2-hydroxybenzoic acid

• ChemBase ID: 812
• Molecular Formular: C7H6O3
• Molecular Mass: 138.12074
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxybenzoic acid
• IUPAC Traditional name: salicylic; salicyclic acid
• Brand Name: 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
• Synonyms: 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; 2-羟基苯甲酸; 水杨酸; 水杨酸; 水杨酸, ACS

Database IDs

• CAS Number: 69-72-7
• EC Number: 200-712-3
• MDL Number: MFCD00002439
• Beilstein Number: 774890
• Merck Index: 148332
• PubChem SID: 24899745; 24854876; 24888186; 24846714; 24899681; 24856524; 46504942; 24901960; 160964275
• PubChem CID: 338
• CHEBI ID: 16914
• ATC CODE: B01AC06; S01BC08; N02BA01; A01AD05; D01AE12
• CHEMBL: 424
• Chemspider ID: 331
• DrugBank ID: DB00936
• FEMA ID: 3985
• KEGG ID: D00097
• Unique Ingredient Identifier: O414PZ4LPZ
• Wikipedia Title: Salicylic_acid
• Flavis Number: 8.112

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.7897391
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.6725287
• LogD (pH = 7.4): -1.5175761
• Log P: 1.9772635
• Molar Refractivity: 35.2951 cm^3
• Polarizability: 13.298781 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.96
• LOG S: -1.09
• Solubility (Water): 1.13e+01 g/l

PROPERTIES

Physical Property

• Solubility: 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
• Apperance: Powder; White Solid
• Melting Point: 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
• Boiling Point: 182 °C at 80 hPa; 211 °C(lit.); 211 °C/20 mmHg; 211°C (20 mmHg); 211°C/20mm; 211°C/20mm
• Flash Point: 157 °C (closed cup); 157 °C; 157°C; 157°C(315°F); 314.6 °F
• Auto Ignition Point: 545 °C; ca. 545 - 549 °C
• Density: 1.44; 1.443; 1.443 g/cm^3
• Vapor Pressure: .31 hPa at 95 °C; 1 mmHg ( 114 °C)
• Vapor Density: 4.8 (vs air)
• Hydrophobicity(logP): 2.4
• pKa: 2.97

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere; Room Temperature (15-30°C), Protect from light
• Storage Warning: Harmful/Irritant/Corrosive/Light Sensitive; Light Sensitive
• RTECS: VO0525000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 1
• Risk Statements: 22-37/38-41; 22-41; R:22-36/37/38; R22 R36 R38 R61
• Safety Statements: 26-36/37/39; 26-36/37/39-60; 26-39; S:25-26-36/37/39; S22 S26 S36 S37 S39
• TSCA Listed: 是
• EU Index: 200-712-3
• GHS Pictograms: GHS05; GHS06; GHS07
• GHS Signal Word: Danger
• NFPA704:
  

  1

  2

  0
• GHS Hazard statements: H301-H315-H335-H318; H302-H318
• GHS Precautionary statements: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A; P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Gene Information: human ... ALB(213), PTPN1(5770)
• Allergens: no known allergens

Product Information

• Purity: ≥98.0% (T); ≥99%; ≥99.0%; ≥99.0% (T); 95+%; 99%; 99.5-100.5% (calc. to the dried substance); 99+%
• Grade: ACS; ACS reagent; Halal; Kosher; Ph Eur; puriss. p.a.; purum; REAGENT; ReagentPlus®; SAJ first grade; TraceCERT®
• Suitability: complies for appearance of solution; complies for identity; plant cell culture tested
• Ignition Residue: ≤0.01%; ≤0.05% (as SO4)
• Impurities: ≤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
• Cation Traces: 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
• Antion Traces: chloride (Cl-): ≤0.001%; chloride (Cl-): ≤100 mg/kg; chloride (Cl-): ≤50 mg/kg; sulfate (SO42-): ≤0.003%; sulfate (SO42-): ≤200 mg/kg
• Loss on Drying: ≤0.3% loss on drying; ≤0.5% loss on drying
• Quality: meets analytical specification of Ph. Eur., BP, USP
• Pharmacopeia: testing & handling conforms to Pharmacopeia
• Pharmacopeia Traceability: traceable to BP 775; traceable to PhEur S020000; traceable to USP 1609002
• Linear Formula: 2-(HO)C6H4CO2H

DETAILS

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

Packaging
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.
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 105910

Packaging
3 kg in poly drum
500 g in poly bottle
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 247588

Packaging
100, 500 g in poly bottle

Toronto Research Chemicals - S088125

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

REFERENCES

• 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)