Azalaic Acid
Azelaic acid
CAS: 123-99-9
Molecular Formula: C9H16O4
Azalaic Acid - Names and Identifiers
| Name | Azelaic acid |
| Synonyms | emerox1144 emerox1110 Emerox 1144 Emerox 1110 Azelaic acid Azalaic Acid nonanedioate Emery's L-110 Azelainic acid ninandioic acid Azelaicacidtech Nonanedioic acid azelaicacid,technicalgrade Heptane-1,7-dicarboxylic acid |
| CAS | 123-99-9 |
| EINECS | 204-669-1 |
| InChI | InChI=1/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13)/p-2 |
| InChIKey | BDJRBEYXGGNYIS-UHFFFAOYSA-N |
Azalaic Acid - Physico-chemical Properties
| Molecular Formula | C9H16O4 |
| Molar Mass | 188.22 |
| Density | 1,029 g/cm3 |
| Melting Point | 98 °C |
| Boling Point | 286°C100mm Hg(lit.) |
| Flash Point | 215 °C |
| Water Solubility | 2.4 g/L (20 ºC) |
| Solubility | Soluble in boiling water and ethanol, soluble in organic solvents, slightly soluble in benzene. |
| Vapor Presure | <1 mm Hg ( 20 °C) |
| Vapor Density | 6.5 (vs air) |
| Appearance | White flakes |
| Color | White to slightly yellow |
| Merck | 14,905 |
| BRN | 1101094 |
| pKa | 4.53, 5.33(at 25℃) |
| PH | 3.5 (1g/l, H2O) |
| Storage Condition | Store below +30°C. |
| Stability | Stable. Combustible. Incompatible with bases, strong oxidizing agents. Readily biodegrades in soil and water with >70% DOC reduction after 28 days. |
| Sensitive | Easily absorbing moisture |
| Refractive Index | 1.4303 |
| MDL | MFCD00004432 |
| Physical and Chemical Properties | Melting point 98-103°C boiling point 286 ° C (100 mmHg) flash point 215°C water-soluble 2.4g/L (20°C) |
| Use | Used as a raw material for the production of plasticizer dioctyl nonanediate and perfume, lubricating oil, oil agent, polyamide resin |
Azalaic Acid - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S24/25 - Avoid contact with skin and eyes. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| WGK Germany | 1 |
| RTECS | CM1980000 |
| TSCA | Yes |
| HS Code | 29171390 |
| Toxicity | LD50 orally in Rabbit: > 4000 mg/kg LD50 dermal Rat > 10 g/kg |
Azalaic Acid - Reference
| Reference Show more | 1. Xie Xiongxiong, Xie Jing, Zeng Jinxiang, Zhang Chenhui, Li Min, Liang Jian, Zhu Jixiao, Zhong Guoyue, Luo Guangming, Yao Pengcheng, Gui Yaqi. Studies on Migration Components in Blood of Tibetan Medicine Short-tube Ear Grass and Their Docking with XOD Molecules [J]. Journal of Jiangxi University of Traditional Chinese Medicine, 2020,32(05):71-76 115. 2. Chau, Siu-Leung, et al. "Comprehensive quantitative analysis of SQ injection using multiple chromatographic technologies." Molecules 21.8 (2016): 1092.https://doi.org/10.3390/molecules21081092 3. [IF = 4.411] Siu-Leung Chau et al. "Comprehensive Quantitative Analysis of SQ Injection Using Multiple Chromatographic Technologies." Molecules. 2016 Aug;21(8): 1092 4. [IF = 3.935] Yi Tao et al. "Towards the identification of alkaline phosphatase binding ligands in Li-Dan-Hua-Shi pills: A Box-Behnken design optimized affinity selection approach tandem with UHPLC-Q-TOF/MS analysis." J Pharmaceut Biomed. 2018 May;154:486 5. [IF = 4.24] Mingxia Wu et al. "Inhibitory effects of acorn (Quercus variabilis Blume) kernel-derived polyphenols on the activities of α-amylase, α-glucosidase, and dipeptidyl peptidase IV." Food Biosci. 2021 Oct;43:101224 |
Azalaic Acid - Introduction
The anhydride is partially formed during distillation above 360°C. It's irritating.
