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Nonanal

Nonanal structure

Nonanal 

structure
  • CAS No:

    124-19-6

  • Formula:

    C9H18O

  • Chemical Name:

    Nonanal

  • Synonyms:

    Nonanal;Nonanaldehyde;Nonaldehyde;Nonylic aldehyde;Pelargonaldehyde;Pelargonic aldehyde;n-Nonanal;n-Nonylaldehyde;Nonanoic aldehyde;Nonylaldehyde;Aldehyde C 9;NSC 5518;Aldehyde C 09;918959-88-3

  • Categories:

    Cosmetic Ingredient  >  Perfuming

Description

n-Nonanal has a strong, fatty odor developing an orange and rose note on dilution. It has a fatty, citrus-like flavor brown liquid Nonanal occurs in citrus and rose oils. It is a colorless liquid with a fatty, rose-like odor and is used in floral compositions, particularly those with rose characteristics.ChEBI: A fatty aldehyde formally arising from reduction of nonanoic acis. Metabolite observed in cancer metabolism.Nonanal has a strong, fatty odor developing an orange and rose note on dilut


Nonanal is a clear brown liquid characterized by a rose-orange odor. Insoluble in water. Found in at least 20 essential oils, including rose and citrus oils and several species of pine oil.|Liquid|colourless to yellow liquid/fruity odour


Nonanal is a clear brown liquid characterized by a rose-orange odor. Insoluble in water. Found in at least 20 essential oils, including rose and citrus oils and several species of pine oil.|Nonanal is a saturated fatty aldehyde formally arising from reduction of the carboxy group of nonanoic acid. Metabolite observed in cancer metabolism. It has a role as a human metabolite and a plant metabolite. It is a saturated fatty aldehyde, a n-alkanal and a medium-chain fatty aldehyde. It derives from a nonanoic acid.

Nonanal Basic Attributes

142.24

142.24

1236701

204-688-5

2L2WBY9K6T

5518

1993

DTXSID9021639

Colorless liquid

29121900

Characteristics

17.1

3.27 (est)

Clear colorless to light yellow Liquid

0.8264 g/cm3 @ Temp: 22 °C

94-95 °C

191 °C

147 °F

n 20/D 1.424(lit.)

Practically insoluble in water;soluble in three volumes 70% alcohol, in mineral oil; insoluble in glycerol

2-8°C

~0.26 mm Hg ( 25 °C)

LD50 orally in Rabbit: > 5000 mg/kg

Orange-rose odor

7.34e-04 atm-m3/mole|Henry's Law constant = 7.34X10-4 atm-cu m/mole at 25 °C

Hydroxyl radical reaction rate constant = 3.31X10-11 cu cm/molec-sec at 25 °C (est)

Sensitive to air. Insoluble in water.

Aldehydes

NONANAL is an aldehyde. Aldehydes are frequently involved in self-condensation or polymerization reactions. These reactions are exothermic; they are often catalyzed by acid. Aldehydes are readily oxidized to give carboxylic acids. Flammable and/or toxic gases are generated by the combination of aldehydes with azo, diazo compounds, dithiocarbamates, nitrides, and strong reducing agents. Aldehydes can react with air to give first peroxo acids, and ultimately carboxylic acids. These autoxidation reactions are activated by light, catalyzed by salts of transition metals, and are autocatalytic (catalyzed by the products of the reaction). The addition of stabilizers (antioxidants) to shipments of aldehydes retards autoxidation. Polymerizes readily with sulfuric acid and oxidized to nonanoic acid. (NTP, 1992)

Critical temperature: 658 K; critical pressure: 2.7 MPA

Safety Information

III

9

3082

2

36/37/38

26-37/39

RA5700000

Xi

Stable. Flammable. Incompatible with strong oxidizing agents.

P261-P305 + P351 + P338

H315-H319-H335

SRP: 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 air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.|Waste treatment methods: Product: This combustible material may be burned in a chemical incinerator equipped with an afterburner and scrubber. Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Contaminated packaging: Dispose of as unused product.

