3D Mol Similar

Butyric Acid

: Iupac Name：butanoic acid; CAS No.: 107-92-6; Molecular Weight：88.106; Modify Date.: 2022-11-29 11:28; Introduction: Butyric acid is a carboxylic acid also classified as a fatty acid. It exists in two isomeric forms as shown previously, but this entry focuses on n-butyric acid or butanoic acid. It is a colorless, viscous, rancid-smelling liquid that is present as esters in animal fats and plant oils. Butyric acid exists as a glyceride in butter, with a concentration of about 4%; dairy and egg products are a primary source of butyric acid. When butter or other food products go rancid, free butyric acid is liberated by hydrolysis, producing the rancid smell. It also occurs in animal fat and plant oils. View more+

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1. Names and Identifiers

: 1.1 Name; Butyric Acid; 1.2 Synonyms; (3R,4S)-1-Benzoyl-3-(1-methoxy-1-methylethoxy)-4-phenyl-2-azetidinone 3-Methylpropionic acid EINECS 203-532-3 MFCD00002814 n-Butyric acid n-Butyric Acid, FCC n-Butyric acid, synthesis grade normal Butyric acid Tetranoic acid (Butyric); View all

1.3 CAS No.: 107-92-6

1.4 CID: 264

1.5 EINECS(EC#): 203-532-3

1.6 Molecular Formula: C4H8O2 (isomer)

1.7 Inchi: InChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6)

1.8 InChIkey: FERIUCNNQQJTOY-UHFFFAOYSA-N

1.9 Canonical Smiles: CCCC(=O)O

1.10 Isomers Smiles: CCCC(=O)O

2. Properties

2.1 Density: 0.958

2.1 Melting point: -7.9℃

2.1 Boiling point: 17.8° F (NTP, 1992)

2.1 Refractive index: 1.3965-1.3995

2.1 Flash Point: 170° F (NTP, 1992)

2.2 Precise Quality: 88.05240

2.2 PSA: 37.30000

2.2 logP: 0.87110

2.2 Viscosity: Viscosity is a measure of a fluid's resistance to flow. It describes the internal friction of a moving fluid.

2.3 VaporDensity: 3.04

2.4 AnalyticLaboratory Methods: Detection of organic acid sweetners, syrup carboxylic acids and carbohydrates by HPLC.

2.5 Appearance: Butyric acid appears as a colorless liquid with a penetrating and unpleasant odor. Flash point 170°F. Corrosive to metals and tissue. Density 8.0 lb /gal.

2.6 AutoIgnition: 842° F (USCG, 1999)

2.7 Storage: Ambient temperatures.

2.8 Chemical Properties: Butyric acid is a combustible, oily liquid withan unpleasant odor. The Odor Threshold is 0.0001 ppm.

2.9 Color/Form: Oily liquid
Colorless liquid

2.10 Corrosivity: Corrosive material

2.11 Heat of Combustion: 521.87 kg cal/gm at 25 deg C

2.12 Heat of Vaporization: 40.45 kJ/mol at 25 deg C

2.13 Odor: Unpleasant, rancid odor

2.14 Odor Threshold: 0.001 mg/cu m (Odor low) 9 mg/cu m (Odor high)

2.15 PH: 2.5 (100g/l, H2O, 20℃)

2.16 Physical: BUTYRIC ACID; is a colorless liquid with a penetrating and unpleasant odor. Flash point 170°F. Corrosive to metals and tissue. Density 8.0 lb /gal.

