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Nonanoic acid

Nonanoic acid structure

Nonanoic acid 

structure
  • CAS No:

    112-05-0

  • Formula:

    C9H18O2

  • Chemical Name:

    Nonanoic acid

  • Synonyms:

    Nonanoic acid;Nonoic acid;n-Nonoic acid;Nonylic acid;1-Octanecarboxylic acid;Pelargonic acid;n-Nonylic acid;n-Nonanoic acid;n-Pelargonic acid;Grantrico;NSC 62787;NSC 65450;NSC 65455;Emery 1203;Thinex;2243464-06-2

  • Categories:

    Cosmetic Ingredient  >  Perfuming

Description

clear colorless liquid Colorless or yellowish, combustible, oily liquid. Faint odor. Nonanoic acid has a fatty, characteristic odor and a corresponding unpleasant taste. May be prepared by oxidation of methylnonyl ketone; by oxidation of oleic acid; or from heptyl iodide via malonic ester synthesis. Nonanoic acid has a fatty, characteristic odor and a corresponding unpleasant taste. This compound is also reported as having a cheese, waxy flavorChEBI: A C9 straight-chain saturated fatty acid w


Liquid; OtherSolid, Liquid|Liquid|colourless to pale yellow liquid


Nonanoic acid is a C9 straight-chain saturated fatty acid which occurs naturally as esters of the oil of pelargonium. Has antifungal properties, and is also used as a herbicide as well as in the preparation of plasticisers and lacquers. It has a role as an antifeedant, a plant metabolite, a Daphnia magna metabolite and an algal metabolite. It is a straight-chain saturated fatty acid and a medium-chain fatty acid. It is a conjugate acid of a nonanoate. It derives from a hydride of a nonane.|Nonanoic Acid is a naturally-occurring saturated fatty acid with nine carbon atoms. The ammonium salt form of nonanoic acid is used as an herbicide. It works by stripping the waxy cuticle of the plant, causing cell disruption, cell leakage, and death by desiccation.

Nonanoic acid Basic Attributes

158.24

158.24

1752351

203-931-2

97SEH7577T

62787

DTXSID3021641

C82932

Colorless, oily liquid at ordinary temp; crystallizes when cooled|Yellowish oil

29159080

Characteristics

37.3

3.42

Clear colorless Liquid

0.9052 g/cm3 @ Temp: 20 °C

12.5 °C

252-253 °C @ Press: 760 Torr

212 °F

n 20/D 1.432(lit.)

H2O: negligible soluble

2-8°C

<0.1 mm Hg ( 20 °C)

5.5 (vs air)

LD50 i.v. in mice: 224±4.6 mg/kg (Or, Wretlind)

0.8-9%(V)

FATTY ODOR

UNPLEASANT TASTE

Henry's Law constant = 1.62X10-6 atm-cu m/mole at 25 °C (est)

pKa = 4.95 at 25 °C

143.33 Ų [M-H]- [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]

Acid value: 351 mg KOH/g|Specific heat: 2.91 J/g (for the solid); Heat of fusion: 20.3 kJ/mol.|Hydroxyl radical reaction rate constant = 9.76X10-12 cu cm/molec-sec at 25 °C (est)

-5,456.1 kJ/mol

Safety Information

III

8

UN 3265 8/PG 3

1

34

26-28-36/37/39-45-28A

RA6650000

C

Stable under normal temperatures and pressures.

P280-P303 + P361 + P353-P304 + P340 + P310-P305 + P351 + P338

H314

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.|Do not contaminate water, food, or feed by ... disposal. ... Pesticide disposal:: Wastes resulting from the use of this product must be disposed of on site or at an approved waste disposal facility. Container disposal: Do not reuse empty container. Triple rinse, then offer for recycling or reconditioning, or puncture and dispose of in a sanitary landfill or by incineration, or if allowed by state and local authorities, by burning. If burned, stay out of smoke. /Scythe herbicide (57% pelargonic acid)/

Nonanoic 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: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.

