Eugenol Chemische Eigenschaften,Einsatz,Produktion Methoden
R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R42/43:Sensibilisierung durch Einatmen und Hautkontakt möglich.
R38:Reizt die Haut.
R40:Verdacht auf krebserzeugende Wirkung.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S24/25:Berührung mit den Augen und der Haut vermeiden.
S23:Gas/Rauch/Dampf/Aerosol nicht einatmen(geeignete Bezeichnung(en) vom Hersteller anzugeben).
Aussehen Eigenschaften
C10H12O2; Eugenol. Gelbliche Flüssigkeit mit charakteristischem Geruch.
Gefahren für Mensch und Umwelt
Gesundheitsschädlich beim Verschlucken.
LD
50 (oral, Ratte): 1950 mg/kg
Schutzmaßnahmen und Verhaltensregeln
Schutzhandschuhe als kurzzeitiger Spritzschutz.
Verhalten im Gefahrfall
Mit flüssigkeitsbindendem Material aufnehmen. Der Entsorgung zuführen. Nachreinigen
Kohlendioxid, Pulver.
Brennbar.
Erste Hilfe
Nach Hautkontakt: Mit reichlich Wasser abwaschen.
Nach Augenkontakt: Bei geöffnetem Lidspalt mit reichlich fliessendem Wasser (Augendusche!) mindestens 15 Minuten ausspülen. Sofort Augenarzt hinzuziehen.
Nach Einatmen: Frischluft. Arzt hinzuziehen.
Nach Verschlucken: Reichlich Wasser trinken. Erbrechen auslösen. Arzt hinzuziehen.
Nach Kleidungskontakt: Kontminierte Kleidung entfernen.
Ersthelfer: siehe gesonderten Anschlag
Sachgerechte Entsorgung
Als halogenfreie, organische Lösemittelabfälle.
Beschreibung
Sensitization to eugenol mainly occurs in those in
dental professions. Eugenol is contained in the "fragrance
mix".
Chemische Eigenschaften
Eugenol is the main component
of several essential oils; clove leaf oil and cinnamon leaf oilmay contain>90%.Eugenol occurs in small amounts in many other essential oils. It is a colorless to
slightly yellow liquid with a spicy, clove odor.
Catalytic hydrogenation (e.g., in the presence of noble metal catalysts) yields
dihydroeugenol. Isoeugenol is obtained fromeugenol by shifting the double bond.
Esterification and etherification of the hydroxy group of eugenol yield valuable
fragrance and flavor materials (e.g., eugenol acetate and eugenol methyl ether).
Occurrence
Reported found as a constituent in several volatile oils: clove oil, laurel and cinnamon leaf oil. Smaller amounts
of eugenol are also present in the oil of camphor, Java citronella, California laurel and acacia flowers; remarkable amounts of eugenol
are found in Ocimum sanctum (70%) and Ocimum gratissimum (60%). Eugenol is also found in the oil from violet flowers (21%);
in some plants, eugenol probably occurs as glucoside. Reported found in apricot, citrus oils, raspberry, strawberry, tomato, anise,
cinnamon (leaf, bark and roots), clove bud and stem, nutmeg, mace, pepper, smoked fish, beer, whiskey, grape wines, cocoa, mango,
tarragon, laurel, myrtle leaf, and pimento berry and leaf.
Verwenden
Eugenol is a dental compound which shows cytotoxicity to human oral squamous cell carcinoma and oral cells. When glucosylated, this compound exhibits anti-inflammatory activity.
synthetische
Since sufficient eugenol can be isolated from cheap essential oils,
synthesis is not industrially important. Eugenol is still preferentially isolated from
clove leaf and cinnamon leaf oil (e.g., by extraction with sodium hydroxide solution).
Nonphenolic materials are then removed by steam distillation. After the
alkaline solution is acidified at low temperature, pure eugenol is obtained by distillation.
Definition
ChEBI: A phenylpropanoid formally derived from guaiacol with an allyl chain substituted para to the hydroxy group.
Allgemeine Beschreibung
Clear colorless pale yellow or amber-colored liquid. Odor of cloves. Spicy pungent taste.
Air & Water Reaktionen
Darkens and thickens on exposure to air. Also darkens with age. Eugenol may decompose on exposure to light. Insoluble in water.
Reaktivität anzeigen
Eugenol is incompatible with strong oxidizers. This includes ferric chloride and potassium permanganate. Eugenol reacts with strong alkalis. Eugenol is incompatible with iron and zinc.
Hazard
Questionable carcinogen.
Brandgefahr
Eugenol is combustible.
Kontakt-Allergie
Eugenol is a fragrance allergen obtained from many
natural sources. Occupational sensitization to eugenol
may occur in dental profession workers. Eugenol is
contained in “fragrance mix” and has to be listed by
name in cosmetics within the EU.
Clinical Use
4-Allyl-2-methoxyphenol is obtained primarily from cloveoil. It is a pale-yellow liquid with a strong aroma of clovesand a pungent taste. Eugenol is only slightly soluble in waterbut is miscible with alcohol and other organic solvents.Eugenol possesses both local anesthetic and antiseptic activityand can be directly applied on a piece of cotton to relievetoothaches. Eugenol is also used in mouthwashes because ofits antiseptic property and pleasant taste. The phenol coefficientof eugenol is 14.4.
Anticancer Research
This compound was tested on a model of skin tumor induced by DMBA croton oilin Swiss mice. The eugenol affects the cellular proliferation by increasing apoptosiscellular death. There is evidence for a downregulation of c-myc, H-ras, and Bcl-2expression and an upregulation of p53, Bax, and active caspase-3 (Grondona et al.2014).
Sicherheitsprofil
Moderately toxic by
ingestion, intraperitoneal, and subcutaneous
routes. Human mutation data reported. A
human skin irritant. Questionable
carcinogen with experimental carcinogenic
and tumorigenic data. Combustible liquid.
When heated to decomposition it emits
acrid smoke and irritating fumes. See also
ALLYL COMPOUNDS.
Stoffwechsel
No absorption of eugenol occurred within 2hr of application to the intact shaved skin of mice (Meyer & Meyer, 1959). Following ip injec tion of [
14C]eugenol into rats, radioactivity was dis tributed in various organs and the presence of
14CO
2 in the expired air indicated the demethylation of eugenol (Weinberg, Rabinowitz, Zanger & Gennaro, 1972). Over 70% of an oral dose of eugenol was excreted in the urine of rabbits (Schr?der & Vollmer, 1932).
läuterung methode
Fractional distillation of eugenol gives a pale yellow liquid which darkens and thickens on exposure to air. It should be stored under N2 at -20o. [Waterman & Priedster Recl Trav Chim Pays-Bas 48 1272 1929, Beilstein 6 H 961, 6 IV 6337.]
Eugenol Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