2.17 pKa: 4.83(at 25℃)

2.18 Water Solubility: Solubility in water: miscible

2.19 Spectral Properties: Index of refraction: 1.3991 at 20 deg C/D
SADTLER REF NUMBER: 125 (IR, PRISM); 37 (IR, GRATING); MAX ABSORPTION (WATER): 208 NM (LOG E= 1.8), 270 (IR, PRISM); 37 (IR, GRATING); MAX ABSORPTION (WATER): 208 NM (LOG E= 1.8), 270 NM (SHOULDER) (LOG E= -0.8)
IR: 4820 (Coblentz Society Spectral Collection)
UV: 2-21 (Philip et al, Organic Electronic Spectral Data, John Wiley & Sons, New York)
1H NMR: 7312 (Sadtler Research Laboratories Spectral Collection)
MASS: 49308 (NIST/EPA/MSDC Mass Spectral Database 1990 version)

2.20 Stability: It has good stability

2.21 StorageTemp: Store below +30°C.

2.22 Surface Tension: 26.05 mN/m at 25 deg C

3. Use and Manufacturing

3.1 Definition: ChEBI: A straight-chain saturated fatty acid that is butane in which one of the terminal methyl groups has been oxidised to a carboxy group.

3.2 GHS Classification: Signal: Danger
GHS Hazard Statements
H314: Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

Precautionary Statement Codes
P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, and P501

3.3 Methods of Manufacturing: Obtained as a by-product from the liquid phase oxidation of n-butane; to acetic acid; or by oxidation of n-butyl alcohol; or normal-butyraldehyde;

3.4 Potential Exposure: In manufacture of butyrate esters,some of which go into artificial flavoring.Incompatibilities: May form explosive mixture with air.Incompatible with sulfuric acid, caustics, ammonia,aliphatic amines; isocyanates, strong oxidizers; alkyleneoxides; epichlorohydrin

3.5 Produe Method: Butyric Acid is industrially 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 butyrates or butanoates. Butyric acid or fermentation butyric acid is also found as a hexyl ester hexyl butyrate in the oil of Heracleum giganteum (a type of hogweed) and as the octyl ester octyl butyrate in parsnip (Pastinaca sativa); it has also been noticed in skin flora and perspiration.

3.6 Purification Methods: Distil the acid, them mix it with KMnO4 (20g/L), and fractionally redistil, discarding the first third of the distillate [Vogel J Chem Soc 1814 1948]. [Beilstein 2 IV 779.]

3.7 Usage: Butyric Acid is a fatty acid that is commonly obtained from butter fat. it has an objectionable odor which limits its uses as a food acid-ulant or antimycotic. it is an important chemical reactant in the manufacture of synthetic flavoring, shortening, and other edible food additives. in butter fat, the liberation of butyric acid which occurs during hydrolytic rancidity makes the butter fat unusable. it is used in soy milk-type drinks and candies.

3.8 Waste Disposal: Dissolve or mix the materialwith a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal,state, and local environmental regulations must be observed. Butyric Acid Preparation Products And Raw materials Preparation Products

4. Safety and Handling

4.1 Symbol: GHS05, GHS07

4.1 Hazard Codes: C,Xi

4.1 Signal Word: Danger

4.1 Risk Statements: R34

4.1 Safety Statements: S26;S36;S45

4.1 Exposure Standards and Regulations: N-Butyric acid used as a synthetic flavoring substance or adjuvant in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice.

4.2 Packing Group: III

4.2 Octanol/Water Partition Coefficient: log Kow= 0.79

4.3 Fire Hazard: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

4.4 Other Preventative Measures: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. ... Avoid breathing vapors. Keep upwind. Avoid bodily contact with the material. Do not handle broken packages without protective equipment. Wash away any material which may have contacted the body with copious amounts of water, or soap and water.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.; View all

4.5 Hazard Class: 8

4.5 Hazard Declaration: H302-H314

4.5 Cleanup Methods: Land spill: Dig a pit, pond, lagoon, or holding area to contain liquid or solid material /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash or cement powder. Neutralize with agricultural lime (slaked lime), crushed limestone, or sodium bicarbonate.
Water spill: Neutralize with agricultural lime (slaked lime), crushed limestone, or sodium bicarbonate. If dissolved, apply activated carbon at ten times the spilled amount in region of 10 ppm or greater concn. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates.
Air spill: Apply water spray or mist to knock down vapors. Vapor knockdown water is corrosive or toxic and should be diked for containment.
Eliminate all ignition sources ... Protect personnel, and dilute spill to form nonflammable mixtures. Control runoff and isolate discharged material for proper disposal ...; View all

4.6 DisposalMethods: SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
The following wastewater treatment technologies have been investigated for butyric acid: Concentration process: Biological treatment.
The following wastewater treatment technologies have been investigated for butyric acid: Concentration process: Activated carbon.
The following wastewater treatment technologies have been investigated for butyric acid: Concentration process: Resin adsorption.