European Chemicals Bureau; IUCLID Dataset, Nonanoic acid (CAS # 112-05-0) (2000 CD-ROM edition). Available from the Database Query page at: http://ecb.jrc.it/esis/esis.php as of January 18, 2008.|USEPA/HPVIS; SCREENING-LEVEL HAZARD CHARACTERIZATION: C7 to C9 Aliphatic Aldehydes and Carboxylic Acids Category (August 2007) Available from http://www.epa.gov/hpvis/hazchar/Category_C7-C9 Aliphatic Aldehydes & Carboxylic Acids_HC_August 2007.pdf as of January 16, 2008.

|Warning|H315: Causes skin irritation [Warning Skin corrosion/irritation]|P264, P273, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362, and P501|Danger|H314 (62.04%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P260, P264, P280, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P332+P313, P337+P313, P362, P363, P405, and P501|Aggregated GHS information provided by 197 companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P260, P264, P273, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P391, P405, and P501|Aggregated GHS information provided by 298 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H314 (92.7%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]|P260, P264, P273, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, and P501|Aggregated GHS information provided by 2493 companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, and P362

Worker Protection Standard (WPS) Uses: Some materials that are chemical-resistant to this product are listed below. If you want more options, follow the instructions for category E on an EPA chemical resistance category selection chart. Applicators and other handlers who handle this pesticide for any use covered by the WPS ... must wear: Coveralls worn over short-sleeved shirt and short pants; chemical-resistant gloves such as barrier laminate, nitrile rubber, or neoprene rubber; chemical-resistant footwear plus socks; protective eyewear (goggles, face shield or safety glasses) /Scythe herbicide (57% pelargonic acid)/|Agricultural Use Requirements: Personal protective equipment required for early entry to treated areas that is permitted under the Worker Protection Standard and that involves contact with anything that has been treated, such as plants, soil, or water, include: Coveralls worn over short-sleeved shirt and short pants; chemical-resistant gloves such as barrier laminate, nitrile rubber, or neoprene rubber; chemical-resistant footwear plus socks; protective eyewear (goggles, face shield or safety glasses... /Scythe herbicide (57% pelargonic acid)/|Non-WPS Uses: Applicators and other handlers who handle this pesticide for any use not covered by the Worker Protection Standard ... must wear: Long-sleeved shirt and long pants; chemical-resistant gloves such as barrier laminate, nitrile rubber, or neoprene rubber; protective eyewear (goggles, face shield or safety glasses) /Scythe herbicide (57% pelargonic acid)/

Combustible

Combustible

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: 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.|Agricultural Use Requirements: Use this product only in accordance with its labeling and with the Worker Protection Standard... . Do not enter or allow worker entry into treated areas during the restricted entry interval (REI) of 12 hours. ./Scythe herbicide (57% pelargonic acid)/|Do not get in eyes, on skin or on clothing. Avoid breathing spray mist. Wash thoroughly with soap and water after handling. Pemove contaminated clothing and wash clothing before reuse. /Scythe herbicide (57% pelargonic acid)/|For more Preventive Measures (Complete) data for NONANOIC ACID (8 total), please visit the HSDB record page.

Pelargonic acid is a skin and eye irritant.|Causes substantial but temporary eye injury. Causes skin irritation. ... /Scythe herbicide (57% pelargonic acid)/

