Grundinformationen
- Standard-SMILES
CCCCCC=O- InChIKey
JARKCYVAAOWBJS-UHFFFAOYSA-N- Summenformel
- C6H12O
- Durchschnittliche Molmasse
- 100,16 g/mol
- Monoisotopische Masse
- 100,088815
Überblick
Hexaldehyde appears as a clear colorless liquid with a pungent odor. Flash point 90 °F. Less dense than water and insoluble in water. Vapors heavier than air.
Namen und Bezeichner
- Bevorzugter Name
- Hexanal
- IUPAC
- hexanal
- Lokaler Name
- Hexanal
- Englischer Name
- Hexanal
- Summenformel
- C6H12O
- Molmasse
- 100.16
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
66-25-1- PubChem CID
- 6184
- DTXSID
DTXSID2021604- ChEMBL
CHEMBL280331- ChEBI
CHEBI:88528- UNII
- 9DC2K31JJQ
- EC Number
- 200-624-5
- Nikkaji
- J1.409E
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,8
- Polarare Oberfläche (TPSA)
- 17,1 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 1
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 7
- Formalladung
- 0
- Komplexität
- 41,4
Experimentelle und physikochemische Eigenschaften
Chemical Classes
Other Classes -> Aldehydes
Flammable agents - 3rd degree
LogP
log kow = 1.78
1.78
Odor
Characteristic fruity odor (on dilution)
Strong, green grass odor
Sharp, aldehyde odor
Taste
Characeteristic fruity taste (on dilution)
Green, woody, vegetative, apple, grassy, citrus and orange with a fresh lingering aftertaste
Density
0.83 at 68 °F (USCG, 1999) - Less dense than water; will float
0.8335 g/cu cm at 20 °C
Bulk density = 6.9 wt/gal at 20 °C
0.808-0.817
0.8335 @ 20°C
Physikochemische Eigenschaften
- Schmelzpunkt
- -56 °C · -56 °C
- Siedepunkt
- 130 · 130-131 °C(lit.)
- Dichte
- 0.816 g/mL · 0.816 g/mL at 20 °C
- Dampfdichte
- 1 · >1 (vs air)
- Dampfdruck
- 10 mm · 10 mm Hg ( 20 °C)
- Brechungsindex
- 20 · n20/D 1.4035(lit.)
- FEMA
- 2557 · 2557 | HEXANAL
- Flammpunkt
- 90 °F · 90 °F
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- 6 g/l · 6g/l
- Aggregatzustand
- Liquid
- Farbe
- Clear colorless to slightly yellow
- PH
- 4 · 4-5 (4.8g/l, H2O, 20℃)
- Geruch (Odor)
- Pungent.
- Odor Threshold
- 0.00028 ppm · 0.00028ppm
- Geruchsart
- green
- Biologische Quelle
- synthetic
- Wasserlöslichkeit
- 4.8 g/L · 4.8 g/L (20 ºC)
- Spezifische Wärmekapazität
- 2.1 J/ · Cp(liquid): 2.1 J/(g·K), at 25℃
- JECFA Number
- 92 · 92
- Merck
- 14 · 14,1760
- BRN
- 506198 · 506198
- Henry's Law Constant
- 4.5 · 4.5×10-2 mol/(m3Pa) at 25℃, Brockbank (2013)
- Stabilität
- Stable. Flammable. Incompatible with oxidizing agents, strong bases, strong reducing agents.
- Major Application
- flavors and fragrances
- Kosmetik-Inhaltsstoffe Funktionen
- FRAGRANCE
- InChI
- 1S/C6H12O/c1-2-3-4-5-6-7/h6H,2-5H2,1H3
- InChIKey
- JARKCYVAAOWBJS-UHFFFAOYSA-N
- SMILES
- CCCCCC=O
- LogP
- 1.97 · 1.97
- CAS Datenbank
- 66 · 66-25-1(CAS DataBase Reference)
- NIST chemische Informationen
- Hexanal(66-25-1)
- EPA chemische Informationen
- Hexaldehyde (66-25-1)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
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 1956 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]
Gefahrenhinweise
Regulatory Information
Chemical: Hexanal
Hexanal is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Hexanal 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: 16-02-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/27720
Hexanal: Does not have an individual approval but may be used under an appropriate group standard
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Fire Hazards
Behavior in Fire: Vapor is heavier than air and may travel to a source of ignition and flash back. (USCG, 1999)
· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.