4.7 DOT Emergency Guidelines: /GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: TOXIC; inhalation, ingestion, or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors, and sewers explosion hazards. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas.
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Evacuation: ... Fire: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions.
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire: Small fires: Dry chemical, CO2 or water spray. Large fires: Dry chemical, CO2, alcohol-resistant foam or water spray. Move containers from fire area if you can do it without risk. Dike fire control water for later disposal; do not scatter the material. Fire involving tanks or car/trailer loads: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire.
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Spill or Leak: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS.
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim warm and quiet. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves.; View all

4.8 RIDADR: UN 2820

4.8 Fire Fighting Procedures: Use water spray, dry chemical, "alcohol resistant" foam, or CO2. Use water to keep fire-exposed containers cool. On large fires, solid streams of water may not be effective.
If material on fire or involved in fire: Use water in flooding quantities as fog. Solid streams of water may be ineffective. ... Apply water from as far a distance as possible.

4.9 FirePotential: ... Combustible liquid

4.10 Safety Profile: Moderately toxic by ingestion, skin contact, subcutaneous, intraperitoneal, and intravenous routes. Human mutation data reported. Severe skin and eye irritant. A corrosive material. Combustible liquid. Could react with oxidizing materials. Incandescent reaction with chromium trioxide above 100'. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

4.11 Caution Statement: P260-P280-P301 + P312 + P330-P303 + P361 + P353-P304 + P340 + P310-P305 + P351 + P338

4.11 Formulations/Preparations: GRADES: 90%; 95%; 99%; edible; synthetic; reagent; Technical; FCC.
Grades or Purity: Commercial, 99.5+%

4.12 WGK Germany: 1

4.12 RTECS: ES5425000

4.12 Protective Equipment and Clothing: Wear self-contained breathing apparatus; wear goggles if eye protection is not provided.
Wear boots and protective gloves. ... If contact with the material anticipated, wear full protective clothing.
Wear special protective clothing and positive pressure self-contained breathing apparatus.

4.13 Reactivities and Incompatibilities: May attack aluminum or other light metals with formation of flammable hydrogen gas.
/Butyric acid/ can react with oxidizing materials.
A mixture of chromium trioxide and butyric acid became incandescent on heating to 100 deg C. /Chromium trioxide/

4.14 Skin, Eye, and Respiratory Irritations: Vapor: Irritating to eyes, nose, and throat. If inhaled will cause coughing or difficult breathing. Liquid: Will burn skin and eyes.

4.15 Safety: Hazard Codes: C,Xi
Risk Statements: 34
R34:Causes burns.
Safety Statements: 26-36-45
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 2820 8/PG 3
WGK Germany: 1
RTECS: ES5425000
Hazard Note: Irritant
HazardClass: 8
PackingGroup: III

4.16 Specification: Butyric acid (CAS NO.107-92-6), its Synonyms are 1-Butyric acid ; 1-Propanecarboxylic acid ; Buttersaeure ; Butyrate ; n-Butanoic acid ; n-Butyric acid ; Propylformic acid ; Kyselina maselna .

