ヘプタナール

FATTY, PUNGENT ODOR

Penetrating fruity odor

0.8495 at 68 °F (NTP, 1992) - Less dense than water; will float

0.82162 g/cu cm at 25 °C

0.814-0.819

less than 1 mg/mL at 70 °F (NTP, 1992)

Miscible with alcohol, ether. Soluble in 3 volumes of 60% alcohol.

1:12 IN 50% ALC, 1:4 IN 60% ALC, 1:2 IN 70% ALC

Slightly soluble in carbon tetrachloride; miscible with ethanol, ethyl ether

In water, 1,250 mg/L at 25 °C

1.25 mg/mL at 25 °C

Warning

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P264, P264+P265, P280, P302+P352, P303+P361+P353, P305+P351+P338, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1692 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H226: Flammable liquid and vapor [Warning Flammable liquids]

Chemical: Heptanal

Heptanal is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Heptanal 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: 11-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/2177

Heptanal: HSNO Approval: HSR001163 Approved with controls

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:

· May cause toxic effects if inhaled or absorbed through skin.

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] Safe when used as a flavoring agent in food; [JECFA] A severe eye irritant; [RTECS] An irritant; [MSDSonline]

Heptanal 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.

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date 9/30/91; Reporting date: 11/27/91.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Heptanal is included on this list. Effective date 9/30/91; Sunset date: 6/30/98.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

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.

General First Aid:

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.

Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:

Immediate precautionary measure

A study of organic chemicals in mother's milk was conducted in 4 urban areas in the US, sites selected in the vicinity of chemical manufacturing plants and/or industrial user facilities that had a high probability of pollutant detection(1). Of the eight samples interpreted, 2 from each area, n-heptanal was present in all samples from Bayonne NJ, Jersey City NJ, Pittsburgh PA, and Baton Rouge LA(1). Aldehydes are believed to be metabolites(1). In EPA's National Human Adipose Tissue Survey (NHATS) for 1982, all 46 composite samples analyzed contained n-heptanal: in all 12 samples for 0-14, in all 17 samples for 15-44, and in all 17 samples for 45 and over years of age(2).

ENVIRONMENTAL: A study of organic chemicals in mother's milk was conducted in 4 urban areas in the US, sites selected in the vicinity of chemical manufacturing plants and/or industrial user facilities that had a high probability of pollutant detection(1). Of the eight samples interpreted, 2 from each area, n-heptanal was present in all samples from Bayonne NJ, Jersey City NJ, Pittsburgh PA, and Baton Rouge LA(1).

LC50; Species: Pimephales promelas (Fathead minnow, 26-34 day old juvenile); Conditions: freshwater, continuous flow through system; Concentration: 37.9 mg/L for 96 hr /metabolic precursor, 1-heptanol/

LC50; Species: Alburnus alburnus (Bleak); Conditions: brackish water, static no aeration; Concentration: 45 mg/L for 96 hr (95% confidence interval: 42-49 mg/L) /metabolic precursor,1-heptanol dissolved in water/

LC50; Species: Nitocra spinipes (harpacticoid); Conditions: brackish water, static; Concentration: 210 mg/L for 96 hr (95% confidence interval: 170-250 mg/L) /metabolic precursor,1-heptanol dissolved in water/

LC50; Species: Oncorhynchus mykiss (Rainbow trout, fingerlings 10 days old); Conditions: freshwater, semi-static (solution were removed daily), 15.1 + or - 1 °C, pH 8.3 + or -0.2, dissolved oxygen 10.1 + or -0.2 mg/L; Concentration: 12 mg/L for 96 hr /98% (methyl hexanoate, 1%)/

For more Ecotoxicity Values (Complete) data for N-HEPTANAL (12 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 86(SRC), determined from a water solubility of 1250 mg/L(2) and a regression-derived equation(3), indicates that n-heptanal is expected to have high mobility in soil(SRC). Volatilization of n-heptanal from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 2.7X10-4 atm-cu m/mole(4). n-Heptanal is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 3.52 mm Hg(5). A theoretical BOD of 14.7% in 1 day using an activated sludge(6) indicates that biodegradation may be an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 86(SRC), determined from a water solubility of 1,250 mg/L(2) and a regression-derived equation(3), indicates that n-heptanal is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 2.7X10-4 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 7 hrs and 5 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 11(SRC), from its water solubility(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). In a groundwater recharge project, CA, 70% of theoretical COD of n-heptanal was removed(6), indicating that biodegradation may be an important environmental fate process in water(SRC). n-Heptanal is easily oxidized(7) and may be oxidized by oxygen and other oxidants present in natural water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), n-heptanal, which has a vapor pressure of 3.52 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase n-heptanal 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 13 hrs(SRC), calculated from its rate constant of 3.0X10-11 cu cm/molecule-sec at 25 °C(3). n-Heptanal contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

n-Heptanal is a plant volatile that has been identified in roasted filberts(1), peanut oil(2), baked potato(3), and ginger oil(4). The concentration of n-heptanal in various sweet corn products were: caned/cream, 6 ppm; canned/kernel, 4 ppm; frozen/kernel, <5 ppm(5). The concentration of heptanal in orange juice was <0.6-3.8 ppb(6). n-Heptanal was found in popcorn using a dry extraction method at 16 ug/kg(7). Commercial rice cakes were found to contain 5 ppb of heptanal(8). n-Heptanal was found in roasted earth almonds (Cyperus esculentus L.)(9). n-Heptanal was detected in the emissions from heated rapeseed oil(10).

n-Heptanal is found in animal products, having been identified in raw beef(1), fried bacon(2), fried chicken(3), duck(4), clams(5), and a French mountain cheese(6). n-Heptanal was measured at 1820 ng/g, and 843 ng/g in big eyed herring paste and hair tail viscera paste, respectively and was not detected in anchovy paste and shrimp paste(7). n-Heptanal was found in full fat and reduced fat frankfurters(8), and Italian-type dry-cured ham(9). n-Heptanal was released from charbroiling meat at 125,000 ug/kg of cooked meat(10).

REPORTED USES: NON-ALCOHOLIC BEVERAGES, 4.9 PPM; ALCOHOLIC BEVERAGES, 4.0 PPM; ICE CREAM, ICES, ETC, 1.2 PPM; CANDY, 2.0 PPM; BAKED GOODS, 2.6 PPM.

ENVIRONMENTAL: A study of organic chemicals in mother's milk was conducted in 4 urban areas in the US, sites selected in the vicinity of chemical manufacturing plants and/or industrial user facilities that had a high probability of pollutant detection(1). Of the eight samples interpreted, 2 from each area, n-heptanal was present in all samples from Bayonne NJ, Jersey City NJ, Pittsburgh PA, and Baton Rouge LA(1).

Uremic toxins such as heptanal are actively transported into the kidneys via organic ion transporters (especially OAT3). Increased levels of uremic toxins can stimulate the production of reactive oxygen species. This seems to be mediated by the direct binding or inhibition by uremic toxins of the enzyme NADPH oxidase (especially NOX4 which is abundant in the kidneys and heart) (A7868). Reactive oxygen species can induce several different DNA methyltransferases (DNMTs) which are involved in the silencing of a protein known as KLOTHO. KLOTHO has been identified as having important roles in anti-aging, mineral metabolism, and vitamin D metabolism. A number of studies have indicated that KLOTHO mRNA and protein levels are reduced during acute or chronic kidney diseases in response to high local levels of reactive oxygen species (A7869).

n-Heptanal has been identified as a volatile in kiwi fruit flowers(1), pineapple guava(2), cassava(3), apricots(4), plums(4), and Bisbee delicious apples(5). n-Heptanal was emitted from rape during the blooming period at a rate of 0.06-0.20 and 0.09-0.27 ppbv on May 8 and 9, 1998, respectively(6). n-Heptanal was found in raw earth almonds (Cyperus esculentus L.)(7). n-Heptanal is a plant volatile, being emitted by vegetation growing under the canopy in northern European forests and particular by a common weed, Bifora radians(8).

