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Heptanal
HEPTANAL · N-HEPTANAL · N-HEPTALDEHYDE · FEMA 2541 · 1-HEPTALDEHYDE · FEMA 2542 · ENANTHALDEHYDE · HEPTYL ALDEHYDE
Identifikatoren & physikalische Daten
| CAS No. | 111-71-7 |
|---|---|
| Summenformel | C7H14O |
| Durchschnittliche Molmasse | 114,19 g/mol |
| Monoisotopische Masse | 114,10446507 g/mol |
| SMILES | CCCCCCC=O |
| InChIKey | FXHGMKSSBGDXIY-UHFFFAOYSA-N |
| PubChem CID | 8130 |
| ChEMBL | CHEMBL18104 |
| ChEBI | CHEBI:34787 |
| EC No. | 203-898-4 |
| DTXSID | DTXSID0021597 |
| Lokaler Name | Heptanal |
Chemische & physikalische Eigenschaften
| XLogP | 2,3 |
|---|---|
| Polarare Oberfläche (TPSA) | 17,1 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 5 |
| Schwere Atome | 8 |
| Formalladung | 0 |
| Komplexität | 50,3 |
| Stoffklassen | Other Classes -> Aldehydes |
| Lipide | Fatty Acyls [FA] -> Fatty aldehydes [FA06] |
| SpringerMaterials Properties | Boiling point |
| Duftstoffe | Fragrance Ingredient (Heptanal) -> IFRA transparency List |
| Geruch | FATTY, PUNGENT ODORPenetrating fruity odor |
| Geschmack | FATTY TASTE |
| Lebensmittelzusatzstoffe | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Dichte | 0.8495 at 68 °F (NTP, 1992) - Less dense than waterwill float0.82162 g/cu cm at 25 °C0.814-0.8190.817 g/mL at 25 °C (lit.) |
| Aromastoffe | EU Flavoring substances |
| Viscosity | 0.977 cP at 15 °C0.791 cP at 30 °C |
| Color/Form | Oily colorless liquid |
| Löslichkeit | 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% ALCSlightly soluble in carbon tetrachloridemiscible with ethanol, ethyl etherIn water, 1,250 mg/L at 25 °C1.25 mg/mL at 25 °C1.25g/l insolubleVery slightly soluble in water, soluble in alcohol and oils. |
| Schmelzpunkt | -43 °C (lit.) |
| Siedepunkt | 153 °C (lit.) |
| Dampfdruck | 3 hPa (20 °C) |
| FEMA | 2540 | HEPTANAL |
| Brechungsindex | n20/D 1.413(lit.) |
| Flammpunkt | 95 °F |
| Lagerbedingungen | Flammables area |
| Aggregatzustand | Powder, Crystals or Chunks |
| Farbe | White to light yellow-beige |
| Geruch | Green-herbaceous, vegetable-like odor |
| Biologische Quelle | synthetic |
| Geruchsart | green |
| Explosionsgrenze | 1.1-5.2%(V) |
| Geruchsschwelle | 0.00018ppm |
| Spezifische Wärmekapazität | Cp(liquid): 2.02 J/(g·K), at 25℃ |
| JECFA Number | 95 |
| Merck | 14,4658 |
| BRN | 1560236 |
| Henry-Konstante | 3.4×10-2 mol/(m3Pa) at 25℃, Brockbank (2013) |
| Dielektrizitätskonstante | 9.1(Ambient) |
| Stabilität | Stable. May be light sensitive. Flammable - readily forms explosive mixtures with air. Incompatible with strong oxidizing agents, strong bases, strong reducing agents. |
| Hauptanwendungen | flavors and fragrances |
| Kosmetik-Inhaltsstoffe Funktionen | PERFUMING |
| InChI | 1S/C7H14O/c1-2-3-4-5-6-7-8/h7H,2-6H2,1H3 |
| InChIKey | FXHGMKSSBGDXIY-UHFFFAOYSA-N |
| SMILES | CCCCCCC=O |
| LogP (Verteilungskoeffizient) | 2.8 at 20℃ |
| CAS Datenbank | 111-71-7(CAS DataBase Reference) |
| NIST chemische Informationen | Heptanal(111-71-7) |
| EPA chemische Informationen | Heptanal (111-71-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH226 (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.H226: Flammable liquid and vapor [Warning Flammable liquids] |
|---|---|
| Regulatorische Informationen | Chemical: HeptanalHeptanal 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/2177Heptanal: HSNO Approval: HSR001163 Approved with controls |
| DOT-Kennzeichnung | Flammable Liquid |
| Brandgefahren | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. |
| Brandpotenzial | Flammable/combustible materialmay be ignited by heat, sparks or flames. |
| Gesundheitsgefahren | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:· May cause toxic effects if inhaled or absorbed through skin. |
| Gefahrenübersicht | Category of C7-C9 aliphatic aldehydes and carboxylic acids: Members and supporting chemicals demonstrate low acute toxicity by oral, dermal, and inhalation exposurestoxicity in repeated-dose studies only at relatively high levelsno 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] |
| DOT-Nummer und Handbuch | 3056 129 |
| FDA-Anforderungen | 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. |
| Reaktive Gruppe | Aldehydes |
| Special Reports | European Chemicals BureauIUCLID Dataset, Heptanal (111-71-7) (2000). Available from the database query page: http://ecb.jrc.ec.europa.eu/ as of January 28, 2009. |
