Azelaic acid

Base Information

• Chemical Name: Azelaic acid
• CAS No.: 123-99-9
• Deprecated CAS: 1219811-33-2,32733-99-6
• Molecular Formula: C9H16O4
• Molecular Weight: 188.224
• Hs Code.: 2917.19
• European Community (EC) Number: 204-669-1
• NSC Number: 757406,19493
• UNII: F2VW3D43YT
• DSSTox Substance ID: DTXSID8021640
• Nikkaji Number: J10.058G
• Wikipedia: Azelaic_acid
• Wikidata: Q413504
• NCI Thesaurus Code: C47407
• RXCUI: 18602
• Metabolomics Workbench ID: 1976
• ChEMBL ID: CHEMBL1238
• Mol file: 123-99-9.mol

Synonyms:1, 9-Nonanedioic acid;Nonanedioic acid;Azelaic acid, technical grade;Lepargylic acid;Heptanedicarboxylic acid;Nonanedioic acid Azelaic acid;Empol 1144;1,7-Heptanedicarboxylic acid;Emerox 1144;Emerox 1110;Ammonium Hydrogen Azelate;Azelaic Acid 99%;

Chemical Property of Azelaic acid

Chemical Property:

• Appearance/Colour: white to cream solid
• Vapor Pressure: <1 mm Hg ( 20 °C)
• Melting Point: 98-103 ºC
• Refractive Index: 1.4303
• Boiling Point: 370.5 ºC at 760 mmHg
• PKA: 4.53, 5.33(at 25℃)
• Flash Point: 192.1 ºC
• PSA: 74.60000
• Density: 1.131 g/cm³
• LogP: 1.88630
• Storage Temp.: 2-8°C
• Solubility.: 2.4g/l
• Water Solubility.: 2.4 g/L (20 ºC)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 188.10485899
• Heavy Atom Count: 13
• Complexity: 147

Purity/Quality:

99%, ^*data from raw suppliers

Azelaic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C(CCCC(=O)O)CCCC(=O)O
• Recent ClinicalTrials: Azelaic Acid as a Novel Treatment for Central Centrifugal Cicatricial Alopecia (CCCA)
• Recent EU Clinical Trials: THE EFFECT OF AZELAIC ACID ON SYMPTOMS OF ACNE IN FEMALE PATIENTS AGE 20-45 WITH MILD TO MODERATE PAPULOPUSTULAR ACNE (ACNE TARDA)
• Description: 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.
• Uses: antiacne, antiproliferative agent antifungal, binds to membrane sterols 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.
• 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.
• Therapeutic Function: Antiacne, Depigmentor
• Clinical Use: Azelaic acid is used for the treatment of mild to moderate acne, particularly in cases characterized by marked inflammation-associated hyperpigmentation.

Technology Process of Azelaic acid

There total 303 articles about Azelaic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

1,3-Dioxa-cyclododecane-4,12-dione → azelaic acid (123-99-9,26776-28-3) + 1,9-Nonanediol (3937-56-2) + 9-hydroxynonanoic acid (3788-56-5)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; at 23 ℃; for 120h;

DOI:10.1080/00397919708004080

Reference yield: 28.0%

9,10-diketostearic acid (656-73-5) → azelaic acid (123-99-9,26776-28-3) + octane-1,8-dioic acid (505-48-6) + nonanoic acid (112-05-0)

Guidance literature:

With 1 wt% Au/Al2O3; oxygen; sodium hydroxide; In water; at 80 ℃; for 4.33333h; under 3750.38 Torr; Autoclave; Inert atmosphere;

DOI:10.1039/c3gc41822g

Reference yield: 27.5%

Methyl oleate (112-62-9) → azelaic acid (123-99-9,26776-28-3) + heptanedioic acid (111-16-0) + octane-1,8-dioic acid (505-48-6) + Octanoic acid (124-07-2) + nonanoic acid (112-05-0)

Guidance literature:

With 7CeO₂*7Nb₂O₅*3La₂O₃*K₂O*2Bi₂O₃; oxygen; at 120 ℃; for 15h; under 6750.68 Torr; Autoclave;

upstream raw materials:

tetrachloromethane

Elaidic acid

tetranitromethane

cycloheptadec-9-en-1-one

Downstream raw materials:

azelaic acid bis-(3-tetrahydro[2]furyl-propyl ester)

formaldehyd

cycloactanone

2-Nonanone

Refernces

• 1、 Karim, Mohammad R.,Sampson, Paul. "A New and Efficient Approach to Macrocyclic Keto Lactones". . p. 598 - 605. Retrieved 1990.
• 2、 Song, Ji-Won,Lee, Jung-Hoo,Bornscheuer, Uwe T.,Park, Jin-Byung. "Microbial synthesis of medium-chain α,ω-dicarboxylic acids and ω-aminocarboxylic acids from renewable long-chain fatty acids". . p. 1782 - 1788. Retrieved 2014.
• 3、 Barger et al.. "-". . p. 90,93. Retrieved 1933.
• 4、 Gunstone,F.D. et al.. "-". . p. 295 - 296. Retrieved 1967.
• 5、 Applewhite,T.H. et al.. "". . p. 3407 - 3409. Retrieved 1966.
• 6、 Cha, Hee-Jeong,Seo, Eun-Ji,Song, Ji-Won,Jo, Hye-Jin,Kumar, Akula Ravi,Park, Jin-Byung. "Simultaneous Enzyme/Whole-Cell Biotransformation of C18 Ricinoleic Acid into (R)-3-Hydroxynonanoic Acid, 9-Hydroxynonanoic Acid, and 1,9-Nonanedioic Acid". . p. 696 - 703. Retrieved 2018.
• 7、 Atapalkar, Ranjit S.,Athawale, Paresh R.,Srinivasa Reddy,Kulkarni, Amol A.. "Scalable, sustainable and catalyst-free continuous flow ozonolysis of fatty acids". supporting information. p. 2391 - 2396. Retrieved 2021/04/07.
• 8、 -. "FLOW CHEMISTRY SYNTHESIS OF ISOCYANATES". Paragraph 0008; 0175; 0180. . Retrieved 2021/06/22.