홈MCP워크벤치Skills
홈워크벤치알림마이페이지
Huagongshe 오픈 프로젝트：[email protected]AI 접속: llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.7.8
돌아가기
Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
HCID 2266생성일: 2026년 10월 27일

노난디 산

노난디산 · 아젤라익애씨드 · 아젤라산 · NONANEDIOIC ACID · azelaic · Azelex · ANCHOIC ACID · Azelaic acid powder

https://huagongshe.com/ko/chemical/2266

노난디 산 분자 구조식

식별자 및 물리적 특성

CAS No.123-99-9
분자식C9H16O4
평균 분자량188.22 g/mol
단동위원소 질량188.10485899 g/mol
SMILESO=C(O)CCCCCCCC(=O)O
InChIKeyBDJRBEYXGGNYIS-UHFFFAOYSA-N
PubChem CID2266
ChEMBLCHEMBL1238
ChEBICHEBI:48131
EC No.204-669-1
DTXSIDDTXSID8021640
현지명노난디 산

화학 및 물리적 성질

XLogP1.6
극성 표면적74.6
수소 결합 공여자 수2
수소 결합 수용자 수4
회전 가능 결합 수8
무거운 원자 수13
형식 전하0
복잡도147
물질 분류Other Classes -> Organic Acids
의약품PharmaceuticalsPharmaceuticals -> Listed in ZINC15
지질Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Dicarboxylic acids [FA0117]
화장품Cosmetic ingredients (Azelaic Acid) -> CIR (Cosmetic Ingredient Review)Buffering
향료Fragrance
LogP(분배 계수)log Kow = 1.57
밀도1.225 g/cu cm at 25 °C1,029 g/cm3
향미제EU Flavoring substances
Color/FormMonoclinic prismatic needlesYellowish to white crystalline powderLeaflets or needles
용해도Slightly soluble in ethy ether, benzene, DMSOsoluble in ethanolSoluble in hot water, alcohol and organic solventsOne liter of water dissolves 1.0 g at 1.0 °C2.4 g at 20 °C8.2 g at 50 °C22 g at 50 °C ... 1000 g ether dissolves 18.8 g at 11 °C and 26.8 g at 15 °CIn water, 2.40X10+3 mg/L at 20 °C2.4 mg/mL2.4g/L
인화점210 °C (closed cup)215 °C
Human DrugsBreast FeedingLactationMilk, HumanAntineoplastic AgentsDermatologic AgentsFDA approved drugs -> Active ingredient
녹는점98 °C
끓는 점286 °C100 mm Hg(lit.)
증기 밀도6.5 (vs air)
증기압<1 mm Hg ( 20 °C)
굴절률1.4303
저장 조건Store below +30°C.
물리적 상태약간의 결정성 분말 또는 플레이크
pKa(산도 계수)4.53, 5.33(at 25℃)
색상흰색에서 약간 노란색
pH3.5 (1g/l, H2O)
용해도2.4g/L(20℃)
Merck14,905
BRN1101094
헨리 상수8.9×107 mol/(m3Pa) at 25℃, Compernolle and Müller (2014)
안정성안정적인. 타기 쉬운. 염기, 강한 산화제와 호환되지 않습니다. 28일 후 70% 이상의 DOC 감소로 토양과 물에서 쉽게 생분해됩니다.
화장품 원료 기능향기버퍼링
InChI1S/C9H16O4/c10-8(11)6-4-2-1-3-5-7-9(12)13/h1-7H2,(H,10,11)(H,12,13)
InChIKeyBDJRBEYXGGNYIS-UHFFFAOYSA-N
SMILESOC(=O)CCCCCCCC(O)=O
LogP(분배 계수)1.57 at 25℃
NISTNonanedioic acid(123-99-9)
EPAAzelaic acid (123-99-9)

화학적 성질

Azelaic acid is an organic compound with the formula (CH2)7(CO2H)2. This saturated dicarboxylic acid exists as a white powder. It is found in wheat, rye, and barley. It is a component of a number of hair and skin conditioners.

