Azelaic acid

Structural formula
General
Surname	Azelaic acid
other names	Nonanedioic acid 1,7-heptanedicarboxylic acid
Molecular formula	C 9 H 16 O 4
Brief description	white, crystalline solid
External identifiers / databases
CAS number 123-99-9 EC number 204-669-1 ECHA InfoCard 100.004.246 PubChem 2266 DrugBank DB00548 Wikidata Q413504
Drug information
ATC code	D10 AX03
Drug class	Acne medication
properties
Molar mass	188.22 g mol −1
Physical state	firmly
density	1.23 g cm −3
Melting point	98-102 ° C
boiling point	237 ° C (20 h Pa )
pK s value	pK s 1 = 4.53 pK s 2 = 5.40
solubility	slightly soluble in water (2.4 g l −1 at 20 ° C)
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances Caution H and P phrases H: 319 P: 305 + 351 + 338
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Azelaic acid (nonanedioic acid, 1,7-heptanedicarboxylic acid) is a chemical compound from the homologous series of dicarboxylic acids . Their salts and esters are called azelates .

properties

As a dibasic acid, it dissociates in water in two stages of protolysis . There are three polymorphic forms, which are divided into α, β and γ.

presentation

Azelaic acid can be made by oxidizing castor oil with potassium permanganate . First the castor oil is hydrolyzed to ricinoleic acid, which is then oxidized to azelaic acid.

The industrial production of azelaic acid is carried out by ozonolysis of oleic acid . By alkali melting of castor oil with NaOH, sebacic acid and 2-octanol (caprylic alcohol) are industrially produced via ricinoleic acid as an intermediate .

use

Azelaic acid is used as an active pharmaceutical ingredient in topical therapy for acne and rosacea . 20% cream and 15% gel preparations are used. Azelaic acid preparations require a prescription.

Various Di ester of azelaic acid, such as with 2-ethylhexanol ( diisooctyl azelate , DIOZ) with butanol ( dibutyl , DBZ) or octanol ( dioctyl azelate , DOZ), are used as plasticizers for plastics .

Trade names

Monopreparations

Skinoren (D, A, CH), generic (A)

Individual evidence

1. ↑ ^{a b c} Azelaic acid data sheet (PDF) from Merck , accessed March 30, 2010.
2. ↑ ^{a b} Azelaic acid data sheet at AlfaAesar, accessed on March 30, 2010 ( PDF )(JavaScript required) .
3. ↑ ^{a b} CRC Handbook of Tables for Organic Compound Identification , Third Edition, 1984, ISBN 0-8493-0303-6 .
4. ↑ ^{a b} Entry on azelaic acid in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
5. ↑ PM Babkov et al. Ukr. Fiz. Zh. (Russ Ed.) 1985.
6. ↑ TW Abraham, R. Höfer, Lipid-Based Polymer Building Blocks and Polymers , In: K. Matyjaszewski, M. Möller (eds.): Polymer Science: A Comprehensive Reference, Vol 10, Polymers for a Sustainable Environment and Green Energy , JE McGrath, MA Hickner, R. Höfer (Vol. Edts.) Elsevier, Amsterdam, Oxford, Waltham (2012) pp. 15-58
7. ↑ External identifiers or database links to diisooctyl azelate : CAS number: 26544-17-2, EC number: 247-774-8, ECHA InfoCard: 100.043.416 , PubChem : 66934 , Wikidata : Q72467323 .
8. ↑ External identifiers from or database links to dibutylazelate : CAS number: 2917-73-9, EC number: 220-850-8, ECHA InfoCard: 100.018.956 , PubChem : 18016 , ChemSpider : 17020 , Wikidata : Q27290265 .

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !