is mainly found in dairy products.
Butyric acid (from Ancient Greek, meaning “butter”), also known under the systematic name butanoic acid, is a straight-chain alkyl carboxylic acid with the chemical formula CH3CH2CH2CO2H.
Butyric acid is an oily, colorless liquid with an unpleasant odor.
Isobutyric acid (2-methylpropanoic acid) is an isomer.
Salts and esters of butyric acid are known as butyrates or butanoates.
The acid does not occur widely in nature, but Butyric acids esters are widespread.
Butyric acid is a common industrial chemical and an important component in the mammalian gut.
Butyric Acid, also known under the systemic name “butanoic acid,” is a carboxylic acid with the structural formal CH3CH2CH2COOH.
Butyric acid is an important flavor compound in a number of foods in addition to beer.
However, at concentrations above Butyric acids beer flavor threshold (2 mg/L), it causes cheesy, rancid, baby vomit, or putrid off-flavors.
Abnormal concentrations in beer Butyric acid can arise from infections by anaerobic spore-forming bacteria of the genus Clostridium.
Butyric acid is a fatty acid that’s created when the good bacteria in your gut break down dietary fiber.
Butyric acid’s also found in animal fats and vegetable oils.
However, the amount of butyric acid found in foods like butter and ghee is small compared to the amount that’s made in your gut.
To date, only limited research has been done, especially on humans, to fully understand the benefits of butyric acid.
Early evidence looks promising, though.
Researchers are continuing to look at the potential that butyric acid has for improving gut health.
Keep reading to learn more about the possible benefits of butyric acid and what researchers have unearthed about it so far.
Butyric acid uses
Butyric acid is used in the preparation of various butyrate esters.
Butyric acid is used to produce cellulose acetate butyrate (CAB), which is used in a wide variety of tools, paints, and coatings, and is more resistant to degradation than cellulose acetate.
However, CAB can degrade with exposure to heat and moisture, releasing butyric acid.
Low-molecular-weight esters of butyric acid, such as methyl butyrate, have mostly pleasant aromas or tastes.
As a consequence, Butyric acid is used as food and perfume additives.
Butyric acid is an approved food flavoring in the EU FLAVIS database (number 08.005).
Due to Butyric acids powerful odor, Butyric acid 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, Butyric acid is not clear whether fish are attracted by the butyric acid itself or the substances added to Butyric acid.
Butyric acid was, however, one of the few organic acids shown to be palatable for both tench and bitterling.
Butyric acid has also been used as a stink bomb by Sea Shepherd Conservation Society to disrupt Japanese whaling crews.
What exactly is butyric acid?
Butyric acid is what’s known as a short-chain fatty acid (SCFA).
Butyric acid’s one of the three most common SCFAs in your gut, along with acetic acid and propionic acid.
These three fatty acids make up between 90 and 95 percentTrusted Source of the SCFAs in your gut.
SCFAs are saturated fatty acids that are created when friendly bacteria break down dietary fiber.
The primary health benefits of butyric acid and other SCFAs are their ability to provide your colon cells with energy.
Butyric acid provides your colon cells with about 70 percentTrusted Source of their total energy needs.
Butyric acid goes by several other names, including butyrate and butanoic acid.
What foods is butyric acid found in?
Most of the butyric acid in your body comes from the bacteria in your gut.
The amount of butyric acid in food is small compared to the amount your gut bacteria produce.
Dietary butyric acid is found in the following foods:
-ghee
-cow’s milk
-butter
-sheep’s milk
-goat’s milk
-breast milk
-parmesan cheese
-red meat
-vegetable oils
-sauerkraut
Butter is one of the best dietary sources of butyric acid.
About 11 percentTrusted Source of the saturated fat in butter comes from SCFAs.
Butyric acid makes up about half of these SCFAs.
You can also take butyric acid as a supplement.
Sodium butyrate is one of the most common forms of the supplement.
You can buy this supplement at most health stores or online.
However, keep in mind that at this time, the benefits of butyric acid supplements aren’t well understood.
Discuss the pros and cons with your doctor.
Increasing your dietary fiber intake is another way to boost the amount of butyric acid in your gut.
The bacteria in your gut primarily feed on resistant starches your body can’t break down.
You can findTrusted Source these resistant starches in fruit, whole grains, legumes, and vegetables, like:
-artichokes
-garlic
-onions
-asparagus
-potatoes
-bananas
-apples
-apricots
-carrots
-oat bran
You can also find resistant starches in carbs that are cooked then cooled, like:
-oats
-beans
-rice
-potatoes
History
Butyric acid was first observed in impure form in 1814 by the French chemist Michel Eugène Chevreul.
By 1818, he had purified it sufficiently to characterize it.
However, Chevreul 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 butyric acid comes from Ancient Greek, meaning “butter”, the substance in which it was first found.
The Latin name butyrum (or buturum) is similar.
Occurrence
Triglycerides of butyric acid compose 3–4% of butter.
When butter goes rancid, butyric acid is liberated from the glyceride by hydrolysis.
Butyric acid is one of the fatty acid subgroup called short-chain fatty acids.
Butyric acid is a typical carboxylic acid that reacts with bases and affects many metals.
Butyric acid is found in animal fat and plant oils, bovine milk, breast milk, butter, parmesan cheese, body odor, vomit, and as a product of anaerobic fermentation (including in the colon).
Butyric acid has a taste somewhat like butter and an unpleasant odor.
