Heptanoic Acid

log Kow = 2.42

2.42

2.42 (estimated)

0.92 at 68 °F (USCG, 1999) - Less dense than water; will float

0.9181 at 20 °C/4 °C

Relative density (water = 1): 0.9

0.915-0.920 (20 °C/20 °C)

0.918 @25 °C

3.40 cP at 30 °C; 0.82 cP at 120 °C

4.8 mm²/s at 20 °C

Danger

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

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

Danger

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

P260, P261, P264, P264+P265, P271, P280, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P321, P363, P403+P233, P405, and P501 (click each P-code to see the statement)

Chemical: Heptanoic acid

Heptanoic acid is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Heptanoic acid 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: 14-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/15829

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

This chemical is probably combustible. (NTP, 1992)

Combustible.

Harmful if swallowed, inhaled, or absorbed through skin. Extremely destructive to mucous membranes, upper respiratory tract, skin, and eyes. Inhalation may be fatal as a result of spasm, inflammation and edema of the larynx and bronchi, chemical pneumonitis, and pulmonary edema. Symptoms of exposure may include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting. (USCG, 1999)

Category of C7-C9 aliphatic aldehydes and carboxylic acids: Members and supporting chemicals demonstrate low acute toxicity by oral, dermal, and inhalation exposures; toxicity in repeated-dose studies only at relatively high levels; no evidence of reproductive toxicity, developmental toxicity, or mutagenicity; [EPA ChAMP: Hazard Characterization] A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause pulmonary edema; [ICSC] Emergency treatment: Irritants; [HSDB] Safe when used as a flavoring agent in food; [JECFA] A corrosive substance that can cause injury to the skin and eyes; [CHEMINFO] A highly corrosive substance that can cause severe injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis and pulmonary edema; [MSDSonline]

European Chemicals Bureau; IUCLID Dataset, Heptanoic acid (CAS # 111-14-8) (2000 CD-ROM edition). Available from the Database Query page at: http://ecb.jrc.it/esis/esis.php as of January 15, 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%20Aliphatic%20Aldehydes%20&%20Carboxylic%20Acids_HC_August%202007.pdf as of January 15, 2008.

HEPTANOIC ACID reacts exothermically with bases. Can react, particularly if moist, with active metals to form gaseous hydrogen and a metal salt. Such reactions are slow if the acid remains dry. Corrodes or dissolves iron, steel, and aluminum parts and containers under ordinary conditions. Reacts with cyanide salts to generate gaseous hydrogen cyanide, particuarly if moist. May generate flammable and/or toxic gases with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Reacts with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Reacts exothermically with carbonates and bicarbonates to generate a harmless gas (carbon dioxide). Can be oxidized exothermically by strong oxidizing agents and reduced exothermically by strong reducing agents. A wide variety of products is possible. May initiate polymerization reactions; may catalyze chemical reactions.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Use water spray, powder, foam, carbon dioxide.

Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Give one or two glasses of water to drink. Rest. Refer for medical attention .

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

... FIRE FIGHTING /with/ Powder, water spray, foam, carbon dioxide.

If material involved in fire: Extinguish fire using agent suitable for type of surrounding fire (Material itself does not burn or burns with difficulty.). Keep run-off water out of sewers and water sources.

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.

SPILLAGE DISPOSAL: Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent and remove to safe place (extra personal protection: complete protective clothing including self-contained breathing apparatus).

Personal protection: complete protective clothing including self-contained breathing apparatus. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

If material not on fire and not involved in fire: Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard.

Personnel protection: Keep upwind. Avoid breathing vapors. ... Avoid bodily contact with the material.

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.

Exposure: PREVENT GENERATION OF MISTS! AVOID ALL CONTACT; Inhalation: Ventilation, local exhaust, or breathing protection; Skin: Protective clothing; Eyes: Face shield or eye protection in combination with breathing protection. Ingestion: Do not eat, drink, or smoke during work. Wash hands before eating.

For more Preventive Measures (Complete) data for HEPTANOIC ACID (6 total), please visit the HSDB record page.

EC50; Species: Xenopus laevis (African clawed frog, embryo); Conditions: freshwater, renewal, pH 7.0-7.8; Concentration: 51.3 mg/L for 96 hr (48000-55000 ug/L); Effect: increased developmental changes, general (craniofacial defects, abnormal gut coiling) /> or =98% purity/

LC50; Species: Xenopus laevis (African clawed frog, embryo); Conditions: freshwater, renewal, pH 7.0-7.8; Concentration: 318.6 mg/L for 96 hr (313000-324000 ug/L) /> or =98% purity/

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 490 for the free acid(SRC), determined from a log Kow of 2.42(2) and a regression-derived equation(3), indicates that undissociated heptanoic acid is expected to have moderate mobility in soil(SRC). The pKa of heptanoic acid is 4.8(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 heptanoic acid from moist soil is not expected to be an important fate process because the acid is in the anion form and anions do not volatilize(SRC). Heptanoic acid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.07X10-2 mm Hg(5). Total organic carbon removal of 96% observed for heptanoic acid using a non-acclimated activated sludge(6), suggesting that biodegradation is an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 490 for the free acid(SRC), determined from a log Kow of 2.42(2) and a regression-derived equation(3), indicates that undissociated heptanoic acid is expected to adsorb to suspended solids and sediment(SRC). A pKa of 4.8(4) indicates heptanoic 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). Heptanoic acid, present at an initial concentration of 500 ppm, was biodegraded 24.6, 36.1, and 49.2% of its theoretical BOD after 72 hours using activated sludge(8), indicating biodegradation may be an important fate process in aqueous environments(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), heptanoic acid, which has a vapor pressure of 1.07X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase heptanoic 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 2.3 days(SRC), calculated from its rate constant of 6.9X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Heptanoic 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).

Heptanoic acid has been identified as a volatile flavor component of mutton, beef, and pork(1). Heptanoic acid has been identified as a volatile component of raw beef(2), fried bacon flavor(3), and baked potato flavor(4). Heptanoic acid was found in popcorn using wet extraction method at 25 ug/kg(5). Heptanoic acid was found as a volatile component of raw and roasted earth-almond (Cyperus esculentus L.)(6). Heptanoic acid was found in gas and particulate matter effluents from commercial-scale meat charbroiling operations at 26,000 and 6,190 ug/kg meat cooked, respectively(7).

Annual consumption is 101.67 lb. Individual consumption is 0.0008651 mg/kg/day.

Fatty acids are an important part of the normal daily diet of mammals, birds and invertebrates.

/AQUATIC SPECIES/ Fathead minnows (Pimephales promelas) were exposed to heptanoic acid for 96 hr at a nominal concentration of 120 mg/L in a semi-static system. Mean measured concentrations decreased during the test: 98% at 0 hr, 96% at 24 hr, 97% at 72 hr and 33% at 96 hr. The mean measured concentration was 92 mg/L. No mortalities or sublethal effects were observed throughout the exposure period. 96-hr LC50 > 92 mg/L.

/OTHER TOXICITY INFORMATION/ No mortality /in Cyprinus carpio/ was seen in a feeding study of n-heptanoic acid at doses of 43-115 mg/kg.

Burning sensation. Cough. Headache. Nausea. Shortness of breath. Vomiting. Wheezing. Symptoms may be delayed.

Skin burns. Pain. Blisters.

Redness. Pain. Severe deep burns.

Abdominal cramps. Further see Inhalation.

Heptanoic acid was detected in the leachate of a sanitary landfill located in Barcelona, Spain at an unreported concn(1). Heptanoic acid was found in oil field waste water samples from a California oil processing facility from not detected (detection limit 1 ug/L) to 1.02 mg/L in samples taken from March 1 to June 16, 1995(2). The acidic fraction of oil shale retort water was found to contain heptanoic acid at a concn of 370 mg/L(3). Heptanoic acid was detected in: product water samples from an in situ coal gasification site in Hanna, WY at a concn of 870 ppm; retort water from in situ oil shale processing in Rock Springs, WY at a concn of 79 ppm; and boiler blowdown water from in situ shale oil processing in DeBeque, CO at a concn of 54 ppm(4). Heptanoic acid was detected in process retort water from the Occidental Oil Shale, Inc facility in Logan Wash, CO at a concn of 149 mg/L(5). Heptanoic acid was detected in industrial effluent samples collected between Nov 1979-81 in the following industrial categories: ore mining, 16 ng/uL; organics and plastics, 34 ng/uL; auto and other laundries, 21 ng/L; mechanical products, 1393 ng/uL; and publicly owned treatment works at an unknown concn(6). Heptanoic acid was detected in the emissions of a municipal waste incineration plant at a concn of 0.50 ug/cu m(7). Heptanoic acid was detected in exhaust from a gasoline engine at a concn of 0.047 ppb(8). Heptanoic acid was found in groundwater samples down gradient from a crude oil spill in Bemidji, MN in 1990: 0.140, 0.68, 0.171, 0.082, 0.072, and <0.020 uM at 0, 24, 36, 46, 56, and 66 meters from spill source(9). Heptanoic acid was detected in groundwater from a landfill well near Norman, OK at an estimated concn of 1.0 ug/L(10). Groundwater samples collected 15.5 feet below the land surface near an area contaminated with gasoline contained heptanoic acid at a concn of 4 ug/L(11).

Heptanoic acid was found in gas and particulate matter effluents from commercial-scale meat charbroiling operations at 26,000 and 6,190 ug/kg meat cooked, respectively(1).

The Koc of undissociated heptanoic acid is estimated as 490(SRC), using a log Kow of 2.42(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that undissociated heptanoic acid is expected to have moderate mobility in soil. The pKa of heptanoic acid is 4.8(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).

Heptanoic acid (CAS # 111-14-8) was evaluated for subchronic dermal toxicity and irritation in New Zealand White rabbits (5/sex/group) exposed to 500 mg/kg/day (25% w/w in mineral oil) for 5 days/week for 2 weeks. Half of the animals (3 males, 2 females) received applications upon abraded skin and half (3 females, 2 males) received applications on intact skin. Applications remained uncovered. A control group of 10 rabbits was treated dermally with 2 g/kg/day mineral oil. A solitary male in the abraded group was found dead on Day 11. Upon gross postmortem necropsy, this animal showed significant antemortem weight loss, while all other treated animals showed slight weight losses in the second week. Severe erythema, slight to severe edema, necrosis, eschar, atonia, desquamation, fissuring and exfoliation of eschar tissue was noted at applications sites in all animals. Hair loss and ocular irritation were also noted in treated rabbits. Treatment-related weight loss and signs of dermal irritation resolved in animals held for 2-week recovery. Upon necropsy of 6 animals (3 rabbits each of treatments upon abraded and intact skin) at 2 weeks, no treatment-related gross pathology was identified. Microscopic examination revealed generally localized necrosis accompanied by epidermal hyperplasia, hyperkeratosis, and occasional diffuse and perifollicular dermal inflammation at both abraded and intact application sites. Treated rabbits held for recovery were reepithelialized and continuous with normal follicular structure and population, and with persisting mild to moderate epidermal hyperplasia and hyperkeratosis. Microscopic examination of select visceral organs from the sole lethality, 6 rabbits at 2 weeks and 3 recovered rabbits at 4 weeks failed to reveal a systemic effect of treatment.

Heptanoic acid (CAS # 111-14-8) was evaluated for primary dermal irritation in 6 New Zealand White rabbits exposed with 2 each 0.5 ml occluded dermal applications on either side of the spinal column (one intact and one abraded site) at either the shoulder or the lumbar region of the shaved back for 4 hours. The application sites were examined at 4.5, 24, and 48 hours after initiation of treatment. A solitary rabbit suffered spontaneous death prior to 48-hour observation. This animal displayed dermal irritation of no greater severity than that seen in all other treated rabbits. Severe erythema with mild to moderate edema were consistent throughout 4.5 to 48 hour observations at abraded and intact sites on all animals. A primary irritation score was 5.6/8 for 6 rabbits and study investigators characterized heptanoic acid as "corrosive". Gross necropsy of the study lethality revealed clear nasal discharge, discolored (green and black) abdomen, mottled dark red lungs, mottled tan liver, irregularly edged, pitted and dark spleen, pale red adrenals, dark red foci in the right kidney, dark red foci on inside walls of the stomach, and extreme vascularization of the intestine with dark red foci.

Heptanoic acid (CAS # 111-14-8) was evaluated for developmental and maternal toxicity in 22 pregnant Crl:COBS, CDBR rats administered doses of 1000 mg/kg bw by oral intubation on gestational days 6 through 15. A control group of 22 female rats received gavage doses of corn oil (vehicle). On Day 20, all rats were sacrificed for Caesarian delivery and determination of fetal/embryotoxicity and teratogenic effects, as well as fertility indices and maternal toxicity. No excess mortality, retarded bodyweight gains, decreased food consumption or other clinical signs of maternal toxicity were observed relative to control. Likewise, gross pathology upon terminal sacrifice identified no treatment-related effects in the pregnant dams. Pregnancy rates, mean number of corpora lutea, implantations, and mean implantation efficiency (implantations per corpora lutea) were comparable to controls, as were gravid and nongravid uterine weights, and mean ovarian, uterine, and litter data. Embryotoxic effects (number of resorptions, number of fetuses, fetal viability, mean fetal bodyweight, mean fetal length) were not observed. Gross pathology and skeletal examinations produced no statistically significant evidence of fetotoxicity or teratogenicity in a viable fetal population similar to that in the control group. Of 80 fetuses from 22 litters of the treated rats, a single incidence of hydroureter and 2 dilated ureters were noted that were not seen in control fetuses and total variant treated fetuses were fewer than variant controls.

METABOLISM OF HEPTANOIC ACID, WHICH OCCURS BY BETA-OXIDATION, FOLLOWS THE SAME PATTERN AS OTHER ODD CARBON NUMBER, STRAIGHT CHAIN, ALIPHATIC ACIDS. THIS RESULTS IN THE APPEARANCE OF KETONE BODIES. METABOLISM OF THE REMAINING PROPIONIC ACID MOIETY RESULTS IN GLUCOSE & GLYCOGEN FORMATION.

THE FATTY ACID COMPOSITION OF THE HEART, LIVER, AND EPIDIDYMAL FAT WAS STUDIED AFTER DIETARY ADMIN OF HEPTANOIC ACID TO RATS DEFICIENT IN FATTY ACID. IT HAD NO EFFECT ON FATTY ACID DEFICIENCY IN RATS. ALL OF THE ODD-NUMBERED FATTY ACIDS TESTED SEEMED TO BE MAINLY OXIDIZED THROUGH THE BETA-OXIDATION SPIRAL.

THE BINDING INTERACTIONS OF BOVINE SERUM ALBUMIN (BSA) WITH THE UNBRANCHED FATTY ACIDS PENTANOATE UP TO NONANOATE WERE EXAMINED. A SINGLE, HIGH-AFFINITY SITE WAS OBSERVED FOR EACH FATTY ACID. FROM BINDING AFFINITY AND COMPETITION DATA, THERE APPEARS TO BE DISTINCT ALBUMIN SITES FOR THE SHORT-CHAIN (LESS THAN OR EQUAL TO C7) FATTY ACIDS.

Found in fusel oils; [Merck Index] Used to make special lubricants for aircraft and brake fluids; Also used as a fragrance, flavoring agent, and alkyd resin comonomer; [HSDB] Present in some plants and rancid oils; [CHEMINFO]

Organic synthesis; production of special lubricants for aircraft and brake fluids

SYNTHETIC FLAVORING INGREDIENT

CHEM INT FOR POLYOL ESTERS FOR LUBE OILS

CHEM INT FOR METAL SALTS USED IN PLASTICS MFR & GREASES

For more Uses (Complete) data for HEPTANOIC ACID (7 total), please visit the HSDB record page.

(1979) 5.45X10+9 GRAMS

(1980) 3.63X10+9 GRAMS

2023: 50,000,000 - <100,000,000 lb

(1980) 7.26X10+9 GRAMS

(1981) PROBABLY GREATER THAN 2.27X10+6 GRAMS

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5426]

Heptanoic 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).

Prepared by the oxidation of heptaldehyde with potassium permanganate in sulfuric acid.

1-Hexene (hydroformylation/carbonyl oxidation)

... /Produced/ by the decomposition of esters made from castor oil. At 500-600 °C, castor oil acid methyl ester decomposes in the presence of water vapor to form oenanthal (heptanal) and undecenoic acid methyl ester. The oenanthal is then oxidized with oxygen to heptanoic acid.

EPA Safer Chemical Functional Use Classes -> Uncategorized

Safer Chemical Classes -> Green half-circle - The chemical is expected to be of low concern

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

Heptanoic acid: ACTIVE

NON-ALCOHOLIC BEVERAGES 2.0 PPM; ICE CREAM, ICES, ETC 2.0 PPM; CANDY 6.0 PPM; BAKED GOODS 8.0 PPM; GELATINS & PUDDINGS 6.0 PPM; PRESERVES & SPREADS 2.0 PPM; MARGARINE 5.0 PPM.

Found in various fusel oils in appreciable amounts.

FEMA NUMBER 3348

HEPTANOIC ACID IS DEEMED GRAS BY FEMA.