| TSCA-Anforderungen | 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 9/30/91Reporting 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 9/30/91Sunset date: 6/30/98. |
| Reactivity Alerts | Highly Flammable |
| Brandbekämpfung | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: |
| Freisetungsmaßnahmen | · 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. |
| Erste Hilfe | 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: |
| Firefighting Hazards | Vapor may travel to a source of ignition and flash back. Container may explode in heat of fire. Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. |
| Expositionsschutz und Persönliche Schutzausrüstung | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| Freisetung ohne Brand | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: |
| Entsorgungsverfahren | 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Isolation and Evacuation | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]:Immediate precautionary measure |
| Personal Protective Equipment (PPE) | Excerpt from ERG Guide 129 [Flammable Liquids (Water-Miscible / Noxious)]: |
| Emergency Response Planning Guidelines | CAUTION: The majority of these products have a very low flash point. Use of water spray when fighting fire may be inefficient. |
| Körperbelastung | 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). |
| Treatment | Kidney dialysis is usually needed to relieve the symptoms of uremic syndrome until normal kidney function can be restored. |
| Gesundheitliche Auswirkungen | Chronic exposure to uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. |
| Ökotoxizitätswerte | LC50Species: Pimephales promelas (Fathead minnow, 26-34 day old juvenile)Conditions: freshwater, continuous flow through systemConcentration: 37.9 mg/L for 96 hr /metabolic precursor, 1-heptanol/Species: Alburnus alburnus (Bleak)Conditions: brackish water, static no aerationConcentration: 45 mg/L for 96 hr (95% confidence interval: 42-49 mg/L) /metabolic precursor,1-heptanol dissolved in water/Species: Nitocra spinipes (harpacticoid)Conditions: brackish water, staticConcentration: 210 mg/L for 96 hr (95% confidence interval: 170-250 mg/L) /metabolic precursor,1-heptanol dissolved in water/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/LConcentration: 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. |
| Umweltverhalten | 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). |
| Lebensmitteluntersuchungswerte | 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 ppmcanned/kernel, 4 ppmfrozen/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 PPMALCOHOLIC BEVERAGES, 4.0 PPMICE CREAM, ICES, ETC, 1.2 PPMCANDY, 2.0 PPMBAKED GOODS, 2.6 PPM. |
| Expositionspfade | Endogenous, Ingestion, Dermal (contact) |
| Milk Concentrations | 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). |
| Toxizitätsübersicht | 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). |
| Average Daily Intake | AIR INTAKE: Assuming mean concentration of n-heptanal in air of 0.15 ppb(1), an average daily uptake of 14 ug is expected(SRC). |
| Plant Concentrations | 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). |
| Signs and Symptoms | 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. |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 3056 |
| Zollcode | 2912 19 00 |
| RTECS-Nr. | MI6900000 |
| R-Sätze (R) | 10-36/37/38-38-50/53 |
| Toxizität | LD50 orally in Rabbit: > 5000 mg/kg LD50 dermal Rabbit > 5000 mg/kg |
| Gefahrensymbole | Xi,N |
| hazard_note | Irritant |
| Sicherheitshinweise (S) | 26-36-37-16-61-60 |
| Gefahrenklasse | 3Aquatic Chronic 3Flam. Liq. 3Skin Irrit. 2 |
| Verpackungsgruppe | III |
| Lagerklasse | 3 - Flammable liquids |
| Gefahrstoffdaten | 111-71-7(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 250 °C |
Anwendungen & Verwendung
Beschreibung
Heptanal has a very strong, fatty, harsh, pungent odor and an unpleasant, fatty taste. Heptanal is obtained by distilling castor oil, preferably under reduced pressure.
Occurrence
Heptanal is a constituent of the essential oils of ylang-ylang, clary sage, California lemon, bitter orange, rose and hyacinth Also reported found in cocoa, buckwheat, elderberry fruit and juice and babaco fruit (Carica pentagona Heilborn)
Verwenden
Labelled Heptanal. Bioconversion of heptanal to heptanol by Saccharomyces cerevisiae and effect of C source maltose.
Herstellung & Synthese
synthetische
Obtained by distilling castor oil, preferably under reduced pressure.