Isovaleric Acid

Other Classes -> Organic Acids

Corrosives

Log Kow = 1.16

1.16

0.931 @ 20 °C/4 °C

0.923-0.928

Danger

H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

P260, P264, P264+P265, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1809 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Chemical: Butanoic acid, 3-methyl-

Regulation (EC) No 1831/2003 (amended)

Butanoic acid, 3-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Butanoic acid, 3-methyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 01-12-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/5729

Isopentanoic acid: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Safe when used as a flavoring agent in food; [JECFA] Mild irritant when administered to eye of rabbit; Corrosive to skin of mice; Caused somnolence and ataxia in lethal-dose feeding studies of rats; [RTECS] Corrosive to tissue; [CAMEO] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; [CHEMINFO] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis and pulmonary edema; [MSDSonline]

Isovaleric acid is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: 1) the quantity added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) when intended for use in or on food it is of appropriate food grade and is prepared and handled as a food ingredient.

ISOPENTANOIC ACID is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in it to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.

/GUIDE 154: SUBSTANCES - TOXIC AND/OR CORROSIVE (NON-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. /Corrosive liquid, NOS/

/GUIDE 154: SUBSTANCES - TOXIC AND/OR CORROSIVE (NON-COMBUSTIBLE)/ Fire or Explosion: Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. /Corrosive liquid, NOS/

/GUIDE 154: SUBSTANCES - TOXIC AND/OR CORROSIVE (NON-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. /Corrosive liquid, NOS/

/GUIDE 154: SUBSTANCES - TOXIC AND/OR CORROSIVE (NON-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. /Corrosive liquid, NOS/

For more DOT Emergency Guidelines (Complete) data for ISOVALERIC ACID (8 total), please visit the HSDB record page.

Skin Corr. 1B (100%)

Corrosives, Flammable agents - 2nd degree

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.

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 100(SRC), determined from a measured log Kow of 1.16(2) and a recommended regression-derived equation(3), indicates that isovaleric acid is expected to have high mobility in soil(SRC). Volatilization of isovaleric acid may be important from moist soil surfaces(SRC) given a measured Henry's Law constant of 8.33X10-7 atm-cu m/mole(4). Isovaleric acid's pKa of 4.78 suggests this process may be attenuated under environmental pHs(6,SRC). Isovaleric acid is not expected to volatilize from dry soil surfaces based it's vapor pressure of 0.44 mm Hg(5). Isovaleric acid was degraded in anaerobic and aerobic biodegradation studies(7,8). A biodegradation study based on oxygen depletion measurements, using a sewage seed and a chemical concentration of 2.0 mg of carbon/l, indicate that isovaleric acid is readily biodegraded(7). An initial isovaleric acid concentration of 30 mg carbon/l was anaerobically biodegraded 91% after 21 days incubation in synthetic sewage(8).

AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 100(SRC), determined from a measured log Kow of 1.16(2) and a recommended regression-derived equation(3), indicates that isovaleric acid is not expected to adsorb to suspended solids and sediment in water(SRC). Isovaleric acid may volatilize from water surfaces(3,SRC) based on a measured Henry's Law constant of 8.33X10-7 atm-cu m/mole(4). Estimated volatilization half-lives for a model river and model lake are 45 and 330 days, respectively(3,SRC). However, a pKa of 4.78 for isovaleric acid(6) indicates that isovaleric acid will not significantly volatilize from water as it will exist predominately in the ionic form under environmental pHs(SRC). According to a classification scheme(5), an estimated BCF value of 4.5(3,SRC), from a measured log Kow(2), suggests that bioconcentration in aquatic organisms is low(SRC). Isovaleric acid was degraded in anaerobic and aerobic biodegradation studies(7,8). A biodegradation study based on oxygen depletion measurements, using a sewage seed and a chemical concentration of 2.0 mg of carbon/l, indicate that isovaleric acid is readily biodegraded(7). An initial isovaleric acid concentration of 30 mg carbon/l was anaerobically biodegraded 91% after 21 days incubation in synthetic sewage(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), isovaleric acid, which has a measured vapor pressure of 0.44 mm Hg at 25 °C(2,SRC), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase isovaleric acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 3.9 days(3,SRC).

