Azelaic acid
- CAS No.
- 123-99-9
- Chemical Name:
- Azelaic acid
- Synonyms
- NONANEDIOIC ACID;Azelex;azelaic;ninandioic acid;ANCHOIC ACID;nonanedioate;Azelaic acid powder;ZK-62498;Azalaic Acid;nonadioic acid
- CBNumber:
- CB6852982
- Molecular Formula:
- C9H16O4
- Molecular Weight:
- 188.22
- MOL File:
- 123-99-9.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/9/3 18:36:42
| Melting point | 98 °C |
|---|---|
| Boiling point | 286 °C100 mm Hg(lit.) |
| Density | 1,029 g/cm3 |
| vapor density | 6.5 (vs air) |
| vapor pressure | <1 mm Hg ( 20 °C) |
| refractive index | 1.4303 |
| Flash point | 215 °C |
| storage temp. | Store below +30°C. |
| solubility | 2.4g/l |
| form | Slightly Crystalline Powder or Flakes |
| pka | 4.53, 5.33(at 25℃) |
| color | White to slightly yellow |
| PH | 3.5 (1g/l, H2O) |
| Water Solubility | 2.4 g/L (20 ºC) |
| Merck | 14,905 |
| BRN | 1101094 |
| Stability | Stable. Combustible. Incompatible with bases, strong oxidizing agents. Readily biodegrades in soil and water with >70% DOC reduction after 28 days. |
| InChIKey | BDJRBEYXGGNYIS-UHFFFAOYSA-N |
| LogP | 1.57 at 25℃ |
| CAS DataBase Reference | 123-99-9(CAS DataBase Reference) |
| NIST Chemistry Reference | Nonanedioic acid(123-99-9) |
| EPA Substance Registry System | Azelaic acid (123-99-9) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H315-H319 | |||||||||
| Precautionary statements | P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313 | |||||||||
| Hazard Codes | Xi | |||||||||
| Risk Statements | 36/37/38 | |||||||||
| Safety Statements | 24/25-36-26 | |||||||||
| WGK Germany | 1 | |||||||||
| RTECS | CM1980000 | |||||||||
| TSCA | Yes | |||||||||
| HS Code | 29171390 | |||||||||
| Toxicity | LD50 orally in Rabbit: > 4000 mg/kg LD50 dermal Rat > 10 g/kg | |||||||||
| NFPA 704 |
|
Azelaic acid price More Price(23)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | A96150 | Azelaic acid technical grade, 80% | 123-99-9 | 2KG | ₹5228.48 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 95054 | Azelaic acid analytical standard | 123-99-9 | 100MG | ₹6365.1 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 8.20116 | Azelaic acid, technical grade for synthesis | 123-99-9 | 100G | ₹2740 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 8.20117 | Azelaic acid for synthesis | 123-99-9 | 25G | ₹5080 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 8.20116 | Azelaic acid, technical grade for synthesis | 123-99-9 | 1KG | ₹7850 | 2022-06-14 | Buy |
Azelaic acid Chemical Properties,Uses,Production
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.
Chemical Properties
Azelaic acid is an organic compound with the formula (CH2)7(CO2H)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.
Uses
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.
Production Methods
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.
Preparation
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.
General Description
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.
Safety Profile
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.
Purification Methods
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.]
Azelaic acid Preparation Products And Raw materials
Raw materials
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chevron_right| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| Anant Pharmaceuticals Pvt Ltd | +91-8550986868 +91-9485998001 | Haryana, India | 461 | 58 | Inquiry |
| SEUTIC | +91-8309787199 +91-8309787199 | Hyderabad, India | 124 | 58 | Inquiry |
| Vadivarhe Speciality Chemicals Limited | +91-9028832204 +91-9028832204 | Maharashtra, India | 38 | 58 | Inquiry |
| GLP Pharma Standards | +91 9866074638 | Hyderabad, India | 1644 | 58 | Inquiry |
| Cefa-Cilinas Biotics Pvt Ltd | +91-7875033155 +91-8080701561 | Maharashtra, India | 121 | 58 | Inquiry |
| JSK Chemicals | +919879767970 | Gujarat, India | 3756 | 58 | Inquiry |
| Glenmark Pharmaceuticals Limited | +912240189999 | Maharashtra, India | 93 | 58 | Inquiry |
| Synergene Active Ingredients Pvt. Ltd. | +91-04023700774 +91-04023700774 | Telangana, India | 96 | 58 | Inquiry |
| BDR Pharmaceuticals International Pvt Ltd | +91-2240560560 +91-7718884418 | Maharashtra, India | 206 | 58 | Inquiry |
| Alfa Aesar | 1 800 209 7001 | Maharashtra, India | 6913 | 58 | Inquiry |
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Related Qustion
- Q:What does Azelaic acid do for the skin?
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