4.17 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LC	inhalation	> 500mg/m3 (500mg/m3)	LUNGS, THORAX, OR RESPIRATION: STRUCTURAL OR FUNCTIONAL CHANGE IN TRACHEA OR BRONCHI	Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 23(5), Pg. 31, 1958.
mouse	LD50	intraperitoneal	3180mg/kg (3180mg/kg)		Journal of Pharmacy and Pharmacology. Vol. 21, Pg. 85, 1969.
mouse	LD50	intravenous	800mg/kg (800mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Acta Pharmacologica et Toxicologica. Vol. 18, Pg. 141, 1961.
mouse	LD50	subcutaneous	3180mg/kg (3180mg/kg)		Journal of Pharmacy and Pharmacology. Vol. 21, Pg. 85, 1969.
mouse	LDLo	oral	500mg/kg (500mg/kg)	GASTROINTESTINAL: NECROTIC GHANGES KIDNEY, URETER, AND BLADDER: OTHER CHANGES BLOOD: CHANGES IN SPLEEN	Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Substances. For English translation, see TNICS*. Vol. 4, Pg. 19, 1962.
rabbit	LD50	skin	530uL/kg (0.53mL/kg)		Union Carbide Data Sheet. Vol. 4/10/1968,
rat	LC	inhalation	> 500mg/m3 (500mg/m3)	LUNGS, THORAX, OR RESPIRATION: STRUCTURAL OR FUNCTIONAL CHANGE IN TRACHEA OR BRONCHI	Toksikologiya Novykh Promyshlennykh Khimicheskikh Veshchestv. Toxicology of New Industrial Chemical Substances. For English translation, see TNICS*. Vol. 4, Pg. 19, 1962.
rat	LD50	oral	2gm/kg (2000mg/kg)		"Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 30, 1982.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin corrosion, Category 1B

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H314 Causes severe skin burns and eye damage
Precautionary statement(s)
Prevention	P260 Do not breathe dust/fume/gas/mist/vapours/spray. P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	P301+P330+P331 IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower]. P363 Wash contaminated clothing before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P310 Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in CDCl3

1H NMR : 90 MHz in CDCl3

Predict 1H proton NMR

IR : liquid film

Mass

7. Synthesis Route

107-92-6Total: 279 Synthesis Route

71-36-3 61 Suppliers

107-92-6 190 Suppliers

Literatures:
Hirai, Yuichirou; Kojima, Takahiko; Mizutani, Yasuhisa; Shiota, Yoshihito; Yoshizawa, Kazunari; Fukuzumi, Shunichi Angewandte Chemie - International Edition, 2008 , vol. 47, # 31 p. 5772 - 5776
Yield: ~99%

57-57-8 61 Suppliers

107-92-6 190 Suppliers

Literatures:
Kawashima, Masatoshi; Sato, Toshio; Fujisawa, Tamotsu Tetrahedron, 1989 , vol. 45, # 2 p. 403 - 412
Yield: ~85%

60-01-5 59 Suppliers

107-92-6 190 Suppliers

Literatures:
Tetrahedron Asymmetry, , vol. 12, # 4 p. 545 - 556
Yield: ~%

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8. Other Information

8.0 Usage: Butyric acid is a useful as precursor for the preparation of various butyrate esters. It is used as a food and perfume additive. It is also used as an animal feed supplement. Due to its powerful odor, it has also been used as a fishing bait additive and as a stink bomb. It is widely used as a flavoring agent for human food and beverages.

8.1 Merck: 14,1593

8.2 BRN: 906770

8.3 Description: Butyric acid is a carboxylic acid also classified as a fatty acid. It exists in two isomeric forms as shown previously, but this entry focuses on n-butyric acid or butanoic acid. It is a colorless, viscous, rancid-smelling liquid that is present as esters in animal fats and plant oils. Butyric acid exists as a glyceride in butter, with a concentration of about 4%; dairy and egg products are a primary source of butyric acid. When butter or other food products go rancid, free butyric acid is liberated by hydrolysis, producing the rancid smell. It also occurs in animal fat and plant oils.

8.4 Chemical Properties: Butyric acid is a combustible, oily liquid with an unpleasant odor. The Odor Threshold is 0.0001 ppm.

