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Azelaic acid supplier in China
Cas No: 123-99-9
USD $ 2356.0-2356.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
High Purity Azelaic acid /ninandioic acid CAS 123-99-9
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Azelaic acid, Nonanedioic Acid, CAS:123-99-9
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Azelaic acid
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Azelaic acid
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123-99-9 Usage

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.

Chemical Properties

white to cream solid

Chemical Properties

Nonanedioic acid is the best known dicarboxylic acid. Its name stems from the action of nitric acid (azote, nitrogen, or azotic, nitric) oxidation of oleic or elaidic acid. It was detected among products of rancid fats. Its origin explains for its presence in poorly preserved samples of linseed oil and in specimens of ointment removed from Egyptian tombs 5000 years old. 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. Azelaic acid is used, as simple esters or branched-chain esters) in the manufacture of plasticizers (for vinyl chloride resins, rubber), lubricants and greases. Azelaic acid is now used in cosmetics (treatment of acne). It displays bacteriostatic and bactericidal properties against a variety of aerobic and anaerobic micro-organisms present on acne-bearing skin. 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.

Originator

Schering AG (W. Germany)

Uses

antiacne, antiproliferative agent

Uses

antifungal, binds to membrane sterols

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.

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.

Application

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 Azelaic acid is used to treat mild to moderate acne, both comedonal acne and inflammatory acne . It belongs to a class of medication called dicarboxylic acids. It works by killing acne bacteria that infect skin pores. It 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 . It clears the bumps and swelling caused by Rosacea. Azelaic acid has been used for treatment of skin pigmentation including melasma and post inflammatory hyper pigmentation , particularly in those with darker skin types. It has been recommended as an alternative to hydroquinone (HQ). As a tyrosinase inhibitor, azelaic acid reduces synthesis of melanin. Brand names AzClear Action ( 20 % lotion, Ego Pharmaceuticals), Azelex (20% cream, Allergan), White Action cream (20 % cream ,2 % glycolic acid), SynCare), Finacea (15 % gel, Intendis/Berlex Laboratories, subsidiaries of Bayer AG), Finevin (20 % cream, Intendis / Berlex Laboratories), Skinoren (20 % cream or 15% gel, Intendis), Melazepam, Strata Dermatologics, 2oz, Mixed Dicarboxylic Acids 20 % Azelaic Acid Cream.,and Azaclear (azelaic acid and niacinamide, Epikinetics LLC). .

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:

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. It 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 it. 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).

Brand name

Azelex (Allergan); Finacea (Intendis);Skinoren.

Therapeutic Function

Antiacne, Depigmentor

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 4846, 1955 DOI: 10.1021/ja01623a048Organic Syntheses, Coll. Vol. 2, p. 53, 1943

General Description

Azelaic acid is used as a therapeutic agent in dermatology.

Biochem/physiol Actions

Azelaic acid is a potent inhibitor of 5α-reductase activity. It is a reversible competitive inhibitor of thioredoxin reductase in human melanoma cells.

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.

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.

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.]

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.

Chemical Properties

white to cream solid

Chemical Properties

Nonanedioic acid is the best known dicarboxylic acid. Its name stems from the action of nitric acid (azote, nitrogen, or azotic, nitric) oxidation of oleic or elaidic acid. It was detected among products of rancid fats. Its origin explains for its presence in poorly preserved samples of linseed oil and in specimens of ointment removed from Egyptian tombs 5000 years old. 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. Azelaic acid is used, as simple esters or branched-chain esters) in the manufacture of plasticizers (for vinyl chloride resins, rubber), lubricants and greases. Azelaic acid is now used in cosmetics (treatment of acne). It displays bacteriostatic and bactericidal properties against a variety of aerobic and anaerobic micro-organisms present on acne-bearing skin. 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.

Originator

Schering AG (W. Germany)

Uses

antiacne, antiproliferative agent

Uses

antifungal, binds to membrane sterols

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.

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.