Health Hazards
Ingestion causes irritation of mouth and stomach. Contact with vapor or liquid irritates eyes. Liquid irritates skin. (USCG, 1999)
· May cause toxic effects if inhaled or absorbed through skin.
Hazards Summary
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] Auto-oxidizes and polymerizes (especially in presence of acid); [Merck Index] A skin, eye, nose, and throat irritant; [HSDB] Highly flammable and polymerizable; A skin and eye irritant; [CAMEO] A skin and eye irritant; [eChemPortal: ERMA] An irritant; Effects in high-dose animal studies include lacrimation; [MSDSonline]
FDA Requirements
Hexanal 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 b) 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.
Reactivity Profile
HEXALDEHYDE 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. May attack some forms of plastics (USCG, 1999).
Sicherheit und Schutzausrüstung
Accidental Release Measures
· 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.
First Aid
INGESTION: give large amount of water and induce vomiting.
General First Aid:
Fire Fighting Procedures
If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may spread fire. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide.
Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.
Storage Conditions
Conditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Recommended storage temperature 2-8 °C Storage class (TRGS 510): Flammable liquids.
Cleanup Methods
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. 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.
Disposal Methods
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.
Product: Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting as this material is highly flammable. 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.
Preventive Measures
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors.
Personnel protection: Avoid breathing vapors. Keep upwind. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water.
Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.
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.
SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits 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.
Isolation and Evacuation
Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]:
Immediate precautionary measure
Toxikologische Informationen
Body Burden
Hexaldehyde has been detected in human adipose tissue from the following age groups: in all 12 samples for 0-14, in all 17 samples for 15-44, and in 16 out of 17 samples for 45 and over years of age; and the following regions: 12 times in the North Central, 9 times in the Northeast, 18 times in the South, and 6 times in the West regions(1). Hexaldehyde was detected not quantified in human milk samples from Bayonne, NJ, Jersey City, NJ, and Pittsburgh, PA(2). Hexaldehyde was detected in the exhaled breath of 3 subjects at 9-13 ppb(3). Hexaldehyde was found in 15 of 15 personal air samples at a mean concentration of 2.2 ppb from samples taken in Helsinki, Finland, tested May to September 1997(4).
Ecotoxicity Values
LC50; Species: Americamysis bahia (Opossum Shrimp) juvenile age 2-8 days; Conditions: saltwater, flow through, 24 °C, pH 8.0, dissolved oxygen 7.5-7.6 mg/L; Concentration: >4300 ug/L for 24 hr /99% purity/
LC50; Species: Americamysis bahia (Opossum Shrimp) juvenile age 2-8 days; Conditions: saltwater, flow through, 24 °C, pH 8.0, dissolved oxygen 7.6 mg/L; Concentration: >4300 ug/L for 48 hr /99% purity/
LC50; Species: Americamysis bahia (Opossum Shrimp) juvenile age 2-8 days; Conditions: saltwater, flow through, 25 °C, pH 7.9, dissolved oxygen 7.5 mg/L; Concentration: 4300 ug/L for 72 hr /99% purity/
LC50; Species: Americamysis bahia (Opossum Shrimp) juvenile age 2-8 days; Conditions: saltwater, flow through, 25 °C, pH 7.9-8.0, dissolved oxygen 7.4-7.7 mg/L; Concentration: 2800 ug/L for 96 hr (95% confidence interval: 1900-4300 ug/L) /99% purity/
For more Ecotoxicity Values (Complete) data for HEXALDEHYDE (18 total), please visit the HSDB record page.
