nonanedioic acid

• ChemBase ID: 430
• Molecular Formular: C9H16O4
• Molecular Mass: 188.22094
• Monoisotopic Mass: 188.10485899
• SMILES: OC(=O)CCCCCCCC(=O)O
• Canonical SMILES: OC(=O)CCCCCCCC(=O)O
• 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)
• InChIKey: BDJRBEYXGGNYIS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: nonanedioic acid
• IUPAC Traditional name: azelaic acid
• Brand Name: Azelex; Emerox 1110; Emerox 1144; Emery's L-110; Finacea; Finevin; Skinoren
• Synonyms: n-Nonanedioic acid; Nonanedioic acid; Lepargylic acid; Heptanedicarboxylic acid; Azalaic Acid; Anchoic acid; Azelainic acid; Azelaic Acid; Nonanedionic acid; 1,7-Heptanedicarboxylic acid; Azelaic acid; 杜鹃花酸; 壬二酸

Database IDs

• CAS Number: 123-99-9
• EC Number: 204-669-1
• MDL Number: MFCD00004432
• Beilstein Number: 1101094
• Merck Index: 14905
• PubChem SID: 24891477; 24278221; 160963893; 46506284
• PubChem CID: 2266
• CHEBI ID: 48131
• ATC CODE: D10AX03
• CHEMBL: 1238
• Chemspider ID: 2179
• DrugBank ID: DB00548
• KEGG ID: D03034
• Unique Ingredient Identifier: F2VW3D43YT
• Wikipedia Title: Azelaic_acid

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.1478105
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.1637566
• LogD (pH = 7.4): -3.6534874
• Log P: 1.8243604
• Molar Refractivity: 46.542 cm^3
• Polarizability: 18.41525 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.37
• LOG S: -1.92
• Solubility (Water): 2.28e+00 g/l

PROPERTIES

Physical Property

• Solubility: 2.14 g/L in water; 2400 mg/L (20 oC)
• Apperance: Crystalline
• Melting Point: 109-111 °C; 109-111 °C(lit.); 109-111°C; ca 102°C
• Boiling Point: 286 °C at 100 mmHg; 286 °C/100 mmHg(lit.); 286.5°C; 286.5°C @ 100 mm; 286°C/100mm; 287°C
• Flash Point: 210 °C; 215°C(419°F); 410 °F
• Density: 1.029 g/ml; 1.225
• Vapor Pressure: <1 mmHg ( 20 °C)
• Vapor Density: 6.5 (vs air)
• Hydrophobicity(logP): 1.7
• pKa: 4.550, 5.498

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: CM1980000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 1
• Risk Statements: R:36/37/38
• Safety Statements: S:20-25-26-37/39
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Admin Routes: Topical
• Bioavailability: Very low
• Half Life: 12 hours
• Legal Status: Rx-only (US)

Product Information

• Purity: ~85% (GC); ~90%; >97%; ≥99.0% (GC); 80%; 95%; 96%; 98%; tech. 80%
• Grade: PRACTICAL; puriss.; technical; technical grade
• Linear Formula: HO2C(CH2)7CO2H

DETAILS

MP Biomedicals - 05225943

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02100855

Crystalline
Purity: >97%

MP Biomedicals - 02150408

Practical Grade
Purity: ~90%
Crystalline

MP Biomedicals - 05215098

MP Biomedicals Rare Chemical collection

DrugBank - DB00548

• Drug Groups: approved
• Description: Azelaic acid is a saturated dicarboxylic acid found naturally in wheat, rye, and barley. It is a natural substance that is produced by Malassezia furfur (also known as Pityrosporum ovale), a yeast that lives on normal skin. It is effective against a number of skin conditions, such as mild to moderate acne, when applied topically in a cream formulation of 20%. It works in part by stopping the growth of skin bacteria that cause acne, and by keeping skin pores clear. Azelaic acid's antimicrobial action may be attributable to inhibition of microbial cellular protein synthesis.
• Indication: For the topical treatment of mild-to-moderate inflammatory acne vulgaris.
• Pharmacology: Azelaic acid is a saturated dicarboxylic acid found naturally in wheat, rye, and barley. It is a natural substance that is produced by Malassezia furfur (also known as Pityrosporum ovale), a yeast that lives on normal skin. It is effective against a number of skin conditions, such as mild to moderate acne, when applied topically in a cream formulation of 20%. It works in part by stopping the growth of skin bacteria that cause acne, and by keeping skin pores clear. Azelaic acid's antimicrobial action may be attributable to inhibition of microbial cellular protein synthesis.
• Toxicity: Oral LD50 in rat: >5 g/kg
• Affected Organisms: Various aerobic and anaerobic microorganisms
• Biotransformation: Mainly excreted unchanged in the urine but undergoes some b-oxidation to shorter chain dicarboxylic acids.
• Absorption: Approximately 4% of the topically applied azelaic acid is systemically absorbed.
• Half Life: The observed half-lives in healthy subjects are approximately 45 minutes after oral dosing and 12 hours after topical dosing, indicating percutaneous absorption rate-limited kinetics.
• Elimination: Azelaic acid is mainly excreted unchanged in the urine, but undergoes some ?-oxidation to shorter chain dicarboxylic acids.
• External Links: RxList; PDRhealth; Drugs.com

Sigma Aldrich - 246379

Packaging
25, 100 g in poly bottle

Sigma Aldrich - A96150

Packaging
2 kg in poly bottle