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Azelaic Acid 123-99-9 Azelaic Acid
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 |
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. |
CAS:
123-99-9
MF:
C9H16O4
MW:
188.22
EINECS:
204-669-1
MDL No.:
MFCD00004432
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
pka
4.53, 5.33(at 25℃)
form
Slightly Crystalline Powder or Flakes
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℃
Xi'an Eastling biotech Co., Ltd. is dedicated to the research and development, production, and sales of natural plant extracts; With nearly 15 years of experience in identifying, researching, developing, and producing active ingredients for medicinal plants, we focus on providing innovative products and services to customers in industries such as pharmaceuticals, health food, and cosmetics.
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