Application

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 Azelaic acid is used to treat mild to moderate acne, both comedonal acne and inflammatory acne . It belongs to a class of medication called dicarboxylic acids. It works by killing acne bacteria that infect skin pores. It 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 . It clears the bumps and swelling caused by Rosacea. Azelaic acid has been used for treatment of skin pigmentation including melasma and post inflammatory hyper pigmentation , particularly in those with darker skin types. It has been recommended as an alternative to hydroquinone (HQ). As a tyrosinase inhibitor, azelaic acid reduces synthesis of melanin. Brand names AzClear Action ( 20 % lotion, Ego Pharmaceuticals), Azelex (20% cream, Allergan), White Action cream (20 % cream ,2 % glycolic acid), SynCare), Finacea (15 % gel, Intendis/Berlex Laboratories, subsidiaries of Bayer AG), Finevin (20 % cream, Intendis / Berlex Laboratories), Skinoren (20 % cream or 15% gel, Intendis), Melazepam, Strata Dermatologics, 2oz, Mixed Dicarboxylic Acids 20 % Azelaic Acid Cream.,and Azaclear (azelaic acid and niacinamide, Epikinetics LLC). .

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:

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. It 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 it. 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).

Brand name

Azelex (Allergan); Finacea (Intendis);Skinoren.

Therapeutic Function

Antiacne, Depigmentor

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 4846, 1955 DOI: 10.1021/ja01623a048Organic Syntheses, Coll. Vol. 2, p. 53, 1943

General Description

Azelaic acid is used as a therapeutic agent in dermatology.

Biochem/physiol Actions

Azelaic acid is a potent inhibitor of 5α-reductase activity. It is a reversible competitive inhibitor of thioredoxin reductase in human melanoma cells.

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.

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.

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.]
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

123-99-9 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (42587)  Azelaic acid, 96%    123-99-9 25g 124.0CNY Detail
Alfa Aesar (42587)  Azelaic acid, 96%    123-99-9 100g 331.0CNY Detail
Alfa Aesar (42587)  Azelaic acid, 96%    123-99-9 500g 1335.0CNY Detail
Alfa Aesar (36308)  Azelaic acid, 98%    123-99-9 25g 158.0CNY Detail
Alfa Aesar (36308)  Azelaic acid, 98%    123-99-9 100g 406.0CNY Detail
Alfa Aesar (36308)  Azelaic acid, 98%    123-99-9 *5x100g 1537.0CNY Detail
Alfa Aesar (A17271)  Azelaic acid, tech. 80%    123-99-9 500g 243.0CNY Detail
Alfa Aesar (A17271)  Azelaic acid, tech. 80%    123-99-9 2500g 911.0CNY Detail
Sigma-Aldrich (95054)  Azelaicacid  analytical standard 123-99-9 95054-100MG 458.64CNY Detail
Aldrich (246379)  Azelaicacid  98% 123-99-9 246379-25G 307.71CNY Detail
Aldrich (246379)  Azelaicacid  98% 123-99-9 246379-100G 1,411.02CNY Detail

123-99-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Azelaic acid

1.2 Other means of identification

Product number -
Other names nonanedioic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:123-99-9 SDS

123-99-9Synthetic route

cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

azelaic acid
123-99-9

azelaic acid

Conditions
ConditionsYield
With phosphotungstic acid; potassium permanganate; N-benzyl-N,N,N-triethylammonium chloride; dihydrogen peroxide; oxygen at 95℃; for 8h; Reagent/catalyst; Concentration; Temperature;99.23%
With potassium permanganate80%
With oleate hydratase from S. maltophilia In aq. buffer at 35℃; for 2h; pH=8; Enzymatic reaction;21%
Dihydroxystearic Acid
120-87-6