Isovaleric acid was detected in garden waste exudate and kitchen waste exudate at unspecified concentrations(1,2). Isovaleric acid was detected in raw and processed waste water from the Lurgi-Process Plant in Sasolburg, South Africa at concentrations of 1 and 5 mg/l, respectively(3). Isovaleric acid was detected in primary and secondary effluents from four sewage treatment plants at concentrations ranging from 17 to 541 ug/l and 0.8 to 524 ug/l, respectively(4). A combined concentration of 151 mg/l of isovaleric acid and 2-methylbutanoic acid was detected in oil-shale process retort water samples from the Occidental Oil Shale, Inc facility at Logan Wash, CO in 1979(5). Groundwater samples contaminated by wood-preserving chemicals in Pensacola, FL contained isovaleric acid at concentrations of 2.01, 0.78, 0.59 mg/l at 6.1, 3.3, and 5.8 m below the surface, respectively(6). Groundwater samples from a landfill well in Norman, OK contained isovaleric acid at an estimated concentration of 0.7 mg/l(7). Isovaleric acid was detected in effluent from a publicly owned treatment works facility located in an industrial area of NJ (industrial contribution to influent is 18%) at a concentration of 35 ppb(8). Isovaleric acid was identified in trench leachate samples collected from low-level radioactive waste disposal sites at Maxey Flats, KY and West Valley, NY at concentrations ranging from 1.8 to 17 mg/l(9).

The Koc of isovaleric acid is estimated as approximately 100(SRC), using a measured log Kow of 1.16(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that isovaleric acid is expected to have high mobility in soil(SRC).

ORIGINALLY REPORTED IN SEAL & DOLPHIN FAT; SUBSEQUENTLY ISOLATED FROM VALERIAN. ALSO REPORTED FOUND IN ESSENTIAL OILS OF: CYPRESS, CITRONELLA, LAUREL LEAVES, CAJEPUT, CYMBOPOGON JAVANENSIS, HOPS, PERSEA PUBESCENS, GERANIUM, AMERICAN PEPPERMINT, NIAOULI, SPEARMINT, ROSEMARY, LEMONGRASS, EUCALYPTUS GONIOCALYX AND OTHER SPECIES, TOBACCO, MONARDA FISTULOSA, THYMUS MASTICHINA, ARTEMISIA FRIGIDA, & PROBABLY IN LAVENDER. /ALSO/...AMONG CONSTITUENTS OF PETITGRAIN LEMON.

Isovaleric acid occurs in hop oil, tobacco and several other plants(1).

A SINGLE DOSE OF HYPOGLYCIN A, MARKEDLY INCREASED RAT PLASMA ISOVALERIC ACID CONCN, & ALPHA-METHYLBUTYRIC ACID, A POSITION ISOMER, ACCUMULATED. ACCUMULATION OF THESE BRANCHED PENTANOIC ACIDS MAY CONTRIBUTE TO PATHOGENESIS OF JAMAICAN VOMITING SICKNESS.

Isovaleric acid's production and use in medicine, flavors, perfumes(1), as a chemical intermediate in fungicides, rodenticides, sedatives, narcotics, and other drugs(2) may result in its release to the environment through various waste streams(SRC).

An anaerobic biodegradation study, using an isovaleric acid concentration of 7.2 mg/l and a mixed bacterial culture isolated from low-level radioactive waste trench leachate from Maxey Flats, KY reported a 5% increase in isovaleric acid concentration after 60 days incubation(1). An aerobic biodegradation study, using an isovaleric acid concentration of 3.7 mg/l and a mixed bacterial culture isolated from low-level radioactive waste trench leachate from Maxey Flats, KY reported a 37% increase in isovaleric acid concentration after 21 days incubation(1). These increases in concentration were attributed to the microbial degradation of complex compounds(1). Isovaleric acid was completely degraded in an aerobic biodegradation study using a chemical concentration of 17.9 mg/l and a mixed bacterial culture isolated from low-level radioactive waste trench leachate from West Valley, NY(1). A biodegradation study based on oxygen depletion measurements, using a sewage seed and a chemical concentration of 2.0 mg of carbon/l, indicate that isovaleric acid is readily biodegraded(2). An initial isovaleric acid concentration of 30 mg carbon/l was anaerobically biodegraded 91% after 21 days incubation in synthetic sewage(3).