Incompatible materials: Strong oxidizing agents, Strong reducing agents, Strong bases

Nonanal 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.

EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program's Robust Summaries and Test Plans. /C6-C10 Aliphatic Aldehydes and Carboxylic Acids/[Available from, as of July 26, 2004: http://www.epa.gov/hpv/pubs/hpvrstp.htm]

This compound is combustible. (NTP, 1992)

|Warning|H315 (21.57%): Causes skin irritation [Warning Skin corrosion/irritation]|P264, P273, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362, and P501|Aggregated GHS information provided by 1811 companies from 20 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H227: Combustible liquid [Warning Flammable liquids]|P210, P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P370+P378, P403+P233, P403+P235, P405, and P501|P210, P261, P264, P271, P273, P280, P302+P352, P304+P340, P312, P321, P332+P313, P362, P370+P378, P403+P233, P403+P235, P405, and P501

Excerpt from ERG Guide 128 [Flammable Liquids (Water-Immiscible)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet). FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent-wash all contaminate surfaces with 70% ethanol followed by washing with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).|Body Protection:impervious clothing, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Skin protection: Handle with gloves.|Eye/face protection: Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).

Combustible liquid.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary. Use water spray to cool unopened containers.|Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

ACCIDENTAL RELEASE MEASURES. Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Remove all sources of ignition. Evacuate personnel to safe areas. Beware of vapors accumulating to form explosive concentrations. Vapors can accumulate in low areas.; Environmental precautions Prevent further leakage or spillage if safe to do so. Do not let product enter drains.; Methods and materials for containment and cleaning up: Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and place in container for disposal according to local regulations. Keep in suitable, closed containers for disposal.

Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.|Precautions for safe handling: Avoid contact with skin and eyes. Avoid inhalation of vapor or mist. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.

A severe skin irritant.

Nonanal has been detected in the exhaust of small, medium, and large commercial Chinese restaurant kitchens at concentrations ranging from 68.8 to 111, 15.0-17.4, and 23.7-71.1 ppb, respectively, and in the exhaust of Sichuan Spicy food kitchens at a concentration range of 49.9 to 60.0 ppb(1). Average concentrations for nonanal from Chinese cooking have been reported as 1365, 2281, 4501, and 1373 ng/mg in Cantonese, Sichuan, Dongbei, and Hunan style cooking, respectively(2). Nonanal was detected in the gases sampled from wells and cover soils at a landfill in Tuscany at concentrations ranging from <2 to 523 ppbv(3).

URBAN/SUBURBAN: Nonanal was detected in one of five ambient air samples collected Sept 8-9, 1993 from locations in southern California - Long Beach, Los Angeles, Claremont, Azusa, and San Nicholas Island; it was detected not quantified in Azusa, CA(1). In a 1983 study sampling air in northern Italy, nonanal exhibited a mean outdoor concentration of <2.0 ug/cu m(2). Nonanal has been detected in air samples collected in Rome and Montelibretti, Italy from September 16-17, 1991 at concentration ranges of 0.2-38 ppbv and 0.15-3.7 ppbv, respectively(3). A mean concentration of 2.8 ng/cu m for nonanal was reported for twenty seven ambient air samples collected from seven locations in Hong Kong in 2003; the range was 0.6 to 9.2 ng/cu m(4).|INDOOR: Nonanal is commonly detected in indoor samples at a relative occurrence of 5%, with reported concentrations ranging from 5-10 ug/cu m(1). In a 1983 study sampling indoor air in northern Italy, nonanal exhibited a mean indoor concentration of 12 ug/cu m(2). Nonanal was present at concentrations of 13, 6, <1, <1, <1, and <1 ug/cu m after 0.5, 1.0, 1.5, 2.5, 3.3, and 4.0 hrs, respectively, after 8.1 g of air freshener was applied in a model room(3). Nonanal was detected in 37 small and medium sized buildings sampled in California; indoor concentrations ranged from not detected to 20.9 ug/cu m with a mean of 4.25 ug/cu m(4).|RURAL/REMOTE: Nonanal was detected in ambient air sampled from September 16-17, 1991 in the Monti Cimini pine forest and a coastal wooded area near the Lido di Ostia, both in Italy(1). Night time levels of nonanal from a pine forest near Storkow, Germany ranged from 0.5, 1.4, and 0.39 ppbv at vertical profiles of 1, 14, and 30 meters, respectively(1).