8.5 Chemical Properties: Butyric acid, C3H7COOH, a colorless liquid with an obnoxious odor, occurring in spoiled butter.It miscible with water, alcohol, and ether.It is used in the synthesis of butyrate ester perfume and flavor ingredients and in disinfectants and pharmaceuticals,

8.6 Chemical Properties: Butyric acid (from Greek meaning "butter"), 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 milk, especially goat, sheep and buffalo's milk, butter, Parmesan cheese, and as a product of anaerobic fermentation (including in the colon and as body odor). It has an unpleasant smell and acrid taste, with a sweetish aftertaste (similar to ether). It 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 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 . The name of butyric acid comes from the Latin word for butter, butyrum (or buturum), the substance in which butyric acid was first found.

8.7 Chemical Properties: Butyric acid is a fatty acid occurring in the form of esters in animal fats. 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. It is an important member of the fatty acid subgroup called short- chain fatty acids. Butyric acid is a medium-strong acid that reacts with bases and strong oxidants, and attacks many metals.
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. It is oxidized to carbon dioxide and acetic acid using potassium dichromate and sulfuric 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.
Butyric acid has a structural isomer called isobutyric acid (2-methylpropanoic acid).

8.8 Chemical Properties: n-Butyric acid has a persistent, penetrating, rancid, butter-like odor and burning, acid taste.

8.9 Occurrence: Normally occurs in butter as a glyceride. It has been reported found in the essential oils of citronella Ceylon, Eucalyptus globules, Araucaria cunninghamii, Lippia scaberrima, Monarda fistulosa, cajeput, Heracleum giganteum, lavender, Hedeoma pulegioides, valerian, nutmeg, hops, Pastinaca sativa, Spanish anise and others. It has been identified in strawberry aroma, apricot, American cranberry, sour cherry, black currants, butter, milk, strawberry jam, cheeses (blue, cheddar, feta, Swiss, Camembert and romano), raspberry, papaya, coffee mutton, beer, rum, bourbon whiskey and cider.

8.10 History: Butyric acid gets its name from the Latin butyrum, or butter. It was discovered by Adolf Lieben (1836–1914) and Antonio Rossi in 1869. Butyric acid is one of the simplest fatty acids.

8.11 Uses: Butyric Acid is a fatty acid that is commonly obtained from butter fat. it has an objectionable odor which limits its uses as a food acid- ulant or antimycotic. it is an important chemical reactant in the manufacture of synthetic flavoring, shortening, and other edible food additives. in butter fat, the liberation of butyric acid which occurs during hydrolytic rancidity makes the butter fat unusable. it is used in soy milk-type drinks and candies.

8.12 Uses: It is used in plastics as a raw material for the cellulose acetate butyrate (CAB). Other uses of butyric acid are in disinfectants, pharmaceuticals, and feed supplements for plant and animals. Butyric acid derivatives play an important role in plant and animal physiology.

8.13 Uses: 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 find use as food and perfume additives. It is also used as an animal feed supplement, due to the ability to reduce pathogenic bacterial colonization. It is an approved food flavoring in the EU FLAVIS database (number 08.005).
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, however, one of the few organic acids shown to be palatable for both tench and bitterling. The substance has also been used as a stink bomb by Sea Shepherd Conservation Society to disrupt Japanese whaling crews, as well as by anti-abortion protesters to disrupt abortion clinics.; View all

8.14 Production Methods: Butyric Acid is industrially 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 butyrates or butanoates.
Butyric acid or fermentation butyric acid is also found as a hexyl ester hexyl butyrate in the oil of Heracleum giganteum (a type of hogweed) and as the octyl ester octyl butyrate in parsnip (Pastinaca sativa); it has also been noticed in skin flora and perspiration.

8.15 Preparation: Obtained by fermentation of starches and molasses with selective enzymes (Granulo saccharobutyricum); it is subsequently isolated as the calcium salt.

8.16 Definition: ChEBI: A straight-chain saturated fatty acid that is butane in which one of the terminal methyl groups has been oxidised to a carboxy group.