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 48(SRC), determined from a log Kow of 1.78(2) and a regression-derived equation(3), indicates that hexaldehyde is expected to have high mobility in soil(SRC). Volatilization of hexaldehyde from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 2.13X10-4 atm-cu m/mole(4). Hexaldehyde is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 11.3 mm Hg(5). According to a fungal growth experiment, hexaldehyde was oxidized but did not support growth(6) which suggests that it may not biodegrade in soil(SRC). However, the straight chain aldehyde structure of hexaldehyde would suggest rapid biodegradation(7). A 50% of theoretical BOD using activated sludge in the Japanese MITI test(8) suggests that biodegradation is an important environmental fate process in soil(SRC).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 50(SRC), determined from a log Kow of 1.78(2) and a regression-derived equation(3), indicates that hexaldehyde 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 2.13X10-4 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 4 hrs and 5 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 7(SRC), from its log Kow(2) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Hexaldehyde is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). According to a fungal growth experiment, hexaldehyde was oxidized but did not support growth(6) which suggests that it may not biodegrade in water(SRC). However, the straight chain aldehyde structure of hexaldehyde would suggest rapid biodegradation(7). A 50% of theoretical BOD using activated sludge in the Japanese MITI test(8) suggests 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), hexaldehyde, which has a vapor pressure of 11.3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase hexaldehyde 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 12 and 14 hrs(SRC), calculated from rate constants of 3.17X10-11 cu cm/molecule-sec at 23 °C(3) and 2.79X10-11 cu cm/molecule-sec at 25 °C, respectively(4). The rate constant for the vapor-phase reaction of hexaldehyde with nitrate radical has been experimentally determined to be 1.64X10-14 cu cm/sec(4) and 1.28X10-14 cu cm/sec(5). These correspond to atmospheric half-lives of about 49 and 63 hrs, respectively, at a concentration of 2.4X10+8 nitrate radicals per cu cm(6). Hexaldehyde does not contain chromophores that absorb at wavelengths >290 nm(7) and, therefore, is not susceptible to direct photolysis by sunlight(SRC).
Food Survey Values
Hexaldehyde occurs as a volatile component of edible Korean Chamchwi(1), peanut oil(2), baked potatoes(3), Beaufort cheese(4), pine sprout and pine needle tea(5), clove essential oil(6), roasted filberts(7), and roasted earth almonds (Cyperus esculentus L.)(8). Hexaldehyde was quantified in sweet corn (cream can corn, 14 ppb; frozen kernel corn, 5 ppb(9), and was identified in paprika oleoresin <0.1 mg/kg(10). Hexaldehyde was found in popcorn using wet extraction method at 80 ug/kg and dry extraction method at 140 ug/kg(11). Commercial rice cakes were found to contain 800-960 ppb of hexaldehyde(12). Fermented soybean (Glycine max) curds were found to contain 499.8-1319.1 ug/kg of hexaldehyde(13). Hexaldehyde was not detected in roasted peanuts at concns of 0.109-0.257 ug/g(14). Hexaldehyde was identified as a volatile component of boiled Chinese chestnuts (Castanea molissima) but not found in roasted chestnuts(15). Hexaldehyde was detected in the emissions from heated rapeseed oil(16).
Hexaldehyde has been found as a volatile component of raw beef(1), chicken breast muscle and caecum(2), fried bacon(3), short-necked clam, clam, and corbicula(4), scrambled eggs (supermarket eggs packed in polystyrene, 39 ng/g; fresh eggs not stored, 32 ng/g; and fresh eggs stored in polystyrene for 2 weeks, 59 ng/g); cooking oil, 3720 and 3039 ng/g; and polystyrene egg cartons(5), mutton, chicken, beef, and pork(6), fried chicken(7), duck meat (19.86 ppb), duck fat (79.81 ppb), Cantonese style roasted duck (67.72 ppb), Cantonese style roasted duck gravy (736.66 ppb)(8), full fat and reduced fat frankfurters(9), and Italian-type dry-cured ham(10). Hexaldehyde was measured at 951 ng/g, 5740 ng/g, and 1080 ng/g in anchovy paste, big eyed herring paste, and hair tail viscera paste, respectively and was not detected in shrimp paste(11). Hexaldehyde was detected as an odorant in cooked mussels (Mytilus edulis)(12). Hexaldehyde was released from char broiling meat at 203,000 ug/kg of cooked meat(13).
Toxicity Summary
IDENTIFICATION AND USE: Hexaldehyde 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. Hexanal is used in fruit flavors and, when highly diluted, in perfumery for obtaining fruity notes. It is also used in organic synthesis of plasticizers, rubber chemicals, dyes, synthetic resins, insecticides. HUMAN EXPOSURE AND TOXICITY: Twelve healthy volunteers were exposed to 0, 2, and 10 ppm n-hexanal for 2 hours at rest in a balanced order. Ratings of discomfort in the eyes and nose, solvent smell, and headache increased significantly with the level of exposure. Frequency of blinking was significantly increased at 10 ppm. No effects on pulmonary function and nasal swelling were detected, except a not-significant tendency to increased nasal obstruction at 10 ppm. No clear effects on plasma inflammatory markers (C-reactive protein and interleukin-6) were observed. /It was concluded that/ two hours of exposure to n-hexanal results in mild irritation at 10 ppm, with no apparent adversity at 2 ppm. n-Hexanal at 0.1% depressed motility of human spermatozoa but never rendered the sperm completely immotile. The increased concentrations of lower molecular weight aldehydes, including hexanal, may interfere with cholesterol transport and gap junctional intercellular communication. ANIMAL STUDIES: Acute exposures to the concentrated vapor for 1 hour or to 2000 ppm for 4 hours result in mortality to rats and is cytotoxic to rat hepatocytes. Rats receiving diets containing hexyl aldehyde for 3 wk showed decrease in serum cholesterol and triglyceride. Hexanal stimulates dopamine release but does not inhibit dopamine uptake in the brain striatum of rats. Hexanal influenced the length of time virgin female mice engage in the maternal crouching behavior. Hexanal was mutagenic in mammalian cells. Hexanal produced DNA single-strand breaks, or lesions which were converted to breaks in alkali.
