Salicylic acid

Salicylic acid
Skeletal formula of salicylic acid
Skeletal formula of salicylic acid
Ball-and-stick model of salicylic acid
Ball-and-stick model of salicylic acid
Salicylic acid
Names
Preferred IUPAC name
2-Hydroxybenzoic acid[1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.648 Edit this at Wikidata
EC Number
  • 200-712-3
KEGG
RTECS number
  • VO0525000
UNII
  • InChI=1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10) checkY
    Key: YGSDEFSMJLZEOE-UHFFFAOYSA-N checkY
  • InChI=1/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)
    Key: YGSDEFSMJLZEOE-UHFFFAOYAQ
  • O=C(O)c1ccccc1O
Properties
C7H6O3
Molar mass 138.122 g/mol
Appearance Colorless to white crystalline powder
Odor Odorless
Density 1.443 g/cm3 (20 °C)[2]
Melting point 158.6 °C (317.5 °F; 431.8 K)
Boiling point 211 °C (412 °F; 484 K)
at 20 mmHg[2][3]
Sublimes at 76 °C[3]
  • 1.24 g/L (0 °C)
  • 2.48 g/L (25 °C)
  • 4.14 g/L (40 °C)
  • 17.41 g/L (75 °C)[3]
  • 77.79 g/L (100 °C)[4]
Solubility Soluble in ether, CCl4, benzene, propanol, acetone, ethanol, oil of turpentine, toluene
Solubility in benzene
  • 0.46 g/100 g (11.7 °C)
  • 0.775 g/100 g (25 °C)
  • 0.991 g/100 g (30.5 °C)
  • 2.38 g/100 g (49.4 °C)
  • 4.4 g/100 g (64.2 °C)[3][4]
Solubility in chloroform
  • 2.22 g/100 mL (25 °C)[4]
  • 2.31 g/100 mL (30.5 °C)[3]
Solubility in methanol
  • 40.67 g/100 g (−3 °C)
  • 62.48 g/100 g (21 °C)[3]
Solubility in olive oil 2.43 g/100 g (23 °C)[3]
Solubility in acetone 39.6 g/100 g (23 °C)[3]
log P 2.26
Vapor pressure 10.93 mPa[3]
Acidity (pKa)
  1. 2.97 (25 °C)[5]
  2. 13.82 (20 °C)[3]
UV-vis (λmax) 210 nm, 234 nm, 303 nm (4 mg/dL in ethanol)[3]
−72.23·10−6 cm3/mol
1.565 (20 °C)[2]
2.65 D
Thermochemistry
−589.9 kJ/mol
-3.025 MJ/mol[6]
Pharmacology
A01AD05 (WHO) B01AC06 (WHO) D01AE12 (WHO) N02BA01 (WHO) S01BC08 (WHO)
Hazards
Occupational safety and health (OHS/OSH):
Eye hazards
 Severe irritation
Skin hazards
 Mild irritation
GHS labelling:[7]
GHS05: Corrosive GHS07: Exclamation mark
Danger
H302, H318
P280, P305+P351+P338
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Flash point 157 °C (315 °F; 430 K)
closed cup[3]
540 °C (1,004 °F; 813 K)[3]
Lethal dose or concentration (LD, LC):
480 mg/kg (mice, oral)
Safety data sheet (SDS) MSDS[dead link]
Related compounds
Related compounds
 Methyl salicylate,
Benzoic acid,
Phenol, Aspirin,
4-Hydroxybenzoic acid,
Magnesium salicylate,
Choline salicylate,
Bismuth subsalicylate,
Sulfosalicylic acid,
Salicylate synthase
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Salicylic acid is an organic compound with the formula HOC6H4COOH.[3] A colorless (or, white), bitter-tasting solid, it is a precursor to and a metabolite of acetylsalicylic acid (aspirin).[3] It is a plant hormone,[8] and has been listed by the EPA Toxic Substances Control Act (TSCA) Chemical Substance Inventory as an experimental teratogen.[9] The name is from Latin salix for willow tree, from which it was initially identified and derived. It is an ingredient in some anti-acne products. Salts and esters of salicylic acid are known as salicylates.[3]

  1. ^ "Front Matter". Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 64. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  2. ^ a b c Haynes WM, ed. (2011). CRC Handbook of Chemistry and Physics (92nd ed.). Boca Raton, FL: CRC Press. p. 3.306. ISBN 1-4398-5511-0.
  3. ^ a b c d e f g h i j k l m n o p "Salicylic acid". PubChem, US National Library of Medicine. 19 Nov 2023. Retrieved 19 Nov 2023.
  4. ^ a b c Atherton Seidell, William F. Linke (1952). Solubilities of Inorganic and Organic Compounds: A Compilation of Solubility Data from the Periodical Literature. Supplement to the third edition containing data published during the years 1939–1949. Van Nostrand.
  5. ^ Wishart DS, Djombou Feunang Y, Guo AC, Lo EJ, Marcu A, Grant JR, Sajed T, Johnson D, Li C, Sayeeda Z, Assempour N, Iynkkaran I, Liu Y, Maciejewski A, Gale N, Wilson A, Chin L, Cummings R, Le D, Pon A, Knox C, Wilson M. "Salycylic acid | DrugBank Online". DrugBank. 5.0.
  6. ^ "Salicylic acid". Archived from the original on 2017-02-15. Retrieved 2014-08-17.
  7. ^ Sigma-Aldrich Co., Salicylic acid.
  8. ^ Boullard O, Leblanc H, Besson B (2000). "Salicylic Acid". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a23_477. ISBN 3-527-30673-0.
  9. ^ Lewis Sr RJ (2008). Hazardous Chemicals Desk Reference. John Wiley & Sons. p. 1217. ISBN 978-0-470-33445-4.