Azelainsure Chemische Eigenschaften,Einsatz,Produktion Methoden
R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S24/25:Berührung mit den Augen und der Haut vermeiden.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Beschreibung
Azelaic acid is a topical antiacne agent which exerts its therapeutic action through a
myriad of antimicrobial, antiproliferative and cytostatic effects. In vitro, azelaic acid hasbeen shown to inhibit DNA polymerases in several tumor cell lines.
Chemische Eigenschaften
Azelaic acid is an organic compound with the formula (CH
2)
7(CO
2H)
2. This saturated dicarboxylic acid exists as a white powder. It is found in wheat, rye, and barley. It is a component of a number of hair and skin conditioners.
Verwenden
Azelaic acid is used in lacquers, alkyd resins, plasticizers,
adhesives, polyamides, urethane elastomers, and organic
syntheses. Azelaic acid is also used in treating of
acne.
Vorbereitung Methode
Azelaic acid is industrially produced by the ozonolysis of oleic acid. The side product is nonanoic acid. It is produced naturally by Malassezia furfur (also known as Pityrosporum ovale), a yeast that lives on normal skin. The bacterial degradation of nonanoic acid gives azelaic acid.
Indications
Azelaic acid (Azelex) is a naturally occurring dicarboxylic
acid produced by the yeast Malassezia furfur.
Azelaic acid inhibits tyrosinase, a rate-limiting enzyme
in the synthesis of the pigment melanin. This may explain
why diminution of melanin pigmentation occurs in
the skin of some patients with pityriasis versicolor, a disease
caused by M. furfur. Azelaic acid is bacteriostatic
against a number of species thought to participate in the
pathogenesis of acne, including Propionibacterium acnes.
The drug may also reduce microcomedo formation
by promoting normalization of epidermal keratinocytes.
synthetische
Azelaic acid is made by the ozonolysis of oleic acid:
Application
Azelaic acid, also known as azalea acid, is a white to slightly yellow powder. Azelaic acid is a medium-long chain dibasic acid[1]. In recent years, with the rapid development of the organic synthetic chemical industry, the demand for medium and long chain dibasic acids is increasing. The medium and long chain dibasic acids and their derivatives have a wide range of industrial applications and a broad product market.
Allgemeine Beschreibung
Azelaic acid is used as a therapeutic agent in dermatology.
Mechanism of action
Naturally occurring dicarboxylic acid that is bacteriostatic
to Propionibacterium acnes. It also decreases conversion of testosterone
to 5{pi}ga-dihydrotestosterone (DHT) and alters keratinization of the microcomedone.
It may also be beneficial in the treatment of melasma. The
mechanism of action is not fully understood. Deoxyribonucleic acid (DNA)
synthesis is reduced, and mitochondrial cellular energy products are inhibited
in melanocytes.
Biotechnological Applications
In plants, azelaic acid serves as a "distress flare" involved in defense responses after infection. It serves as a signal that induces the accumulation of salicylic acid, an important component of a plant's defensive response.
Clinical Use
Azelaic acid is used for the treatment of mild to
moderate acne, particularly in cases characterized by
marked inflammation-associated hyperpigmentation.
Sicherheitsprofil
Low toxicity by ingestion. A skinand eye irritant. Closely related to glutaric acid and adipicacid. Combustible when exposed to heat or flame; canreact with oxidizing materials.
läuterung methode
Recrystallise it from H2O(charcoal) or thiophene-free *benzene. The acid can be dried by azeotropic distillation with toluene, the residual toluene solution is then cooled and filtered, and the precipitate is dried in a vacuum oven. It has been purified by zone refining or by sublimation onto a cold finger at 10-3torr. It distils above 360o with partial formation of the anhydride. The dimethyl ester has m –3.9o and b 140o/8mm. [Hill & McEwen Org Synth Coll Vol II 53 1943, Beilstein 2 IV 2055.]
Azelainsure Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