Mammals with good scent detection abilities, such as dogs, can detect Butyric acid at 10 parts per billion, whereas humans can detect it only in concentrations above 10 parts per million.
In food manufacturing, Butyric acid is used as a flavoring agent.
In humans, butyric acid is one of two primary endogenous agonists of human hydroxycarboxylic acid receptor 2 (HCA2), a Gi/o-coupled G protein-coupled receptor.
Butyric acid is present as Butyric acids octyl ester in parsnip (Pastinaca sativa) and in the seed of the ginkgo tree.
Butyric acid (C3H7COOH) is a clear, colorless liquid, with a strong pungent odor. Butyric acid is a naturally occurring short-chain fatty acid found in the human body, butter, and numerous other sources.
Esters and salts of butyric acid are used in a variety of applications including perfumes, flavorings, and animal feeds.
Butyric acid, also known as butanoic acid or butyrate, belongs to the class of organic compounds known as straight chain fatty acids.
These are fatty acids with a straight aliphatic chain.
Butyric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Butyric acid is a potentially toxic compound.
CAS Number
Butyric acid: 107-92-6
Butyrate: 461-55-2
ChEBI: Butyric acid: CHEBI:30772
ChEMBL: Butyric acid: ChEMBL14227
ChemSpider:
Butyric acid: 259
Butyrate: 94582
DrugBank:
Butyric acid: DB03568
ECHA InfoCard: 100.003.212
EC Number
Butyric acid: 203-532-3
IUPHAR/BPS
Butyric acid: 1059
KEGG
Butyric acid: C00246 check
MeSH: Butyric+acid
PubChem CID
Butyric acid: 264
Butyrate: 104775
RTECS number
Butyric acid: ES5425000
UNII
Butyric acid: 40UIR9Q29H check
UN number: 2820
CompTox Dashboard (EPA)
Butyric acid: DTXSID8021515
Butyric acid (BA) is a carboxylic acid with the formula CH3-CH2-CH2-COOH.
Butyric acid is frequently used in the veterinary field, especially in ruminant animals.
Together with other short-chain fatty acids (propionic acid and acetic acid), BA is the principal source of energy produced by ruminal fermentation of cellulose and starch.
In the field of zootechnics, butyric acid is used to improve the growth of bovine animals.
In humans, BA is synthesised by the colonic microflora (microbiota) during fermentation of digestible fibre, such as cereal flour, inulin, and psyllium.
Production
Industrial
In industry, butyric acid is produced by hydroformylation from propene and syngas, forming butyraldehyde, which is oxidised to the final product.
H2 + CO + CH3CH=CH2 → CH3CH2CH2CHO → butyric acid
Butyric acid can be separated from aqueous solutions by saturation with salts such as calcium chloride.
The calcium salt, Ca(C4H7O2)2·H2O, is less soluble in hot water than in cold.
What are the benefits of butyric acid?
You’ve likely heard that eating fiber is good for your digestion.
Part of the reason why eating more fiber may improve your gut health is because it leads to your colon producing more butyric acid.
Although clinical evidence is limited, early research suggests butyric acid could have several benefits, as outlined below.
Preferred IUPAC name: Butanoic acid
Other names:
Ethylacetic acid
1-Propanecarboxylic acid
Propylformic acid
C4:0 (Lipid numbers)
Chemical formula: C3H7COOH
Molar mass: 88.106 g·mol−1
Appearance: Colorless liquid
Odor: Unpleasant, similar to vomit or body odor
Density:
1.135 g/cm3 (−43 °C)
0.9528 g/cm3 (25 °C)
Melting point: −5.1 °C (22.8 °F; 268.0 K)
Boiling point: 163.75 °C (326.75 °F; 436.90 K)
Sublimation
conditions: Sublimes at −35 °C
ΔsublHo = 76 kJ/mol
Solubility in water: Miscible
Solubility: Miscible with ethanol, ether. Slightly soluble in CCl4
log P: 0.79
Vapor pressure: 0.112 kPa (20 °C)
0.74 kPa (50 °C)
9.62 kPa (100 °C)
Henry’s law
constant (kH): 5.35·10−4 L·atm/mol
Acidity (pKa): 4.82
Magnetic susceptibility (χ): −55.10·10−6 cm3/mol
Thermal conductivity: 1.46·105 W/m·K
Refractive index (nD): 1.398 (20 °C)
Viscosity: 1.814 cP (15 °C)
1.426 cP (25 °C)
Butyric acid has many uses in different industries, and currently there is a great interest in using it as a precursor to biofuels.
Due to increases in petroleum prices as well as a continuous reduction in petroleum availability and a growing need for clean energy sources, research has recently been directed towards alternative fuel sources.
Biofuels in general offer many advantages including sustainability, a reduction of greenhouse gas emissions, and security of supply.
The term biofuel generally refers to solid, liquid, or gaseous fuels that are predominantly produced from biomass and will be used as such throughout this paper.
Furthermore, liquid biofuels can be broadly classified into (a) bioalcohols, (b) vegetable oils and biodiesels, and (c) biocrude and synthetic oils.
As Butyric acid is one of the most promising biofuels for replacing gasoline in the future, a lot of attention these days is paid toward biobutanol.
Butyric acids primary use is as an industrial solvent, but it also offers several advantages over ethanol as a transportation fuel.
For instance, the three carbon-carbon bonds in butanol provide more energy when burned than the two bonds present in two molecules of ethanol, that is, four carbons total for each fuel.