안전 및 규제

GHS 분류This chemical does not meet GHS hazard criteria for 6.5% (71 of 1087) of reports.WarningH315 (40.2%): Causes skin irritation [Warning Skin corrosion/irritation]P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)Aggregated GHS information provided per 1087 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
규제 정보Chemical: Nonanedioic acidCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Nonanedioic acid is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Nonanedioic acid are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 27-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/13411Azelaic acid: Does not have an individual approval but may be used under an appropriate group standard
기타 안전 정보Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
화재 가능성Slightly flammable to flammable in presence of heat.
유해성 요약Linear alkyl diacids cluster: Group members and supporting chemicals demonstrate eye irritation in rabbitsno evidence of skin sensitizationlow oral repeated dose systemic toxicity and developmental toxicityno adverse effects to reproductive organs in repeated-dose studiesno evidence of mutagenicity[EPA ChAMP: Hazard Characterization] May cause irritation[Acros Organics MSDS]
FDA 요건The 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.
EPA Safer Chemical

용도

개요

Azelaic acid is a topical antiacne agent which exerts its therapeutic action through a myriad of antimicrobial, antiproliferative and cytostatic effects. In vitro, azelaic acid hasbeen shown to inhibit DNA polymerases in several tumor cell lines.

용도

Azelaic acid is used in lacquers, alkyd resins, plasticizers, adhesives, polyamides, urethane elastomers, and organic syntheses. Azelaic acid is also used in treating of acne.

일반 설명

Azelaic acid is used as a therapeutic agent in dermatology.

제조 및 합성 방법

생산 방법

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.

제조 방법

Azelaic acid is made by the ozonolysis of oleic acid:

