2-hydroxybenzoic acid

• ChemBase编号: 812
• 分子式: C7H6O3
• 平均质量: 138.12074
• 单一同位素质量: 138.03169405
• SMILES: Oc1c(cccc1)C(=O)O
• Canonical SMILES: OC(=O)c1ccccc1O
• InChI: InChI=1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)
• InChIKey: YGSDEFSMJLZEOE-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-hydroxybenzoic acid
• IUPAC传统名: salicylic; salicyclic acid
• 商标名: Advanced pain relief callus removers; Advanced pain relief corn removers; Clear away wart remover; Compound W; Dr. Scholl's Callus Removers; Dr. Scholl's Corn Removers; Dr. Scholl's Wart Remover Kit; Duofil Wart Remover; Duoplant; Freezone; Ionil; Keralyt; Kyselina 2-hydroxybenzoova; Kyselina salicylova; Psoriacid-s-stift; Retarder SAX; Retarder W; Rutranex; SAX; Salicylic acid collodion; Salicylic acid soap; Saligel; Salonil; Stri-dex
• 别名: 2-羟基苯甲酸; 水杨酸; 水杨酸; 水杨酸, ACS; Salicylic acid; Acidum salicylicum; Salicylic acid 99%; Salicylic acid, ACS; 2-Hydroxybenzoic acid; Rutranex; Saligel; Salonil; Salvona Nanosal; Stri-Dex; Trans-Ver-Sal; Verrugon; SALICYLIC ACID, ACS; SALICYLIC ACID; 2-Carboxyphenol; 2-Hydroxybenzenecarboxylic acid; 2-Hydroxybenzoic acid; Acido salicilico; O-carboxyphenol; O-hydroxybenzoic acid; Orthohydroxybenzoic acid; Phenol-2-carboxylic acid; SA; Salicylate; Salicylic acid; Salicyclic acid

登记号

• CAS号: 69-72-7
• EC号: 200-712-3
• MDL号: MFCD00002439
• Beilstein号: 774890
• 默克索引号: 148332
• PubChem SID: 24856524; 24901960; 160964275; 24846714; 24899681; 24899745; 46504942; 24854876; 24888186
• PubChem CID: 338
• CHEBI ID: 16914
• ATC码: N02BA01; A01AD05; D01AE12; B01AC06; S01BC08
• CHEMBL: 424
• Chemspider ID: 331
• DrugBank ID: DB00936
• FEMA编号: 3985
• KEGG ID: D00097
• 美国药典/FDA物质标识码: O414PZ4LPZ
• 维基百科标题: Salicylic_acid
• Flavis Number: 8.112

理论计算性质

JChem

• Acid pKa: 2.7897391
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): -0.6725287
• LogD (pH = 7.4): -1.5175761
• Log P: 1.9772635
• 摩尔折射率: 35.2951 cm^3
• 极化性: 13.298781 Å^3
• 极化表面积: 57.53 Å^2
• 可自由旋转的化学键: 1
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.96
• LOG S: -1.09
• 溶解度: 1.13e+01 g/l

分子性质

理化性质

• 溶解度: 2 g/L (20 °C) in water; 2.24 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; 96% ethanol: soluble0.1 g/mL, clear; Chloroform; ethanol: soluble1 M at 20 °C, clear, colorless; Soluble in alcohol, acetone, ether. Slightly soluble in cold water. More soluble in boiling water. Water solubility increased by Na3PO4, alkali acetates or alkali citrates
• 外观: Powder; White Solid
• 熔点: 154-156°C; 158-160°C; 158-161 °C; 158-161 °C(lit.); 158-161°C; 158-162 °C; 159.0°C; ca. 157 - 159 °C with sublimation
• 沸点: 182 °C at 80 hPa; 211 °C(lit.); 211 °C/20 mmHg; 211°C (20 mmHg); 211°C/20mm; 211°C/20mm
• 闪点: 157 °C (closed cup); 157 °C; 157°C; 157°C(315°F); 314.6 °F
• 自燃点: 545 °C; ca. 545 - 549 °C
• 密度: 1.44; 1.443; 1.443 g/cm^3
• 蒸汽压: .31 hPa at 95 °C; 1 mmHg ( 114 °C)
• 蒸汽密度: 4.8 (vs air)
• 疏水性(logP): 2.4
• pKa: 2.97

安全信息

• 保存条件: Hygroscopic, Refrigerator, Under Inert Atmosphere; Room Temperature (15-30°C), Protect from light
• 保存注意事项: Harmful/Irritant/Corrosive/Light Sensitive; Light Sensitive
• RTECS编号: VO0525000
• 欧盟危险性物质标志: X; 有害性(Harmful) (Xn)
• 德国WGK号: 1
• 危险公开号: 22-37/38-41; 22-41; R:22-36/37/38; R22 R36 R38 R61
• 安全公开号: 26-36/37/39; 26-36/37/39-60; 26-39; S:25-26-36/37/39; S22 S26 S36 S37 S39
• TSCA收录: 是
• 欧盟危险品索引: 200-712-3
• GHS危险品标识: GHS05; GHS06; GHS07
• GHS警示词: Danger
• NFPA704:
  

  1

  2

  0
• GHS危险声明: H301-H315-H335-H318; H302-H318
• GHS警示性声明: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A; P280-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves

药理学性质

• 相关基因信息: human ... ALB(213), PTPN1(5770)
• 过敏源: no known allergens

产品相关信息

• 纯度: ≥98.0% (T); ≥99%; ≥99.0%; ≥99.0% (T); 95+%; 99%; 99.5-100.5% (calc. to the dried substance); 99+%
• 级别: ACS; ACS reagent; Halal; Kosher; Ph Eur; puriss. p.a.; purum; REAGENT; ReagentPlus®; SAJ first grade; TraceCERT®
• 适用性: complies for appearance of solution; complies for identity; plant cell culture tested
• 燃烧残渣: ≤0.01%; ≤0.05% (as SO4)
• 杂质: ≤0.001% heavy metals (as Pb); ≤0.005% Phosphorus (P); ≤0.1% Insoluble matter; ≤0.2% related subst. (HPLC); H2SO4, passes test(darkened); residual solvents, complies
• 痕量阳离子: Al: ≤0.005%; Ca: ≤0.0005%; Ca: ≤10 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤0.0005%; Cu: ≤5 mg/kg; Fe: ≤0.0005%; Fe: ≤2 ppm; Fe: ≤5 mg/kg; heavy metals (as Pb): ≤5 ppm; K: ≤0.005%; K: ≤50 mg/kg; Mg: ≤0.0005%; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Na: ≤0.01%; Na: ≤500 mg/kg; NH4+: ≤0.05%; Ni: ≤5 mg/kg; Pb: ≤0.001%; Pb: ≤5 mg/kg; Zn: ≤0.0005%; Zn: ≤5 mg/kg
• 痕量阴离子: chloride (Cl-): ≤0.001%; chloride (Cl-): ≤100 mg/kg; chloride (Cl-): ≤50 mg/kg; sulfate (SO42-): ≤0.003%; sulfate (SO42-): ≤200 mg/kg
• 干燥失重: ≤0.3% loss on drying; ≤0.5% loss on drying
• 品质说明: meets analytical specification of Ph. Eur., BP, USP
• 药典: testing & handling conforms to Pharmacopeia
• Pharmacopeia Traceability: traceable to BP 775; traceable to PhEur S020000; traceable to USP 1609002
• 线性分子式: 2-(HO)C6H4CO2H

详细说明

MP Biomedicals - 02191089

Free Acid
Purity: 99%
m.p. 177°C (dec)
CAUTION: STRONG IRRITANT!

MP Biomedicals - 02152570

ACS Reagent Grade
Melting Point: 158.0-161.0°C
CAUTION: STRONG IRRITANT!

DrugBank - DB00936

• Drug Groups: approved
• Description: A compound obtained from the bark of the white willow and wintergreen leaves, and also prepared synthetically. It has bacteriostatic, fungicidal, and keratolytic actions. Its salts, the salicylates, are used as analgesics.
• Indication: Key additive in many skin-care products for the treatment of acne, psoriasis, callouses, corns, keratosis pilaris and warts.
• Pharmacology: Salicylic acid treats acne by causing skin cells to slough off more readily, preventing pores from clogging up. This effect on skin cells also makes salicylic acid an active ingredient in several shampoos meant to treat dandruff. Use of straight salicylic solution may cause hyperpigmentation on unpretreated skin for those with darker skin types (Fitzpatrick phototypes IV, V, VI), as well as with the lack of use of a broad spectrum sunblock. Subsalicylate in combination with bismuth form the popular stomach relief aid known commonly as Pepto-Bismol. When combined the two key ingredients help control diarrhea, nausea, heartburn, and even gas. It is also very mildly anti-biotic.
• Toxicity: Oral rat LD50: 891 mg/kg. Inhalation rat LC50: > 900 mg/m3/1hr. Irritation: skin rabbit: 500 mg/24H mild. Eye rabbit: 100 mg severe. Investigated a mutagen and reproductive effector.
• Affected Organisms: Humans and other mammals
• References: Vane JR: Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs. Nat New Biol. 1971 Jun 23;231(25):232-5. [Pubmed] ; Flower R, Gryglewski R, Herbaczynska-Cedro K, Vane JR: Effects of anti-inflammatory drugs on prostaglandin biosynthesis. Nat New Biol. 1972 Jul 26;238(82):104-6. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - S5922

包装
100, 500 g in poly bottle

Sigma Aldrich - W398500

包装
1 kg in poly bottle
1 sample in glass bottle
10, 25 kg in fiber drum

Sigma Aldrich - 52341

General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
法律信息
TraceCERT 注册商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - 105910

包装
3 kg in poly drum
500 g in poly bottle
3kg 开口塑料桶包装；500g 塑料瓶包装
法律信息
ReagentPlus 注册商标 Sigma-Aldrich Co. LLC

Sigma Aldrich - 247588

包装
100, 500 g in poly bottle

Toronto Research Chemicals - S088125

Salicylic Acid is an impurity of Acetylsalicylic Acid (A187780). Acetylsalicylic acid Impurity B.

参考文献

• Flower R, Gryglewski R, Herbaczynska-Cedro K, Vane JR: Effects of anti-inflammatory drugs on prostaglandin biosynthesis. Nat New Biol. 1972 Jul 26;238(82):104-6. Pubmed
• Vane JR: Inhibition of prostaglandin synthesis as a mechanism of action for aspirin-like drugs. Nat New Biol. 1971 Jun 23;231(25):232-5. Pubmed
• Walter, M., et al.: Eur. J. Biochem., 1996, 239, 281 (1996)
• Bantignies, B., et al.: Plant Mol. Biol., 42, 871 (1996)
• Bais, H., et al.: J. Biol. Chem., 278, 32413 ( 2003), Finkler, C., et al.: Genetica, 124, 117 (1996)