Dihydroxystearic Acid

A

azelaic acid
123-99-9

azelaic acid

B

nonanoic acid
112-05-0

nonanoic acid

Conditions
ConditionsYield
With 1 wt% Au/Al2O3; oxygen; sodium hydroxide In water at 80℃; under 3750.38 Torr; for 4.33333h; Autoclave; Inert atmosphere;A 86%
B 99%
With copper(II) ferrite; oxygen In neat (no solvent) at 80℃; under 18751.9 Torr; for 5h; Reagent/catalyst; Temperature; Pressure; Autoclave;A 57.24%
B 46.65%
With sodium stannate; dihydrogen peroxide; tungsten(VI) oxide In water; tert-butyl alcohol at 130℃; for 4h; Sealed tube;
Elaidic Acid
112-79-8

Elaidic Acid

A

azelaic acid
123-99-9

azelaic acid

B

nonanoic acid
112-05-0

nonanoic acid

Conditions
ConditionsYield
With sodium periodate; RuCl3*2.9H2O In water at 20℃; for 8h; Sonication;A 62%
B 98%
With dihydrogen peroxide In tert-butyl alcohol at 85℃; for 3.5h; Catalytic behavior; Reagent/catalyst;
cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

A

azelaic acid
123-99-9

azelaic acid

B

nonanoic acid
112-05-0

nonanoic acid

Conditions
ConditionsYield
With potassium permanganate; sodium hydroxide In water at 50℃; for 8h; Reagent/catalyst; Temperature;A 96%
B 81%
With oxygen; ozone In water; acetone at 0℃; for 0.333333h; Reagent/catalyst; Solvent; Temperature; Flow reactor;A 89%
B 74%
With cetylpyridinium peroxotungstophosphate; dihydrogen peroxide In water at 80℃; for 1h;A 86%
B 82%
dec-9-enoic acid
14436-32-9

dec-9-enoic acid

azelaic acid
123-99-9

azelaic acid

Conditions
ConditionsYield
With sodium periodate; RuCl3*2.9H2O In water at 20℃; for 0.5h; Sonication;96%
With dihydrogen peroxide; cetyltrimethylammonim bromide; ortho-tungstic acid at 50 - 77℃; Inert atmosphere;76%
9-hydroxynonanoic acid
3788-56-5

9-hydroxynonanoic acid

azelaic acid
123-99-9

azelaic acid

Conditions
ConditionsYield
With sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In water; acetonitrile at 20℃; for 8h; Reagent/catalyst; Solvent; Temperature;94%
1,3-Dioxa-cyclododecane-4,12-dione

1,3-Dioxa-cyclododecane-4,12-dione

A

azelaic acid
123-99-9

azelaic acid

B

1,9-Nonanediol
3937-56-2

1,9-Nonanediol

C

9-hydroxynonanoic acid
3788-56-5

9-hydroxynonanoic acid

Conditions
ConditionsYield
With sodium tetrahydroborate In tetrahydrofuran at 23℃; for 120h;A n/a
B 2%
C 92%
With sodium tetrahydroborate In tetrahydrofuran at 65℃; for 6h;A n/a
B 6%
C 87%
8-cyano-octanoic acid
37056-34-1

8-cyano-octanoic acid

azelaic acid
123-99-9

azelaic acid

Conditions
ConditionsYield
With sulfuric acid at 100℃; for 6h;90%
With sulfuric acid at 100℃; for 6h;90%
In anhydrous ethylene glycol dimethyl ether
In sulfuric acid
nonanedinitrile
1675-69-0

nonanedinitrile

azelaic acid
123-99-9

azelaic acid

Conditions
ConditionsYield
With water for 48h; Rhodococcus rhodochrous AJ270;88%
With potassium phosphate buffer; Rhodococcus sp. AJ270 at 30℃; for 48h;88%
concentrated H2 SO4