n-Heptanal is a plant volatile that has been identified in pineapple, guava(1), cassava(2), apricots(3), plums(3), Bisbee delicious apples(4), and Korean chamchwi(5). The concentration of n-heptanal in fresh/kernel sweet corn was <1 ppm(6). n-Heptanal was found in raw earth almonds (Cyperus esculentus L.)(7). n-Heptanal was detected in whole and ground musty sorghum with direct helium-purge method and with supercritical fluid extraction method(8).

As a uremic toxin, this compound can cause uremic syndrome. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. Abnormal bleeding, such as bleeding spontaneously or profusely from a very minor injury can also occur. Heart problems, such as an irregular heartbeat, inflammation in the sac that surrounds the heart (pericarditis), and increased pressure on the heart can be seen in patients with uremic syndrome. Shortness of breath from fluid buildup in the space between the lungs and the chest wall (pleural effusion) can also be present.

Heptanal 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.

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date 9/30/91; Reporting date: 11/27/91.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Heptanal is included on this list. Effective date 9/30/91; Sunset date: 6/30/98.

Aldehydes are readily oxidized to organic acids, which, in turn, can serve as substrates for fatty acid oxidation pathways and the Krebs cycle. ... Oxidation of aldehydes is catalyzed by aldehyde dehydrogenase, which has been found in the brain, erythrocytes, liver, kidney, heart, and placenta. /Aldehydes/

... The detoxification of aldehydes can be seen to proceed basically via two routes: (1) an oxidation to yield readily metabolized acids; (2) inactivation by reaction with sulfhydryl groups, particularly glutathione. Under conditions that either deplete glutathione levels, or that result in an inhibition of aldehyde dehydrogenase (for example, Antabuse treatment), the acute and chronic effects of aldehyde toxicity might be more fully expressed. /Aldehydes/

Heptanal and nonanal are identified from in vitro studies as potential biomarkers of exposure to ozone the former resulting from ozonation of palmitoleic acid and the latter from oleic acid. These molecules also are present in the lung lavage of Sprague-Dawley rats exposed to 1.3 ppm ozone for 10 hr. Aldehydes may be useful dosimeters for ozone and indicate that unsaturated fatty acids in the lung lining fluid layer undergo ozonation in vivo.

Heptanal is oxidized to pimelic or heptanoic acid, then CO2 and water.

Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Most uremic toxins are metabolic waste products and are normally excreted in the urine or feces.

A plant volatile found in various essential oils, fruits, and other natural sources; Used in flavors and fragrances and to make other chemicals; [HSDB]

Manufacture of 1-heptanol; ethyl oenanthate

Manufacture of 1-heptanol, organic synthesis, perfumery, pharmaceuticals, flavoring

Reported uses (ppm): (FEMA, 2005)

CHEM INT FOR HEPTANOIC ACID AND 1-HEPTANOL

For more Uses (Complete) data for N-HEPTANAL (7 total), please visit the HSDB record page.

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

Heptanal 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).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5632]

Obtained by distilling castor oil under reduced pressure; ... catalytic dehydration of ricinoleic acid methyl ester yields heptanal as cleavage product in almost quantitative yield.

PYROLYSIS OF CASTOR OIL TO N-HEPTANAL & UNDECYLENIC ACIDS; REACTION OF 1-HEXENE WITH CARBON MONOXIDE & HYDROGEN IN PRESENCE OF A RHODIUM CATALYST (OXO PROCESS)

Pyrolytic cleavage of ricinoleic acid.

Hydroformylation of 1-hexene in the presence of modified rhodium catalysts.

For more Methods of Manufacturing (Complete) data for N-HEPTANAL (6 total), please visit the HSDB record page.

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

Heptanal: ACTIVE

Flavor useful in: citrus, vegetable flavors, melon.