8.17 Production Methods: Butyric acid is produced by oxidation of butyraldehyde (CH₃(CH₂)₂CHO) or butanol (C₄H₉OH). It can also be formed biologically by the oxidation of sugar and starches using bacteria.

8.18 Definition: A colorless liquid carboxylic acid. Esters of butanoic acid are present in butter.

8.19 Aroma threshold values: Detection: 240 ppb to 4.8 ppm

8.20 Taste threshold values: Taste characteristics at 250 ppm: acidic, sour, cheesy, dairy, creamy with a fruity nuance.

8.21 General Description: A colorless liquid with a penetrating and unpleasant odor. Flash point 170°F. Corrosive to metals and tissue. Density 8.0 lb /gal.

8.22 Air & Water Reactions: Water soluble.

8.23 Reactivity Profile: (3R,4S)-1-Benzoyl-3-(1-methoxy-1-methylethoxy)-4-phenyl-2-azetidinone can react with oxidizing agents. Incandescent reactions occur with chromium trioxide above 212°F. Also incompatible with bases and reducing agents. May attack aluminum and other light metals .

8.24 Hazard: Strong irritant to skin and tissue.

8.25 Health Hazard: Inhalation causes irritation of mucous membrane and respiratory tract; may cause nausea and vomiting. Ingestion causes irritation of mouth and stomach. Contact with eyes may cause serious injury. Contact with skin may cause burns; chemical is readily absorbed through the skin and may cause damage by this route.

8.26 Fire Hazard: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.

8.27 Biotechnological Applications: Butyrate 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.
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 waste products from the cell.

8.28 Safety Profile: Moderately toxic by ingestion, skin contact, subcutaneous, intraperitoneal, and intravenous routes. Human mutation data reported. Severe skin and eye irritant. A corrosive material. Combustible liquid. Could react with oxidizing materials. Incandescent reaction with chromium trioxide above 100'. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

8.29 Safety: The United States Environmental Protection Agency rates and regulates butyric acid as a toxic substance.
Personal protective equipment such as rubber or PVC gloves, protective eye goggles, and chemical-resistant clothing and shoes are used to minimize risks when handling butyric acid.
Inhalation of butyric acid may result in soreness of throat, coughing, a burning sensation and laboured breathing. Ingestion of the acid may result in abdominal pain, shock, and collapse. Physical exposure to the acid may result in pain, blistering and skin burns, while exposure to the eyes may result in pain, severe deep burns and loss of vision.

8.30 Potential Exposure: In manufacture of butyrate esters, some of which go into artificial flavoring. Incompatibilities: May form explosive mixture with air. Incompatible with sulfuric acid, caustics, ammonia, aliphatic amines; isocyanates, strong oxidizers; alkylene oxides; epichlorohydrin

8.31 Environmental Fate: The most probable mechanism of toxicity is the formation of an acid proteinate following exposure to high concentrations. Such complexes result in an inhibition of protein function and disruption of cellular homeostasis. Butyric acid induces apoptosis by production of ceramide and reactive oxygen species in the mitochondria followed by activation of JNK in mitogen activated protein (MAP) kinase cascades. Butyric acid has two contrasting functional roles. As a product of fermentation within the human colon, it serves as the most important energy source for normal colorectal epithelium. It also promotes differentiation of cultured malignant cells. A switch from aerobic to anaerobic metabolism accompanies neoplastic transformation in the colorectum. The separate functional roles for n-butyrate may reflect the different metabolic activities of normal and neoplastic tissues. Deficiency of n-butyrate, coupled with the increased energy requirements of neoplastic tissue, may promote the switch to anaerobic metabolism. n-Butyrate was previously found to increase epidermal growth factor receptor binding in primary cultures of rat hepatocytes. It was shown that butyrate and dexamethasone synergistically modulate the surface expression of epidermal growth factor receptors. The butyrate-induced enhancement of highaffinity epidermal growth factor bindingwas slight in the absence of glucocorticoid, but was strongly and dose-dependently amplified by dexamethasone. Butyrate counteracted the inhibition by insulin of the dexamethasone-induced increase in epidermal growth factor binding. The results indicate that the glucocorticoid has a permissive effect on a butyrate-sensitive process that determines the surface expression of the high-affinity class of epidermal growth factor receptors.; View all

