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Salicylic acid information


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
CAS Number
  • 69-72-7 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:16914 checkY
ChEMBL
  • ChEMBL424 checkY
ChemSpider
  • 331 checkY
DrugBank
  • DB00936
ECHA InfoCard 100.000.648 Edit this at Wikidata
EC Number
  • 200-712-3
IUPHAR/BPS
  • 4306
KEGG
  • D00097 checkY
PubChem CID
  • 338
RTECS number
  • VO0525000
UNII
  • O414PZ4LPZ checkY
CompTox Dashboard (EPA)
  • DTXSID7026368 Edit this at Wikidata
InChI
  • 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
SMILES
  • O=C(O)c1ccccc1O
Properties
Chemical formula
C7H6O3
Molar mass 138.122 g/mol
Appearance Colorless to white crystals
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]
Sublimation
conditions
Sublimes at 76 °C[3]
Solubility in water
  • 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]
Magnetic susceptibility (χ)
−72.23·10−6 cm3/mol
Refractive index (nD)
1.565 (20 °C)[2]
Dipole moment
2.65 D
Thermochemistry
Std enthalpy of
formation fH298)
−589.9 kJ/mol
Std enthalpy of
combustion cH298)
-3.025 MJ/mol[6]
Pharmacology
ATC code
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]
Pictograms
GHS05: Corrosive GHS07: Exclamation mark
Signal word
Danger
Hazard statements
H302, H318
Precautionary statements
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]
Autoignition
temperature
540 °C (1,004 °F; 813 K)[3]
Lethal dose or concentration (LD, LC):
LD50 (median dose)
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 ?)
Infobox references

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 (inactive 2024-04-11). ISBN 978-0-85404-182-4.{{cite book}}: CS1 maint: DOI inactive as of April 2024 (link)
  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.

and 25 Related for: Salicylic acid information

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Salicylic acid

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Salicylic acid is an organic compound with the formula HOC6H4COOH. A colorless (or, white), bitter-tasting solid, it is a precursor to and a metabolite...

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Medical uses of salicylic acid

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Salicylic acid is used as a medicine to help remove the outer layer of the skin. As such it is used to treat warts, skin tags, calluses, psoriasis, dandruff...

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Aspirin

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esterification reaction. Salicylic acid is treated with acetic anhydride, an acid derivative, causing a chemical reaction that turns salicylic acid's hydroxyl group...

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Acne

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applied directly to the affected skin, such as azelaic acid, benzoyl peroxide, and salicylic acid, are commonly used. Antibiotics and retinoids are available...

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Plant hormone

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abscisic acid, auxins, brassinosteroids, cytokinins and ethylene. This list was later expanded, and brassinosteroids, jasmonates, salicylic acid, and strigolactones...

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Plantar wart

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Treatment is only needed if it is causing symptoms. This may include salicylic acid, cryotherapy, chemo-based fluorouracil or bleomycin, and surgical removal...

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Wart

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months to years. A number of treatments may speed resolution, including salicylic acid applied to the skin and cryotherapy. In those who are otherwise healthy...

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Phenolates

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CH3I → C6H5OCH3 + NaI C6H5ONa + (CH3O)2SO2 → C6H5OCH3 + (CH3O)SO3Na Salicylic acid is produced in the Kolbe–Schmitt reaction between carbon dioxide and...

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History of aspirin

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1838 chemists identified salicylic acid in the bark of White Willow. After many years, it was synthesised as acetylsalicylic acid, now known as aspirin.'...

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Chemical peel

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treat acne.. Salicylic acid also has the ability to reduce the spots and bumps associated with acne. It is becoming common for beta hydroxy acid (BHA) peels...

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Azelaic acid

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after infection. It serves as a signal that induces the accumulation of salicylic acid, an important component of a plant's defensive response. The mechanism...

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Bismuth subsalicylate

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hydrolysis of bismuth salicylate (Bi(C6H4(OH)CO2)3). As a derivative of salicylic acid, bismuth subsalicylate displays anti-inflammatory and bactericidal action...

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Keratosis pilaris

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preparations of moisturizers and medications such as glycolic acid, lactic acid, salicylic acid, urea, or retinoids to the skin. Fractional carbon dioxide...

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Carboxylic acid

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production of vinegar. The Kolbe–Schmitt reaction provides a route to salicylic acid, precursor to aspirin. Preparative methods for small scale reactions...

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Cutibacterium acnes

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C. acnes. Some other antimicrobials like salicylic acid have been proven to inhibit C. acnes. Salicylic acid is a naturally occurring substance derived...

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Methyl salicylate

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organic compound with the formula C8H8O3. It is the methyl ester of salicylic acid. It is a colorless, viscous liquid with a sweet, fruity odor reminiscent...

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Salicylate poisoning

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the advantage of restoring electrolyte and acid-base abnormalities while removing salicylate. Salicylic acid has a small size (low molecular mass), has...

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Treatment of warts by keratolysis

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keratolytic treatment of warts available over-the-counter involves salicylic acid. These products are readily available at most drugstores and supermarkets...

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Dandruff

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dandruff. Antifungal cream, such as ketoconazole, or the keratolytic agent salicylic acid may be used to try to improve the condition. Dandruff affects about...

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Shilajit

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linoleic acid, lauric acid, saturated fatty acids), ichthyridine, salicylic acid, resins, triterpenes, sterols, aromatic carboxylic acids, 3,4-benzocoumarins...

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Sodium salicylate

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Sodium salicylate is a sodium salt of salicylic acid. It can be prepared from sodium phenolate and carbon dioxide under higher temperature and pressure...

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Willow

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Willows all have abundant watery bark sap, which is heavily charged with salicylic acid, soft, usually pliant, tough wood, slender branches, and large, fibrous...

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Carmex

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being metabolized into salicylic acid. It is often incorrectly thought to be a drying agent; however, this is not true. Salicylic acid works as a keratolytic...

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Neutrogena

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Salicylic Acid," while in the United Kingdom, they sell the "Clear & Defend 2% Salicylic Acid Face Wash." Although both products contain 2% salicylic...

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Keratolytic

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swelling and hydrolysis of skin), salicylic acid, urea, lactic acid, allantoin, glycolic acid, and trichloroacetic acid. While cytostatic agents such as...

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