Chemical: Azelaic acid
Hazard Classes and CategoriesSkin Irrit. 2 (40.2%)
Skin, Eye, and Respiratory IrritationsSkin: May cause mild skin irritation. Eyes: May cause mild eye irritation. Inhalation: May cause respiratory tract irritation.
Hazardous Reactivities and IncompatibilitiesReactive with oxidizing agents.
소화 절차SMALL FIRE: Use DRY chemical powder. LARGE FIRE: Use water spray, fog or foam. Do not use water jet.
보관 조건Precautions: Keep away from heat. Keep away from sources of ignition. Ground all equipment containing material. Do not ingest. Do not breathe dust. If ingested, seek medical advice immediately and show the container or the label. Keep away from incompatibles such as oxidizing agents. Storage: Keep container tightly closed. Keep container in a cool, well-ventilated area. Sensitive to light. Store in light-resistant containers.
정리 방법Small 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.
처리 방법SRP: 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.
Preventive MeasuresSRP: 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.
Personal Protective Equipment (PPE)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 sufficientconsult 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.
상호 작용The cytotoxic effect of azelaic acid on murine melanoma cells in culture is due, at least in part, to an antimitochondrial action. ...The possibility that the addition of carnitine to the medium may increase the transport of azelaic acid into the mitochondria and thereby increase its cytotoxic effect /was investigated/. Using mitochondrial cross-sectional area measured from electron micrographs as a criterion for mitochondrial damage, /it was/ found that the addition of L-carnitine to the culture medium had no effect either alone or with a low (10-3 M) concentration of azelaic acid. At a high concentration (5 X 10-2 M) azelaic acid caused swelling and disruption of the mitochondria to such an extent that this was not increased by carnitine. At 10-2 M azelaic acid, however, some swelling of the mitochondria occurred which was significantly increased by the addition of carnitine. This indicates that carnitine-mediated transport of the diacid into the mitochondria had occurred. ...Carnitine may reduce the time or concentration needed for azelaic acid to have a toxic effect on the malignant melanocyte.Chemotherapy for melanoma results in low response and must be reinforced with sensitizer compounds. We believed that azelaic acid (AZA) could modulate melanomas' resistance to antineoplastics. Therefore we tried to compare in vitro treatment with antineoplastics alone versus AZA treatment followed by antineoplastics. We carried out MTT assays to evaluate the cytotoxicity of melphalan, lomustine (CCNU), fotemustine, and 4-Hydroxyanisole (4-HA) on three melanoma lines (B16F10, SK-MEL-28, and SK-MEL-1), and the modulating effect of pretreatment with AZA (1 mM). AZA showed a dose-dependent antineoplastic activity on the three lines. Melphalan was the most active drug followed by CCNU, fotemustine, and 4-HA. The most sensitive line was B16F10 and the least sensitive was SK-meL-1. Previous treatment with AZA of B16F10 reinforced the effect of melphalan (2.5 times), CCNU (10 times), and fotemustine (14 times)whereas for SK-MEL-28 and SK-MEL-1, only the cytotoxicity of CCNU and fotemustine increased. An antagonist effect was produced by 4-HA on all three lines. We concluded that AZA enhances in vitro cytotoxicity of CCNU and fotemustine.
환경 거동TERRESTRIAL 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 °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 °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).
노출 경로Approximately 4% of the topically applied azelaic acid is systemically absorbed.
Milk ConcentrationsEquilibrium dialysis was used to assess human milk partitioning in vitro. At an 1,7-heptanecarboxylic 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 1,7-heptanecarboxylic acid into maternal milk is not expected to cause a significant change from baseline 1,7-heptanecarboxylic acid levels in the milk.
독성 요약Safe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.orgThe exact mechanism of action of azelaic acid is not known. It is thought that azelaic acid manifests its antibacterial effects by inhibiting the synthesis of cellular protein in anaerobic and aerobic bacteria, especially <i>Staphylococcus epidermidis</i> and <i>Propionibacterium acnes</i>. In aerobic bacteria, azelaic acid reversibly inhibits several oxidoreductive enzymes including tyrosinase, mitochondrial enzymes of the respiratory chain, thioredoxin reductase, 5-alpha-reductase, and DNA polymerases. In anaerobic bacteria, azelaic acid impedes glycolysis. Along with these actions, azelaic acid also improves acne vulgaris by normalizing the keratin process and decreasing microcomedo formation. Azelaic acid may be effective against both inflamed and noninflamed lesions. Specifically, azelaic acid reduces the thickness of the stratum corneum, shrinks keratohyalin granules by reducing the amount and distribution of filaggrin (a component of keratohyalin) in epidermal layers, and lowers the number of keratohyalin granules.