concentrated H2 SO4

cyclohexanone-2-propionitrile
4594-78-9

cyclohexanone-2-propionitrile

3-(2-oxocyclohexyl)propionic acid
2275-26-5

3-(2-oxocyclohexyl)propionic acid

dihydrogen peroxide
7722-84-1

dihydrogen peroxide

azelaic acid
123-99-9

azelaic acid

Conditions
ConditionsYield
With hydrogenchloride; acetic acid In methanol88%
Conditions
ConditionsYield
With phosphotungstic acid; dihydrogen peroxide; cetylpyridinium bromide In water at 85℃; for 5h; Green chemistry;A 86.5%
B 87.3%
With tungstophosphoric acid *15.4 H2O; cetylpyridinium chloride; dihydrogen peroxide In water at 85℃; for 5h;
With sodium stannate; dihydrogen peroxide; tungsten(VI) oxide In water; tert-butyl alcohol at 130℃; for 4h; Sealed tube;
Elaidic acid
112-79-8

Elaidic acid

A

azelaic acid
123-99-9

azelaic acid

B

nonanoic acid
112-05-0

nonanoic acid

Conditions
ConditionsYield
With oxygen; ozone In water; acetone at 0℃; Flow reactor;A 87%
B 76%
With dihydrogen peroxide; methyltrioctylammonium tetrakis(oxodiperoxotungsto)phos In water at 85℃; for 5h;A 79 % Chromat.
B 82 % Chromat.
C9H12O6

C9H12O6

azelaic acid
123-99-9

azelaic acid

Conditions
ConditionsYield
With hydrogen In water at 200℃; under 15001.5 Torr; for 12h;86%
1-hepten-3-ol
4938-52-7

1-hepten-3-ol

carbon monoxide
201230-82-2

carbon monoxide

azelaic acid
123-99-9

azelaic acid

Conditions
ConditionsYield
With HeMaRaphos; water; toluene-4-sulfonic acid; palladium dichloride In tetrahydrofuran at 125℃; under 30003 Torr; for 24h; Autoclave; Green chemistry; regioselective reaction;86%
Ricinoleic acid
141-22-0

Ricinoleic acid

A

azelaic acid
123-99-9

azelaic acid

Conditions
ConditionsYield
With oxygen; ozone In water; acetone at 0℃; Flow reactor;A 86%
B 70%
(Z)-12-hydroxyoctadec-9-enoic acid
81212-19-3

(Z)-12-hydroxyoctadec-9-enoic acid

A

azelaic acid
123-99-9

azelaic acid

C

12-hydroxy-9,10-epoxyoctadecanoic acid
47244-76-8, 118201-32-4

12-hydroxy-9,10-epoxyoctadecanoic acid

Conditions
ConditionsYield
With cetylpyridinium peroxotungstophosphate; dihydrogen peroxide In water at 80℃; for 1h;A 84%
B 84%
C 4%
cis-9-hexadecenoic acid
373-49-9

cis-9-hexadecenoic acid

A

azelaic acid
123-99-9

azelaic acid

B

oenanthic acid
111-14-8

oenanthic acid

Conditions
ConditionsYield
With ozone In water; acetonitrile at 0℃;A 84%
B 83%
Ricinoleic acid
141-22-0

Ricinoleic acid

A

azelaic acid
123-99-9

azelaic acid

B

(R)-3-hydroxynonanoic acid
33796-87-1

(R)-3-hydroxynonanoic acid

Conditions
ConditionsYield
With phosphotungstic acid; dihydrogen peroxide; cetylpyridinium bromide In water at 85℃; for 5h; Green chemistry;A 83.2%
B 60.8%
With tungstophosphoric acid *15.4 H2O; cetylpyridinium chloride; dihydrogen peroxide In water at 85℃; for 5h;
9-dodecenoic acid
2382-40-3

