Isovaleric Acid

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.

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.