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Azelaic acid information


Azelaic acid
Skeletal formula of azelaic acid
Ball-and-stick model of the azelaic acid molecule
Names
Preferred IUPAC name
Nonanedioic acid
Identifiers
CAS Number
  • 123-99-9 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
1101094
ChEBI
  • CHEBI:48131 checkY
ChEMBL
  • ChEMBL1238 checkY
ChemSpider
  • 2179 checkY
DrugBank
  • DB00548 checkY
ECHA InfoCard 100.004.246 Edit this at Wikidata
EC Number
  • 204-669-1
Gmelin Reference
261342
IUPHAR/BPS
  • 7484
KEGG
  • D03034 checkY
PubChem CID
  • 2266
UNII
  • F2VW3D43YT checkY
CompTox Dashboard (EPA)
  • DTXSID8021640 Edit this at Wikidata
InChI
  • InChI=1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13) checkY
    Key: BDJRBEYXGGNYIS-UHFFFAOYSA-N checkY
  • InChI=1/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13)
    Key: BDJRBEYXGGNYIS-UHFFFAOYAK
SMILES
  • O=C(O)CCCCCCCC(=O)O
Properties
Chemical formula
C9H16O4
Molar mass 188.22 g/mol
Appearance white solid
Density 1.443 g/mL
Melting point 109 to 111 °C (228 to 232 °F; 382 to 384 K)[1]
Boiling point 286 °C (547 °F; 559 K) at 100 mmHg[1]
Solubility in water
2.14 g/L[2]
Acidity (pKa) 4.550, 5.498[2]
Pharmacology
ATC code
D10AX03 (WHO)
Routes of
administration
Topical
Pharmacokinetics:
Bioavailability
Very low
Biological half-life
12 h
Legal status
  • AU: S2 (Pharmacy Only)
  • US: ℞-only
Hazards
GHS labelling:
Pictograms
GHS07: Exclamation mark
Signal word
Warning
Hazard statements
H315, H319
Precautionary statements
P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Azelaic acid (AzA) is an organic compound with the formula HOOC(CH2)7COOH.[3] This saturated dicarboxylic acid exists as a white powder. It is found in wheat, rye, and barley. It is a precursor to diverse industrial products including polymers and plasticizers, as well as being a component of a number of hair and skin conditioners.[4] AzA inhibits tyrosinase.[5]

  1. ^ a b Sigma-Aldrich catalog Archived April 9, 2008, at the Wayback Machine
  2. ^ a b Bretti, C.; Crea, F.; Foti, C.; Sammartano, S. (2006). "Solubility and Activity Coefficients of Acidic and Basic Nonelectrolytes in Aqueous Salt Solutions. 2. Solubility and Activity Coefficients of Suberic, Azelaic, and Sebacic Acids in NaCl(aq), (CH3)4NCl(aq), and (C2H5)4NI(aq) at Different Ionic Strengths and at t = 25 °C". J. Chem. Eng. Data. 51 (5): 1660–1667. doi:10.1021/je060132t.
  3. ^ Del Rosso, James Q. (2006-02-01). "The use of topical azelaic acid for common skin disorders other than inflammatory rosacea". Cutis. 77 (2 Suppl): 22–24. ISSN 0011-4162. PMID 16566285.
  4. ^ Cite error: The named reference Boy was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference TyrosinaseInhibitor was invoked but never defined (see the help page).

and 29 Related for: Azelaic acid information

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Azelaic acid

Last Update:

Azelaic acid (AzA) is an organic compound with the formula HOOC(CH2)7COOH. This saturated dicarboxylic acid exists as a white powder. It is found in wheat...

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Acne

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Treatments applied directly to the affected skin, such as azelaic acid, benzoyl peroxide, and salicylic acid, are commonly used. Antibiotics and retinoids are...

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Dicarboxylic acid

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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...

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Oleic acid

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carboxylic acid group yields oleyl alcohol. Ozonolysis of oleic acid is an important route to azelaic acid. The coproduct is nonanoic acid: H17C8CH=CHC7H14CO2H...

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Anal bleaching

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hydroquinone, however it is less effective at lightening and also carcinogenic. Azelaic acid is another option. Mercury was commonly used as a skin lightening agent...

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Sebacic acid

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candles. Sebacic acid is a derivative of castor oil. In the industrial setting, sebacic acid and its homologues such as azelaic acid can be used as a...

