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Azelaic acid(CAS No. 123-99-9)

Azelaic acid C9H16O4 (cas 123-99-9) Molecular Structure

123-99-9 Structure

Identification and Related Records

【Name】
Azelaic acid
【CAS Registry number】
123-99-9
【Synonyms】
1, 9-Nonanedioic acid
Nonanedioic acid
Azelaic acid, technical grade
Lepargylic acid
Heptanedicarboxylic acid
Nonanedioic acid Azelaic acid
Empol 1144
1,7-Heptanedicarboxylic acid
Emerox 1144
Emerox 1110
Ammonium Hydrogen Azelate
Azelaic Acid 99%
【EINECS(EC#)】
204-669-1
【Molecular Formula】
C9H16O4 (Products with the same molecular formula)
【Molecular Weight】
188.22
【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)
【InChIKey】
BDJRBEYXGGNYIS-UHFFFAOYSA-N
【Canonical SMILES】
C(CCCC(=O)O)CCCC(=O)O
【MOL File】
123-99-9.mol

Chemical and Physical Properties

【Appearance】
white flake
【Density】
23720
【Melting Point】
98-103℃
【Boiling Point】
286℃ (100 mmHg)
【Vapour】
1.66E-06mmHg at 25°C
【Refractive Index】
1.42808 (107.3 C)
【Flash Point】
215℃
【Water】
2.4 g/L (20℃)
【Solubilities】
2.4 g/L
【Color/Form】
Monoclinic prismatic needles
Yellowish to white crystalline powder
Leaflets or needles
【Stability】
Stable. Combustible. Incompatible with bases, strong oxidizing agents. Readily biodegrades in soil and water with >70% DOC reduction after 28 days.
【HS Code】
29171390
【Storage temp】
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
【Spectral properties】
Index of refraction = 1.4303 at 111 deg C
MASS: 8107 (NIST/EPA/MSDC Mass Spectral dtabase, 1990 version); 2785 (National Bureau of Standards)
IR: 5912 (Coblentz Society spectral collection)
1H NMR: 6060 (Sadtler Research Laboratories spectral collection)
【Computed Properties】
Molecular Weight:188.22094 [g/mol]
Molecular Formula:C9H16O4
XLogP3:1.6
H-Bond Donor:2
H-Bond Acceptor:4
Rotatable Bond Count:8
Exact Mass:188.104859
MonoIsotopic Mass:188.104859
Topological Polar Surface Area:74.6
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
Feature 3D Acceptor Count:4
Feature 3D Anion Count:2
Effective Rotor Count:8
Conformer Sampling RMSD:0.8
CID Conformer Count:103

Safety and Handling

【Hazard Codes】
Xi: Irritant;
【Risk Statements】
R36/37/38
【Safety Statements 】
S24/25
【Safety】

Hazard Codes:?IrritantXi
Risk Statements: 36/37/38?
R36/37/38: Irritating to eyes, respiratory system and skin
Safety Statements: 24/25-36-26?
S24/25: Avoid contact with skin and eyes
S36: Wear suitable protective clothing
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
WGK Germany: 1
RTECS: CM1980000
HS Code: 29171390
Low toxicity by ingestion. A skin and eye irritant. Closely related to glutaric acid and adipic acid. Combustible when exposed to heat or flame; can react with oxidizing materials.

【PackingGroup 】
Z01
【Skin, Eye, and Respiratory Irritations】
Skin: May cause mild skin irritation. Eyes: May cause mild eye irritation. Inhalation: May cause respiratory tract irritation.
【Cleanup Methods】
Small spill: Use appropriate tools to put the spilled solid in a convenient waste disposal container. Finish cleaning by spreading water on the contaminated surface and dispose of according to local and regional authority requirements. Large spill: Use a shovel to put the material into a convenient waste disposal container. Finish cleaning by spreading water on the contaminated surface and allow to evacuate through the sanitary system.
【Transport】
25kgs
【Fire Fighting Procedures】
SMALL FIRE: Use DRY chemical powder. LARGE FIRE: Use water spray, fog or foam. Do not use water jet.
【Fire Potential】
Slightly flammable to flammable in presence of heat.
【Formulations/Preparations】
Topical: Cream: 20% Azelex (with propylene glycol) (Allergan), Finevin (with propylene glycol) (Berlex). Gel: 15% Finacea (with propylene glycol) (Berlex).
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl azelaic acid, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
Azelaic acid is an indirect food additive for use only as a component of adhesives.
【Reactivities and Incompatibilities】
Reactive with oxidizing agents.
【Other Preventative Measures】
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.
【Protective Equipment and Clothing】
Personal Protection: Safety glasses. Lab coat. Dust respirator. Be sure to use an approved/certified respirator or equivalent. Gloves.
Personal Protection in Case of a Large Spill: Splash goggles. Full suit. Dust respirator. Boots. Gloves. A self contained breathing apparatus should be used to avoid inhalation of the product. Suggested protective clothing might not be sufficient; consult a specialist BEFORE handling this product.
Engineering controls: Use process enclosures, local exhaust ventilation, or other engineering controls to keep airborne levels below recommended exposure limits. If user operations generate dust, fume or mist, use ventilation to keep exposure to airborne contaminants below the exposure limit.
【Specification】

?Azelaic acid (CAS NO.123-99-9) is also called as?Azelaic acid [USAN:INN]?; 1,7-Heptanedicarboxylic acid ; 1,9-Nonanedioic acid ;?Acide azelaique ; Acide azelaique [French]?;?Acidum azelaicum ;?Azelaic acid, technical grade ;?Heptanedicarboxylic acid?;?Nonanedioic acid .

【Octanol/Water Partition Coefficient】
log Kow = 1.57
【Report】

Reported in EPA TSCA Inventory.

【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Prepared by disruptive oxidation of ricinoleic acid
Oxidation of oleic acid by ozone
... Generally produced from naturally occurring fatty acids via oxidative cleavage of a double bond in the 9-position, eg, from oleic acid.
U.S. Production

Nonanedioic acid is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. Year Production Range (pounds) 1986 >10 million - 50 million 1990 >10 million - 50 million 1994 >10 million - 50 million 1998 >10 million - 50 million 2002 >10 million - 50 million
【Usage】

Effective against a number of skin conditions, such as mild to moderate acne, when applied topically in a cream.

