Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
코직산
코직산 · 코직애씨드 · kojic acid powder · kojic · 5-HYDROXY-2-(HYDROXYMETHYL)-4H-PYRAN-4-ONE · KAD · 4H-Pyran-4-one, 5-hydroxy-2-(hydroxymethyl)- · Kojic acid 99%
식별자 및 물리적 특성
| CAS No. | 501-30-4 |
|---|---|
| 분자식 | C6H6O4 |
| 평균 분자량 | 142.11 g/mol |
| 단동위원소 질량 | 142.02660867 g/mol |
| SMILES | O=c1cc(CO)occ1O |
| InChIKey | BEJNERDRQOWKJM-UHFFFAOYSA-N |
| PubChem CID | 3840 |
| ChEMBL | CHEMBL287556 |
| ChEBI | CHEBI:43572 |
| EC No. | 207-922-4 |
| DTXSID | DTXSID2040236 |
| 현지명 | 코직산 |
화학 및 물리적 성질
| XLogP | -0.9 |
|---|---|
| 극성 표면적 | 66.8 |
| 수소 결합 공여자 수 | 2 |
| 수소 결합 수용자 수 | 4 |
| 회전 가능 결합 수 | 1 |
| 무거운 원자 수 | 10 |
| 형식 전하 | 0 |
| 복잡도 | 214 |
| 의약품 | Pharmaceuticals -> Listed in ZINC15 |
| 화장품 | Cosmetic ingredients (Kojic Acid) -> CIR (Cosmetic Ingredient Review)Antioxidant |
| SpringerMaterials Properties | Crystal structure |
| LogP(분배 계수) | log Kow = -0.64 |
| Color/Form | Prismatic needles from acetone, ethanol+ether or methanol+ethyl acetateCrystalsPrisms, needles from acetone |
| 용해도 | Soluble in ethanol, ethyl ether, acetone, DMSOslightly soluble in benzeneSoluble in water, acetoneslightly solluble in etherinsoluble in benzeneSparingly soluble in pyridineDMSO(약간 용해됨), 메탄올(약간 용해됨, 초음파처리) |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| 녹는점 | 153.5 °C161 °C152-155 °C (lit.) |
| Physical Description | Solid |
| Dissociation Constants | pKa = 7.66 (approx., at 25 °C) |
| Collision Cross Section | 121.9 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| 끓는 점 | 179.65°C (rough estimate) |
| 밀도 | 1.1712 (rough estimate) |
| 굴절률 | 1.4434 (estimate) |
| 저장 조건 | Store below +30°C. |
| 물리적 상태 | 결정성 분말 |
| pKa(산도 계수) | 7.9(at 25℃) |
| 색상 | 흰색에서 베이지색 갈색 |
| 용해도 | 녹는 |
| Merck | 14,5317 |
| BRN | 120895 |
| 헨리 상수 | 4.1×101 mol/(m3Pa) at 25℃, HSDB (2015) |
| 안정성 | 안정적인. 타기 쉬운. 강한 산화제와 호환되지 않습니다. |
| 주요 응용 | 청소용품화장품음식 및 음료개인 위생 관리 |
| 화장품 원료 기능 | 항산화제피부의 멜라닌 생성을 줄입니다 |
| InChI | 1S/C6H6O4/c7-2-4-1-5(8)6(9)3-10-4/h1,3,7,9H,2H2 |
| InChIKey | BEJNERDRQOWKJM-UHFFFAOYSA-N |
| SMILES | OCC1=CC(=O)C(O)=CO1 |
| LogP(분배 계수) | -0.640 |
| NIST | 5-Hydroxy-2-(hydroxymethyl)-4h-pyran-4-one(501-30-4) |
| EPA | Kojic acid (501-30-4) |
화학적 성질
tan powder
안전 및 규제
| GHS 분류 | This chemical does not meet GHS hazard criteria for 86.2% (69 of 80) of all reports.WarningH351 (13.8%): Suspected of causing cancer [Warning Carcinogenicity]P203, P280, P318, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 80 reports by companies from 4 notifications to the ECHA C&L Inventory. |
|---|---|
| 규제 정보 | 4H-Pyran-4-one, 5-hydroxy-2-(hydroxymethyl)-: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Carc. 2 (13.8%) |
| 처리 방법 | 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. |
| 상호 작용 | Kojic acid (5-hydroxy-2-hydroxymethyl-gamma-pyrone) is a bacterial metabolic product used intensively in the food industry. In the presence of visible light and molecular oxygen it was found to cause breakage of calf thymus DNA. Such degradation was considerably enhanced in the presence of the transition metal ions Fe(III), Fe(II) and Cu(II). The cleavage of DNA in the presence of Fe(III) did not appear to have any preferred site(s) or sequence(s) for strand scission. Kojic acid catalysed the reduction of transition metal which in the case of Cu(II) was found to play an essential role in the degradation of DNA. Kojic acid also reduced oxygen to superoxide and hydroxyl radicals were formed in the presence of metal ions. The involvement of these active oxygen species in the reaction was established by the inhibition of DNA breakage by superoxide dismutase, catalase, iodide, mannitol, formate and sodium azide.... The anti-wrinkling activity of kojic acid /was evaluated/ by using hairless mice exposed to chronic solar-simulating ultraviolet (UV) irradiation as a model animal. At the end of a 20-week irradiation period, topical application of kojic acid before UV irradiation was observed to dramatically prevent: (1) the wrinkling, (2) hyperplasia of the epidermis, (3) fibrosis of the lower dermis, and (4) the increase of extracellular matrix