Nonanal has been identified in emissions of volatile organic compounds from furniture coatings(1) and carpet cushions(2). Nonanal was emitted from three day old floor coverings at rates of 5, 9, 24, and 12 ug/sq m-hr for varnished parquet, waxed parquet, used linoleum floorings, and cushioned vinyl, respectively(3). The emission rates at 28 days old for varnished parquet, waxed parquet and cushioned vinyl were 5, 8, and 9 ug/sq m-hr(3). Nonanal was detected in whole building emissions of 37 small and medium sized buildings sampled in California at rates ranging from 1.44 to 277 ug/hr/sq m with a mean rate of 7.8 ug/h/sq m(4). Nonanal has been detected in the interior air of parked used vehicles at a concentration of 32.0 ug/cu m; no detection of nonanal was reported for new parked vehicles examined in the study(5). Nonanal was detected in the vehicles of 50 late shift patrol cars of nonsmokers monitored between August 13 through October 11, 2001(6).|Nonanal has been identified in cigarette smoke at 3 ug/cu m(1). It is a component of tobacco, tobacco smoke, and tobacco smoke substitutes(2).

Toxicity

IDENTIFICATION AND USE: Nonanal is a colorless liquid. It is not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses. It is used in perfume industry and as a flavoring agent. HUMAN EXPOSURE AND TOXICITY: Ozone exposure resulted in a significant early increase in nonanal in the airway epithelial lining fluid of humans. Nonanal levels returned to baseline by 18 hr after exposure. Nonanal produced in vitro by ozonation of liposomes induced hemolysis of human red blood cells, and combination of nonanal and H2O2 was significantly more hemolytic than nonanal alone. It was negative for unscheduled DNA synthesis in adult human hepatocytes assay at 3-100 mM. ANIMAL STUDIES: Single dermal dose of nonanal 5 g/kg applied on 3 rabbits with intact skin and 3 rabbits with abraded skin produced one death and severe edema and burns at site of application. There was no evidence of embryotoxicity, fetal toxicity, or teratogenesis when pregnant female rats were given 1500 mg/kg bw/day of nonanoic acid (metabolite of nonanal on days 6-15 of pregnancy. It was positive for sister chromatid exchange in rat hepatocytes at 0.1-100 uM, and negative for unscheduled DNA synthesis in adult rat hepatocytes assay at 3-100 mM. It was positive for forward mutation assay in V79 Chinese hamster lung cells at 0.1-0.3 mM and negative in modified Ames test (preincubation method) using S. typhmiurium TA98, TA100 and TA1535 at 1-666 ug/plate. It was also negative in Ames test using S. typhmiurium TA102 and TA104 at up to 1 mg/plate, and negative in the chromosomal aberration test using rat hepatocytes at 0.4 ug/mL.

LD50 Rat oral >5,000 mL/kg bw /from table/|LD50 Rabbit dermal >5,000 mL/kg bw /from table/|LC50 Rat inhalation >0.46 mg/L but <3.8 mg/L/4 hr /Nonanoic acid, 97%/

Nonanal has been identified as a plant volatile(1-4) and is a constituent in various tissues of several plant species(5).

Nonanal's production and use in perfumery and as a flavoring agent(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 40(SRC), determined from a structure estimation method(2), indicates that nonanal is expected to have very high mobility in soil(SRC). Volatilization of nonanal from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 7.3X10-4 atm-cu m/mole(3). Even though the vapor pressure is low environmentally at standard temperature and pressure, 0.37 mm Hg(4), there is a detectable odor; therefore, nonanal may volatilize from dry soil. Utilizing the Japanese MITI test, 44% of the Theoretical BOD was reached in 4 weeks(5) indicating that biodegradation is an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 40(SRC), determined from a structure estimation method(2), indicates that nonanal 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 7.34X10-4 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 2 hours and 5 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 67(SRC), from an estimated log Kow of 3.27(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Utilizing the Warburg respirometry test, a theoretical BOD range of 8 to 21% using activated sludge(6) indicating that 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), nonanal, which has a vapor pressure of 0.37 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase nonanal 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 day(SRC), calculated from its rate constant of 3.31X10-11 cu cm/molecule-sec at 25 °C(SRC) Nonanal does not contain chromophores that absorb at wavelengths >290 nm(3) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of nonanal with photochemically-produced hydroxyl radicals has been estimated as 3.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 1 day at an atmospheric concentration of 5X10+6 hydroxyl radicals per cu cm(2). Nonanal is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(3). Nonanal does not contain chromophores that absorb at wavelengths >290 nm(3) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 67 was calculated in fish for nonanal(SRC), using an estimated log Kow of 3.27(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of nonanal can be estimated to be 40(SRC). According to a classification scheme(2), this estimated Koc value suggests that nonanal is expected to have very high mobility in soil.

The Henry's Law constant for nonanal is 7.34X10-4 atm-cu m/mole(1). This Henry's Law constant indicates that nonanal is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 2 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 5 days(SRC). Nonanal's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Nonanal is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.37 mm Hg(3) and the detectable odor.

GROUNDWATER: Nonanal was detected at a maximum concentration of 20 ng/L in groundwater samples collected from Otis Air Base approximately 100 km southeast of Boston(1). Contaminated groundwater has resulted from continuous disposal of secondary treated sewage effluent into a shallow, unconfined aquifer since 1936(1).|DRINKING WATER: Under the National Water-Quality Assessment Program, nonanal is considered low or or no priority (Tier 3) for National- or Regional-scale ambient monitoring of water or sediment in the United States(1).|SURFACE WATER: Nonanal was detected at trace levels in seawater samples from the Peru upwelling region (Santa Ana, San Nicolas, San Juan, South America) collected at six stations in March 1978(1). Samples of estuary surface waters from the UK were taken from the Tees, Tyne, Humber, Thames, Solent, Plymouth Sound, Dee and Mersey as well as two waste disposal sites in Liverpool Bay in May/June 1988 and November/December 1989; nonanal was found in samples from the Humber, Tyne, Tees, Liverpool Bay and Plymouth Sound(2).|RAIN/SNOW/FOG: Nonanal was detected in Antarctic snow samples collected during a 1993/1994 expedition at concentrations ranging from 16 to 227 ng/L(1).