Nonanoic acid was detected in aqueous industrial effluent extracts collected between Nov 1979-81 in the following industrial categories (concentration in one effluent extract): ore mining (12 ng/uL); auto and other laundries (34 ng/uL); porcelain/enameling (28 ng/uL); electronics (3084 ng/uL); mechanical products (1954 ng/uL); and publicly owned treatment works at an unknown concn(1). Nonanoic acid was identified in the acidic fraction of sewage and sludge from the Iona Island Sewage Treatment Plant, British Columbia(2). The acidic fraction of oil shale retort water from the Kerosene Creek seam of the Rundle deposit, Queensland, Australia, was found to contain nonanoic acid at a concn of 200 mg/L(3). A grab sample, obtained in April 1980, of the final effluent from the Addison, IL Publicly Owned Treatment Works was found to contain nonanoic acid at an unreported concn(4). Groundwater samples contaminated by industrial pollution near Barcelona, Spain were found to contain nonanoic acid at concns ranging from <5 to 75 ng/L(5). Nonanoic acid was detected in trench leachate from a low-level radioactive waste disposal site in West Valley, NY at an average concn of 4.5 mg/L(6). Nonanoic acid was detected in process retort water from the Occidental Oil Shale, Inc facility in Logan Wash, CO at a concn of 81 mg/L(7). Nonanoic acid was detected in: process water from in situ coal gasification in Gillette, WY at a concn of 5 ppm; retort water from in situ oil shale processing in Rock Springs, WY at a concn of 493 ppm; and boiler blowdown water from in situ shale oil processing in DeBeque, CO at a concn of 132 ppm(8). Nonanoic acid was detected in emissions from a municipal waste incineration plant at an unspecified concn(9).|Nonanoic acid was emitted from medium duty diesel trucks at 240 ug/km(1). Nonanoic acid was measured in the emissions of gasoline powered motor vehicles at a rate of 27.9 ug/km and 80.6 ug/km for catalyst equipped engines and non-catalyst equipped engines(2). Fine aerosol emission rates of nonanoic acid from heavy-duty diesel trucks, noncatalyst-equipped, and catalyst-equipped automobiles were 146.9, 8.6, and 196.2 ug/km, respectively(3). Nonanoic acid was detected in road dust particles collected from paved streets in a residential area of Pasadena, CA in May 1988 at a concn of 135.4 ug/g of particle sample; brake lining particles at a concn of 87.4 ug/g of particle sample; and tire wear particles at a concn of 90.9 ug/g of particle sample(4). Nonanoic acid was detected in exhaust from a gasoline engine at a concn of 0.052 ppb(5).|Nonanoic acid was identified as a fine particle released from a natural gas-fired space heater and water heater; emission rates were 225.2 pg/kJ and 482.6 pg/kJ for the first series of filters and backup filters within the samplers, respectively(1). Nonanoic acid was found in candle smoke from paraffin and beeswax at 0.25 and 0.31 mg/g of organic compounds(2). Nonanoic acid was found in the fine aerosols from boilers burning number 2 distillate fuel oil at a rate of 184.8 pg/kJ (burning at 58% capacity with 6.5% excess oxygen in stack gases) and not detected (burning at 54% capacity with 7.1% excess oxygen in stack gases)(3). Nonanoic acid was not detected in wood smoke from pine, and detected in smoke from oak and synthetic logs at 0.24 and 0.97 mg/kg of wood burnt(4). Nonanoic acid was found at 1312 ug/g from heated roofing tar pot fumes(5). Nonanoic acid was found in gas and particulate matter effluents from commercial-scale meat charbroiling operations at 42,400 and 6,030 ug/kg meat cooked, respectively(6).

SEDIMENT: Nonanoic acid was detected, not quantified in sediment samples collected from Dokai Bay, Japan on Sept 28 1990(1). Nonanoic acid was identified in sediment samples taken Sept 1995 at the mouth of 3 rivers and in 1 port in Niigata, Japan(2).

URBAN/SUBURBAN: Nonanoic acid was identified in air samples collected along the Niagara River in Sept 1982 at an unreported concn(1). The average ambient annual concn of nonanoic acid in fine particles collected from West Los Angeles, downtown Los Angeles, Pasadena, and Rubidoux,, CA in 1982 was 3.3, 6.6, 5.3, and 9.9 ng/cu m, respectively(2). Nonanoic acid had an average concentration of 4.9 ng/cu m in 4 urban sites from southern CA from samples taken Sept 8-9, 1993(3). Nonanoic acid was found at 0.002-0.009, 0.002-0.008, 0.007-0.013, and 0.005-0.006 ppbv at UCLA campus, Newberry Park, Monterey Park, and La Habra, CA in Oct 1984(4). Air samples collected in Los Angeles between July and Sept 1984 contained 0.0009 to 0.011 ppb nonanoic acid(5). Nonanoic acid was detected at 0.09, 0.11, 0.14 and 0.13 ug/cu m in Long Beach, Los Angeles, Azusa and Claremont, CA, respectively, Sept 8-9, 1993(6).|RURAL/REMOTE: The average ambient annual concn of nonanoic acid in fine particles collected from San Nicolas Island , CA in 1982 was 0.24 ng/cu m(1). Nonanoic acid was detected at 0.01 ug/cu m on San Nicolas Island, CA, Sept 8-9, 1993(2). Nonanoic acid was detected at an unreported concn in air samples collected in a spruce forest in Eggegebirge, North-Rhine Westphalia(3). Remote aerosol samples collected from the North Pacific Ocean, heavily vegetated areas of American Samoa, and the Marshall Islands contained a nonanoic acid concn of 0.031, 4.91, and 0.060 mg/cu m, respectively(4).