Biomedical Effects and Toxicity

【Pharmacological Action】
- Substances that inhibit or prevent the proliferation of NEOPLASMS.
- Drugs used to treat or prevent skin disorders or for the routine care of skin.
【Therapeutic Uses】
Azelaic acid 20% cream is used topically in the treatment of mild to moderate inflammatory acne vulgaris. The drug is not indicated in the treatment of noninflammatory acne vulgaris. Therapy of acne vulgaris must be individualized and frequently modified depending on the types of acne lesions that predominate and the response to therapy. Results of several studies indicate that topical azelaic acid 20% cream is more effective than vehicle placebo in the treatment of mild to moderate inflammatory acne and as effective as topical tretinoin or benzoyl peroxide. Limited data indicate that topical azelaic acid also may be as effective as oral tetracycline hydrochloride in the management of acne vulgaris. A decrease in the number of inflammatory lesions occurs in most patients within 1-2 months of topical azelaic acid therapy, although maximum benefit generally requires more prolonged treatment.
Azelaic acid 15% gel is used topically for the treatment of inflammatory lesions (papules and pustules) associated with mild to moderate rosacea in adults. In 2 clinical studies in adults with mild to moderate papulopustular rosacea, therapy with azelaic acid 15% gel (applied twice daily for 12 weeks) resulted in a 50-58% reduction in the number of papules and pustules compared with a 38-40% reduction in patients receiving vehicle alone. Patients were instructed to avoid spicy foods, thermally hot foods and drinks, and alcoholic beverages during the treatment period, as well as to use only very mild soaps or soapless cleansing lotion for facial cleaning. Azelaic acid 20% cream also has been used with some success in the treatment of papulopustular rosacea. /Use is not currently included in the labeling approved by the US Food and Drug Administration/
The physiopathologic mechanism of acne seems to be dependent on four main factors: a) sebum production and excretion; b) type of keratinization of the follicular channel; c) microbial colonization of the pilosebaceous unit and d) inflammatory reaction of the perifollicular area. Azelaic acid is effective in the treatment of acne because it possesses an activity against all of these factors. Azelaic acid is a competitive inhibitor of mitochondrial oxidoreductases and of 5 alpha-reductase, inhibiting the conversion of testosterone to 5-dehydrotestosterone. It also possesses bacteriostatic activity to both aerobic and anaerobic bacteria including Propionibacterium acnes. Azelaic acid is an anti-keratinizing agent, displaying antiproliferative cytostatic effects on keratinocytes and modulating the early and terminal phases of epidermal differentiation. [Passi S et al; G Ital Dermatol Venereol 24 (10): 455-63 (1989)]
【Biomedical Effects and Toxicity】
...Azelaic acid (AA, C9 dicarboxylic acid)... when administered perorally to humans, at the same concentrations as the other /dicarboxylic acids/ (DA), it reaches much higher serum and urinary concentrations. Serum concentrations and urinary excretion obtained with intravenous or intra-arterial infusions of AA are significantly higher than those achievable by oral administration. Together with AA, variable amounts of its catabolites, mainly pimelic acid, are found in serum and urine, indicating an involvement of mitochondrial beta-oxidative enzymes. Short-lived serum levels of AA follow a single 1 hr intravenous infusion, but prolonging the period of infusion with successive doses of similar concentration produces sustained higher levels during the period of administration. These levels are consistent with the concentrations of AA capable of producing a cytotoxic effect on tumoral cells in vitro. AA is capable of crossing the blood-brain barrier: its concentration in the cerebrospinal fluid is normally in the range of 2-5% of the values in the serum. [Passi S et al; Acta Derm Venereol Suppl (Stockh) 143: 8-13 (1989)] PubMed Abstract
Azelaic acid was the first dicarboxylic acid proposed as an alternative energy substrate in total parenteral nutrition. In this study, the pharmacokinetics of azelaic acid were investigated in 12 healthy volunteers, 7 receiving a constant infusion (10 g over 90 min) and 5 a bolus dose (1g). The 24 hr urinary excretion and plasma concentration in blood samples taken at regular intervals were assayed by gas-liquid chromatography. Experimental data were analysed by a 2-compartment nonlinear model that describes both tubular secretion and cellular uptake in Michaelis-Menten terms. A high value of urinary excretion (mean 76.9% of infused dose) and a mean clearance of 8.42 L/hr were found, suggesting the presence of tubular secretion. Estimating the population mean of the pharmacokinetic model parameters gave a maximal cellular uptake of 0.657 g/hr. The model predicts that 90% of the maximal uptake should be reached in the plateau phase of a constant infusion of 2.2 g/hr. The presence of extensive and rapid losses through urinary excretion, and the low estimated value of the maximal cellular uptake, indicate that azelaic acid is not suitable as an energy substrate for total parenteral nutrition. [Bertuzzi A et al; Clin Pharmacokinet 20 (5): 411-9 (1991)] PubMed Abstract