Isovaleric acid is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: 1) the quantity added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) when intended for use in or on food it is of appropriate food grade and is prepared and handled as a food ingredient.

(14)C-LABELED ISOVALERIC ACID ADMIN ORALLY TO RATS SHOWED ISOPROPYL GROUP WAS MORE EFFICIENTLY UTILIZED FOR CHOLESTEROL SYNTH THAN CARBOXYL GROUPS, & ALSO MORE EFFICIENTLY UTILIZED THAN FATTY ACID SYNTH. CLEAVAGE OF ACID INTO 2 FRAGMENTS OCCURS BEFORE CHOLESTEROL SYNTH. (14)C-LABELED ISOVALERIC ACID ADMIN ORALLY TO RATS APPEARS TO ENHANCE THE INCORPORATION OF CARBON DIOXIDE INTO CHOLESTEROL.

All liver mitochondrial preparations were affected by 1.19 mM isovalerate. Isovaleryl CoA is a potent inhibitor of succinate:CoA ligase (SCL) with positive cooperativity and half-maximal inhibition at 273 +/-11 uM isovaleryl CoA. The investigators suggested that inhibition of the citric acid cycle at the SCL step may be a general mechanism of organic acid toxicity to mitochondria.

In contrast to valeric acid, isovaleric acid is ketogenic. ...Is metabolized by the liver to give two- and three-carbon fragments. The isopropyl fragment of isovaleric acid is readily converted to acetoacetate and is an efficient source of carbon atoms for fatty acid and cholesterol synthesis. Isovaleric acid ... has been identified in the fermentative organs of ruminant animals.

Isovaleric acid is an intermediate in leucine metabolism. High blood concentrations of isovaleric acid occur in patients with the clinical disorder "isovaleric acidemia." This is a genetic defect of leucine metabolism in which the enzyme isovaleryl-coenzyme A dehydrogenase is inhibited or absent. The disease is characterized by episodic acidosis, slight mental retardation, and an unpleasant body odor.

RATS RECEIVING LABELED ISOVALERIC ACID EXCRETED NONRADIOACTIVE ISOVALTHINE.

Isovalerate given iv to normal rats was rapidly metabolized, with a 50% decr in plasma concn after 11 min, and this time was shortened to 5 min by the simultaneous admin of glycine. The hypoglycin metabolite methylenecyclopropylacetate-CoA inhibited butyryl-CoA dehydrogenase and isovaleryl-CoA dehydrogenase in liver.

Gas chromatographic and mass spectrometric parameters of isovaleryl-beta-D-glucuronide, a new metabolite in the urine of patients with isovaleric acidemia, were presented. The significance of this metabolite for the detoxication of isovalerate in isovaleric acid media is discussed.

Found in hop oil, tobacco, and other plants; [Merck Index] Used as a fragrance and flavor and to make fungicides, rodenticides, sedatives, narcotics, and other drugs; [HSDB] Used to make esters for solvents, softeners, and perfumes; [CHEMINFO]

FRAGRANCE INGREDIENT IN PERFUMES; FLAVOR INGREDIENT IN PERFUMES, NON-ALC BEVERAGES, FOODS; CHEM INT FOR SEDATIVES

Medicine, flavors, perfume.

In sedative manufacture.

Used to make fungicides, rodenticides, sedatives, narcotics, and other drugs.

CALDWELL, US PATENT 2,484,486 (1949 TO KODAK); GUSTAK, SAJKO, ARKIV KEMI 24, 11 (1952); CA 49, 163E (1955); L'VOV ET AL, ZH PRIKL KIM 35, 700 (1962).

With other valeric acids, by distillation from valerian, by oxidation of isoamyl alcohol.

Oxidation of isovaleradehyde.

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

All Other Basic Organic Chemical Manufacturing

Butanoic acid, 3-methyl-: ACTIVE

"VALERIC" ACID OF COMMERCE IS ISOVALERIC ACID.

OF THE 3 POSSIBLE ISOMERS OF N-VALERIC ACID, ONLY ISOVALERIC ACID FINDS EXTENSIVE APPLICATION IN FLAVORING. ... REPORTED USES /IN/ NON-ALCOHOLIC BEVERAGES: 1.2 PPM; ICE CREAMS, ICES: 14 PPM; CANDY: 12 PPM; BAKED GOODS: 5.5 PPM; CHEESE: 2.4 PPM.