Dust samples collected from 12 households in three urban areas of central Finland contained nonanoic acid at an unreported concn(1). Nonanoic acid was found in unburned paraffin and beeswax at 0.33 and 0.30 mg/g of wax(2).

Toxicity

Skin reactions to 40% nonanoic acid in propanol (NON) ... were evaluated by image analysis of 20 MHz B scan recordings (Dermascan C, Cortex Technology). 18 women, aged 18 to 45, were patch tested with 24-hr application time, and clinical and instrumental evaluations were performed at the beginning of the experiment, and 24 and 48 hr after patch testing. To check possible regional variations ... /NON/ was applied 2 x on the same forearm. As control tests, saline solution, propanol and sodium lauryl sulfate (SLS) 3% were applied. Echographic images were processed by a program enabling numerical representation of picture data, based on attribution of fictional values to the echoes' amplitudes, selection of amplitude bands of interest, binary transformation of the image, and calculation of the extension of areas reflecting within the same amplitude range. Sonographic recordings were evaluated by an amplitude interval marking hyporeflecting parts of the dermis (corresponding to edema and inflammatory infiltration), and by a band highlighting the entrance echo (epidermis) ... Evaluations showed that extension of the hypoechogenic area of the dermis increases according to intensity of inflammatory reaction for all irritant substances. A clear decrease in reflectivity of the epidermis echo at 24 hr was visible at SLS patch test test sites, whereas at patch test sites performed with NON ... there was a trend towards an increase in values of hyperreflecting pixels. No significant variations between data recorded at proximal compared to distal skin sites were observed ... /40% Nonanoic acid in propanol/

LD50 Mouse oral 15000 mg/kg|LD50 Mouse iv 224 mg/kg|LD50 Rabbit dermal >5000 mg/kg

/AQUATIC SPECIES/ PELARGONIC ACID INHIBITED CLEAVAGE OF HEMICENTROTUS PULCHERRIMUS EGGS AT A CONCN OF 200 PPM.|/OTHER TERRESTRIAL SPECIES/ Pelargonic acid inhibited pollen germination and pollen tube elongation in Camellia sinensis (tea plant).|/PLANTS/ PELARGONIC ACID INHIBITED POLLEN GERMINATION (AVG GERMINATION 0-1.1%) AND POLLEN TUBE ELONGATION (AVG TUBE LENGTH 0-0.2 NM) IN CAMELLIA SINENSIS AND MITOTIC DIVISION OF GENERATIVE NUCLEUS IN ORNITHOGALUM VIRENS (AVG MITOSIS 0-40.6%).

...AS AN ESTER IN OIL OF PELARGONIUM.|...IN SEVERAL ESSENTIAL OILS, EITHER FREE OR ESTERIFIED: ROSE, GERANIUM, ORRIS, LITSEA CUBEBA, ARTEMISIA ARBORESCENS L, HOPS, CHAMAECYPARIS PISIFERA ENDL, EREMOCITRUS GLAUCA L, FRENCH LAVENDER, AND IN OAK MUSK.|Nonanoic acid was identified as a volatile constituent of the kiwi fruit flower(1) and of raw earth-almond (Cyperus esculentus L.)(2). Nonanoic acid was found in fine particulate matter released (by resuspension and agitation of the leaf composites) from green and dead plant leaves at concentrations of 444.7 and 596.8 ug/g, respectively(3). The compound is a carboxylic acid that is also known as a fatty acid because fatty acids were first isolated by the hydrolysis of naturally occurring fats(4). Fatty acids are widely distributed in nature as components of animal and vegetable fats(5) including lipids such as oils and fats, waxes, sterol esters and other minor compounds(4).