In addition, butanol is less volatile than ethanol, can replace gasoline in internal combustion engines without any mechanical modifications, does not attract water like ethanol so it can be transported in existing pipelines, is not miscible with water, and is less sensitive to colder temperatures.
butyric acid
butanoic acid
107-92-6
n-Butyric acid
n-Butanoic acid
propylformic acid
ethylacetic acid
Butanic acid
1-propanecarboxylic acid
1-Butyric acid
Buttersaeure
butanoate
Butyric acid (natural)
Kyselina maselna
Propanecarboxylic acid
Buttersaeure [German]
1-butanoic acid
FEMA Number 2221
Kyselina maselna [Czech]
MFCD00002814
FEMA No. 2221
Butyric acid is an important chemical currently produced from petrochemical feedstocks.
Butyric acids production from renewable, low-cost biomass in fermentation has attracted large attention in recent years.
In this study, the feasibility of corn husk, an abundant agricultural residue, for butyric acid production by using Clostridium tyrobutyricum immobilized in a fibrous bed bioreactor (FBB) was evaluated.
Insulin sensitivity
People with type 2 diabetes often have low amountsTrusted Source of butyric acid–producing bacteria in their gut.
However, at this point in time, there’s limited evidence to suggest increasing butyric acid in humans has the same effect on insulin sensitivity.
How much butyric acid do you need?
At this time, there aren’t any guidelines around how much butyric acid you need.
Increasing your fiber intake may be the best strategy for boosting the amount of butyric acid in your gut.
Even the richest food sources contain relatively little of this fatty acid compared to the amount your gut bacteria create.
How to Use Butyric acid:
An increased intake of highly processed, low-fiber, high-sugar foods has been shown to decrease levels of butyrate production in the large intestine.
Supplementing with butyric acid might be a good idea if you’re unable to obtain enough of it from your diet.
A butyric acid supplement is typically available at health stores or online.
Butyric acid’s most commonly found in capsule or tablet form.
Dosage recommendations vary by product.
Some recommend one to six capsules/tablets after meals while others suggest taking one capsule three times daily with meals, a few hours before or after taking other medications.
Butyric acid’s best to read product labels carefully and consult your doctor if you feel unsure.
If you prefer to get your butyric acid from foods, then the following are good choices: butter, ghee, raw milk and parmesan cheese.
When looking for a high-quality butter, raw and cultured is best.
This might be hard to find, however.
Organic butter from grass-fed cows is your next best option.
Some properly made kombucha (a fermented tea drink) can also contain butyric acid.
To naturally increase the butyric acid production in your body, you can up your intake of healthy prebiotics like raw Jerusalem artichokes, raw dandelion greens, raw jicama and under-ripe bananas.
Scientific research has found that fecal butyrate levels can vary greatly among individuals, but eating a diet high in resistance starches (like an under-ripe banana) typically increases butyric acid levels and may help maintain colorectal health.
Related: Gymnema Sylvestre: An Ayurvedic Herb That Helps Fight Diabetes, Obesity & More
Butyric acid applications/uses:
-Commerical printing inks
-Feed ingredients
-Feed intermediates
-Food flavors & food fragrances
-Intermediates
-Pharmaceutical chemicals
-Plasticizer
Butyric Acid Interesting Facts
Butyric acid gets its name from the Greek which means butter.
Butyric acid makes up about 3 percent to 4 percent of butter.
Ever smell rancid butter?
That unpleasant odor is the result of the chemical breakdown of the BTA glyceride.
While on the topic of gross odors, butyric acid is actually responsible for human vomit’s distinctive scent too.
During his extremely long life (102 years plus), a French organic chemist named Michel Eugène Chevreul is said to have first observed butyric acid in its impure form in 1814.
Butyric acid was by the acidification of animal fat soaps that he was able to identify butyric acid along with several other fatty acids for the first time, including oleic acid, capric acid (naturally occurs in coconut oil) and valeric acid.
Substituents
-Straight chain fatty acid
-Monocarboxylic acid or derivatives
-Carboxylic acid
-Carboxylic acid derivative
-Organic oxygen compound
-Organic oxide
-Hydrocarbon derivative
-Organooxygen compound
-Carbonyl group
-Aliphatic acyclic compound
Butyric acid (CH3CH2CH2CO2H), also called butanoic acid, a fatty acid occurring in the form of esters in animal fats and plant oils.
As a glyceride (an ester containing an acid and glycerol), it makes up 3–4 percent of butter; the disagreeable odour of rancid butter is that of hydrolysis of the butyric acid glyceride.
The acid is of considerable commercial importance as a raw material in the manufacture of esters of lower alcohols for use as flavouring agents; its anhydride is used to make cellulose butyrate, a useful plastic.
Butyric acid is manufactured by catalyzed air oxidation of butanal (butyraldehyde).
CCRIS 6552
HSDB 940
butoic acid
2-butanoate
NSC 8415
UNII-40UIR9Q29H
UN2820
AI3-15306
C4:0
CH3-[CH2]2-COOH
40UIR9Q29H
CHEBI:30772
NSC8415
butanate
propylformate
Butyrate sodium
1-butanoate
propanecarboxylate
1-butyrate
Butyric acid [UN2820] [Corrosive]
Sodium n-butyrate
1-propanecarboxylate
Irritable bowel syndrome and Crohn’s disease
Some research suggests taking butyric acid supplements could potentially be used as a treatment for irritable bowel syndrome (IBS) and Crohn’s disease.
