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3-ヒドロキシアントラニル酸
3-ヒドロキシアントラニル酸 · 2-アミノ-3-ヒドロキシベンゼンカルボン酸 · 3-ヒドロキシ-2-アミノ安息香酸 · 2-アミノ-3-ヒドロキシ安息香酸 · 2-AMINO-3-HYDROXYBENZOIC ACID · 3-HYDROXY-ANTHRANILATE · 3-HYDROXYANTHRANILLIC ACID · 3-Ohaa
識別子と物理属性
| CAS No. | 548-93-6 |
|---|---|
| 分子式 | C7H7NO3 |
| 平均分子量 | 153.14 g/mol |
| 単同位体質量 | 153.04259308 g/mol |
| SMILES | Nc1c(O)cccc1C(=O)O |
| InChIKey | WJXSWCUQABXPFS-UHFFFAOYSA-N |
| PubChem CID | 86 |
| ChEMBL | CHEMBL445304 |
| ChEBI | CHEBI:15793 |
| EC No. | 208-962-5 |
| DTXSID | DTXSID40203290 |
| 現地名 | 3-ヒドロキシアントラニル酸 |
化学・物理的性質
| XLogP | 0.9 |
|---|---|
| 極性表面積 | 83.6 |
| 水素結合供与体数 | 3 |
| 水素結合受容体数 | 4 |
| 回転可能結合数 | 1 |
| 重原子数 | 11 |
| 形式電荷 | 0 |
| 複雑度 | 160 |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| Color/Form | LEAFLETS IN WATER |
| 溶解度 | SLIGHTLY SOL IN WATER, SOL IN HOT WATER, ALCOHOL, ETHERSOL IN CHLOROFORMDMSO（微量）、メタノール（微量、加温） |
| 融点 | 164 °C240 °C (dec.)(lit.) |
| Physical Description | Solid |
| Collision Cross Section | 131.2 Ų [M+H]+ [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]131.3 Ų [M+H]+ |
| 沸点 | 276.03°C (rough estimate) |
| 密度 | 1.3585 (rough estimate) |
| 屈折率 | 1.5500 (estimate) |
| 貯蔵条件 | Keep in dark place,Sealed in dry,Room Temperature |
| 外観・状態 | 液体または低融点固体 |
| pKa（酸解離定数） | pK1: 2.5(+1)pK2: 5.192(0)pK3: 10.118(OH) (25°C) |
| 色 | 無色透明～白色～黄色～橙色 |
| 主な用途 | ペプチド合成 |
| InChI | InChI=1S/C7H7NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,9H,8H2,(H,10,11) |
| InChIKey | WJXSWCUQABXPFS-UHFFFAOYSA-N |
| SMILES | C(O)(=O)C1=CC=CC(O)=C1N |
| CAS データベース | 548-93-6(CAS DataBase Reference) |
安全性と法規制
| GHS 分類 | WarningH302 (97.6%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 41 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (97.6%) |
| 相互作用 | TRYPTOPHAN ADMIN RAISED OUTPUT OF FREE FORM /OF 3-HYDROXYANTHRANILIC ACID/ PRINCIPALLY IN HUMAN URINE...EFFECT OF CIGARETTE SMOKING ON (CARCINOGEN) 3-HYDROXY ANTHRANILIC ACID EXCRETION WAS STUDIED ON 20 NORMAL INDIVIDUALS IN FASTING STATE. SMOKING INCR EXCRETION OF THIS METABOLITE IN URINE SIGNIFICANTLY. |
| Human Toxicity Excerpts | SINCE FREE FORM WITH CARCINOGENIC POTENTIAL WAS EXCRETED...& INCR ONLY IN SUBJECTS TREATED WITH TRYPTOPHAN, RELATIONSHIP /WITH/...CARCINOGENESIS... RELEVANT TO MAN. ... INTAKE OF TRYPTOPHAN &/OR RATE OF TRYPTOPHAN METAB... IMPORTANT, SINCE RATES OF HYDROLYSIS OF 3-HYDROXYANTHRANILIC ACID CONJUGATES ARE TOO SLOW...PATTERNS OF URINARY EXCRETION OF FREE & CONJUGATED FORMS OF 3-HYDROXYANTHRANILIC ACID CHANGE STRIKINGLY IN DIFFERENT SPECIES OF MAMMALS, & THIS MAY BE IMPORTANT SINCE 3-HYDROXYANTHRANILIC ACID, A TRYPTOPHAN METABOLITE, IS SUSPECTED OF CAUSING BLADDER CANCER.THE POSSIBLE ROLE OF ENDOGENOUS TRYPTOPHAN METABOLITES & OF 1 TYROSINE METABOLITE IN INDUCING BLADDER CANCER IN HUMANS IS DISCUSSED. |
| Non-Human Toxicity Excerpts | ...REPORTED TO INDUCE CHROMATID BREAKS IN CULTURED HUMAN EMBRYO CELLS @ CONCN OF 30 MG/L. ONE CHROMOSOME TRANSLOCATION WAS OBSERVED IN 338 METAPHASE CELLS EXAMINEDNONE WERE SEEN IN 300 CONTROL METAPHASE CELLS.CARCINOGENIC EFFECT WAS SHOWN BY 3-HYDROXYANTHRANILIC ACID IMPLANTED INTO THE BLADDER WALL IN MICE.RESULTS DID NOT SUPPORT HYPOTHESIS THAT TRYPTOPHAN METABOLITES PRODUCED BY INTESTINAL MICROFLORA ARE MAJOR ETIOLOGIC FACTORS IN CANCER OF COLON, THEY WERE NEG IN AMES TEST.3-HYDROXYANTHRANILIC ACID ADMIN SC TO MICE @ 2.5 MG TWICE WEEKLY FOR 10 WK INDUCED TUMORS IN THE URINARY BLADDER.PRESENCE OF 20% 3-HYDROXYANTHRANILIC ACID IN THE PELLETS MADE NO CHANGE IN THE INCIDENCE OF TUMORS. |
| Probable Routes of Human Exposure | HYDROXYANTHRANILIC ACID WAS FOUND IN BOTH SERUM & BLOOD CLOTS OF WORKERS CONTACTING ANILINE DYES. |
| 水環境危害等級（WGK） | 3 |
| RTECS 番号 | DG2625000 |
| 税関コード | 29225000 |
| 危険文句（R） | 20/21/22-36/37/38-40 |
| 危険表示 | Xn |
| 安全措置（S） | 22-26-36 |
| 危険等級 | Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralCarc. 2Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
| 貯蔵分類 | 11 - Combustible Solids |
| 有害物質データ | 548-93-6(Hazardous Substances Data) |
用途
使用
3-Hydroxyanthranilic Acid is one of the tryptophan’s metabolites along the kynurenine pathway. 3-Hydroxyanthranilic Acid has been shown to induce apoptosis in T cells.
製法・合成法
純化方法
The hydrochloride has m 227o (from dilute HCl). [Beilstein 14 H 587, 14 III 1463, 14 IV 2071.] Possible carcinogen.