Nonanoic acid's production and use in organic syntheses, lacquers, plastics, in the production of hydrotropic salts, pharmaceuticals, synthetic flavors and odors, esters for turbojet lubricants, as a flotation agent, vinyl plasticizer, and as a gasoline additive(1) may result in its release to the environment through various waste streams. Its use as a herbicide(2) will result in its direct release to the environment.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,700 for the free acid(SRC), determined from a log Kow of 3.42(2) and a regression-derived equation(3), indicates that undissociated nonanoic acid is expected to have low mobility in soil(SRC). The pKa of nonanoic acid is 4.95(4), indicating that this compound will exist almost entirely in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of nonanoic acid from moist soil surfaces is not expected to be an important fate process(SRC) given the pKa. Nonanoic acid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.65X10-3 mm Hg(6). Biodegradation studies of nonanoic acid show a total organic carbon removal ratio of 99% using a non-acclimated activated sludge(7), and a BOD of 0.59 (g/g) after 5 days incubation using a sewage inoculum(8), suggesting biodegradation is an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,700 for the free acid(SRC), determined from a log Kow of 3.42(2) and a regression-derived equation(3), indicates that undissociated nonanoic acid is expected to adsorb to suspended solids and sediment(SRC). A pKa of 4.95(4) indicates nonanoic acid will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation studies of nonanoic acid show a total organic carbon removal ratio of 99% using a non-acclimated activated sludge(8), and a BOD of 0.59 (g/g) after 5 days incubation using a sewage inoculum(9), suggesting biodegradation is an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), nonanoic acid, which has a vapor pressure of 1.65X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase nonanoic 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 1.6 days(SRC), calculated from its rate constant of 9.8X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Nonanoic acid does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(4).

The rate constant for the vapor-phase reaction of nonanoic acid with photochemically-produced hydroxyl radicals has been estimated as 9.8X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1.6 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Nonanoic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Nonanoic acid does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(3).

An estimated BCF of 3 was calculated in fish for nonanoic acid(SRC), using a log Kow of 3.42(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Koc of undissociated nonanoic acid is estimated as 1,700 for the free acid(SRC), using a log Kow of 3.42(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that undissociated nonanoic acid is expected to have low mobility in soil. The pKa of nonanoic acid is 4.95(4), indicating that this compound will exist almost entirely in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5).

A pKa of 4.95(1) indicates nonanoic acid will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces and moist soil is not expected to be an important fate process(2). Nonanoic acid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.65X10-3 mm Hg(3).

DRINKING WATER: Nonanoic acid was quantitatively detected in drinking water in: Cincinnati, OH in Oct 1978; New Orleans, LA in Jan 1976; Philadelphia, PA in Feb 1976; Ottumwa, IA in Sept 1976; and Seattle, WA in Nov 1976(1). Nonanoic acid was identified in the initial survey of raw and treated water taken at waterworks treating lowland river water in the UK between March and December 1976(2). In the survey of treated water, nonanoic acid was identified in 3 of 14 samples taken between Feb and June 1979 after new treatment procedures were implemented(2). Nonanoic acid was identified as a byproduct of chlorine dioxide disinfection of drinking water at a pilot plant in Evansville, IN(3). Nonanoic acid was identified as an ozone disinfection by-product in drinking water samples from a pilot plant in Jefferson Parish, LA which uses Mississippi River as the raw water source; samples were collected following 4 rounds of ozonation treatment performed in January, 1994, August 1994, May 1995, and September 1996(4).|SURFACE WATER: Nonanoic acid was detected at a concn of 0.01 ppb in a water sample from the Inner Harbor Navigation Canal, Lake Pontchartain, New Orleans, LA collected at a depth of 10 m on the flood tide on June 23, 1980(1).|RAIN/SNOW: Nonanoic acid was detected in rainwater samples collected in a suburb of Hannover, Germany at an unspecified concn(1). Rain and snow samples collected from nine different locations in southern CA between 1982 and 1984 contained nonanoic acid at concns ranging from 0.007 to 0.14 uM(2). Rainwater samples collected in west Los Angeles between 1982 and 1983 contained nonanoic acid at concns ranging from 0.01 to 0.13 uM(2). Nonanoic acid was identified at 6 of 10 snow sample sites; 0.11 ug/kg at Nellim (Lapland, Finland), 0.12 ug/kg at Muonio (Lapland, Finland), 0.56 ug/kg at Levi (Lapland, Finland), 0.05 ug/kg at Butovo (Moscow, Russia), 0.53 ug/kg at Moscow State University (Moscow, Russia), and 1.51 ug/kg at Baikal'sk (Lake Baikal, Siberia)(3).