In one double-blind, randomized placebo studyTrusted Source, 66 adults with IBS received a daily dose of either 300 milligrams (mg) of sodium butyrate or a placebo.
After 4 weeks, participants in the butyric acid group reported significantly less abdominal pain.
In another studyTrusted Source, researchers gave 13 patients with Chron’s disease 4 grams of butyric acid a day for 8 weeks.
At the end of the 8-week treatment, 9 of the 13 participants had improved symptoms.
Formula: C4H8O2 / CH3CH2CH2COOH
Molecular mass: 88.1
Boiling point: 164°C
Melting point: -7.9°C
Relative density (water = 1): 0.96
Solubility in water: miscible
Vapour pressure, Pa at 20°C: 57
Relative vapour density (air = 1): 3
Flash point: 72°C c.c.
Auto-ignition temperature: 452°C
Explosive limits, vol% in air: 2-10
Octanol/water partition coefficient as log Pow: 0.79
Colon cancer
Most of the research looking at butyric acid’s ability to prevent or treat colon cancer has been done on animals or isolated cells.
In one studyTrusted Source, researchers found that sodium butyrate blocked the growth of colorectal cancer cells.
The same study also found it increased the rate of cell death.
Researchers suggest a higher intake of dietary fiber, which could increase the amount of butyric acid the gut produces, may help reduce the risk of colon cancer.
However, more human studies are needed to explore this.
DSSTox_CID_1515
n-Butyric acid, 99+%
DSSTox_RID_76192
DSSTox_GSID_21515
67254-79-9
BUA
acide butyrique
CAS-107-92-6
Butyric Acid (Normal)
EINECS 203-532-3
BRN 0906770
sodium-butyrate
acide butanoique
Fatty acids
Honey robber
ethyl acetic acid
1ugp
3umq
What Is Butyric Acid?
Butyric acid is a colorless liquid that is soluble in water.
Scientifically speaking, Butyric acids structure is four carbon fatty acids with the molecular formula C4H8O2 or CH3CH2CH2COOH.
Butyric acid has other chemical names, including butanoic acid, n-butyric acid, n-butanoic acid and propylformic acid.
Along with acetic and propionic acids, Butyric acid account for approximately 83 percent of the short chain fatty acids in the human colon.
On its own, BTA has an unpleasant smell and bitter, pungent taste, with a somewhat sweet aftertaste.
Butyric acid occurs as esters in animal fats and plant oils.
Butyric is also known as “rancid”, “piquant”, or “baby’s breath”.
Butyric acids causative compound, butyric acid, can be found in many different cheeses at low amounts and is an important part of total flavor profile.
When in higher concentrations, Butyric acids own flavor begins to dominate and becomes much more prominent.
Butyric acid comes about through the breakdown of fat. Enzymes called lipases clip off fatty acids from the fat molecule as we’ve already discussed here.
Some of these fatty acids will be butyric acid.
The lipase enzymes can be found naturally in raw milk or are sometimes added by the cheese maker.
Excessive handling of the milk could also lead to rancid defects due to damaging the fat globules and exposing them to the endogenous lipases.
Butyric acid is a four carbon acid.
Butyric acids small size makes it quite volatile.
Butyric acid can usually be strongly perceived in headspace of packages or after swallowing.
What’s an ester?
An ester is an organic compound that reacts with water to produce alcohols and organic or inorganic acids.
Esters derived from carboxylic acids like butyric acid are the most common type of esters.
BTA is generated in the large intestine together with other short chain fatty acids from the fermentation of dietary carbohydrates, specifically prebiotics like resistant starches, fructooligosaccharides and other dietary fiber.
The names “butyric acid” and “butyrate” are commonly used interchangeably even in scientific articles and studies.
Technically, they have slightly different structures, but they’re still very similar.
Butyrate or butanoate is the traditional name for the conjugate base of butyric acid.
Put simply, butyrate is almost identical to butyric acid, but it just has one less proton.
Judging by scientific studies, they appear to be pretty much identical in their health benefits.
Quality Level: 200
vapor density: 3.04 (vs air)
vapor pressure: 0.43 mmHg ( 20 °C)
assay: ≥99%
form: liquid
autoignition temp.: 824 °F
expl. lim.: 10 %
application(s): HPLC: suitable
refractive index: n20/D 1.398 (lit.)
pH:
2 (25 °C, 10 g/L)
3 (20 °C, 10 g/L)
bp: 162 °C (lit.)
mp: −6-−3 °C (lit.)
density: 0.964 g/mL at 25 °C (lit.)
SMILES string: CCCC(O)=O
InChI: 1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6)
InChI key: FERIUCNNQQJTOY-UHFFFAOYSA-N
Gene Information: human … HDAC1(3065)
Health Benefits of Butyric acid:
1. Weight Loss
Butyric has gained popularity for its ability to possibly help people shed unwanted pounds.
Scientific evidence has shown that people who are obese (as well as people who have type II diabetes) have a different composition of gut bacteria.
Short chain fatty acids are believed to play a positive role along with probiotics in preventing metabolic syndrome, which almost always includes abdominal obesity.
Short chain fatty acids like butyric acid help regulate the balance between fatty acid synthesis and the breakdown of fats.
In a 2007 animal study, after five weeks of treatment with BTA, obese mice lost 10.2 percent of their original body weight, and body fat was reduced by 10 percent.
Butyric acid was also shown to improve insulin sensitivity, which helps guard against weight gain.
Most of the evidence for linking BTA supplementation specifically to weight loss is based on animal research so far, but it does show positive effects in treating obesity naturally.
