123-99-9

Basic information

• Product Name: Azelaic acid
• Synonyms: 1,7-Dicarboxyheptane;azelaic;Azelaic acid, technical grade;azelaicacid,technicalgrade;Azelainic acid;Emerox 1110;Emerox 1144;emerox1110
• CAS NO: 123-99-9
• Molecular Formula: C₉H₁₆O₄
• Molecular Weight: 188.22
• EINECS: 204-669-1
• Product Categories: API intermediates;alpha,omega-Alkanedicarboxylic Acids;alpha,omega-Bifunctional Alkanes;Monofunctional & alpha,omega-Bifunctional Alkanes;Building Blocks;C9;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks;MYCOSTATIN;Food additive and acidulant;Inhibitors
• Mol File: 123-99-9.mol
• Article Data: 90

Chemical Properties

• Melting Point: 98 °C
• Boiling Point: 286 °C100 mm Hg(lit.)
• Flash Point: 215 °C
• Appearance: White to slightly yellow/Slightly Crystalline Powder or Flakes
• Density: 1,029 g/cm3
• Vapor Density: 6.5 (vs air)
• Vapor Pressure: <1 mm Hg ( 20 °C)
• Refractive Index: 1.4303
• Storage Temp.: 2-8°C
• Solubility: 2.4g/l
• PKA: 4.53, 5.33(at 25℃)
• Water Solubility: 2.4 g/L (20 ºC)
• Stability: Stable. Combustible. Incompatible with bases, strong oxidizing agents. Readily biodegrades in soil and water with >70% DOC reduc
• Merck: 14,905
• BRN: 1101094
• CAS DataBase Reference: Azelaic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Azelaic acid(123-99-9)
• EPA Substance Registry System: Azelaic acid(123-99-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 1
• RTECS: CM1980000
• TSCA: Yes
• Hazardous Substances Data: 123-99-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Azelaic acid is used as an anti-acne agent for treating mild to moderate acne, both comedonal acne and inflammatory acne. It belongs to a class of medication called dicarboxylic acids and works by killing acne bacteria that infect skin pores. It also decreases the production of keratin, which promotes the growth of acne bacteria.
Azelaic acid is used as an antiproliferative agent, inhibiting DNA polymerases in several tumor cell lines, and as an antifungal agent, binding to membrane sterols.
Used in Cosmetics Industry:
Azelaic acid is used in cosmetics for the treatment of acne, displaying bacteriostatic and bactericidal properties against various aerobic and anaerobic microorganisms present on acne-bearing skin. It is also used as a topical gel treatment for rosacea, reducing inflammation and clearing bumps and swelling caused by the condition. Additionally, it has been used for the treatment of skin pigmentation, including melasma and post-inflammatory hyperpigmentation, particularly in those with darker skin types.
Used in Chemical Industry:
Azelaic acid is used in the manufacture of plasticizers for vinyl chloride resins and rubber, as well as lubricants and greases. Esters of this dicarboxylic acid find applications in lubrication and as components of hair and skin conditioners.
Used in Polymers and Related Materials:
Azelaic acid forms Nylon-6,9 when combined with hexamethylenediamine, which finds specialized uses as a plastic. Esters of this dicarboxylic acid are also used in the production of lacquers, alkyd resins, adhesives, polyamides, urethane elastomers, and organic syntheses.
Used in Agriculture:
In plants, azelaic acid serves as a "distress flare" involved in defense responses after infection. It acts as a signal that induces the accumulation of salicylic acid, an important component of a plant's defensive response and enhances the resistance of plants to infections.
Brand names of azelaic acid-based products include AzClear Action, Azelex, White Action cream, Finacea, Finevin, Skinoren, Melazepam, and Azaclear.

Originator

Schering AG (W. Germany)

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).

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

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.

