Non-2-enal
2-TRANS-NONENAL · Nsc20746 · 2-nonenal · FEMA 3213 · NON-2-ENAL · T2 NONENAL · 2-NONEN-1-AL · β-Hexylacrolein
Identifikatoren & physikalische Daten
| CAS No. | 2463-53-8 |
|---|---|
| Summenformel | C9H16O |
| Durchschnittliche Molmasse | 140,22 g/mol |
| Monoisotopische Masse | 140,12011513 g/mol |
| SMILES | CCCCCCC=CC=O |
| InChIKey | BSAIUMLZVGUGKX-UHFFFAOYSA-N |
| PubChem CID | 17166 |
| EC No. | 219-562-5 |
| DTXSID | DTXSID3047219 |
| Lokaler Name | Non-2-enal |
Chemische & physikalische Eigenschaften
| XLogP | 3,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 17,1 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 6 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 94,9 |
| Dichte | 0.855-0.8650.846 g/mL at 25 °C(lit.) |
| Aromastoffe | EU Flavoring substances |
| Löslichkeit | Soluble in most fixed oilsInsoluble in waterSoluble (in ethanol) |
| Siedepunkt | 88-90 °C (12 mm Hg)88-90 °C12 mm Hg(lit.) |
| Brechungsindex | 1.454-1.460n20/D 1.453(lit.) |
| Physical Description | White to slightly yellow liquidPowerful, penetrating fatty, violet aroma |
| Schmelzpunkt | -28°C (estimate) |
| Dampfdichte | >1 (vs air) |
| FEMA | 3213 | 2-NONENAL |
| Flammpunkt | 184 °F |
| Farbe | White to sltly yellow liquid |
| Geruch | fatty, violet odor |
| Geruchsart | fatty |
| JECFA Number | 1362 |
| Kosmetik-Inhaltsstoffe Funktionen | PERFUMING |
| LogP (Verteilungskoeffizient) | 3.17 |
| CAS Datenbank | 2463-53-8(CAS DataBase Reference) |
| NIST chemische Informationen | 2-Nonenal(2463-53-8) |
| EPA chemische Informationen | 2-Nonenal (2463-53-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)Aggregated GHS information provided per 1550 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Regulation (EC) No 1831/2003 (amended) |
| Hazard Classes and Categories | Skin Irrit. 2 (100%) |
| 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. |
| Expositionspfade | Endogenous, Ingestion, Dermal (contact) |
| Toxizitätsübersicht | Uremic toxins such as 2-Nonenall 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). |
| 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. |
Anwendungen & Verwendung
Beschreibung
2-Nonenal has a very powerful, penetrating fatty odor in concentrated form. It is orris-like, waxy, and quite pleasant on dilution. The odor is reminiscent of dried orange peels. Prepared by oxidation of 9,10,12-trihydroxy stearic acid (Criegee reaction).
Occurrence
Reported found in orris oil, melon, peach, asparagus, carrot, peas, tomato, wheat and crisp breads, Russian cheeses, caviar, butter, fish oil, cooked beef, mutton, pork, and their fats, hop oil, cognac, roasted filberts and peanuts, soybean, beans, sesame seed, mango, rice, beer, and potato chips
Verwenden
The concentration in a perfume oil may be of the order of magnitude of 0.01 to 0.03%. An addition of 0.02% of 2-Nonenal to a normal grade of "gamma" -Methylionone will produce a distinctly ("orrisy") perceptible effect, desirable and attractive in the opinion of many perfumers.
Herstellung & Synthese
synthetische
By oxidation of 9,10,12-trihydroxystearic acid (Criegee reaction)