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Azelainsure
NONANEDIOIC ACID · azelaic · Azelex · ANCHOIC ACID · Azelaic acid powder · ninandioic acid · nonanedioate · Azalaic Acid
Identifikatoren & physikalische Daten
| CAS No. | 123-99-9 |
|---|---|
| Summenformel | C9H16O4 |
| Durchschnittliche Molmasse | 188,22 g/mol |
| Monoisotopische Masse | 188,10485899 g/mol |
| SMILES | O=C(O)CCCCCCCC(=O)O |
| InChIKey | BDJRBEYXGGNYIS-UHFFFAOYSA-N |
| PubChem CID | 2266 |
| ChEMBL | CHEMBL1238 |
| ChEBI | CHEBI:48131 |
| EC No. | 204-669-1 |
| DTXSID | DTXSID8021640 |
| Lokaler Name | Azelainsure |
Chemische & physikalische Eigenschaften
| XLogP | 1,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 74,6 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 8 |
| Schwere Atome | 13 |
| Formalladung | 0 |
| Komplexität | 147 |
| Stoffklassen | Other Classes -> Organic Acids |
| Arzneimittel | PharmaceuticalsPharmaceuticals -> Listed in ZINC15 |
| Lipide | Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Dicarboxylic acids [FA0117] |
| Kosmetika | Cosmetic ingredients (Azelaic Acid) -> CIR (Cosmetic Ingredient Review)Buffering |
| Duftstoffe | Fragrance |
| LogP (Verteilungskoeffizient) | log Kow = 1.57 |
| Dichte | 1.225 g/cu cm at 25 °C1,029 g/cm3 |
| Aromastoffe | EU Flavoring substances |
| Color/Form | Monoclinic prismatic needlesYellowish to white crystalline powderLeaflets or needles |
| Löslichkeit | Slightly soluble in ethy ether, benzene, DMSOsoluble in ethanolSoluble in hot water, alcohol and organic solventsOne liter of water dissolves 1.0 g at 1.0 °C2.4 g at 20 °C8.2 g at 50 °C22 g at 50 °C ... 1000 g ether dissolves 18.8 g at 11 °C and 26.8 g at 15 °CIn water, 2.40X10+3 mg/L at 20 °C2.4 mg/mL2.4g/l2.4 g/L (20 ºC) |
| Flammpunkt | 210 °C (closed cup)215 °C |
| Human Drugs | Breast FeedingLactationMilk, HumanAntineoplastic AgentsDermatologic AgentsFDA approved drugs -> Active ingredient |
| Schmelzpunkt | 98 °C |
| Siedepunkt | 286 °C100 mm Hg(lit.) |
| Dampfdichte | 6.5 (vs air) |
| Dampfdruck | <1 mm Hg ( 20 °C) |
| Brechungsindex | 1.4303 |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | Slightly Crystalline Powder or Flakes |
| pKa (Säurekonstante) | 4.53, 5.33(at 25℃) |
| Farbe | White to slightly yellow |
| pH | 3.5 (1g/l, H2O) |
| Merck | 14,905 |
| BRN | 1101094 |
| Henry-Konstante | 8.9×107 mol/(m3Pa) at 25℃, Compernolle and Müller (2014) |
| Stabilität | Stable. Combustible. Incompatible with bases, strong oxidizing agents. Readily biodegrades in soil and water with >70% DOC reduction after 28 days. |
| Kosmetik-Inhaltsstoffe Funktionen | FRAGRANCEBUFFERING |
| InChI | 1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13) |
| InChIKey | BDJRBEYXGGNYIS-UHFFFAOYSA-N |
| SMILES | OC(=O)CCCCCCCC(O)=O |
| LogP (Verteilungskoeffizient) | 1.57 at 25℃ |
| CAS Datenbank | 123-99-9(CAS DataBase Reference) |
| NIST chemische Informationen | Nonanedioic acid(123-99-9) |
| EPA chemische Informationen | Azelaic acid (123-99-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 6.5% (71 of 1087) of reports.WarningH315 (40.2%): 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 1087 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Nonanedioic acidCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Nonanedioic acid is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Nonanedioic acid 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: 27-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/13411Azelaic acid: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment |
| Brandpotenzial | Slightly flammable to flammable in presence of heat. |
| Gefahrenübersicht | Linear alkyl diacids cluster: Group members and supporting chemicals demonstrate eye irritation in rabbitsno evidence of skin sensitizationlow oral repeated dose systemic toxicity and developmental toxicityno adverse effects to reproductive organs in repeated-dose studiesno evidence of mutagenicity[EPA ChAMP: Hazard Characterization] May cause irritation[Acros Organics MSDS] |
| FDA-Anforderungen | The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl azelaic acid, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. |
Anwendungen & Verwendung
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.
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.
Herstellung & Synthese
synthetische
Azelaic acid is made by the ozonolysis of oleic acid: