Azelaic acid

Azelaic acid
Compound Structure:
Synonyms: azelaic acid;NONANEDIOIC ACID;Finacea;Anchoic acid;Azelex;Lepargylic acid;1,7-Heptanedicarboxylic acid;Skinoren;1,9-Nonanedioic acid;Heptanedicarboxylic acid;n-Nonanedioic acid;Emerox 1110;Emerox 1144;azelate;acide azelaique;acidum azelaicum
Compound ID: NMPC-609
PubChem ID:

2266
Molecular Formula: C9H16O4
Canonical SMILES: C(CCCC(=O)O)CCCC(=O)O
InChIKey: BDJRBEYXGGNYIS-UHFFFAOYSA-N
About the compound:

Azelaic acid is a saturated dicarboxylic acid with the chemical formula HOOC(CH2)7COOH. It is found naturally in wheat, rye, and barley, as well as being produced by the fungus Malassezia furfur (Pityrosporum ovale), which is commonly found on human skin. Azelaic acid has various applications and benefits: Skin Conditions: Azelaic acid is effective in treating mild to moderate acne when applied topically in a cream formulation with a concentration of 20%. It works by inhibiting the growth of skin bacteria that contribute to acne and by keeping skin pores clear. Antimicrobial Action: Azelaic acid's antimicrobial action is attributed to its ability to inhibit microbial cellular protein synthesis, making it effective against the bacteria associated with acne. Skin Lightening: Azelaic acid can also help in reducing skin hyperpigmentation and improving uneven skin tone. It inhibits tyrosinase, an enzyme involved in melanin production, which can lead to a more even complexion. Industrial Uses: Azelaic acid serves as a precursor to various industrial products, including polymers and plasticizers. It is also used in some hair and skin conditioners.

GHS Hazard Statements

• H315 (49.41%): Causes skin irritation [Warning Skin corrosion/irritation]

• H319 (99.91%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

188.22 g/mol

XLogP3

1.6

Hydrogen Bond Donor Count

2

Hydrogen Bond Acceptor Count

4

Rotatable Bond Count

8

Exact Mass

188.10485899 g/mol

Monoisotopic Mass

188.10485899 g/mol

Topological Polar Surface Area

74.6Ų

Heavy Atom Count

13

Formal Charge

0

Complexity

147

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Yellowish to white solid; [HSDB] White flakes; [Acros Organics MSDS]

Boiling Point

286.5°C at 1.00E+02 mm Hg

Melting Point

106.5°C

Density

1.225 g/cu cm at 25 °C

Solubility 

Slightly soluble in ethy ether, benzene, DMSO; soluble in ethanol

Vapor Pressure

0.00000001 [mmHg]

Source: PubChem
Source Species: Strychnos innocua
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