Nonanal has been identified as a volatile component in the following food items: common pineapple guava, 0.10 ug/g(1); popcorn, 41 ug/kg(2); rice cakes, 9-11 ppb(3); detected, not quantified in raw but not roasted earth-almond (Cyperus esculentus L.)(4). Concentrations in bisbee delicious apples (1990 harvest date) were 435.5 (8/14), 1474.5 (8/21), 3288.0 (8/24), 222.6 (9/4), 361.2 (9/11), 274.8 (9/18), 83.6 (9/25), and 206.1 (10/2)(5). Nonanal has also been identified as a volatile component in heated peanut oil, with 0.15, 1.02, 1.11, and 2.01% identified in the GC peak area at 50, 100, 150, and 200 °C, respectively(6). It is a volatile component of Idaho Russet Burbank baked potatoes(7); fresh tree-ripened apricots (Prunus armeniaca L.), and plums (Prunus salicina), at not detected to 8, and 14 and 51 ug/kg, respectively(8); and in roasted filberts(9). Nonanal was identified as a volatile component in unpasteurized, fresh orange juice samples at concentrations of 0.022-0.082, 0.087, and 0.025 ppm in mechanically pressed valencia, pineapple, and ambersweet oranges, respectively(10). Concentrations of 0.001, 0.003, 0.003-0.004, 0.007-0.25, trace, and 0.007 ppm were measured in hand pressed valencia, pineapple, hamlin, navel, pera, and ambersweet oranges, respectively(10).|Nonanal has been identified in the head-space at concentrations of 8,880, 9,130, and 24,200 relative peak areas following analysis of frankfurters with 30%, 12%, and 5% fat content, respectively(1). Nonanal has been identified, not quantified as a volatile component in scrambled eggs(2). The compound is one of the aroma components identified in uncured beef and chicken at concentrations of 1.44 and 11.59 mg/kg, respectively(3). Nonanal is one of the volatile components of water-boiled duck meat, duck fat, Cantonese-style roasted duck, and Cantonese-style roasted duck gravy at concentrations of 31.79, 24.97, 8.04, and 48.87 ppb, respectively(4). Nonanal was identified as one of the characteristic odorants in fresh rhizomes of ginger (Zingiber officinale Roscoe)(5).

According to the 2012 TSCA Inventory Update Reporting data, 5 reporting facilities estimate the number of persons reasonably likely to be exposed during the manufacturing, processing, or use of nonanal in the United States may be as low as <10 workers and as high as 9999 workers per plant; the data may be greatly underestimated due to confidential business information (CBI) or unknown values(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 8,081 workers (1,350 of these are female) were potentially exposed to nonanal in the US(1). Occupational exposure to nonanal may occur through inhalation and dermal contact with this compound at workplaces where nonanal is produced or used. Nonanal was detected in 37 small and medium sized buildings such as restaurants, retail establishments, hair salons, and fitness gyms sampled in California; indoor concentrations ranged from not detected to 20.9 ug/cu m with a mean of 4.25 ug/cu m(2). Monitoring data indicate that the general population may be exposed to nonanal via inhalation of ambient air, ingestion of food and drinking water, and dermal contact with consumer products containing nonanal(SRC).

Drug Information

Aldehyde dehydrogenase (ALDH) specific activity was measured in crude homogenates, post-mitochondrial supernatants, cytosolic and microsomal fractions of /Rainbow trout (Oncorhynchus mykiss)/ liver, using a number of endogenous and xenobiotic aldehydes and both NAD+ and NADP+ as co-factors. All the activity found in the crude homogenate could be accounted for by the sum of the cytosolic and microsomal activities. Highest activities were found with the medium chain length substrates hexanal and nonanal in all fractions. The ,-unsaturated aldehydes, (E,E)-2,4-nonadienal-1-al, and trans, trans-2,4-decadienal, were also good substrates for both fractions, while the hydroxylated , unsaturated trans-4-hydroxy-2-nonenal was a good substrate only for the microsomal fraction. Short chain and aromatic xenobiotic substrates were metabolized at much lower rates, and only the microsomal fraction was effective against acetaldehyde, acrolein, and benzaldehyde. Neither fraction metabolized 2,5-dihydroxy benzaldehyde. NAD+ was the preferred co-factor for most substrates. Apparent affinity (Km) for hexanal and nonanal in the cytosolic fraction were comparable to that found in rats, but the theoretical maximal velocity (Vmax) for these substrates, and the specific activities for the other substrates, were much lower than found in mammals. The biochemical results suggest that trout are well adapted to detoxify products of endogenous lipid peroxidation, but are poorly adapted to detoxify xenobiotic aldehydes.

SYMPTOMS: This compound will cause skin and eye irritation; it is a strong irritant. ACUTE/CHRONIC HAZARDS: Local irritant. (NTP, 1992)

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

/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. /Aldehydes 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 ventilations if necessary. Aggressive airway management may be necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Anticipate seizures and treat if necessary ... . Monitor for shock and treat if necessary ... . Monitor for pulmonary edema 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. Administer activated charcoal ... . /Aldehydes and Related Compounds/|/SRP:/ Advanced treatment: Consider Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Intubation should be considered at the first sign of upper airway obstruction caused by edema. 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 ... . 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 ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aldehydes and Related Compounds/

/BIOMONITORING/ The authors hypothesized that exposure of healthy humans to ozone at concentrations found in ambient air causes both ozonation and peroxidation of lipids epithelial lining fluid. Smokers (12) and nonsmokers (15) were exposed once to air and twice to 0.22 ppm ozone for 4 hr with exercise in an environmental chamber; each exposure was separated by at least three weeks. Bronchoalveolar lavage (BAL) was performed immediately after one ozone exposure and 18 hr after the other ozone exposure. Lavage fluid was analyzed for two aldehyde products of ozonation and lipid peroxidation, nonanal and hexanal, as well as for total protein, albumin, and immunoglobulin M (IgM) as markers of changes in epithelial permeability. Ozone exposure resulted in a significant early increase in nonanal (p<0.0001), with no statistically significant relationship between increases in nonanal and lung function changes, airway inflammation, or changes in epithelial permeability. Increases in hexanal levels were not statistically significant (p=0.16). Both nonanal and hexanal levels returned to baseline by 18 hr after exposure. These studies confirm that exposure to ozone with exercise at concentrations relevant to urban outdoor air results in ozonation of lipids in the airway epithelial lining fluid of humans.|/GENOTOXICITY/ ...Negative for unscheduled DNA synthesis in adult human hepatocytes assay at 3-100 mM... /from table/|/ALTERNATIVE and IN VITRO TESTS/ Dioleoyl phosphatidylcholine (PC) liposomes were ozonized and the ozonized liposomes were tested for their lytic potency on human red blood cells (RBC). Ozonation of PC liposomes generated approximately 1 mole equivalent of hydrogen peroxide (H2O2) and 2 mole equivalents of aldehydes, based on the moles of ozone consumed. The time necessary for 50% hemolysis induced by ozonized liposomes (a convenient measure of hemolytic activity) was found to depend on the extent of ozonation of the PC liposomes, indicating the formation and accumulation of hemolytic agents during ozonation. Hemolysis was also observed when RBC were incubated with nonanal, the expected product of the ozonation of oleic acid, the principle unsaturated fatty acid in the liposomes. Hydrogen peroxide, another product of PC ozonation, did not induce hemolysis; however, a combination of H2O2 and nonanal was significantly more hemolytic than nonanal alone. A ratio of 1:2 H2O2/nonanal (the ratio observed in the ozonized liposomes) provided hemolytic activity comparable to that observed with ozonized dioleoyl PC. Among different antioxidants tested, ascorbate, catalase, and glutathione peroxidase partially inhibited hemolysis induced by ozonized liposomes and by H2O2/nonanal mixtures, but they were not protective against the nonanal-induced hemolysis. Identification of H2O2 and aldehydes as cytotoxic chemical species generated from the ozonation of unsaturated fatty acids may have an important bearing on the in vivo toxicity of ozone on the lung as well as on extrapulmonary tissues.|/ALTERNATIVE and IN VITRO TESTS/ Mutations in human Retinol Dehydrogenase 12 (RDH12) are known to cause photoreceptor cell death but the physiological function of RDH12 in photoreceptors remains poorly understood. In vitro, RDH12 recognizes both retinoids and medium-chain aldehydes as substrates. Our previous study suggested that RDH12 protects cells against toxic levels of retinaldehyde and retinoic acid. Here, we investigated whether RDH12 can also protect cells against highly reactive medium-chain aldehydes. Analysis of cell survival demonstrated that RDH12 was protective against nonanal but not against 4-hydroxynonenal. At high concentrations, nonanal inhibited the activity of RDH12 towards retinaldehyde, suggesting that nonanal was metabolized by RDH12. 4-Hydroxynonenal did not inhibit the RDH12 retinaldehyde reductase activity, but it strongly inhibited the activities of lecithin:retinol acyl transferase and aldehyde dehydrogenase, resulting in decreased levels of retinyl esters and retinoic acid and accumulation of unesterified retinol. Thus, the results of this study showed that RDH12 is more effective in protection against retinaldehyde than against medium-chain aldehydes, and that medium-chain aldehydes, especially 4-hydroxynonenal, severely disrupt cellular retinoid homeostasis. Together, these findings provide a new insight into the effects of lipid peroxidation products and the impact of oxidative stress on retinoid metabolism.|/OTHER TOXICITY INFORMATION/ We have used multiple analytical methods to characterize the gas-phase products formed when ozone was added to cabin air during simulated 4-hour flights that were conducted in a reconstructed section of a B-767 aircraft containing human occupants. Two separate groups of 16 females were each exposed to four conditions: low air exchange (4.4 (hr-1)), <2 ppb ozone; low air exchange, 61-64 ppb ozone; high air exchange (8.8 hr(-1)), <2 ppb ozone; and high air exchange, 73-77 ppb ozone. The addition of ozone to the cabin air increased the levels of identified byproducts from approximately 70 to 130 ppb at the lower air exchange rate and from approximately 30 to 70 ppb at the higher air exchange rate. Most of the increase was attributable to acetone, nonanal, decanal, 4-oxopentanal (4-OPA), 6-methyl-5-hepten-2-one (6-MHO), formic acid, and acetic acid, with 0.25-0.30 mol of quantified product volatilized per mol of ozone consumed. Several of these compounds reached levels above their reported odor thresholds. Most byproducts were derived from surface reactions with occupants and their clothing, consistent with the inference that occupants were responsible for the removal of >55% of the ozone in the cabin. The observations made in this study have implications for other indoor settings. Whenever human beings and ozone are simultaneously present, one anticipates production of acetone, nonanal, decanal, 6-MHO, geranyl acetone, and 4-OPA.