Uremic toxins such as hexanal 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).
Plant Concentrations
Hexaldehyde has been detected as an emission from agricultural and natural plants (most dominant plant types) found in California's Central Valley(1). Hexaldehyde was detected in the emissions from northern red oak, dawn redwood, bass wood and tulip poplar trees(2). Hexaldehyde was detected in the emissions of Quercus ilex (oak) from the Mediterranean(3). Hexaldehyde was emitted from rape (Brassica napus) during the blooming period at a rate of 0.09 and 0.25 ppbv during May 8 and 9, 1998(4). Hexaldehyde was detected in as a volatile component from the leaves of Callicarpa japonica, an indigenous plant of Korea, Japan, China, and Taiwan(5).
Hexaldehyde occurs as a volatile component of ripening kiwi fruit(1), pineapple, guava(2), fresh grapefruit juice(3), Welsh onions and scallions(4), edible Korean Chamchwi(5), cassava, gari, and farine(7), delicious apples(8), chickpea seed(9, raw earth almonds (Cyperus esculentus L.)(10) and kogyoku apples(11). Hexaldehyde was quantified in sweet corn (kernel corn, 24 ppb; fresh kernel corn, 4 ppb)(12); mature (13183.4 ug/kg) and ripe (8398.0 ug/kg) guava fruit(13); nectarine cultivars (Sunfre, 580 ug/kg; P89-56, 740 ug/kg; P62-27, 600 ug/kg; Flavortop, 1950 ug/kg)(14);, beans (103 ppb), split peas (110 ppb), and lentils (59 ppb)(15); apricots (9, 5, and 8 ug/kg) and plums (19 and 6 ug/kg)(16). Hexaldehyde was not detected in raw peanuts (detection limit 0.02 ug/g)(17). Hexaldehyde was detected in the emissions from heated rapeseed oil(18). Hexaldehyde was detected in whole and ground musty sorghum with direct helium-purge method and with supercritical fluid extraction method(19).
Hexaldehyde detections in various plants(1).[Table#1644]
Regulatorische Informationen
FDA Requirements
Hexanal 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 b) 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.
Sicherheitsdaten
- F
- 13
- wgk
- 1
- tsca
- TSCA listed
- ridadr
- UN 1207
- hs_code
- 2912 19 00
- RTECS-Nr.
- MN7175000
- risk_code
- 10-36-36/37/38
- Toxizität
- LD50 orally in rats: 4.89 g/kg (Smyth)
- hazard_code
- Xi
- hazard_note
- Irritant
- safety_code
- 37/39-26-16-9
- hazard_class
- 3
- packing_group
- III
- Speicherklasse
- 3 - Flammable liquids
- Giftige Stoffe Daten
- 66-25-1(Hazardous Substances Data)
- Hazard Classifications
- Eye Irrit. 2Flam. Liq. 3Skin Irrit. 2
- Selbstentzündungstemperatur
- 220 °C
Chemie und Industrie
Pharmakologische Informationen
Mechanism of Action
Inhibition of intercellular communication is an important feature in the tumor promotion phase of a multistage carcinogenesis model. In atherosclerosis inhibition of cell-cell communication by atherogenic compounds, e.g., low density lipoproteins (LDL), also seems to be important. For testing atherogenic compounds we used an atherosclerosis relevant cell type, namely human smooth muscle cells. In order to investigate which part of the LDL particle would be involved in inhibition of metabolic co-operation between human smooth muscle cells in culture ... several fatty acids and their breakdown products /were tested/, namely aldehydes. Unsaturated C-18 fatty acids markedly influenced gap-junctional intercellular communication (GJIC), whereas saturated (C18:0, C16:0) and unsaturated fatty acids with > 20 carbon atoms did not inhibit GJIC. In the case of oleic and elaidic acid, orientation seemed important; however, after exposure to palmitoleic and palmitelaidic acid no differences were found. The most potent inhibitor of GJIC was linoleic acid, which inhibited GJIC by 75%. No correlation was found between degrees of unsaturation and ability to inhibit GJIC. Of the tested aldehydes, hexanal, propanal, butanal and 4-hydroxynonenal did significantly inhibit GJIC, while pentanal had no effect. Since modification of LDL was shown to be important in order for LDL to inhibit GJIC, these results show that fatty acids and their oxidative breakdown products may be of importance for the inhibition of GJIC by LDL.