9-dodecenoic acid

azelaic acid
123-99-9

azelaic acid

Conditions
ConditionsYield
With dihydrogen peroxide; cetyltrimethylammonim bromide; ortho-tungstic acid In water at 50 - 77℃; for 16h; Inert atmosphere;79%
cis-9-hexadecenoic acid
373-49-9

cis-9-hexadecenoic acid

azelaic acid
123-99-9

azelaic acid

Conditions
ConditionsYield
With sodium periodate; ruthenium trichloride In water; ethyl acetate; acetonitrile for 2h;75%
cyclooct-4-enecarboxaldehyde
19835-69-9

cyclooct-4-enecarboxaldehyde

azelaic acid
123-99-9

azelaic acid

Conditions
ConditionsYield
With sodium hydroxide In water at 330 - 350℃; for 6h; autoclave;73.5%
methyl 10-acetoxy-9-oxodecanoate
101171-32-8

methyl 10-acetoxy-9-oxodecanoate

azelaic acid
123-99-9

azelaic acid

Conditions
ConditionsYield
With oxygen; sodium t-butanolate In diethyl ether; water for 4h; Ambient temperature;70%
hydrous cobalt chloride

hydrous cobalt chloride

H2 WO4

H2 WO4

linoleic acid
60-33-3

linoleic acid

dihydrogen peroxide
7722-84-1

dihydrogen peroxide

azelaic acid
123-99-9

azelaic acid

Conditions
ConditionsYield
In water70%
cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

A

azelaic acid
123-99-9

azelaic acid

B

N-hydroxynonan-1-imine
2243-24-5

N-hydroxynonan-1-imine

C

nonanoic acid
112-05-0

nonanoic acid

D

9-(hydroxyimino)nonanoic acid

9-(hydroxyimino)nonanoic acid

Conditions
ConditionsYield
Stage #1: cis-Octadecenoic acid With oxygen; ozone at 0 - 20℃;
Stage #2: With hydroxylamine hydrochloride In methanol at 0℃; Solvent; Reagent/catalyst;
A 66%
B 45%
C 46%
D 26%
hept-2-en-1-ol
22104-77-4

hept-2-en-1-ol

carbon monoxide
201230-82-2

carbon monoxide

azelaic acid
123-99-9

azelaic acid

Conditions
ConditionsYield
With HeMaRaphos; water; toluene-4-sulfonic acid; palladium dichloride In tetrahydrofuran at 125℃; under 30003 Torr; for 24h; Autoclave; Green chemistry; regioselective reaction;65%
9,10-dihydroxyoctadecane-1,18-dioic acid
137-21-3

9,10-dihydroxyoctadecane-1,18-dioic acid

azelaic acid
123-99-9

azelaic acid

Conditions
ConditionsYield
With sodium hypochlorite at 20℃; for 5h; Reagent/catalyst;50%
heptane-1,1,7,7-tetracarboxylic acid

heptane-1,1,7,7-tetracarboxylic acid

azelaic acid
123-99-9

azelaic acid

Conditions
ConditionsYield
With methanesulfonic acid In water at 125℃; for 4h; Inert atmosphere;40%
at 120 - 130℃; for 16h; Temperature;11 g
With trimethylamine In toluene for 12h; Dean-Stark; Inert atmosphere; Reflux; Industrial scale;3406 kg
methanol
67-56-1

methanol

azelaic acid
123-99-9

azelaic acid

Dimethyl azelate
1732-10-1

Dimethyl azelate

Conditions
ConditionsYield
With boron trifluoride at 65℃; for 0.333333h;100%
With sulfuric acid In dichloromethane Dean-Stark; Heating;95%
With sulfuric acid80%
azelaic acid
123-99-9

azelaic acid

azelaoyl chloride
123-98-8

azelaoyl chloride

Conditions
ConditionsYield
With thionyl chloride at 80℃; for 36h; Inert atmosphere;100%
With thionyl chloride at 80℃; for 24h;96%
With thionyl chloride at 20℃;96%
azelaic acid
123-99-9

azelaic acid

vinyl propionate
105-38-4

vinyl propionate

azelaic acid divinyl ester
10355-49-4

azelaic acid divinyl ester

Conditions
ConditionsYield
With sulfuric acid; mercury(II) diacetate at 20 - 50℃; for 4h;100%
azelaic acid
123-99-9

azelaic acid

C9H14O4(2-)*Mg(2+)*3H2O

C9H14O4(2-)*Mg(2+)*3H2O

Conditions
ConditionsYield
With magnesium hydroxide; water for 0.583333h; Milling;100%
azelaic acid
123-99-9

azelaic acid

[K2(H2AZE)(AZE)]