n-nonylaldehyde

Nonanal Use and Manufacturing

Methods of Manufacturing

From the reduction of n-nonanoic acid. Catalyzed by n-nonanol.

Uses

A component of essential oils, Nonanal possesses a strong fruity odor. Essential oils have varying effects from antibacterial activity to hypolipidemic activity.


Intermediates


Air care products

Production

10,000,000 - 50,000,000 lb|Nonanal 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 volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Nonanal. Aggregated National Production Volume: 10 to < 50 million pounds.|Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Nonanal. National Production Volume: 21,932,784 lb/yr.

Grade: Technical, Food Chemical Codex

All other basic organic chemical manufacturing|Nonanal: ACTIVE

Method: EPA-TSC/NERL 556; Procedure: gas chromatography with electron capture detector; Analyte: nonanal; Matrix: finished drinking water and raw source water; Detection Limit: 0.74 ug/L.|Method: EPA-OGWDW/TSC 556.1; Procedure: fast gas chromatography system equipped with an electron capture detector; Analyte: nonanal; Matrix: finished drinking water and raw source water; Detection Limit: 0.62 ug/L.

EPA Safer Chemical Functional Use Classes -> Fragrances|Safer Chemical Classes -> Yellow triangle - The chemical has met Safer Choice Criteria for its functional ingredient-class, but has some hazard profile issues|Food additives -> Flavoring Agents|Flavouring Agent -> FLAVOURING_AGENT; -> JECFA Functional Classes|Flavoring Agents -> JECFA Flavorings Index|Fatty Acyls [FA] -> Fatty aldehydes [FA06]

Flavoring Agents|Flavouring Agent -> FLAVOURING_AGENT;

Computed Properties

Molecular Weight:142.24
XLogP3:3.3
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:7
Exact Mass:142.135765193
Monoisotopic Mass:142.135765193
Topological Polar Surface Area:17.1
Heavy Atom Count:10
Complexity:69.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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