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

Synthetic route

cis-Octadecenoic acid (112-80-1) → azelaic acid (123-99-9)

Conditions	Yield
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 permanganate	80%
With oleate hydratase from S. maltophilia In aq. buffer at 35℃; for 2h; pH=8; Enzymatic reaction;	21%

Dihydroxystearic Acid (120-87-6) → azelaic acid (123-99-9) + nonanoic acid (112-05-0)

Conditions	Yield
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) → azelaic acid (123-99-9) + nonanoic acid (112-05-0)

Conditions	Yield
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) → azelaic acid (123-99-9) + nonanoic acid (112-05-0)

Conditions	Yield
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) → azelaic acid (123-99-9)

Conditions	Yield
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) → azelaic acid (123-99-9)

Conditions	Yield
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 → azelaic acid (123-99-9) + 1,9-Nonanediol (3937-56-2) + 9-hydroxynonanoic acid (3788-56-5)

Conditions	Yield
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) → azelaic acid (123-99-9)

Conditions	Yield
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) → azelaic acid (123-99-9)

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

concentrated H2 SO4 + cyclohexanone-2-propionitrile (4594-78-9) + 3-(2-oxocyclohexyl)propionic acid (2275-26-5) + dihydrogen peroxide (7722-84-1) → azelaic acid (123-99-9)

Conditions	Yield
With hydrogenchloride; acetic acid In methanol	88%

9,10-epoxystearic acid (2443-39-2, 13980-07-9, 16833-55-9, 17682-84-7, 17682-85-8, 24560-98-3, 38003-74-6, 38003-76-8) → azelaic acid (123-99-9) + nonanoic acid (112-05-0)

Conditions	Yield
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) → azelaic acid (123-99-9) + nonanoic acid (112-05-0)

Conditions	Yield
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 → azelaic acid (123-99-9)

Conditions	Yield
With hydrogen In water at 200℃; under 15001.5 Torr; for 12h;	86%

1-hepten-3-ol (4938-52-7) + carbon monoxide (201230-82-2) → azelaic acid (123-99-9)

Conditions	Yield
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) → azelaic acid (123-99-9) + β-hydroxynonanoic acid (33796-87-1, 45023-83-4, 88930-09-0, 40165-87-5)

Conditions	Yield
With oxygen; ozone In water; acetone at 0℃; Flow reactor;	A 86% B 70%

(Z)-12-hydroxyoctadec-9-enoic acid (81212-19-3) → azelaic acid (123-99-9) + β-hydroxynonanoic acid (33796-87-1, 45023-83-4, 88930-09-0, 40165-87-5) + 12-hydroxy-9,10-epoxyoctadecanoic acid (47244-76-8, 118201-32-4)

Conditions	Yield
With cetylpyridinium peroxotungstophosphate; dihydrogen peroxide In water at 80℃; for 1h;	A 84% B 84% C 4%

cis-9-hexadecenoic acid (373-49-9) → azelaic acid (123-99-9) + oenanthic acid (111-14-8)

Conditions	Yield
With ozone In water; acetonitrile at 0℃;	A 84% B 83%

Ricinoleic acid (141-22-0) → azelaic acid (123-99-9) + (R)-3-hydroxynonanoic acid (33796-87-1)

Conditions	Yield
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) → azelaic acid (123-99-9)

Conditions	Yield
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) → azelaic acid (123-99-9)

Conditions	Yield
With sodium periodate; ruthenium trichloride In water; ethyl acetate; acetonitrile for 2h;	75%

cyclooct-4-enecarboxaldehyde (19835-69-9) → azelaic acid (123-99-9)

Conditions	Yield
With sodium hydroxide In water at 330 - 350℃; for 6h; autoclave;	73.5%

methyl 10-acetoxy-9-oxodecanoate (101171-32-8) → azelaic acid (123-99-9)

Conditions	Yield
With oxygen; sodium t-butanolate In diethyl ether; water for 4h; Ambient temperature;	70%

hydrous cobalt chloride + H2 WO4 + linoleic acid (60-33-3) + dihydrogen peroxide (7722-84-1) → azelaic acid (123-99-9)

Conditions	Yield
In water	70%

cis-Octadecenoic acid (112-80-1) → azelaic acid (123-99-9) + N-hydroxynonan-1-imine (2243-24-5) + nonanoic acid (112-05-0) + 9-(hydroxyimino)nonanoic acid

Conditions	Yield
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) + carbon monoxide (201230-82-2) → azelaic acid (123-99-9)