components in the upper dermis. These findings indicate that kojic acid is a typical agent preventing wrinkling of the skin due to chronic photodamage.The individual and combined effects of kojic acid and aflatoxin were studied in male broiler chicks (Peterson x Hubbard). The experiment had a two by two factorial arrangement of treatments with dietary treatments of 0 and 2,500 mg kojic acid/kg feed and 0 and 2.5 mg aflatoxin/kg feed. The broilers were obtained at 1 day of age and housed in electrically heated batteries with feed and water available for ad libitum intake until they reached 3 wk of age. The toxicity of kojic acid was characterized by significant (P less than .05) reductions in body weight, the relative weight of the bursa of Fabricius, serum cholesterol concentration, and serum alkaline phosphatase activity, and by significant (P less than .05) increases in the relative weight of the pancreas, proventriculus, and gizzard, and serum concentrations of uric acid and triglycerides. Aflatoxicosis was characterized by significant (P less than .05) reductions in body weight, serum concentrations of total protein, albumin, cholesterol, and inorganic phosphorus, serum glutamic oxalacetic transaminase activity, and mean corpuscular volume, mean corpuscular hemoglobin, and mean corpuscular hemoglobin concentration. Significant (P less than .05) increases in the relative weight of the liver, kidney, spleen, pancreas, proventriculus, and heart, and the serum pyruvic transaminase activity were also caused by aflatoxin alone. The only significant (P less than .05) interaction between kojic acid and aflatoxin, which can best be described as antagonistic, was seen through an increase in mean corpuscular hemoglobin and mean corpuscular hemoglobin concentration. These data indicate that kojic acid is not an aflatoxin synergist at the levels used in the present study. |
| 건강 영향 | Animals studies have shown that kojic acid increases the occurrence of thyroid cancer and thyroid adenomas, though it is not known whether this is also true in humans. (A3073) |
| 환경 거동 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 11(SRC), determined from a log Kow of -0.64(2) and a regression-derived equation(3), indicates that kojic acid is expected to have very high mobility in soil(SRC). Volatilization of kojic acid from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.4X10-7 atm-cu m/mole(SRC), using a fragment constant estimation method(4). Kojic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.2X10-6 mm Hg(SRC), determined from a fragment constant method(5). Biodegradation data were not available(SRC, 2008).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 11(SRC), determined from a log Kow of -0.64(2) and a regression-derived equation(3), indicates that kojic acid is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.4X10-7 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2008).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), kojic acid, which has an estimated vapor pressure of 3.2X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase kojic 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 6 hours(SRC), calculated from its rate constant of 6.4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Vapor-phase kojic acid is degraded in the atmosphere by reaction with ozone radicals(SRC)the half-life for this reaction in air is estimated to be 21 hours(SRC), calculated from its rate constant of 1.3X10-17 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase kojic acid may be removed from the air by wet or dry deposition(SRC). Kojic acid contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC). |
| 식품 조사 수치 | Kojic acid is a fungal metabolite commonly produced by many species of Aspergillus, Acetobacter, and Penicillium. The Aspergillus flavus group has traditionally been used in the production of a number of foods, including miso (soybean paste), shoyu (soy sauce), and sake.... Because kojic acid is often produced during the fermentation of historically used dietary staples, it has a long history of consumption. |