8.32 Shipping: UN2820 Butyric acid, Hazard class: 8; Labels: 8—Corrosive material. UN2529 Isobutyric acid, Hazard Class: 3; Labels: 3—Flammable liquid, 8—Corrosive material

8.33 Purification Methods: Distil the acid, them mix it with KMnO4 (20g/L), and fractionally redistil, discarding the first third of the distillate [Vogel J Chem Soc 1814 1948]. [Beilstein 2 IV 779.]

8.34 Toxicity evaluation: Butyric acid is not environmentally persistent as it is biodegradable in aqueous media, volatilizes from surface waters at a moderate rate, and readily undergoes photodegradation in the atmosphere. n-Butanoic acid may be susceptible to biodegradation in terrestrial and aquatic environments based on the observed degradation of 72% after 5 h when incubated with activated sludge. At an initial concentration of 100 mg l^-1, n-butanoic acid displayed a 72% theoretical biological oxygen demand (BODT) after 5 h when incubated with activated sludge. n-Butanoic acid at an initial concentration of 5 ppm displayed a BODT of 76.6% in freshwater and 72.4% in seawater after 5 days. n-Butanoic acid had a BODT of 17.4, 23.8, 26.2, and 27.7% after 6, 12, 18, and 24 h, respectively, when incubated with an activated sludge seed at an initial concentration of 500 ppm. In a screening study, the BODT of n-butanoic acid was 46, 48, and 58% after 2, 10, and 30 days, respectively, using a sewage seed. In a screening study using a sewage seed, n-butanoic acid had a 5-day BODT of 72–78% and a 20-day BODT of 92–99%.
Butyric acid must be separated from strong oxidants, strong bases, food, and feedstuffs for long-range transport (UN Hazard Class 8; UN Packing Group III; stable during transport). It should be stored in a cool, dry, well-ventilated location, away from any area where fire hazard may be acute. Outside or detached storage is preferred, separate from oxidizing materials, heat, oxidizers, and sunlight.; View all

8.35 Waste Disposal: Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

8.36 Storage features: Separated from strong oxidants, strong bases and food and feedstuffs.

9. Computational chemical data

Molecular Weight: 88.106g/mol
Molecular Formula: C₄H₈O₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 88.052429494
Monoisotopic Mass: 88.052429494
Complexity: 49.5
Rotatable Bond Count: 2
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 37.3
Heavy Atom Count: 6
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBgMAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGgAACAAACACAgAACCAAAAgAIAACQCAAAAAAAAAAAAAEAAAAAABAAAAAAQAAEAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

10. Question & Answer

What are the characteristics of Butyric Acid Clostridium? May 25 2024
Butyric Acid Clostridium, also known as Butyric Acid Clostridium, is a Gram-positive anaerobic bacterium that is widely present in nature and in the intestines of humans and animals. The morphology of..
The Versatile Uses and Environmental Impact of Butyric Acid Can Butyric Acid Revolutionize Industries and Protect the Environment? Dec 03 2021
Title: The Versatile Uses and Environmental Impact of Butyric Acid Can Butyric Acid Revolutionize Industries and Protect the Environment? Butyric acid, a four-carbon acid known for its unpleasant odor..
Why is Butyric Acid Important for Gut Health? Oct 19 2020
Butyric acid plays a vital role in gut health and has powerful functions. Especially in China, after the decision to ban the use of growth-promoting antibiotics in animal feed by 2020, endogenous buty..
What are the uses of Butyric Acid? Jul 05 2019
Butyric Acid, also known as butanoic acid or butyrate, is a saturated monocarboxylic acid with four carbon atoms. It is a typical volatile short-chain fatty acid. Its molecular formula is CH3(CH2)2C00..

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