Conditions	Yield
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) → azelaic acid (123-99-9)

Conditions	Yield
With sodium hypochlorite at 20℃; for 5h; Reagent/catalyst;	50%

heptane-1,1,7,7-tetracarboxylic acid → azelaic acid (123-99-9)

Conditions	Yield
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) + azelaic acid (123-99-9) → Dimethyl azelate (1732-10-1)

Conditions	Yield
With boron trifluoride at 65℃; for 0.333333h;	100%
With sulfuric acid In dichloromethane Dean-Stark; Heating;	95%
With sulfuric acid	80%

azelaic acid (123-99-9) → azelaoyl chloride (123-98-8)

Conditions	Yield
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) + vinyl propionate (105-38-4) → azelaic acid divinyl ester (10355-49-4)

Conditions	Yield
With sulfuric acid; mercury(II) diacetate at 20 - 50℃; for 4h;	100%

azelaic acid (123-99-9) → C9H14O4(2-)*Mg(2+)*3H2O

Conditions	Yield
With magnesium hydroxide; water for 0.583333h; Milling;	100%

azelaic acid (123-99-9) → [K2(H2AZE)(AZE)]

Conditions	Yield
With water; potassium hydroxide for 0.166667h; Milling;	100%

azelaic acid (123-99-9) → C9H14O4(2-)*2Na(1+)*H2O

Conditions	Yield
With water; sodium hydroxide for 0.166667h; Milling;	100%

azelaic acid (123-99-9) → C9H14O4(2-)*Mg(2+)*3H2O

Conditions	Yield
With magnesium hydroxide; water for 0.25h; Milling;	100%

azelaic acid (123-99-9) + 2-Ethylhexyl alcohol (104-76-7) → bis(2-ethylhexyl) azelaate (103-24-2)

Conditions	Yield
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) + 1,1'-bis(4-pyridinyl)ferrocene (459142-93-9) → [(Fe(η5-C5H4-1-(4-C5H4N))2)2(1-azelaic acid)2]

Conditions	Yield
In methanol 1:1 mixt. ground for 5 min, dissolved in methanol; crystd.;	99%

azelaic acid (123-99-9) → dibromoazelaic acid (3479-83-2)

Conditions	Yield
With bromine; phosphorus tribromide at 80℃; for 8h; Temperature; Time;	98%

methanol (67-56-1) + azelaic acid (123-99-9) → α,α'-dibromoazelaiate de dimethyle (18281-62-4)

Conditions	Yield
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) + 1,10-Decanediol (112-47-0) → poly(decamethylene azelate), degree of polymerization > 200, Mn=2.69E4, Mw=5.83E4; monomers: azelaic acid; 1,10-decanediol

Conditions	Yield
tetrachlorobis(tetrahydrofuran)hafnium(IV) In o-xylene for 24h; Heating;	97%

azelaic acid (123-99-9) + 1,10-Decanediol (112-47-0) → Reaxys ID: 11364959

Conditions	Yield
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) + lead(II) acetate trihydrate (6080-56-4) → lead(II) azelate (7717-58-0, 14489-30-6, 25725-29-5, 87720-72-7)

Conditions	Yield
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) + 1,7-heptandiol (629-30-1) → 1,9-dioxacyclooctadecane-10,18-dione (660-63-9)

Conditions	Yield
With hafnium(IV) trifluoromethanesulfonate In toluene at 110℃; for 48h; Inert atmosphere;	96%

azelaic acid (123-99-9) + n-butyl formate (592-84-7) → Nonanedioic acid monobutyl ester (4753-32-6)

Conditions	Yield
With DOWEX 50W-X2 In Petroleum ether for 4.5h; Heating;	95%

azelaic acid (123-99-9) + 1-Chloropropane (540-54-5) → dipropyl azelate (6624-68-6)

Conditions	Yield
With sodium hydrogencarbonate In propan-1-ol at 40℃; for 1.5h;	95%

azelaic acid (123-99-9) + L-arginine (74-79-3) + germanium dioxide → C21H40GeN8O8

Conditions	Yield
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) + C15H16O4 → C39H44O10