2. Potential Colorectal Cancer Treatment
Multiple studies have shown butyric acid’s potential ability to fight cancer, especially cancer in the colon.
Butyric acid’s actually shown an ability to “modify nuclear architecture” and induce the death of colon cancer cells.
This is likely a huge reason why increased fiber intake has been linked with less colon cancer since higher fiber intake can typically equate to more butyric acid present in the colon.
According to 2011 research published in the International Journal of Cancer, “the role of short chain fatty acids, particularly butyrate, in colon cancer therapy has been extensively studied, and its tumor suppressive functions are believed to be due to their intracellular actions.”
This laboratory study further shows that butyrate treatment led to an increase in the programmed cell death of colon cancer cells.
According to a 2014 scientific article, it looks like “a high-fiber diet protects against colorectal tumors in a microbiota- and butyrate-dependent manner.”
What does that mean?
Butyric acid means that most likely getting plenty of fiber isn’t what fends off cancer on its own.
Butyric acid’s eating a diet rich in healthy fiber AND having enough good gut flora AND enough BTA present in the body that can provides cancer defense in the colon.
3. Irritable Bowel Syndrome (IBS) Relief
In general, butyric acid can have a very positive impact on gut health, which greatly affects the health of your entire body.
Short chain fatty acids like butyric acid can help keep the gut ling healthy and sealed, which prevents leaky gut syndrome and all kinds of issues linked to a leaky gut like IBS symptoms.
This is a type of digestive disorder that’s characterized by a group of common symptoms, including changes in bowel movements and abdominal pain.
A scientific article published in the Gastroenterology Review looked at butyric acid’s potential as an IBS diet therapy based on numerous studies conducted to date.
Researchers conclude that “butyrate supplementation seems to be a promising therapy for IBS.”
Some notable 2012 research included in the article was a double-blind, randomized, placebo-controlled study involving 66 adult patients with IBS who were given microencapsulated butyric acid at a dose of 300 milligrams per day or a placebo in addition to receiving standard therapy.
After four weeks, researchers found that subjects who took the butyric acid had a statistically significant decrease in the frequency of abdominal pain during bowel movements.
After 12 weeks, subjects in the BTA group experienced decreases in the frequency of spontaneous abdominal pain, postprandial abdominal pain, abdominal pain during defecation and urge after defecation.
4. Crohn’s Disease Treatment
Crohn’s disease is a type of inflammatory bowel disease (IBD) characterized by inflammation of the lining of the GI tract, abdominal pain, severe diarrhea, fatigue, weight loss and malnutrition.
Again, this is a disease related to a leaky gut.
A 2005 study published in the journal Alimentary Pharmacology & Therapeutics was small, but it found that “oral butyrate is safe and well tolerated, and may be effective in inducing clinical improvement/remission in Crohn’s disease.”
Another 2013 study showed that butyric acid can reduce pain during bowel movements and inflammation in the gut, both of which are extremely helpful to Crohn’s disease and other inflammatory bowel diseases.
Short chain fatty acids like BTA truly play a crucial role in the maintenance of gut barrier integrity, which can help ward off a leaky gut and avoid an IBDs like Crohn’s.
5. Combats Insulin Resistance
A 2009 study published by the American Diabetes Foundation looked at butyric acid’s effect on the regulation of insulin sensitivity in mice consuming a diet high in fat.
The study concluded that “dietary supplementation of butyrate can prevent and treat diet-induced insulin resistance in mouse.”
Researchers also found that the mice treated with butyrate did not have any increase in body fat and the butyrate supplement actually appeared to prevent obesity.
Researchers agree that more studies need to be conducted to further explore how butyrate affects insulin levels in humans, but it looks promising so far, which could have profound effects on treating diabetes.
6. General Anti-inflammatory Effects
Studies have shown the broad anti-inflammatory powers of butyric acid.
Butyric acid’s believed that not only can BTA help inflammatory conditions, but Butyric acidv might also have a helpful ability to manage immune responses.
As we’ve said before, inflammation is the root of most diseases, which is why having more butyric acid in your body could likely benefit many people with various health problems with inflammatory roots.
butanoic acid, 4
Nat. Butyric Acid
Fatty Acid,Vegetable
TNFa + NaBut
Butyrate, sodium salt
Butyric acid [UN2820] [Corrosive]
156779-02-1
BUTYRIC_ACID
n-C3H7COOH
TNFa + Sodium Butyrate
Butyric acid, >=99%
bmse000402
EC 203-532-3
NATURAL BUTYRIC ACID
NCIMech_000707
Butyric acid, a four-carbon fatty acid, is formed in the human colon by bacterial fermentation of carbohydrates (including dietary fiber), and putatively suppresses colorectal cancer (CRC).
Butyrate has diverse and apparently 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.
In humans, the relationship between luminal butyrate exposure and CRC has been examined only indirectly in case-control studies, by measuring fecal butyrate concentrations, although this may not accurately reflect effective butyrate exposure during carcinogenesis.
Perhaps not surprisingly, results of these investigations have been mutually contradictory.
The direct effect of butyrate on tumorigenesis has been assessed in a no. of in vivo animal models, which have also yielded conflicting results.
In part, this may be explained by methodology: differences in the amount and route of butyrate administration, which are likely to significantly influence delivery of butyrate to the distal colon.
Butyric acid is a carboxylic acid 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 is a fatty acid occurring in the form of esters in animal fats and plant oils.