Effluent Concentrations1,7-Heptanecarboxylic acid was detected in automobile exhausts from a 1982 Toyota Corolla Model 1.8 Liter gasoline engine and a 1971 Mercedes Benz 220 Model 2.2 Liter diesel engine which was rebuilt in 1982, at 3.9 and 51 nmol/cu m, respectively(1).1,7-Heptanecarboxylic acid was identified as a directly emitted component in gas and particulate phases of pinene photooxidation aerosol products over a forest area at concentrations of 2.59 (6AM-12PM), 0.69 (12PM-6PM), 0.22 (6PM-6AM) ng/cu m, respectivelyin aerosols - 0.47 (6AM-12PM), 0.16 (12PM-6PM), 0.31 (6PM-6AM) ng/cu m, respectively(1).
Soil Adsorption/MobilityThe Koc of 1,7-heptanecarboxylic acid is estimated as 170(SRC), using a log Kow of 1.57(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 1,7-heptanecarboxylic acid is expected to have moderate mobility in soil. The pKa of 1,7-heptanecarboxylic acid is 4.55(4), indicating that this compound will almost entirely exist 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).
Natural Pollution SourcesOccurs in rancid oleic acid
Atmospheric ConcentrationsURBAN/SUBURBAN: 1,7-Heptanecarboxylic acid exhibited seasonal variations in the atmosphere in Tokyo, Japan, as evidenced by concentrations ranging from 6.9 to 73 ng/cu m in samples collected from 1988-1989(1). 1,7-Heptanecarboxylic acid was detected in air samples from west Los Angeles, CA at concentrations of 0.12, 0.04, 0.07, 0.09, 0.11, 0.03, 0.02 and 0.15 nmol/cu m, on Jun 12, Jun 13-14, Oct 20-22, Oct 24, Oct 24-25, Oct 25-26, Oct 26-29 and Oct 29-30, 1984, respectively(2). It was detected in air samples from downtown Los Angeles, CA at concentrations of 0.27 and 0.13 nmol/cu m, on Oct 24 and Oct 24-25, 1984, respectively(2). 1,7-heptanecarboxylic acid was tested for in 12 air samples from various locations in southern California as part of that area's Children's Health Study (SCCHS) in 1995concentrations of 0.9, 0.93, 0.35, 0.87, 0.76, 0.25, 1.07 ,1.28, 0.95, 0.92, 0.61 and 1.3 ng/cu m from an Alpine location, Atascadero, Lake Arrowhead, Lake Elsinore, Lancaster, Lompoc, Long Beach, Mira Loma, Riverside, San Dimas, Santa Maria and an Upland locations were reported(3). Sources quantified were gasoline-powered motor vehicle exhaust, diesel vehicle exhaust, wood smoke, vegetative detritus, tire wear and natural gas combustion(3). 1,7-Heptanecarboxylic acid was detected in 4 samples collected in winter and summer of 1992 in Tokyo, Japan at concentrations of 41, 46 ng/cu m (February 24-26), 43 and 48 ng/cu m (July 22-23)(4).INDOOR: 1,7-Heptanecarboxylic acid was detected in air samples from a greenhouse in Los Angeles, CA at concentrations of 0.03 nmol/cu m, sampled on Dec 12, 1984it was not detected on Dec 13, 1984(1).
Human Toxicity Excerpts/HUMAN EXPOSURE STUDIES/ 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./HUMAN EXPOSURE STUDIES/ Six healthy male volunteers received a single topical treatment with 5 g of an anti-acne cream containing 20% azelaic acid onto the face, the chest and the upper back. One week later 1 g of azelaic acid 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 azelaic acid from the cream was assessed to 3.6% of the dermally applied dose./SIGNS AND SYMPTOMS/ Acute Potential Health Effects: Skin: May cause mild skin irritation. Eyes: May cause mild eye irritation. Inhalation: May cause respiratory tract irritation. Ingestion: May cause digestive tract irritation./ALTERNATIVE and IN VITRO TESTS/ The effects of zinc sulfate and azelaic acid on 5 alpha-reductase activity in human skin were studied using an in vitro assay with 1,2[3H]-testosterone as substrate. When added at concentrations of 3 or 9 mmol/L, zinc was a potent inhibitor of 5 alpha-reductase activity. At high concentrations, zinc could completely inhibit the enzyme activity. Azelaic acid was also a potent inhibitor of 5 alpha-reductaseinhibition was detectable at concentrations as low as 0.2 mmol/L and was complete at 3 mmol/L. An additive effect of the two inhibitors was observed. Vitamin B6 potentiated the inhibitory effect of zinc, but not of azelaic acid, suggesting that two different mechanisms are involved. When the three substances were added together at very low concentrations which had been shown to be ineffective alone, 90% inhibition of 5 alpha-reductase activity was obtained. If this inhibition is confirmed in vivo, zinc sulfate combined with azelaic acid could be an effective agent in the treatment of androgen related pathology of human skin.
Artificial Pollution Sources1,7-Heptanecarboxylic acid's production and use in organic synthesis, lacquers, alkyd resins, polyamides, polyester adhesives, low-temperature plasticizers and in urethane elastomers(1) may result in its release to the environment through various waste streams(SRC).
Environmental BiodegradationAEROBIC: Biodegradation data for 1,7-heptanecarboxylic acid were not available(SRC, 2008) but straight chain carboxylic acids are expected to readily biodergade(1).
수질 위해 등급(WGK)1
TSCA 등재 상태TSCA listed
RTECS 번호CM1980000
독성LD50 orally in Rabbit: > 4000 mg/kg LD50 dermal Rat > 10 g/kg
관세 코드29171390
위험 문구(R)36/37/38
위험 표시Xi
안전 문구(S)24/25-36-26
기존화학 물질KE-26092
위험 등급Eye Irrit. 2Skin Irrit. 2
저장 분류11 - Combustible Solids
유해 물질 데이터123-99-9(Hazardous Substances Data)