Conditions	Yield
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane	95%

azelaic acid (123-99-9) + 1,2-dimethoxybenzene (91-16-7) → 1,7-bis(3,4-dimethoxyphenyl)heptane-1,7-dione (32246-69-8)

Conditions	Yield
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) + diphenylamine (122-39-4) → 1,7-bis(9-acridinyl)heptane

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

azelaic acid (123-99-9) + tetramethyl ammoniumhydroxide (75-59-2) → bis(tetramethylammonium) azelate

Conditions	Yield
In methanol at 21℃; for 48h;	94%

azelaic acid (123-99-9) + sulfanilamide (63-74-1) → C21H28N4O6S2 (123351-07-5)

Conditions	Yield
With sulfuric acid at 30 - 40℃; for 0.5h;	93%

methanol (67-56-1) + azelaic acid (123-99-9) → azelaic monomethyl ester (2104-19-0)

Conditions	Yield
With sulfuric acid	92%

Upstream product

• 112-80-1 cis-Octadecenoic acid 
• 544-72-9 9-cis,11-trans,13-cis-octadecatrienoic acid 
• 506-23-0 eleostearic acid 
• 544-73-0 (9E,11E,13E)-9,11,13-octadecatrienoic acid 
• 106-14-9 12-Hydroxystearic acid 
• 112-62-9 Methyl oleate 
• 60-33-3 linoleic acid 
• 29204-02-2 gadoleic acid 
• 141-22-0 Ricinoleic acid 
• 120-87-6 Dihydroxystearic Acid 
• 23224-20-6 methyl ricinoleate 
• 20701-68-2 (9Z)-octadec-9-enedioic acid 
• 20701-67-1 9-octadecenedioic acid 
• 1095618-59-9 12-hydroxy-9-octadecenoic acid ethyl ester 

Downstream Products

• 83912-91-8 nonanedioic acid di-p-tolyl ester 
• 38223-57-3 1,6-dioxacyclopentadecane-7,15-dione 
• 13926-70-0 1,8-dioxa-cycloheptadecane-9,17-dione 
• 1593-55-1 azelaic acid monoethyl ester 
• 624-17-9 diethyl azelate 
• 105-03-3 di-2-ethylbutyl azelate 
• 98422-15-2 nonanedioic acid bis-(3-methyl-benzyl ester) 
• 1842-72-4 1,7-heptanedicarboxamide 
• 502-49-8 cycloactanone 
• 124-07-2 Octanoic acid 
• 123-98-8 azelaoyl chloride 
• 53185-69-6 pimelaldehyde 
• 1941-79-3 1,9-diperoxynonanedioic acid 
• 142-82-5 n-heptane 

Related news

Olfactory receptor Olfr544 responding to Azelaic acid (cas 123-99-9) regulates glucagon secretion in α-cells of mouse pancreatic islets09/27/2019

Olfactory receptors (ORs) are extensively expressed in olfactory as well as non-olfactory tissues. Although many OR transcripts are expressed in non-olfactory tissues, only a few studies demonstrate the functional role of ORs. Here, we verified that mouse pancreatic α-cells express potential OR...detailed

New effective Azelaic acid (cas 123-99-9) liposomal gel formulation of enhanced pharmaceutical bioavailability09/10/2019

Azelaic acid is a naturally occurring saturated C9-dicarboxylic acid which has been shown to be effective in the treatment of comedonal acne and inflammatory acne, as well as hiperpigmentary skin disorders. The aim of the present study is to compare new developed liposomal hydrogel (lipogel) and...detailed

Preparation of in situ hydrogels loaded with Azelaic acid (cas 123-99-9) nanocrystals and their dermal application performance study09/09/2019

Azelaic acid (AZA) is a dicarboxylic acid that is topically used in the treatment of acne and rosacea since it possesses antibacterial and keratolytic activity. The primary objective of this study was to develop an AZA nanocrystal suspension. It is expected that improved solubility and dissoluti...detailed

Preparation of antibacterial TiO2 particles by hybridization with Azelaic acid (cas 123-99-9) for applications in cosmetics09/08/2019