Interestingly, low-molecular-weight esters of butyric acid, such as methyl butyrate, have mostly pleasant aromas or tastes.
As a consequence, they find use as food and perfume additives.
Butyrate is produced as end-product of a fermentation process solely performed by obligate anaerobic bacteria.
What is Butyric Acid?
Butyric acid is known as a short-chain fatty acid (SCFA), which is one among the three most common SCFA’s in the gut, along with acetic acid and propionic acid.
These saturated fatty acids comprise about 90-95 % of the SCFAs in the gut that is produced when gut-friendly bacteria break down dietary fibre.
Butyric acid is well-known to support digestive health, reduce inflammation and lowers the risk of diseases and promote overall health.
Butyric acid holds a significant role in providing colon cells with the needed energy to carry out its normal functions and also regulates blood sugar and cholesterol levels.
Butyric acid goes by other names such as butyrate and butanoic acid.
Appearance: colorless clear liquid (est)
Assay: 99.00 to 100.00 sum of isomers
Food Chemicals Codex Listed: Yes
Specific Gravity: 0.85200 to 0.95600 @ 25.00 °C.
Pounds per Gallon – (est).: 7.089 to 7.955
Refractive Index: 1.39700 to 1.39900 @ 20.00 °C.
Melting Point: -7.00 to -5.00 °C. @ 760.00 mm Hg
Boiling Point: 162.00 to 164.00 °C. @ 760.00 mm Hg
Boiling Point: 90.00 to 91.00 °C. @ 50.00 mm Hg
Vapor Pressure: 1.650000 mmHg @ 25.00 °C.
Vapor Density: 3.04 ( Air = 1 )
Flash Point: 167.00 °F. TCC ( 75.00 °C. )
logP (o/w): 0.790
Shelf Life: 36.00 month(s) or longer if stored properly.
Storage: store in cool, dry place in tightly sealed containers, protected from heat and light.
Butyrate is produced by several fermentation processes performed by obligate anaerobic bacteria.
This fermentation pathway was discovered by Louis Pasteur in 1861.
Examples of butyrate-producing species of bacteria:
Clostridium butyricum
Clostridium kluyveri
Clostridium pasteurianum
Faecalibacterium prausnitzii
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 oxidized into acetyl coenzyme A catalyzed by pyruvate:ferredoxin oxidoreductase.
Two molecules of carbon dioxide (CO2) and two molecules of elemental hydrogen (H2) are formed as waste products.
Subsequently, ATP is produced 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 + 2 CO2 + 2 H2
Other pathways to butyrate include succinate reduction and crotonate disproportionation.
WLN: QV3
ACMC-1C12J
4-02-00-00779 (Beilstein Handbook Reference)
CCCC([O])=O
CHEMBL14227
Butyric acid, >=99%, FG
GTPL1059
BUTYRIC-3,3-D2 ACID
DTXSID3095692
DTXSID8021515
BDBM26109
Butyric acid, analytical standard
Bio1_000444
Bio1_000933
Bio1_001422
N-butyric acid, ethyl acetic acid
ZINC895132
BUTYRIC-1,2-13C2 ACID
Butyric acid (butanoic acid) belongs to a group of short-chain fatty acids and is thought to play several beneficial roles in the gastrointestinal tract.
Butyric anion is easily absorbed by enteric cells and used as a main source of energy.
Moreover, butyric acid is an important regulator of colonocyte proliferation and apoptosis, gastrointestinal tract motility and bacterial microflora composition in addition to its involvement in many other processes including immunoregulation and anti-inflammatory activity.
The pathogenesis of irritable bowel syndrome (IBS), the most commonly diagnosed functional gastrointestinal condition, is complex, and its precise mechanisms are still unclear.
NSC-8415
STR06290
Tox21_202382
Tox21_300164
ANW-15867
CCG-35836
LMFA01010004
STL169349
AKOS000118961
DB03568
MCULE-4116382006
UN 2820
NCGC00247914-01
NCGC00247914-02
NCGC00247914-05
NCGC00253919-01
NCGC00259931-01
Butyric acid is notably found in rancid butter, parmesan cheese, and vomit, and has an unpleasant odor and acrid taste, with a sweetish aftertaste.
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.
Butyric acid is an important member of the fatty acid sub-group called short chain fatty acids.
Fatty acids are a carboxylic acid with a long unbranched aliphatic tail (chain), which is either saturated or unsaturated.
Fatty acids derived from natural fats and oils may be assumed to have at least 8 carbon atoms.
Most of the natural fatty acids have an even number of carbon atoms, because their biosynthesis involves acetyl-CoA, a coenzyme carrying a two-carbon-atom group.
Saturated fatty acids do not contain any double bonds or other functional groups along the chain.
The term “saturated” refers to hydrogen, in that all carbons (apart from the carboxylic acid [-COOH] group) contain as many hydrogens as possible.
Saturated fatty acids form straight chains and, as a result, can be packed together very tightly, allowing living organisms to store chemical energy very densely.
The fatty tissues of animals contain large amounts of long-chain saturated fatty acids.
Butyric acid is a GRAS food additive for chronic consumption when used in accordance with good manufacturing practice.
Chronic exposure also occurs through endogenous production as n-butyric acid is an important metabolite in the breakdown of carbohydrates, fats, and proteins, and is produced in the human colon by fermentation.
n-Butyric acid is present in butter as an ester (4–5%).
Butyric acid is toxic to the lungs, the nervous system, and mucous membranes.
Frequent and prolonged exposure can lead to target organ damage.