Follicular concentrations of azelaic acid (AzA) were determined in vivo using a rapid, non-invasive method, after a single topical application of 20% (w/w) AzA cream, in order to establish whether the in vitro antimicrobial effects observed in previous studies are relevant in vivo. Preweighed amounts of 20% (w/w) AzA cream were applied over demarcated areas on the forehead and back of nine young adults, and samples were taken over a period of 5 hr. AzA was removed from the skin surface by washing with acetone, and follicular casts were collected using cyanacrylate gel. The samples were centrifuged to remove particulate matter, and the supernatants derivatized for analysis by HPLC. Although the results showed wide-ranging variability, the follicular concentration increased as the amount present on the surface declined. The maximum follicular concentrations of AzA attained ranged from 7.5 to 52.5 ng (micrograms of follicular casts)-1 and 0.5 to 23.4 ng/(ug of follicular casts) in samples taken from the back and forehead, respectively. Assuming an average density of follicular material of 0.9 g/mL, the mean maximum follicular concentration attained on the back was between 36 and 251 mmol/L, and on the forehead was between 2 and 112 mmol/L, and indicates that the concentration of AzA attained in follicular casts after a single topical application is comparable with the concentration required to inhibit the growth of Propionibacterium acnes and Staphylococcus epidermidis, in vitro. [Bojar RA et al; Br J Dermatol 129 (4): 399-402 (1993)] PubMed Abstract
Six healthy male volunteers received a single topical treatment with 5 g of an anti-acne cream containing 20% azelaic acid (AzA) onto the face, the chest and the upper back. One week later 1 g of AzA was given orally to the same subjects as aqueous microcrystalline suspension. Following the two treatments the renal excretion of the unchanged compound was measured. Analysis included ether extraction of the urine, derivatization of extract and HPLC with UV detection. After topical application 2.2 +/- 0.7%, and after oral administration 61.2 +/- 8.8% of the dose had been excreted unchanged with the urine. By comparing both amounts, the percutaneous absorption of AzA from the cream was assessed to 3.6% of the dermally applied dose. [Tauber U et al; Exp Dermatol 1 (4): 176-9 (1992)] PubMed Abstract
Equilibrium dialysis was used to assess human milk partitioning in vitro. At an azelaic acid concentration of 25 ug/mL, the milk/plasma distribution coefficient was 0.7 and the milk/buffer distribution was 1.0, indicating that passage of drug into maternal milk may occur. Since less than 4% of a topically applied dose is systemically absorbed, the uptake of azelaic acid into maternal milk is not expected to cause a significant change from baseline azelaic acid levels in the milk.
Following a single application of Azelex Cream to human skin in vitro, azelaic acid penetrates into the stratum corneum (approximately 3 to 5% of the applied dose) and other viable skin layers (up to 10% of the dose is found in the epidermis and dermis). Negligible cutaneous metabolism occurs after topical application. Approximately 4% of the topically applied azelaic acid is systemically absorbed. Azelaic acid is mainly excreted unchanged in the urine but undergoes some beta-oxidation to shorter chain dicarboxylic acids. 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.
Azelaic acid is a dietary constituent (whole grain cereals and animal products), and can be formed endogenously from longer-chain dicarboxylic acids, metabolism of oleic acid, and oxidation of monocarboxylic acids. Endogenous plasma concentration (20 to 80 ng/mL) and daily urinary excretion (4 to 28 mg) of azelaic acid are highly dependent on dietary intake. After topical treatment with Azelex Cream in humans, plasma concentration and urinary excretion of azelaic acid are not significantly different from baseline levels.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 170(SRC), determined from a log Kow of 1.57(2) and a regression-derived equation(3), indicates that 1,7-heptanecarboxylic acid is expected to have moderate mobility in soil(SRC). The pKa of 1,7-heptanecarboxylic acid is 4.55(4), indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization from moist soil is not expected because the acid exists as an anion and anions do not volatilize. 1,7-Heptanecarboxylic acid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.07X10-8 mm Hg(6). Biodegradation data were not available(SRC, 2008) but straight chain carboxylic acids are expected to readily biodergade(7).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 170(SRC), determined from a log Kow of 1.57(2) and a regression-derived equation(3), indicates that 1,7-heptanecarboxylic acid is expected to adsorb to suspended solids and sediment(SRC). A pKa of 4.55(4) indicates 1,7-heptanecarboxylic acid will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(5). According to a classification scheme(6), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2008) but straight chain carboxylic acids are expected to readily biodergade(8).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,7-heptanecarboxylic acid, which has a vapor pressure of 1.07X10-8 mm Hg at 25 deg C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 1,7-heptanecarboxylic acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 40 hrs(SRC), calculated from its rate constant of 9.8X10-12 cu cm/molecule-sec at 25 deg C(SRC) that was derived using a structure estimation method(3). Particulate-phase 1,7-heptanecarboxylic acid may be removed from the air by wet or dry deposition(SRC). 1,7-Heptanecarboxylic acid does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

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