To apply as the antimicrobial agent in cosmetics, azelaic acid, a skin lightening material with anti-inflammatory and antimicrobial properties, has been employed to functionalize TiO2 microspheres. Prior to the functionalization process, TiO2 microspheres were modified with NaOH to introduce hyd...detailed

Relevant articles and documents

A New and Efficient Approach to Macrocyclic Keto Lactones

A new and efficient method for macrolactonization has been developed.The intramolecular nucleophilic displacement of chloride from the highly electrophilic α-chloro ketone moiety in 15 by a remote carboxylate nucleophile resulted in the clean formation of the 11-membered keto lactone 1.Relatively high substrate concentrations (up to 18 mM) could be employed without formation of dimeric or oligomeric byproducts.The slow mixing of substrate and base was not required.This macrolactonization reaction was studied in various solvents at a number of substrate concentrations and reaction temperatures in order to evaluate its scope and limitations.A low-temperature Ti(III) ion/peroxide induced radical addition reaction has been developed.The lowering of the reaction temperature from 0 deg C to -78 deg C consistently afforded a dramatic increase in product yield from such reactions.This lowering of the reaction temperature proved essential when the highly functionalized acetoxymethyl vinyl ketone was employed as the radical acceptor.

γ-hydroxyalkenals are oxidatively cleaved through Michael addition of acylperoxy radicals and fragmentation of intermediate β-hydroxyperesters

Oxidative cleavage of arachidonate (C20) and linoleate (C 18) phospholipids generates truncated C8 or C12 γ-hydroxyalkenal phospholipids as well as C5 or C9 carboxyalkanoate phospholipids,

Microbial synthesis of medium-chain α,ω-dicarboxylic acids and ω-aminocarboxylic acids from renewable long-chain fatty acids

Biotransformation of long-chain fatty acids into medium-chain α,ω-dicarboxylic acids or ω-aminocarboxylic acids could be achieved with biocatalysts. This study presents the production of α,ω-dicarboxylic acids (e.g., C9, C11, C 12, C13) and ω-aminocarboxylic acids (e.g., C 11, C12, C13) directly from fatty acids (e.g., oleic acid, ricinoleic acid, lesquerolic acid) using recombinant Escherichia coli-based biocatalysts. ω-Hydroxycarboxylic acids, which were produced from oxidative cleavage of fatty acids via enzymatic reactions involving a fatty acid double bond hydratase, an alcohol dehydrogenase, a Baeyer-Villiger monooxygenase and an esterase, were then oxidized to α,ω- dicarboxylic acids by alcohol dehydrogenase (ADH, AlkJ) from Pseudomonas putida GPo1 or converted into ω-aminocarboxylic acids by a serial combination of ADH from P. putida GPo1 and an ω-transaminase of Silicibacter pomeroyi. The double bonds present in the fatty acids such as ricinoleic acid and lesquerolic acid were reduced by E. coli-native enzymes during the biotransformations. This study demonstrates that the industrially relevant building blocks (C9 to C13 saturated α,ω- dicarboxylic acids and ω-aminocarboxylic acids) can be produced from renewable fatty acids using biocatalysis.

Preparation, characterization, and theoretical studies of azelaic acid derived from oleic acid by use of a novel ozonolysis method

Environmentally friendly manufacture of organic compounds has been intensively reexamined in recent years. Many excellent methods have been devised to produce organic compounds from renewable resources. Azelaic acid has been produced by ozonolysis of oleic acid. The reaction was performed in a Bach bubbling reactor, with fine bubbles, at high temperature (150 °C) without utilizing any catalyst or any solvent. Yield of the reaction was 20% after 2 h. Production of azelaic acid was confirmed by use of FT-IR and 1H NMR spectroscopic data and high-performance liquid chromatography of both synthesized and reference azelaic acid. A theoretical study was performed to obtain quantum chemical data for azelaic acid and to optimize the molecule's geometry. Springer Science+Business Media B.V. 2011.