Butyric acid was discovered in 1869 by Lieben and Rossi.
In Latin, butyric acid means the acid of butter, as Butyric acid was first discovered in rancid butter (butyric acid is hydrolyzed from the glyceride and causes a very unpleasant odor).
Butyric acid is a short chain saturated fatty acid found in the form of esters in animal fats and plant oils.
Butyric acid is utilized in the production of various butyrate esters (e.g., methyl butyrate), which have pleasant aromas and tastes and are used as additives in foods, perfumes, flavorings, varnishes, pharmaceuticals, and disinfectants.
Butyric acid is also used for the production of plastics, plasticizers, surfactants, and textile auxiliaries.
Butyric acid and its derivatives (e.g., tributyrin) are also being considered as potential anticancer agents; the acid induces cytodifferentiation of a wide variety of neoplastic cells.
Butyric acid has several industrial applications, and recently, in the light of increasing petroleum prices and rising need for clean energy resources, butyric acid is being considered as a precursor to biofuels.
Butyric acid may emerge as an effective alternative for gasoline in the near future.
Butyric acid has a wide demand in the transportation sector, owing to the variety of advantages butyric acid has over ethanol.
For instance, butanol is far less volatile compared to ethanol, does not attract water which makes it ideal for transportation in pipelines, and is also less sensitive to low temperatures.
Moreover, butyric acid has uses in the chemical and pharmaceutical industries since it has been associated with several anticancer properties.
Several research institutes are engaged in the development of prodrugs containing butyric acid which can be used as a potential treatment of cancers, leukemia, and side effects of alopecia caused by chemotherapy.
In the chemical industry, butyric acid has primary application in the manufacture of cellulose acetate butyrate plastics.
In end use industries such as cosmetics, and food and beverages, butyric acid esters are used to add fragrance and flavor to products.
These factors are expected to drive demand for butyric acid over the forecast period.
However, environmental and health concerns associated with the handling of butyric acid are projected to restrain growth of the global butyric acid market.
Inhaling butyric acid can cause coughing, soreness of the throat, and respiratory problems.
Furthermore, ingesting butyric acid can result in abdominal pain, and collapse.
Physical contact with butyric acid causes skin irritation, burns, blistering, and prolonged exposure can impair the vision.
BP-21420
BUTYRIC-3,3,4,4,4-D5 ACID
NCI60_001424
Butyric acid, natural, >=99%, FCC, FG
B0754
FT-0623295
FT-0686717
V2319
Butyric acid 1000 microg/mL in Acetonitrile
Butyric acid, SAJ special grade, >=99.5%
C00246
24113-EP2272827A1
24113-EP2275401A1
24113-EP2281819A1
24113-EP2284146A2
24113-EP2284147A2
24113-EP2292611A1
24113-EP2292619A1
24113-EP2298763A1
24113-EP2298772A1
24113-EP2305633A1
24113-EP2305659A1
24113-EP2305808A1
24113-EP2308839A1
24113-EP2311810A1
Found in fresh and cooked apples, banana, sour cherry, papaya, strawberries, wheat bread, cheeses, butter and coffee.
Flavouring agent Butyric acid, also known under the systematic name butanoic acid, is a carboxylic acid with the structural formula CH3CH2CH2-COOH.
Salts and esters of butyric acid are known as butyrates or butanoates.
Butyric acid is found in rancid butter, parmesan cheese, vomit, and body odor and has an unpleasant smell and acrid taste, with a sweetish aftertaste (similar to ether).
Butyric acid can be detected by mammals with good scent detection abilities (such as 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 triglyceride 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.
Butyric acid 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.
The similar strength of these acids results from their common -CH2COOH terminal structure.
Pure butyric acid is 10.9 molar.; Butyric acid, a four-carbon fatty acid, is formed in the human colon by bacterial fermentation of carbohydrates (including dietary fiber), and putatively suppresses colorectal cancer (CRC).
Butyrate has diverse and apparently 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.
In humans, the relationship between luminal butyrate exposure and CRC has been examined only indirectly in case-control studies, by measuring fecal butyrate concentrations, although this may not accurately reflect effective butyrate exposure during carcinogenesis.
Perhaps not surprisingly, results of these investigations have been mutually contradictory.
The direct effect of butyrate on tumorigenesis has been assessed in a no. of in vivo animal models, which have also yielded conflicting results.
In part, this may be explained by methodology: differences in the amount and route of butyrate administration, which are likely to significantly influence delivery of butyrate to the distal colon.
Butyric acid is a carboxylic acid 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 is a fatty acid occurring in the form of esters in animal fats and plant oils.
Interestingly, low-molecular-weight esters of butyric acid, such as methyl butyrate, have mostly pleasant aromas or tastes.
As a consequence, they find use as food and perfume additives.
Butyrate is produced as end-product of a fermentation process solely performed by obligate anaerobic bacteria.;
The acid is an oily colorless liquid that is easily soluble in water, ethanol, and ether, and can be separated from an aqueous phase by saturation with salts such as 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.
24113-EP2311818A1
24113-EP2311825A1
24113-EP2311840A1
24113-EP2314590A1
24113-EP2380661A2
31560-EP2292597A1
31560-EP2295053A1
31560-EP2308858A1
31560-EP2311816A1
31560-EP2311817A1
81544-EP2275407A1
81544-EP2305687A1
81544-EP2305808A1
81544-EP2305825A1
Butyric acid in silage signifies clostridia contamination during the ensiling process.