Metabolism/Metabolites
Aldehyde dehydrogenase specific activity was measured in crude homogenates, post-mitochondrial supernatants, cytosolic and microsomal fractions of trout live, 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. Apparent affinity for hexanal and nonanal in the cytosolic fraction were comparable to that found in rats, but the theoretical maximal velocity for these substrates, and the specific activities for the other substrates, were much lower than found in mammals. In another study with carcinogen fed fish, aldehyde dehydrogenase distribution was evaluated histochemically in cryostat sections. In control trout, aldehyde dehydrogenase was uniformly distributed without an apparent zonal pattern. However, in hepatic tumors, aldehyde dehydrogenase was apparently induced with hexanal, nonanal, and propionaldehyde giving the strongest reaction products.
the substrate preference of an aldehyde dehydrogenase induced in rat liver cytosol by 3-methylcholanthrene was examined. This enzyme, T-ALDH, is identical to the aldehyde dehydrogenase inducible in rat liver by 2,3,7,8-tetrachloro-dibenzo-p-dioxin and the tumor associated aldehyde dehydrogenase found in rat hepatocellular neoplasms. With either NAD or NADP as coenzyme, the preferred substrates were the aliphatic aldehydes n-hexanal, n-nonanal, and isobutyraldehyde and the aromatic aldehydes 2,5-dihydroxybenzaldehyde, benzaldehyde, and 3-hydroxybenzaldehyde. T-ALDH may play a role in oxidizing a variety of aldehydes produced in physiological lipid metabolism. On the contrary, this isozyme does not seem to participate in the oxidation of small aliphatic aldehydes generated during lipid peroxidation.
Alcohol dehydrogenase classes exhibit differences in both substrate specificity and tissue distribution which suggest distinct physiological functions. The kinetic constants of the rat alcohol dehydrogenase classes, purified from liver (classes I and III) and from stomach (class IV), with three groups of relevant physiological compounds: cytotoxic aldehydes generated in lipid peroxidation, omega-hydroxy fatty acids, and retinoids /have been studied/. Classes I and IV actively reduce 4-hydroxynonenal, 2-hexenal, and hexanal, which are toxic compounds known to be produced in significant amounts during lipid peroxidation. Class III shows poor activity with these aldehydes. Class IV exhibits the best kcat/Km values (2150 mM-1 X min-1 for 4-hydroxynonenal), which suggest a role for this enzyme in the elimination of the cytotoxic aldehydes in tissues that are susceptible to lipid peroxidation, such as skin, cornea, and mucosa of the respiratory and digestive tracts, where class IV is localized.
Similar to saturated aldehydes, hexanal is oxidized to the corresponding caboxylic acid by aldehyde dehydrogenase mainly in the liver, but also in other tissues and cells. The acid can serve as a substrate for the Krebs cycle or is excreted as a salt. Alternatively, it can conjugate with glutathione or the sulfhydryl group of other proteins.
Free radical induced lipid peroxidation may play a role in neurodegeneration and peroxidation leads to the formation of hexanal from omega-6 fatty acids. We have previously demonstrated in vitro that pyruvate dehydrogenase (PDH) catalyzes the condensation of saturated aldehydes with pyruvate to form acyloins. We have further shown in perfused rat heart that hexanal, presumably via PDH, is converted to 3-hydroxyoctan-2-one and that it in turn can be reduced to 2,3-octanediol. We now extend this work using intra-striatal microdialysis to show that this reaction also occurs in rat brain. The reduction of hexanal to hexanol was also evaluated. Microdialysis probes were implanted bilaterally in the striatum and were infused with hexanal with and in the absence of added pyruvate. Analysis of microdialysis samples showed a release of 3-hydroxyoctan-2-one (9.5-10.5 pmol/min), 2,3-octanediol (2.2-2.7 pmol/min) and hexanol (64-74 pmol/min). Pyruvate addition did not increase 3-hydroxyoctan-2-one or 2,3-octanediol production. In a second series of experiments where no exogenous hexanal was infused, endogenous production of 3-hydroxyoctan-2-one (1.0-1.3 pmol/min) and 2,3-octanediol (1.0-1.2 pmol/min) was still observed, although no hexanol was detected. We also investigated the possibility that oxidative stress induced by 1-methyl-4-phenylpyridinium (MPP+) would increase lipid peroxidation resulting in increased production of 3-hydroxyoctan-2-one. Analysis of samples collected following MPP+ infusion indicated no additional increase suggesting that brief exposure to MPP+ does not increase hexanal formation over baseline levels during the experimental period.
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.
MeSH Pharmacological Classification
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.
Pesticides designed to control insects that are harmful to man. The insects may be directly harmful, as those acting as disease vectors, or indirectly harmful, as destroyers of crops, food products, or textile fabrics.
Verwendung und Herstellung
Uses
Used as flavoring agent; to make plasticizers, rubber chemicals, dyes, synthetic resins, and insecticides; in perfumery (at low concentrations); [HSDB] Used in fruity flavors and perfumes; [Ullmann]
For hexanal (USEPA/OPP Pesticide Code: 128950) there are 0 labels match. /SRP: 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./
Reported uses (ppm):
Organic synthesis of plasticizers, rubber chemicals, dyes, synthetic resins, insecticides.
Hexanal is used in fruit flavors and, when highly diluted, in perfumery for obtaining fruity notes.
Naturally produced by the body (endogenous).
U.S. Production
2023: 100,000 - <250,000 lb
Production volumes for non-confidential chemicals reported under the Inventory Update Rule.[Table#1645]
Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Hexanal. Aggregated National Production Volume: < 500,000 pounds.
Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Hexanal. National Production Volume: Withheld.
Methods of Manufacturing
... prepared by the hydroformylation of 1-pentene.
Prepared from calcium salt of caproic acid and formic acid.
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing Information
All Other Basic Organic Chemical Manufacturing
Hexanal: ACTIVE
Natural volatile hexanal was studied as an antifungal agent on the major postharvest fungal pathogens Botrytis cinerea, Monilinia fructicola, Sclerotinia sclerotiorum, Alternaria alternata, and Colletotrichum gloeosporioides. ... The antifungal effect of hexanal vapor was further tested on raspberry fruit naturally infected with B. cinerea and on peach fruit inoculated with spores of M. fructicola. Decay was markedly reduced in raspberry and almost completely controlled in peach ... .
Anwendungen
BeschreibungHexanal has a fatty, green, grassy, powerful, penetrating characteristic fruity odor and taste (on dilution). It is prepared from the calcium salt of caproic acid and formic acid.
OccurrenceReported found that hexanal occurs naturally in in some natural aromas of apple, strawberry, camphor oil, tea extracts, tobacco leaves, Eucalyptus globulus, dwarf pine, bitter orange and coffee. Also reported found in nearly 300 natural sources including apple, apricot, banana, sweet and sour cherry, citrus peel oils and juices, berries, guava, melon, raisins, peach, pear, papaya, pineapple, asparagus, cabbage, celery, carrot, lettuce, shallots, onion, leek, ginger, parsley, bread, cheeses, butter, milk, fish, meats, cocoa, coffee, tea, nuts, popcorn, potato chips, oat products, honey, soybean, plum, cauliflower, beetroot, celery root, figs, cardamom, coriander seed and leaf, brussel sprouts, rice, quince, radish, lovage, corn oil, laurel and malt
VerwendenHexanal occurs naturally inmany foods, such as in ripening fruits, or because of addition as a flavorant; it has an apple taste. It can also be produced in foods because of lipid peroxidation during cooking. It is mainly used as a food flavorant, in fragrances, and in the manufacture of dyes, plasticizers, synthetic resins, and pesticides. It is released to air and water during production or use for the manufacture of other products or during the use of these products themselves. It undergoes oxidation and polymerization readily. Feron et al. identified hexanal in about 80 different types of food.
Darstellung
synthetischePrepared from the calcium salt of caproic acid and formic acid
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Nachgelagerte Produkte
Anbieter50 Anbieter
Ergänzende Hinweise
DefinitionChEBI: A fatty aldehyde that is hexane in which one of the terminal methyl group has been mono-oxygenated to form the corresponding aldehyde.
Zugehörige Reaktionen
Verknüpfte Notizen
Wird geladen…