Last Update：2022-10-16 17:12:54
Azalaic Acid - Reference Information
| LogP | 1.57 at 25℃ |
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| overview | azelaic acid is a skin disease prevention and treatment drug, mainly used to treat acne, chloasma and skin melanin deposition. It is also an important organic synthesis intermediate, used in plastics, rubber and other industries to synthesize plasticizers, in aviation oil for the synthesis of low-temperature high-speed lubricating oil, electrolytic capacitor manufacturing and other aspects of important applications. Using unsaturated fatty acids such as oleic acid and corresponding triglycerides such as castor oil and cotton seed oil to prepare azelaic acid is the main production method at present. |
| pharmacological action | azelaic acid can inhibit or kill anaerobic bacteria and aerobic bacteria in skin. In vivo tests show that topical application of azelaic acid cream for 2-3 months can significantly reduce the number of skin bacteria and propionibacterium in hair follicles, indicating that this product has direct antibacterial effect. In addition, topical application of azelaic acid can reduce the composition of free fatty acids and lipids on the skin surface. It shows anti-keratinization effect on the skin of normal people or acne patients. Its principle of action is mainly due to reducing the synthesis of filamentous keratin, thereby reducing hyperkeratosis of hair follicles. Azelaic acid selectively acts on abnormal melanocytes and inhibits their excessive activity. Therefore, topical application of azelaic acid for a long time can reduce the production of skin melanin in patients with senile plaque. But this product has no depigmentation effect on the pigment of normal skin. Azelaic acid also has anti-cell proliferation and anti-cytotoxic effects. Its principle of action is mainly through the destruction of mitochondrial respiratory pathway and cell DNA synthesis. |
| indications | for melanosis, chloasma, malignant nevus, melanoma, sunburn, etc. It has a good effect on acne vulgaris, and it is also effective on rosacea and seborrheic dermatitis. |
| Preparation | A method for preparing azelaic acid catalyzed by solid acid, characterized in that it has the following process and steps: unsaturated fatty acids or mixed fatty acids produced by hydrolysis of animal and vegetable oils, solid acid catalyst, and hexyltrimethyl ammonium chloride are mixed, stirred and heated to 50-70°C, A mixed gas with an ozone concentration of 2-10g/L is introduced at a flow rate of 500 ml/min, a hydrogen peroxide solution with a weight percentage of 20-40% is added in batches, and the reaction temperature is controlled to not exceed 70 ℃; after the raw materials are added, the temperature is raised to 95 ℃ ~ 110 ℃ for 5-12 hours; after the reaction, the reaction mixture is placed in a separatory funnel to separate the solid acid catalyst layer, oil layer and water layer; the water layer is refrigerated and crystallized at 3°C, and white azelaic acid is precipitated, filtered, and dried; the oil layer is extracted with boiling water and then refrigerated and crystallized at 3°C, and azelaic acid is also obtained after suction filtration; the azelaic acid is combined After recrystallization with hot water, purified azelaic acid is obtained; the amount of the solid acid catalyst is 5-20% of the weight of unsaturated fatty acids or mixed fatty acids; the amount of hydrogen peroxide solution is 2-5 times the volume of unsaturated fatty acid or mixed fatty acid; the amount of decyltrimethylammonium chloride is 1%-5% of the weight of unsaturated fatty acid or mixed fatty acid. |
| use | most azelaic acid is used to produce dioctyl azelate (DOZ) plasticizer, and other uses are used as raw materials for perfume, lubricating oil, oil and polyamide resin. DOZ is used for cold resistance and plasticity of cables, films, artificial leather, etc., with low volatility and aging resistance. DOZ can also be used as a softener for synthetic rubber. The azelaic acid used in the production of DOZ in Japan accounts for about 70% of the total consumption of azelaic acid. Azelaic acid is dehydrated by ammonia, and nondinitrile can be produced. Azelaic acid can be used as a reagent and also used in organic synthesis. For example, it can be used as a raw material for the production of plasticizer dioctyl azelate and perfumes, lubricants, oils, and polyamide resins. In addition, azelaic acid is widely used in medicine and cosmetics. |
| production method | is obtained by oxidation of oleic acid by nitric acid or ozone. It can also be obtained by cracking industrial castor as a raw material. 1, 5-dibromopentane is condensed with acetonitrile, or azelaic acid can be prepared from dimethyl azelaic by ketone dimethyl azelic acid using monomethyl methyl glutarate as raw material. |
| category | flammable liquid |
| toxicity classification | low toxicity |
| acute toxicity | oral-rat LD50:>5000 mg/kg |
| stimulation data | skin-rabbit 500 mg/24 hours mild; Eye-rabbit 3 mg mild |
| Explosive hazard characteristics | Intense reaction with oxidant |
| flammability hazard characteristics | open flame burns when heated; combustion produces stimulating smoke |
| storage and transportation characteristics | ventilation and low temperature drying; separate from oxidant |
| fire extinguishing agent | dry powder, foam, sand, carbon dioxide, mist water |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:29:15
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