Record Information
Version1.0
Creation date2010-04-08 22:04:45 UTC
Update date2020-04-21 18:04:07 UTC
Primary IDFDB000882
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSalicylic acid
DescriptionPreservative, fungicide (superseded), prohibited in milk and wine Salicylic acid is a colorless, crystalline organic carboxylic acid. Salicylic acid is toxic if ingested in large quantities, but in small quantities is used as a food preservative and antiseptic in toothpaste. It is also the key additive in many skin-care products for the treatment of acne, psoriasis, callouses, corns, keratosis pilaris and warts. The carboxyl group (COOH) can react with alcohols, forming several useful esters. The name derives from the latin word for the willow tree (Salix), from whose bark it can be obtained.; --Wikipedia; 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. Salicylic acid is found in many foods, some of which are sourdock, horned melon, sesame, and cloud ear fungus.
CAS Number69-72-7
Structure
Thumb
Synonyms
SynonymSource
2-CarboxyphenolChEBI
2-HYDROXYBENZOIC ACIDChEBI
O-CarboxyphenolChEBI
O-Hydroxybenzoic acidChEBI
2-HYDROXYBENZOateGenerator
O-HydroxybenzoateGenerator
SalicylateGenerator
2-HydroxybenzenecarboxylateHMDB
2-Hydroxybenzenecarboxylic acidHMDB
Advanced pain relief callus removersHMDB
Advanced pain relief corn removersHMDB
Clear away wart removerHMDB
Compound WHMDB
Dr. scholl's callus removersHMDB
Dr. scholl's corn removersHMDB
Dr. scholl's wart remover kitHMDB
Duofil wart removerHMDB
DuoplantHMDB
FreezoneHMDB
IonilHMDB
Ionil plusHMDB
K 537HMDB
K 557HMDB
Phenol-2-carboxylateHMDB
Phenol-2-carboxylic acidHMDB
Psoriacid-S-stiftHMDB
Retarder WHMDB
RutranexHMDB
Salicylic acid collodionHMDB
Salicylic acid soapHMDB
SaligelHMDB
SalonilHMDB
Stri-dexHMDB
trans-Ver-salHMDB
2 Hydroxybenzoic acidHMDB
Acid, O-hydroxybenzoicHMDB
O Hydroxybenzoic acidHMDB
Acid, 2-hydroxybenzoicHMDB
Ortho hydroxybenzoic acidHMDB
Acid, salicylicHMDB
Acid, ortho-hydroxybenzoicHMDB
Ortho-hydroxybenzoic acidHMDB
SAPhytoBank
2 Hydroxybenzoic Acidbiospider
2-Hydroxybenzoatebiospider
54-21-7 (SODIUM SALT)biospider
Acid, 2-Hydroxybenzoicbiospider
Acid, o-hydroxybenzoicbiospider
Acido salicilicobiospider
Acidum salicylicumbiospider
Alpha/beta hydroxy acids (glycolic acid, salicylic acid)biospider
Benzoic acid, 2-hydroxy-biospider
Benzoic acid, 2-hydroxy- (9CI)biospider
Benzoic acid, o-hydroxy-biospider
Compound wbiospider
Domerinebiospider
DR. scholl's callus removersbiospider
DR. scholl's corn removersbiospider
DR. scholl's wart remover kitbiospider
Duofilmbiospider
Ionil-plusbiospider
Keralytbiospider
O hydroxybenzoic acidbiospider
O-carboxyphenolbiospider
O-hydroxybenzoatebiospider
O-hydroxybenzoic acidbiospider
Occlusalbiospider
Orthohydroxybenzoic acidbiospider
Pernoxbiospider
phenol derivative, 7biospider
Psoriacid-s-stiftbiospider
Retarder saxbiospider
Retarder wbiospider
SALbiospider
Salicyclic acidbiospider
Salicylic aciddb_source
Salicylic acid (6CI,8CI)biospider
Salicylic acid (see also alpha hydroxy acids)biospider
Salicylic acid [usan:jan]biospider
Salicylic acid, acsbiospider
SAXbiospider
Sebucarebiospider
Sebulexbiospider
Trans-ver-salbiospider
Verrugonbiospider
Predicted Properties
PropertyValueSource
Water Solubility11.3 g/LALOGPS
logP1.96ALOGPS
logP1.98ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)2.79ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.3 m³·mol⁻¹ChemAxon
Polarizability12.81 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC7H6O3
IUPAC name2-hydroxybenzoic acid
InChI IdentifierInChI=1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)
InChI KeyYGSDEFSMJLZEOE-UHFFFAOYSA-N
Isomeric SMILESOC(=O)C1=CC=CC=C1O
Average Molecular Weight138.122
Monoisotopic Molecular Weight138.031694053
Classification
Description belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentSalicylic acids
Alternative Parents
Substituents
  • Salicylic acid
  • Benzoic acid
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Vinylogous acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Foods
  • Cocoa and cocoa products
  • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionC 60.87%; H 4.38%; O 34.75%DFC
    Melting PointMp 159°DFC
    Boiling PointBp20 211°DFC
    Experimental Water Solubility2.24 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
    Experimental logP2.26HANSCH,C ET AL. (1995)
    Experimental pKapKa2 13.6 (25°)DFC
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV Data302 () (MeOH) (Berdy)DFC
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    Spectra
    Spectrum TypeDescriptionSplash KeyView
    GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-014i-3890000000-62eae168a9d7ab3ada6fJSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00du-9700000000-e1e2ee6b61d86c596403JSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-3890000000-62eae168a9d7ab3ada6fJSpectraViewer | MoNA
    GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-2960000000-1b6b46cbb2b643b71448JSpectraViewer | MoNA
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0079-8900000000-e8ee46d81fcc1ce3766eJSpectraViewer
    Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-006x-8950000000-9ed3a56f2b2654ba281fJSpectraViewer
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-059j-9600000000-54545731fceee84be340JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00xu-9500000000-2f1c989b672669aaf083JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0gb9-9000000000-a0049e982e8ecd7ab730JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0900000000-f1e71df6894bcc8dda74JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-9200000000-f9fd317c182ec7ca90dcJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-9000000000-2b17aea4ee0ddd6321cfJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-320b7cd879b61439cf42JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-7d1b96d60026076a7eccJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-002b-0496100000-97708001d2a6d031beffJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-002b-0496100000-97708001d2a6d031beffJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-002b-0496100000-97708001d2a6d031beffJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0900000000-f88c693bac9b89416a52JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-00di-0900000000-2aeace8112266d938c2bJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9400000000-b0fb5458dfa73429b976JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9400000000-b0fb5458dfa73429b976JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9100000000-237ee14e8af5262c0dabJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9000000000-3ec5d7a9114e37b8af2aJSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9000000000-d8fdab29114453b10280JSpectraViewer | MoNA
    LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9000000000-4a337e3639c9f42a9000JSpectraViewer | MoNA
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2900000000-23d1cf43d4dedc979389JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0076-8900000000-f8b39b175209523386d0JSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-549ee40f4c3d2a965b2dJSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-6900000000-06bd3bf75f92d507fd8dJSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9100000000-fd107d170618784f2f1fJSpectraViewer
    Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-3fc7a3b941f5e3e4f7ddJSpectraViewer
    MSMass Spectrum (Electron Ionization)splash10-00du-9600000000-6d4a0ff2d48d814b5c54JSpectraViewer | MoNA
    1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
    1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
    1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
    2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
    2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
    ChemSpider ID331
    ChEMBL IDCHEMBL424
    KEGG Compound IDC00805
    Pubchem Compound ID338
    Pubchem Substance IDNot Available
    ChEBI ID16914
    Phenol-Explorer ID428
    DrugBank IDDB00936
    HMDB IDHMDB01895
    CRC / DFC (Dictionary of Food Compounds) IDBLP36-T:BLP36-T
    EAFUS ID3361
    Dr. Duke IDO-HYDROXYBENZOIC-ACID|SALICYLIC-ACID
    BIGG IDNot Available
    KNApSAcK IDC00000206
    HET IDSAL
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDrw1097271
    SuperScent IDNot Available
    Wikipedia IDSalicylic acid
    Phenol-Explorer Metabolite ID428
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / Bioactivities
    DescriptorIDDefinitionReference
    aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
    analgesic35480 An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.DUKE
    anti arthritic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
    anti dandruffDUKE
    anti dermatotic50177 A drug used to treat or prevent skin disorders or for the routine care of skin.DUKE
    anti eczemic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    anti ichthyosicDUKE
    anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
    anti neuralgic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    anti oncychomycoticDUKE
    antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
    anti periodicDUKE
    anti podagricDUKE
    anti psoriac52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    anti pyretic35493 A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.DUKE
    anti rheumatic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    anti seborrheic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
    antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    anti tympaniticDUKE
    cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
    comedolyticDUKE
    cyclooxygenase-2 inhibitor50629 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.DUKE
    cyclooxygenase inhibitor35544 A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.DUKE
    dermatitigenicDUKE
    fungicide24127 A substance used to destroy fungal pests.DUKE
    hypoglycemic35526 A drug which lowers the blood glucose level.DUKE
    insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
    keratolyticDUKE
    pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
    thermogenicDUKE
    tineacide52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
    ulcerogenicDUKE
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    Flavours
    FlavorCitations
    faint
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    phenolic
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    nutty
    1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
    Files
    MSDSshow
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
    — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.