Nonanoic acid was identified as a volatile component of raw beef(1). Nonanoic acid has been identified as a volatile flavor component of mutton and beef(2). Aerosol emission rates of nonanoic acid from frying hamburger meat was 10.2 mg/kg of meat cooked; emission rates from charbroiling hamburger was 30.6 mg/kg of meat cooked for extra lean hamburger (approx. 10.0% fat) and 47.1 mg/kg of meat cooked for regular hamburger (approx. 21% fat)(3). Nonanoic acid was found in popcorn using wet extraction method at 29 ug/kg(4). Nonanoic acid was detected, not quantified as a volatile component of raw and roasted earth-almond (Cyperus esculentus L.)(5). Nonanoic acid was found in gas and particulate matter effluents from commercial-scale meat charbroiling operations at 42,400 and 6,030 ug/kg meat cooked, respectively(6).

NIOSH (NOES Survey 1981-1983) has statistically estimated that 76,346 workers (6,777 of these were female) were potentially exposed to nonanoic acid in the US(1). Occupational exposure to nonanoic acid may occur through inhalation and dermal contact with this compound at workplaces where nonanoic acid is produced or used(SRC). Monitoring data indicate that the general population may be exposed to nonanoic acid via inhalation of ambient air, ingestion of food and drinking water, and dermal contact with this compound or other products containing nonanoic acid(SRC).

Drug Information

/EXPL THER/ The treatment for patients with genetic disorders of mitochondrial long-chain fatty acid beta-oxidation is directed toward providing sufficient sources of energy for normal growth and development, and at the same time preventing the adverse effects that precipitate or result from metabolic decompensation. Standard of care treatment has focused on preventing the mobilization of lipids that result from fasting and providing medium-chain triglycerides (MCT) in the diet in order to bypass the long-chain metabolic block. MCTs that are currently available as commercial preparations are in the form of even-chain fatty acids that are predominately a mixture of octanoate and decanoate. Recently, the use of odd-chain fatty acids has been proposed as an alternative treatment ... /The authors/ have shown previously that the even-numbered medium-chain fatty acids (MCFAs) that are found in MCT preparations can reduce the accumulation of potentially toxic long-chain metabolites of fatty acid oxidation (FAO). In the current study ... /they/ found that provision of odd-chain species does decrease the build-up of long-chain FAO intermediates in ... in vitro skin fibroblast model, but to a lesser extent than even-numbered MCFAs. /Odd-numbered medium-chain fatty acids (MCFAs)/

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)

INFUSION OF AN EMULSION CONTAINING 20% TRINONANOATE, 0.9% SODIUM CHLORIDE, & 1% SOYBEAN LECITHINS INTO DOGS RESULTED IN OXIDN OF NONANOIC ACID.|NONANOIC ACID IS METABOLIZED BY THE LIVER TO PRODUCE KETONE BODIES. METABOLISM OCCURS VIA BETA-OXIDATION, AND NO EVIDENCE WAS FOUND IN RATS OF CHAIN ELONGATION OR TISSUE STORAGE OF THE ACID. METAB OF THE TERMINAL PROPIONIC ACID RESIDUE RESULTS IN INCREASED GLUCOSE AND GLYCOGEN SYNTHESIS.