Most likely these bacteria hopped onto the forage from either soil or manure sources entering the bunker or silo with the forage.
Clostridia can only produce butyric acid when the pH of the forage is greater than 5.0 and there is sufficient moisture.
When pH is below 5.0, lactic acid bacteria inhibit clostridia’s ability to produce butyric acid.
Maintaining dry matter at 35 to 45 per cent and wilting grass prior to ensiling ensures that the water soluble carbohydrate concentration of the grass is sufficient to prevent increases in the clostridia population.
If a moisture tester is unavailable to do a quick dry matter check prior to ensiling grass, a rough estimate of the dry matter can be determined through balling the grass in your hand and giving it a squeeze.
If the grass is in the ballpark of the proper dry matter no fluid will leak out of your hand from the grass, but the grass will leave your hand feeling slightly damp.
Maintaining optimal ensiling conditions will produce high quality ensiled forage.
Butyric acid can take its toll on cows just as much as it alters the forage quality.
Due to the unpleasant smell associated with silage high in butyric acid, cows will typically reduce their dry matter intake.
Reduced dry matter intake coupled with lower digestible energy from high butyric acid silage puts transition cows at a greater risk for developing metabolic issues while reducing lactational and reproductive performance.
A cow cannot determine if the butyric acid circulating in her blood stream comes from ruminal fermentation, body fat mobilization, or from silage.
Cows convert excess butyric acid regardless of origin, to ketones increasing the overall concentration of ketones in the blood increasing the risk for ketosis and other metabolic issues.
To circumvent the negative health and performance impacts, intake of butyric acid by transition cows should be limited to less than 50 g/d, while cows in early lactation should consume less than 150 g/d to minimize reductions in intake and performance.
Cows that are farther along in lactation can tolerate up to 200 g/d of butyric acid.
Even with the best-laid plans and management, butyric acid may still develop in silage resulting in the need for quick action.
The first step is to confirm the presence of butyric acid through visual and odor assessment.
Follow up with lab analysis to determine how much butyric acid is present in the silage, then calculate the daily intake of butyric acid.
Determine if alternate feeding plans need to be made for at-risk groups if the daily intake of butyric acid exceeds guidelines.
Due to the sensitivity of transition cows, don’t feed these cows forages that contain greater than 50 g/d butyric acid, while the remainder of the herd should be fed a ration that dilutes the butyric acid containing silage.
If dilution is not practical for a farm, silage can be knocked down from the bunk face and spread out in an open area to air out for several days reducing the overall butyric acid content while maintaining the stability of the forage.
Finally, if the butyric content of the forage is greater than 2 per cent it is recommended to dispose of the silage.
Butyrate is a major short-chain fatty acid produced during gut flora-mediated fermentation of dietary fibers.
Legumes (beans, peas, and soybeans), fruits, nuts, cereals, and whole grains are good sources of dietary fibers.
Butyrate is also found in butter and cheese.
Q193213
W-108732
BRD-K05878375-236-02-4
9B27B3D0-9643-40EC-9A5F-7CA1A6ED7F9F
F2191-0094
Z955123634
64833-96-1
butanoic acid, butanic acid, n-butyric acid, ethylacetic acid, propylformic acid, 1-propanecarboxylic acid
n-Butyric acid is a saturated four-carbon carboxylic acid which is a clear liquid, with a suffocating odor and with melting point -6 C and boiling point 164 C.
Butyric acid occurs naturally in rancid butter, in much animal fat and in plant oil.
Butyric acid is soluble in water, ethanol and ether.
Butyric acid can be obtained by the fermentation of sugar or starch, brought about by the addition calcium carbonate or by the oxidation of butanol in the presence of potassium permanganate.
There is a structural formula called isobutyric acid which can not be obtained by the fermentation but by the oxidation of isopropyl alcohol with potassium bichromate and sulfuric acid.
Isobutyric acid melts at -47 C and boils at 154 C.
Butyric acid is slightly soluble in water but soluble in ethanol, ether and organic solvents.
Butyric acid is a strong acid and reacts with bases, strong oxidants and metals.
Butyric acid is used to eliminate calcium in leather industry.
Butyric acid family products, such as their esters, are used for the production of plastics, plasticizers, surfactants and textile auxiliaries.
Butyric acids are used in food additives, flavorings, varnishes, perfumes, pharmaceuticals and disinfectants.
Aminobutyric acid is a four-carbon carboxylic acid, to which an amino group is attached.
There are three structural isomers, alpha, beta, gamma-.
Alpha-aminobutyric acid is has an amino group substituted at the alpha, or 1 position on the carbon atom next to the acid group, while gamma-aminobutyric acid (GABA) at the terinal carbon (the gamma, or 4 position).
Natural GABA exits in L-form only and can be found in plant and animal tissues.
Butyric acid is formed in the metabolism of L-glutamic acid.
Butyric acid is the central nervous system postsynaptic inhibitory transmitter in the brain but is also found in several extraneural tissues, including kidney and pancreatic islet beta cells.
Gamma- hydroxy butyric acid is an intermediate occurring in metabolism of GABA.
There are several hydroxy butyric acid occur at elevated levels in some metabolic disorders.
In biological systems The GABA family products are the parent compounds for a number of psychoactive drugs covering sedation/hypnosis, anxiolysis, anticonvulsant activity, muscle relaxation and anterograde amnesia.
Some examples are benzodiazepines, baclofen, bicuculline, barbiturates, picrotoxin, neurosteroids and the general anesthetics.