[K2(H2AZE)(AZE)]

Conditions
ConditionsYield
With water; potassium hydroxide for 0.166667h; Milling;100%
azelaic acid
123-99-9

azelaic acid

C9H14O4(2-)*2Na(1+)*H2O

C9H14O4(2-)*2Na(1+)*H2O

Conditions
ConditionsYield
With water; sodium hydroxide for 0.166667h; Milling;100%
azelaic acid
123-99-9

azelaic acid

C9H14O4(2-)*Mg(2+)*3H2O

C9H14O4(2-)*Mg(2+)*3H2O

Conditions
ConditionsYield
With magnesium hydroxide; water for 0.25h; Milling;100%
azelaic acid
123-99-9

azelaic acid

2-Ethylhexyl alcohol
104-76-7

2-Ethylhexyl alcohol

bis(2-ethylhexyl) azelaate
103-24-2

bis(2-ethylhexyl) azelaate

Conditions
ConditionsYield
With [HSO3-pmim]+[HSO4]-catalyst for 0.333333h; Reagent/catalyst; Microwave irradiation;99.1%
In 5,5-dimethyl-1,3-cyclohexadiene at 160℃; for 2h;94%
azelaic acid
123-99-9

azelaic acid

1,1'-bis(4-pyridinyl)ferrocene
459142-93-9

1,1'-bis(4-pyridinyl)ferrocene

[(Fe(η5-C5H4-1-(4-C5H4N))2)2(1-azelaic acid)2]

[(Fe(η5-C5H4-1-(4-C5H4N))2)2(1-azelaic acid)2]

Conditions
ConditionsYield
In methanol 1:1 mixt. ground for 5 min, dissolved in methanol; crystd.;99%
azelaic acid
123-99-9

azelaic acid

dibromoazelaic acid
3479-83-2

dibromoazelaic acid

Conditions
ConditionsYield
With bromine; phosphorus tribromide at 80℃; for 8h; Temperature; Time;98%
methanol
67-56-1

methanol

azelaic acid
123-99-9

azelaic acid

α,α'-dibromoazelaiate de dimethyle
18281-62-4

α,α'-dibromoazelaiate de dimethyle

Conditions
ConditionsYield
Stage #1: azelaic acid With thionyl chloride at 75℃; for 1.5h; Sealed tube;
Stage #2: With bromine for 12h; Irradiation;
Stage #3: methanol for 1.5h; Cooling with ice;
98%
(i) SOCl2, (ii) Br2, I2, (iii) /BRN= 1098229/; Multistep reaction;
(i) SOCl2, (ii) Br2, (iii) /BRN= 1098229/; Multistep reaction;
azelaic acid
123-99-9

azelaic acid

1,10-Decanediol
112-47-0

1,10-Decanediol

poly(decamethylene azelate), degree of polymerization > 200, Mn=2.69E4, Mw=5.83E4; monomers: azelaic acid; 1,10-decanediol

poly(decamethylene azelate), degree of polymerization > 200, Mn=2.69E4, Mw=5.83E4; monomers: azelaic acid; 1,10-decanediol