| 노출 경로 | Oral, dermal, inhalation, and parenteral (contaminated drugs). (A3101) |
| 독성 요약 | The CIR Expert Panel concluded that kojic acid is safe for use in cosmetic products up to a concentration of 1%.Safe for use in cosmetics, with qualificationsKojic acid acts as a competitive and reversible inhibitor of animal and plant polyphenol oxidases (tyrosinases), xanthine oxidase, and D- and some L-amino acid oxidases. Inhibition of tyrosinases prevents melanosis, while inhibition of the oxidases prevents metabolism of certain amino acids. Kojic acid also reversibly affects thyroid function by inhibiting iodine uptake, leading to decreases in thyroid hormones T3 and T4 and increases in thyroid-stimulating hormone (TSH). Increased TSH from pituitary gland in turn stimulates thyroid hyperplasia. (A3073, A3074) |
| Signs and Symptoms | Sensitive individuals may develop contact dermatitis. (A3073) |
| Soil Adsorption/Mobility | The Koc of kojic acid is estimated as 11(SRC), using a log Kow of -0.64(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that kojic acid is expected to have very high mobility in soil. |
| Natural Pollution Sources | Kojic acid is a fungal metabolite commonly produced by many species of Aspergillus, Acetobacter, and Penicillium. ... Different Aspergillus species are known to produce variable amounts of kojic acid.Kojic acid is an antibiotic substance produced in an aerobic process by a variety of microorganisms from a wide-range of carbon sources(1). |
| Human Toxicity Excerpts | /ALTERNATIVE and IN VITRO TESTS/ To discover safe and effective topical skin-lightening agents ... alkyl esters of the natural product gentisic acid (GA) ... , four putative tyrosinase inhibitors, /were evaluated/ utilizing mammalian melanocyte cell cultures and cell-free extracts. Desirable characteristics include the ability to inhibit melanogenesis in cells (IC50 less than 100 ug/mL) without cytotoxicity, preferably due to tyrosinase inhibition. Of the six esters synthesized, the smaller esters (e.g. methyl and ethyl) were more effective enzyme inhibitors (IC50 approximately 11 and 20 ug/mL, respectively). For comparison, hydroquinone (HQ), a commercial skin "bleaching" agent, was a less effective enzyme inhibitor (IC50 approximately 72 ug/mL), and was highly cytotoxic to melanocytes in vitro at concentrations substantially lower than the IC50 for enzymatic inhibition. Kojic acid was a potent inhibitor of the mammalian enzyme (IC50 approximately 6 ug/mL), but did not reduce pigmentation in cells. Both arbutin and magnesium ascorbyl phosphate were ineffective in the cell-free and cell-based assays... . |
| Artificial Pollution Sources | Kojic acid's production and use as a flavoring agent, food additive(1), chemical intermediate and antimicrobial(2) may result in its release to the environment through various waste streams(SRC). |
| Carcinogen Classification | Kojic acidGroup 3: Not classifiable as to its carcinogenicity to humansVolume 79: (2001) Some Thyrotropic Agents20003, not classifiable as to its carcinogenicity to humans. (L135) |
| 수질 위해 등급(WGK) | 3 |
| RTECS 번호 | UQ0875000 |
| 관세 코드 | 29329995 |
| 위험 문구(R) | 40-68 |
| 위험 표시 | Xn |
| 안전 문구(S) | 22-24/25-36/37-36 |
| 기존화학 물질 | 2014-3-5741 |
| 저장 분류 | 11 - Combustible Solids |
| 유해 물질 데이터 | 501-30-4(Hazardous Substances Data) |
용도
용도
kojic acid is a skin-lightening agent that acts through anti-oxidant activity. Kojic acid is a tyrosinase inhibitor, although it is not as effective as licorice extract. When combined with allantoin and other proper ingredients in sunscreen preparations, the mixture can inhibit uV-caused erythema and accelerate wound healing. It is also found to be skin sensitizing and can be irritating.
일반 설명
Kojic acid, a tyrosinase inhibitor, is produced by several fungi species, including Aspergillus oryzae. It exhibits skin-lightening property, due to its ability to chelate the copper-containing enzyme tyrosinase in the formation of melanin. Kojic acid is also commonly used as a whitening agent in regular cosmetics, bleaching cosmetics, etc. It is found to be a therapeutic agent and helps in preventing pigmentation.