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Mupirocin

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viable antibiotic against MuH strains. Other antibiotic agents, such as azelaic acid, nitrofurazone, silver sulfadiazine, and ramoplanin have been shown to...

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Hyperpigmentation

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such as hydroquinone, azelaic acid, and kojic acid. Some are available without prescription, such as niacinamide, l-ascorbic acid,[citation needed] retinoids...

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Fatty acid

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is practiced in the production of azelaic acid ((CH2)7(CO2H)2) from oleic acid. Short- and medium-chain fatty acids are absorbed directly into the blood...

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Hydroquinone

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available or under research, including azelaic acid, kojic acid, retinoids, cysteamine, topical steroids, glycolic acid, and other substances. One of these...

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Comedo

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Some research suggests that the common acne medications retinoids and azelaic acid are beneficial and do not cause increased pigmentation of the skin. If...

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Melasma

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due to risk of harm to the fetus. Azelaic acid (20%) is thought to decrease the activity of melanocytes. Tranexamic acid by mouth has shown to provide rapid...

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Ozonolysis

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unsaturated fatty acids to value-added derivatives. Ozonolysis of oleic acid is an important route to azelaic acid. The coproduct is nonanoic acid: CH3(CH2)7CH=CH(CH2)7CO2H}...

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Benzoyl peroxide

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benzoyl peroxide, antibiotics and azelaic acid]" [Acne therapy with topical benzoyl peroxide, antibiotics and azelaic acid]. Journal der Deutschen Dermatologischen...

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Liver spot

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agents, such as hydroquinone, tretinoin, topical cysteamine, azelaic acid, or alpha hydroxy acids. Differently from the melanotic nevi and the verrucous nevi...

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Rosacea

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Medications with good evidence include topical metronidazole, ivermectin and azelaic acid. Good evidence medications taken by mouth include brimonidine, and doxycycline...

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Tinea versicolor

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furfur, lightening of the skin occurs due to the fungus's production of azelaic acid, which has a slight bleaching effect. Tinea versicolor may be diagnosed...

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Postinflammatory hyperpigmentation

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may include topical agents like hydroquinone, retinoids, ascorbic acid, and azelaic acid, as well as chemical peels or laser therapy to promote skin renewal...

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Pimple

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medications, anti-androgen medications, hormonal treatments, alpha hydroxy acid, azelaic acid, and keratolytic soaps. Historically, antibiotics such as tetracyclines...

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Pelargonic acid

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contains esters of the acid. Together with azelaic acid, it is produced industrially by ozonolysis of oleic acid. CH 3 ( CH 2 ) 7 CH = CH ( CH 2 ) 7 CO 2...

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Edible oil refining

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produce pelargonic acid, and azelaic acid. In another application it was possible to recover oleic acid, linoleic acid and linolenic acid and fermented, using...

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Lentigo

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depigmentation agents. Some common depigmentation agents such as azelaic acid and kojic acid seem to be inefficient in this case, however other agents might...

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Acetone

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chemical peeling are salicylic acid, glycolic acid, azelaic acid, 30% salicylic acid in ethanol, and trichloroacetic acid (TCA). Prior to chemexfoliation...

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Hidradenitis

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approved by the FDA include alpha hydroxy acids (naturally available in small amounts in citrus fruits), Azelaic acid, and zinc. It is not thought that they...

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Cosmetics

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exfoliants include azelaic acid, citric acid, acetic acid, malic acid, mandelic acid, glycolic acid, lactic acid, salicylic acid, papain, and bromelain...

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Cat pheromone

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α-methylbutyric acid 6–9 0 0 0 5–8 palmitic acid 0 17–49 13–24 0 28–37 propionic acid 0 11–23 0 0 0 p-hydroxyphenylacetic acid 0 6–15 0 0 8–19 azelaic acid 0 0 6–13...

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Metronidazole

Last Update:

Maybury C (October 2023). "A systematic review to evaluate the efficacy of azelaic acid in the management of acne, rosacea, melasma and skin aging". J Cosmet...

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Drugs in pregnancy

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Frank (1 May 2020). "Topical azelaic acid, salicylic acid, nicotinamide, sulphur, zinc and fruit acid (alpha-hydroxy acid) for acne". The Cochrane Database...

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Tyrosinase

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inhibitors are the following: Azelaic acid 4-Butylresorcinol Hydroquinone L-ascorbic acid - Vitamin C Tranexamic acid While albinism is common, there...

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