Thermoplastic polyester amides derived from oleic acid

Three lipid-based Polyester Amides (PEAs) with varying ratios of ester and amide linkages were synthesized. Oleic acid was used as the starting material to produce the intermediates, characterized by MS and NMR, used for polymerization. PEAs were characterized by FTIR and GPC. The PEAs were constrained to have similar number average molecular weights, in the 2 × 104 range, thereby enabling comparison of their physical properties from a structural perspective. The thermal behavior of the polymers was assessed by DSC, DMA and TGA. Thermal degradation was not affected by ester/amide ratios, but Tg increased non-linearly with decreasing ester/amide ratios and correlated with hydrogen-bond density and repeating unit chain length. Crystallinity was studied by XRD and DSC. Degree of crystallization and multiple melting behavior as a function of cooling kinetics were explained well by hydrogen-bond density, repeating unit chain length and density of ester moieties. Mechanical properties were investigated by DMA and Tensile Analysis, with a non-linear increase of storage and tensile moduli recorded as a function of decreasing ester/amide ratios. The findings suggest how approaches to the synthesis of lipid-based PEAs can be targeted to the delivery of specific physical properties.

Simultaneous Enzyme/Whole-Cell Biotransformation of C18 Ricinoleic Acid into (R)-3-Hydroxynonanoic Acid, 9-Hydroxynonanoic Acid, and 1,9-Nonanedioic Acid

Regiospecific oxyfunctionalization of renewable long chain fatty acids into industrially relevant C9 carboxylic acids has been investigated. One example was biocatalytic transformation of 10,12-dihydroxyoctadecanoic acid, which was produced from ricinoleic acid ((9Z,12R)-12-hydroxyoctadec-9-enoic acid) by a fatty acid double bond hydratase, into (R)-3-hydroxynonanoic acid, 9-hydroxynonanoic acid, and 1,9-nonanedioic acid with a high conversion yield of ca. 70%. The biotransformation was driven by enzyme/whole-cell biocatalysts, consisting of the esterase of Pseudomonas fluorescens and the recombinant Escherichia coli expressing the secondary alcohol dehydrogenase of Micrococcus luteus, the Baeyer-Villiger monooxygenase of Pseudomonas putida KT2440 and the primary alcohol/aldehyde dehydrogenases of Acinetobacter sp. NCIMB9871. The high conversion yields and the high product formation rates over 20 U/g dry cells with insoluble reactants indicated that various (poly-hydroxy) fatty acids could be converted into multi-functional products via the simultaneous enzyme/whole-cell biotransformations. This study will contribute to the enzyme-based functionalization of hydrophobic substances. (Figure presented.).

Process for preparing azelaic acid

A process for preparing azelaic acid is disclosed. In particular, the process for preparing azelaic acid is an ozone free process. The process for preparing azelaic acid comprises a step of decarboxylation of tetra-carboxylic acid in the presence of a organic sulfonic acid.

Scalable, sustainable and catalyst-free continuous flow ozonolysis of fatty acids

A simple and efficient catalyst-free protocol for continuous flow synthesis of azelaic acid is developed from the renewable feedstock oleic acid. An ozone and oxygen mixture was used as the reagent for oxidative cleavage of double bond without using any metal catalyst or terminal oxidant. The target product was scaled up to more than 100 g with 86% yield in a white powder form. Complete recycling and reuse of the solvent were established making it a green method. The approach is significantly energy efficient and also has a very small chemical footprint. The methodology has been successfully tested with four fatty acids making it a versatile platform that gives value addition from renewable resources.

FLOW CHEMISTRY SYNTHESIS OF ISOCYANATES

The disclosure provides, inter alia, safe and environmentally-friendly methods, such as flow chemistry, to synthesize isocyanates, such as methylene diphenyl diisocyanate, toluene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, and tetramethylxylene diisocyanate.

METHOD FOR MANUFACTURING PELARGONIC ACID AND AZELAIC ACID

The present invention relates to a method for producing pelargonic acid and azelaic acid, and more specifically, provides a method for producing pelargonic acid and azelaic acid, which comprises the following steps of: a) reacting an unsaturated carboxylic acid compound under a tungstic acid catalyst to obtain an intermediate product comprising vicinal diol; and b) reacting the intermediate product under a transition metal hydroxide catalyst to obtain the pelargonic acid and azelaic acid. The production method is capable of producing the pelargonic acid and azelaic acid in a high yield from the unsaturated carboxylic acid compound.