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Nonanedioic acid (Azelaic Acid) is an alpha,omega-dicarboxylic acid that is heptane substituted at positions 1 and 7 by carboxy groups.
Nonanedioic acid (Azelaic Acid) has a role as an antibacterial agent, an antineoplastic agent, a dermatologic drug and a plant metabolite.
Nonanedioic acid (Azelaic Acid) is a dicarboxylic fatty acid and an alpha,omega-dicarboxylic acid.
CAS: 123-99-9
MF: C9H16O4
MW: 188.22
EINECS: 204-669-1
Synonyms
azelaicacid,technicalgrade;Azelainic acid;Emerox 1110;Emerox 1144;emerox1110;emerox1144;Emery's L-110;ninandioic acid
Nonanedioic acid (Azelaic Acid), formally nonanedioic acid, is a white crystalline solid with a melting point of 106.5 °C.
Nonanedioic acid (Azelaic Acid) occurs naturally in grains such as wheat, rye, and barley and is produced industrially by ozonolyzing oleic acid.
Nonanedioic acid (Azelaic Acid) is used topically to treat acne and rosacea.
Some plants release azelaic acid as a "distress flare" to signal cells to activate their defenses against attacking pathogens.
Nonanedioic acid (Azelaic Acid) is used to treat mild to moderate acne, both comedonal acne and inflammatory acne.
Nonanedioic acid (Azelaic Acid) belongs to a class of medication called dicarboxylic acids.
Nonanedioic acid (Azelaic Acid) is an alpha,omega-dicarboxylic acid that is heptane substituted at positions 1 and 7 by carboxy groups.
Nonanedioic acid (Azelaic Acid) has a role as an antibacterial agent, an antineoplastic agent, a dermatologic drug and a plant metabolite.
Nonanedioic acid (Azelaic Acid) is a dicarboxylic fatty acid and an alpha,omega-dicarboxylic acid.
Nonanedioic acid (Azelaic Acid) is a conjugate acid of an azelaate(2-) and an azelaate.
Nonanedioic acid (Azelaic Acid) is a naturally occurring saturated binary carboxylic acid containing nine carbon atoms, which is an important medium and long chain dibasic acid.
Nonanedioic acid (Azelaic Acid) has been used in cosmetics for a long time.
Nonanedioic acid (Azelaic Acid) has the function of inhibiting excessive secretion of oil, removing acne and freckles, and whitening skin, and it is very safe.
Nonanedioic acid (Azelaic Acid) is an organic compound with the formula (CH2)7(CO2H)2.
This saturated dicarboxylic acid exists as a white powder.
Nonanedioic acid (Azelaic Acid) is found in wheat, rye, and barley.
Nonanedioic acid (Azelaic Acid) Chemical Properties
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
Fp: 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 (Azelaic Acid)(123-99-9)
EPA Substance Registry System: Nonanedioic acid (Azelaic Acid) (123-99-9)
Nonanedioic acid (Azelaic Acid) is the best known dicarboxylic acid.
Nonanedioic acid (Azelaic Acid)'s name stems from the action of nitric acid (azote, nitrogen, or azotic, nitric) oxidation of oleic or elaidic acid.
Nonanedioic acid (Azelaic Acid) was detected among products of rancid fats.
Nonanedioic acid (Azelaic Acid)'s origin explains for its presence in poorly preserved samples of linseed oil and in specimens of ointment removed from Egyptian tombs 5000 years old.
Nonanedioic acid (Azelaic Acid) was prepared by oxidation of oleic acid with potassium permanganate, but now by oxidative cleavage of oleic acid with chromic acid or by ozonolysis.
Nonanedioic acid (Azelaic Acid) is used, as simple esters or branched-chain esters) in the manufacture of plasticizers (for vinyl chloride resins, rubber), lubricants and greases.
Nonanedioic acid (Azelaic Acid) is now used in cosmetics (treatment of acne).
Nonanedioic acid (Azelaic Acid) displays bacteriostatic and bactericidal properties against a variety of aerobic and anaerobic micro-organisms present on acne-bearing skin.
Nonanedioic acid (Azelaic Acid) was identified as a molecule that accumulated at elevated levels in some parts of plants and was shown to be able to enhance the resistance of plants to infections.
Uses
Nonanedioic acid (Azelaic Acid) is used in lacquers, alkyd resins, plasticizers, adhesives, polyamides, urethane elastomers, and organic syntheses.
Nonanedioic acid (Azelaic Acid) is also used in treating of acne.
Most of the sebacic acid is used to produce dioctyl sebacate (DOZ) plasticizers, and other uses are as raw materials for perfumes, lubricating oils, oils, and polyamide resins.
The Nonanedioic acid (Azelaic Acid) is dehydrated by ammonia to obtain azelonitrile.
Polymers and related materials
Esters of this dicarboxylic acid find applications in lubrication and plasticizers.
With hexamethylenediamine azelaic acid forms Nylon - 6,9, which finds specialized uses as a plastic.
Medical
Nonanedioic acid (Azelaic Acid) is used to treat mild to moderate acne, both comedonal acne and inflammatory acne.
Nonanedioic acid (Azelaic Acid) belongs to a class of medication called dicarboxylic acids.
Nonanedioic acid (Azelaic Acid) works by killing acne bacteria that infect skin pores.
Nonanedioic acid (Azelaic Acid) also decreases the production of keratin, which is a natural substance that promotes the growth of acne bacteria Azelaic acid is also used as a topical gel treatment for rosacea, due to its ability to reduce inflammation.
Nonanedioic acid (Azelaic Acid) clears the bumps and swelling caused by Rosacea.
Nonanedioic acid (Azelaic Acid) has been used for treatment of skin pigmentation including melasma and post inflammatory hyper pigmentation , particularly in those with darker skin types.
Nonanedioic acid (Azelaic Acid) has been recommended as an alternative to hydroquinone (HQ).
As a tyrosinase inhibitor, Nonanedioic acid (Azelaic Acid) reduces synthesis of melanin.
Production Methods
Nonanedioic acid (Azelaic Acid) is industrially produced by the ozonolysis of oleic acid.
The side product is nonanoic acid.
Nonanedioic acid (Azelaic Acid) 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.
Manufacturing Process
Two step oxidation of tall oil fatty acid using peroxyformic acid and nitric acid/sodium metavanadate were used to produce azelaic acid.
Step 1 (derivatization of the double bond):
A hydroxy acyloxy derivative of tall oil fatty acid (TOFA) was prepared by mixing 200 g of TOFA (63% oleic acid, 31% linoleic acid) with 500 mL of formic acid.
The resulting mixture was vigorously stirred by magnetic action.
Hydrogen peroxide solution, 180 mL of 35% by weight, was added in aliquots to the mixture throughout the course of the reaction.
A third of the total amount of peroxide solution was added at once to initiate the reaction.
The peroxyformic acid in this case was prepared in situ.
The start of the reaction was signalled by heat evolution and a dramatic color change, from pale yellow to deep rust red.
The exothermicity of the reaction required external cooling to control the temperature.
The reaction was maintained at 40°C to minimize oxygen loss through the decomposition of the peroxide.
As required, the temperature of the reaction was maintained with an external heating source.
A total reaction time of 5 to 6 hours was necessary for complete reaction.
The end of the reaction was indicated by a color change, the reaction mixture changed from rust red back to yellow.
One last aliquot of peroxide solution was added at the end of the reaction period to provide a peroxide atmosphere during the reaction work-up.
TOFA as a substrate produced a mixture of mono- and dihydroxy formoxystearic acid from the oleic and linoleic acid components, respectively.
The final product was obtained in essentially 100% yield by removing the unreacted formic acid and hydrogen peroxide as well as water.
Nonanedioic acid (Azelaic Acid) was obtained as a viscous, syrupy yellow oil that upon gas chromatographic analysis of the methyl esters of the reaction mixture gave no evidence of unreacted substrate.
Step 2 (oxidation of derivative obtained from step 1):
A 2 L three neck flask fitted with an air condenser attached to a gas scrubbing apparatus was filled with 500 mL of concentrated nitric acid (70% by weight).
The acid was stirred by magnetic action and 1 g of sodium metavanadate was added to Nonanedioic acid (Azelaic Acid).
The resulting mixture was heated slowly to 40°-50°C.
At this point a small amount of product as obtained from Step 1 was added to the acid-catalyst mixture.
Heating was continued until a sharp temperature increase accompanied by evolution of NOx gases was observed.
The reaction temperature was self-sustained with the addition of aliquots of the hydroxy formoxy ester mixture obtained from Step 1.
(External cooling may be required throughout the substrate addition period to keep the temperature within 65°-70°C).
At the end of the addition period the reaction temperature was maintained for an additional 1.5 to 2 hours, for a total reaction time of 3 hours.
The final products were obtained by quenching the reaction by adding excess water and extracting the organic layer with purified diethyl ether.
The ether extract was dried over anhydrous sodium sulfate overnight before its removal with a roto-vap apparatus.
Addition of petroleum ether (boiling range 35°- 60°C) to the product mixture caused precipitation of the diacid component.
Vacuum filtration was used to remove the solid diacids from the liquid monoacid mixture.
The latter was obtained by removing the excess petroleum ether from the resulting filtrate.
Quantitative analysis by gas chromatography of the methyl esters showed that the products to be 96% yield of diacid (66% azelaic, 30% suberic).