Conditions
ConditionsYield
tetrachlorobis(tetrahydrofuran)hafnium(IV) In o-xylene for 24h; Heating;97%
azelaic acid
123-99-9

azelaic acid

1,10-Decanediol
112-47-0

1,10-Decanediol

Reaxys ID: 11364959

Reaxys ID: 11364959

Conditions
ConditionsYield
With molecular sevies 4A; tetrachlorobis(tetrahydrofuran)hafnium(IV) In o-xylene for 24h; Heating / reflux;97%
With molecular sevies 4A; tetrachlorobis(tetrahydrofuran)hafnium(IV) In o-xylene for 24h; Heating / reflux;96%
azelaic acid
123-99-9

azelaic acid

lead(II) acetate trihydrate
6080-56-4

lead(II) acetate trihydrate

Conditions
ConditionsYield
In water High Pressure; placed in a bomb, heated to 220°C (3 h), held for 3 h; cooled to room temp. (3 h), crysts., washed (water), air dried; elem. anal.;96%
azelaic acid
123-99-9

azelaic acid

1,7-heptandiol
629-30-1

1,7-heptandiol

1,9-dioxacyclooctadecane-10,18-dione
660-63-9

1,9-dioxacyclooctadecane-10,18-dione

Conditions
ConditionsYield
With hafnium(IV) trifluoromethanesulfonate In toluene at 110℃; for 48h; Inert atmosphere;96%
azelaic acid
123-99-9

azelaic acid

n-butyl formate
592-84-7

n-butyl formate

Nonanedioic acid monobutyl ester
4753-32-6

Nonanedioic acid monobutyl ester

Conditions
ConditionsYield
With DOWEX 50W-X2 In Petroleum ether for 4.5h; Heating;95%
azelaic acid
123-99-9

azelaic acid

1-Chloropropane
540-54-5

1-Chloropropane

dipropyl azelate
6624-68-6

dipropyl azelate

Conditions
ConditionsYield
With sodium hydrogencarbonate In propan-1-ol at 40℃; for 1.5h;95%
azelaic acid
123-99-9

azelaic acid

L-arginine
74-79-3

L-arginine

germanium dioxide

germanium dioxide

C21H40GeN8O8

C21H40GeN8O8

Conditions
ConditionsYield
Stage #1: L-arginine; germanium dioxide In water at 85 - 95℃; for 1h;
Stage #2: azelaic acid In water for 2h;
95%
azelaic acid
123-99-9

azelaic acid

C15H16O4

C15H16O4

C39H44O10

C39H44O10

Conditions
ConditionsYield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane95%
azelaic acid
123-99-9

azelaic acid

1,2-dimethoxybenzene
91-16-7

1,2-dimethoxybenzene

1,7-bis(3,4-dimethoxyphenyl)heptane-1,7-dione
32246-69-8

1,7-bis(3,4-dimethoxyphenyl)heptane-1,7-dione

Conditions
ConditionsYield
Stage #1: azelaic acid With thionyl chloride In dichloromethane for 4.5h; Reflux;
Stage #2: 1,2-dimethoxybenzene With aluminum (III) chloride In dichloromethane at 0℃; for 5h; Friedel-Crafts Acylation;
95%
azelaic acid
123-99-9

azelaic acid

diphenylamine
122-39-4

diphenylamine

1,7-bis(9-acridinyl)heptane

1,7-bis(9-acridinyl)heptane

Conditions
ConditionsYield
With toluene-4-sulfonic acid In 1-methyl-pyrrolidin-2-one at 170 - 230℃; for 18h; Temperature;95%
azelaic acid
123-99-9

azelaic acid

tetramethyl ammoniumhydroxide
75-59-2

tetramethyl ammoniumhydroxide

bis(tetramethylammonium) azelate

bis(tetramethylammonium) azelate

Conditions
ConditionsYield
In methanol at 21℃; for 48h;94%
azelaic acid
123-99-9

azelaic acid

sulfanilamide
63-74-1

sulfanilamide

C21H28N4O6S2
123351-07-5

C21H28N4O6S2

Conditions
ConditionsYield
With sulfuric acid at 30 - 40℃; for 0.5h;93%
methanol
67-56-1

methanol

azelaic acid
123-99-9

azelaic acid

azelaic monomethyl ester
2104-19-0

azelaic monomethyl ester

Conditions
ConditionsYield
With sulfuric acid92%

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