The epidermal response to 2 different irritants, nonanoic acid (NAA) and sodium lauryl sulfate (SLS), was investigated with 2 different methods. NAA 80% and SLS 4% were applied under occlusion for up to 24 hr. Elemental changes were determined in cryosections by x-ray microanalysis. Compared to unexposed skin a significantly higher sodium/potassium ratio was found after 6 hr in NAA-exposed skin and a lower ratio in SLS-exposed. At 24 hr both substances had induced similar changes, compatible with a cell injury. The findings demonstrate a time-dependent NAA and SLS response. With reverse transcription polymerase chain reaction, the mRNA expression of interleukin-1 alpha (IL-1 alpha), -1 beta (IL-1 beta), -6 (IL-6), and -8 (IL-8), tumor necrosis factor alpha (TNF alpha) and granulocyte macrophage colony stimulating factor (GM-CSF) in shave biopsies from irritated and unexposed skin was studied at 0, 4, 8, and 24 hr. NAA, but not SLS, induced an increase in mRNA expression for IL-6. mRNA-expression for GM-CSF was increased after SLS exposure, but not after NAA. These findings indicate a time and substance dependent difference in the up-regulation of mRNA for different cytokines in epidermis during the first 24 hr of the irritants' reaction. This might be the effect of differences in the irritants action on the cell membranes, which is also reflected by the differences found in the elemental content at 6 hr.|It has been shown that polyunsaturated fatty acids such as arachidonic and docosahexanoic acids but not monounsaturated and saturated long-chain fatty acids promote basal and nerve growth factor (NGF)-induced neurite extension of PC12 cells, a line derived from a rat pheochromocytoma. On the other hand, short-chain fatty acids and valproic acid (2-propylpentanoic acid) enhance the growth of neurite processes of the cells only in the presence of inducers. In this study, /investigators/ demonstrated that straight medium-chain fatty acids (MCFAs) at millimolar concentrations alone potently induced neuronal differentiation of PC12 cells. ... Nonanoic, decanoic, and dodecanoic acids also induced growth of neurite processes, but their maximal effects were less marked than that of octanoic acid. ...

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Organic acids and related compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist respirations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Activated charcoal is not effective ... . Do not attempt to neutralize because of exothermic reaction. Cover skin burns with dry, sterile dressings after decontamination ... . /Organic acids and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Early intubation, at the first sign of upper airway obstruction, may be necessary. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic acids and related compounds/

/HUMAN EXPOSURE STUDIES/ A 12% soln of nonanoic acid in petrolatum produced no irritation on human skin after a 48-hr closed patch test. ... no sensitization reactions were produced in 25 volunteers after patch testing with nonanoic acid (12% in petrolatum).|/HUMAN EXPOSURE STUDIES/ Various concn of nonanoic acid in 1-propanol were applied to 116 healthy volunteers and 75 dermatitis patients as a positive control for patch testing. A dose of 20% produced skin reactions in 90.1-93.9% of subjects. Lesions consisted of erythema at 48 hr & pigmentation @ 96 hr.|/HUMAN EXPOSURE STUDIES/ ...(0.5 OR 1.0 Molar in propanol) caused irritation /in humans/ when applied under occlusive patches.|/HUMAN EXPOSURE STUDIES/ Skin reactions to 40% nonanoic acid in propanol (NON) ... were evaluated by image analysis of 20 MHz B scan recordings (Dermascan C, Cortex Technology). 18 women, aged 18 to 45, were patch tested with 24-hr application time, and clinical and instrumental evaluations were performed at the beginning of the experiment, and 24 and 48 hr after patch testing. To check possible regional variations ... /NON/ was applied 2 x on the same forearm. As control tests, saline solution, propanol and sodium lauryl sulfate (SLS) 3% were applied. Echographic images were processed by a program enabling numerical representation of picture data, based on attribution of fictional values to the echoes' amplitudes, selection of amplitude bands of interest, binary transformation of the image, and calculation of the extension of areas reflecting within the same amplitude range. Sonographic recordings were evaluated by an amplitude interval marking hyporeflecting parts of the dermis (corresponding to edema and inflammatory infiltration), and by a band highlighting the entrance echo (epidermis) ... Evaluations showed that extension of the hypoechogenic area of the dermis increases according to intensity of inflammatory reaction for all irritant substances. A clear decrease in reflectivity of the epidermis echo at 24 hr was visible at SLS patch test sites, whereas at patch test sites performed with NON ... there was a trend towards an increase in values of hyperreflecting pixels. No significant variations between data recorded at proximal compared to distal skin sites were observed ... /40% Nonanoic acid in propanol/|For more Human Toxicity Excerpts (Complete) data for NONANOIC ACID (13 total), please visit the HSDB record page.

nonanoic acid

Nonanoic acid Use and Manufacturing

Methods of Manufacturing

It is derived from the oxidation of nonanol or nonanal or methyl nonanone. Oleic acid is obtained by ozone oxidation.

Uses

In the production of hydrotropic salts (hydrotropic salts form aqueous solutions which dissolve sparingly soluble substances to a greater extent than water); in the manufacture of lacquers, plastics.


Agricultural chemicals (non-pesticidal)|Commercial and industrial products.|Intermediates


Adhesives and sealants|Industrial organic chemicals used in commercial and consumer products.

Production

10,000,000 - 50,000,000 lb|1,000,000 - 10,000,000 lb|(1980) 9.75X10+9 GRAMS (EST CONSUMPTION)|(1981) PROBABLY GREATER THAN 6.81X10+6 GRAMS|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5435]|Nonanoic acid is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Grade: Technical 99%|Econosan Acid Sanitizer: Active Ingredients 8.50% Phosphoric acid, 10.0% Propionic acid, 9.50% Sulfuric acid, 3.00% Capric acid; 3.00% Nonanoic acid|Mandate Plus: Active Ingredients 1.09% Capric acid and 6.30% Nonanoic acid|MON 78999 Herbicide: Active Ingredients 2.00% Glyphosate, isopropylamine salt, and 2.00% Nonanoic acid|For more Formulations/Preparations (Complete) data for NONANOIC ACID (10 total), please visit the HSDB record page.

Adhesive manufacturing|Nonanoic acid: ACTIVE|All other basic organic chemical manufacturing|Fatty acids, C8-10: ACTIVE|Fatty acids, C6-12: ACTIVE|FLAVORS USEFUL IN COCONUT, BERRY.|PELARGONIC ACID SHOWED STRONG ANTIBACTERIAL ACTIVITY AGAINST STREPTOCOCCUS FAECALIS IN SILKWORM LARVAE.|PLAQUE SAMPLES COLLECTED AFTER A NONANOATE-GLUCOSE MOUTH RINSE @ PH 8.0 SHOWED LESS ACID FORMATION AND GLYCOLYSIS. NONANOATE IS EFFECTIVE IN THE PRESENCE OF SUGAR IN INHIBITING GLYCOLYSIS & PREVENTING LOW PH PRODN FROM CARBOHYDRATES WHICH ARE LIKELY TO BE HIGHLY CARIOGENIC.|FEMA NUMBER 2784|For more General Manufacturing Information (Complete) data for NONANOIC ACID (6 total), please visit the HSDB record page.

SIMULTANEOUS GAS CHROMATOGRAPHIC SEPARATION OF A MIXT OF FATTY ACIDS, PHENOLS AND INDOLES INCL NONANOIC ACID IN CIGARETTE SMOKE IS DESCRIBED.

Analyte: nonanoic acid; matrix: blood (plasma); procedure: high-performance liquid chromatography with fluorescence detection at 365 nm (excitation) and 460 nm (emission); limit of quantitation: 5 pmole|Analyte: nonanoic acid; matrix: blood (serum); procedure: high-performance liquid chromatography with fluorescence detection at 350 nm (excitation) and 530 nm (emission)

EPA Safer Chemical Functional Use Classes -> Uncategorized|Safer Chemical Classes -> Green half-circle - The chemical is expected to be of low concern|Food additives -> Flavoring Agents|Agrochemicals -> Acaricides, Herbicides, Insecticides, Plant Growth Regulators|Flavoring Agents -> JECFA Flavorings Index|Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Straight chain fatty acids [FA0101]|Herbicides, Insecticides, Other substances, Repellents, Adjuvants, Fungicides|Cosmetics -> Solvent

Flavoring Agents

Computed Properties

Molecular Weight:158.24
XLogP3:3.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:7
Exact Mass:158.130679813
Monoisotopic Mass:158.130679813
Topological Polar Surface Area:37.3
Heavy Atom Count:11
Complexity:99.7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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