チオサリチル酸
チオサリチル酸 · 2-メルカプト安息香酸 · o-スルフヒドリル安息香酸 · o-チオサリチル酸 · o-メルカプト安息香酸 · チオサリチル酸 メルカプト安息香酸 · 2-スルファニル安息香酸 · 2-MERCAPTOBENZOIC ACID
識別子と物理属性
| CAS No. | 147-93-3 |
|---|---|
| 分子式 | C7H6O2S |
| 平均分子量 | 154.19 g/mol |
| 単同位体質量 | 154.00885043 g/mol |
| SMILES | O=C(O)c1ccccc1S |
| InChIKey | NBOMNTLFRHMDEZ-UHFFFAOYSA-N |
| PubChem CID | 5443 |
| ChEMBL | CHEMBL119888 |
| ChEBI | CHEBI:59124 |
| EC No. | 205-704-3 |
| DTXSID | DTXSID4049032 |
| 現地名 | チオサリチル酸 |
化学・物理的性質
| XLogP | 2.4 |
|---|---|
| 極性表面積 | 38.3 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 1 |
| 重原子数 | 10 |
| 形式電荷 | 0 |
| 複雑度 | 136 |
| 物質分類 | Other Classes -> Benzoic Acid Derivatives |
| 医薬品 | Pharmaceuticals -> Listed in ZINC15 |
| 化粧品 | AntioxidantKeratolyticReducing |
| SpringerMaterials Properties | Chemical shift |
| Color/Form | SULFUR-YELLOW FLAKES, PLATES, NEEDLES FROM GLACIAL ACETIC ACID OR ALCOHOLLEAVES OR NEEDLES FROM WATERCRYSTALS /SODIUM SALT/ |
| 溶解度 | SOL IN WATER /SODIUM SALT/SOL IN HOT WATER, ALCOHOL, ETHER, ACETIC ACIDSLIGHTLY SOLUBLE IN PETROLEUM ETHERDMSO（微量）、メタノール（微量）熱湯に溶ける |
| 融点 | 168-169 °C162-165 °C (lit.) |
| Physical Description | Sulfur-yellow solidSlightly soluble in hot water[Merck Index] Yellow powder, soluble in water[MSDSonline] |
| Stability/Shelf Life | EXPOSURE TO AIR YIELDS DITHIOSALICYLIC ACID |
| Other Experimental Properties | WHEN AN ALCOHOLIC SOLN OF THIOSALICYLIC ACID COMES IN CONTACT WITH FERRIC CHLORIDE, DITHIOSALICYLIC ACID IS PRODUCEDSOFTENS AT 158 °CSUBLIMES |
| 沸点 | 247.55°C (rough estimate) |
| 密度 | 1.49 |
| 屈折率 | 1.5100 (estimate) |
| 引火点 | 150 °C |
| 貯蔵条件 | Store below +30°C. |
| pKa（酸解離定数） | pK1:4.05(0) (20°C) |
| 外観・状態 | 微結晶性粉末 |
| 色 | 白から黄色 |
| Merck | 14,9360 |
| BRN | 508507 |
| 化粧品成分の機能 | 還元剤抗酸化物質角質溶解性 |
| InChI | 1S/C7H6O2S/c8-7(9)5-3-1-2-4-6(5)10/h1-4,10H,(H,8,9) |
| InChIKey | NBOMNTLFRHMDEZ-UHFFFAOYSA-N |
| SMILES | OC(=O)c1ccccc1S |
| LogP（分配係数） | 2.390 |
| CAS データベース | 147-93-3(CAS DataBase Reference) |
| NISTの化学物質情報 | Benzoic acid, 2-mercapto-(147-93-3) |
| EPAの化学物質情報 | Benzoic acid, 2-mercapto- (147-93-3) |
化学的特性
Thiosalicylic acid, (o-mercapto benzoic acid), a sulfur-yellow solid that softens at 158 °C (316 °F), has a melting point of 164 °C (327 °F). It sublimes, is slightly soluble in hot water but freely soluble in glacial acetic acid and alcohol, and yields dithiosalicylic acid, upon exposure to air.
安全性と法規制
| GHS 分類 | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 50 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Chemical: Benzoic acid, 2-mercapto-Thiosalicylic acid: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Skin Irrit. 2 (100%) |
| Protective Action Criteria (PAC) | 0.16 [mg/m3]1.8 [mg/m3]11 [mg/m3] |
| Non-Human Toxicity Excerpts | UNCOUPLING OF OXIDATIVE PHOSPHORYLATION IN RAT LIVER MITOCHONDRIA WAS INVESTIGATED WITH THIO ANALOGS OF SALICYLIC ACID. SIGNIFICANT ACTIVITY WAS OBSERVED. |
| F | 9-23 |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | DH3325000 |
| 毒性 | mouse,LD50,intraperitoneal,50mg/kg (50mg/kg),National Technical Information Service. Vol. AD277-689, |
| 税関コード | 29309070 |
| 危険文句（R） | 36/37/38-20/21/22 |
| 化審法 | (3)-1657 |
| 危険表示 | Xi,Xn,N |
| 安全措置（S） | 26-36/37/39-36 |
| 危険等級 | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
| 貯蔵分類 | 11 - Combustible Solids |
| 有害物質データ | 147-93-3(Hazardous Substances Data) |
用途
解説
C6H4(SH)COOH．一般にチオサリチル酸とよばれるが，サリチル酸のどの酸素が硫黄に置き換わったのかはっきりしないので，安息香酸のオルト位に－SHが置換したことを示す名称が正式名とされている．分析試薬として，また医薬や染料合成の原料として使われる．
用途
分析試薬、医薬・染料中間体、重金属キレート剤、塩ビ安定剤、感光性樹脂原料。
使用
Thiosalicylic acid acts as a trapping agent, which is useful in the desulfenylation of 3-indolyl sulfides. It is used to prepare macrocyclic diamides by condensation with diamines. Further, it is used as a precursor to drug, which finds application for the treatment of atherosclerosis and melanoma. In addition to this, it is involved in the preparation of vaccine preservative thiomersal and thioindigo dyestuff.
製法・合成法
製造方法
Thiosalicylic acid can be prepared from anthranilic acid via diazotization followed by the addition of sodium sulfide and then reduction with zinc. It can also prepared by heating o-halogenated benzoic acids with alkaline hydrosulfide in presence of copper.
合成方法
2-ハロ安息香酸と水硫化ナトリウムとの反応
純化方法
Crystallise the thio acid from hot EtOH (4mL/g), after adding hot distilled water (8mL/g) and boiling with charcoal. The hot solution is filtered, cooled, the solid is collected and dried in vacuo (P2O5). Crystallise it from AcOH and sublime in vacuo.[Beilstein 10 IV 272.]