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Salicylic acid (FDB000882)

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DescriptionPreservative, fungicide (superseded), prohibited in milk and wine Salicylic acid is a colorless, crystalline organic carboxylic acid.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
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
    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
    EI-MS/GC-MS
    TypeDescriptionSplash KeyView
    EI-MSMass Spectrum (Electron Ionization)splash10-00du-9600000000-6d4a0ff2d48d814b5c542014-09-20View Spectrum
    GC-MSSalicylic acid, 2 TMS, GC-MS Spectrumsplash10-014i-3890000000-62eae168a9d7ab3ada6fSpectrum
    GC-MSSalicylic acid, non-derivatized, GC-MS Spectrumsplash10-00du-9700000000-e1e2ee6b61d86c596403Spectrum
    GC-MSSalicylic acid, non-derivatized, GC-MS Spectrumsplash10-014i-3890000000-62eae168a9d7ab3ada6fSpectrum
    GC-MSSalicylic acid, non-derivatized, GC-MS Spectrumsplash10-014i-2960000000-1b6b46cbb2b643b71448Spectrum
    Predicted GC-MSSalicylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0079-8900000000-e8ee46d81fcc1ce3766eSpectrum
    Predicted GC-MSSalicylic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006x-8950000000-9ed3a56f2b2654ba281fSpectrum
    Predicted GC-MSSalicylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    Predicted GC-MSSalicylic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
    MS/MS
    TypeDescriptionSplash KeyView
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-059j-9600000000-54545731fceee84be3402012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-00xu-9500000000-2f1c989b672669aaf0832012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0gb9-9000000000-a0049e982e8ecd7ab7302012-07-24View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0900000000-f1e71df6894bcc8dda742012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-9200000000-f9fd317c182ec7ca90dc2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0006-9000000000-2b17aea4ee0ddd6321cf2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-320b7cd879b61439cf422012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0006-9000000000-7d1b96d60026076a7ecc2012-08-31View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-002b-0496100000-97708001d2a6d031beff2017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-002b-0496100000-97708001d2a6d031beff2017-08-14View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-002b-0496100000-97708001d2a6d031beff2017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0900000000-f88c693bac9b89416a522017-09-12View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9400000000-b0fb5458dfa73429b9762017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9400000000-b0fb5458dfa73429b9762017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9100000000-237ee14e8af5262c0dab2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9000000000-3ec5d7a9114e37b8af2a2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9000000000-d8fdab29114453b102802017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9000000000-4a337e3639c9f42a90002017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-9000000000-2deb0e843e099fdcea992017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00kf-9000000000-951b374b351c5534628a2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-014l-9000000000-4ea52d5aa4344a40c0072017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0900000000-f1e71df6894bcc8dda742017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9200000000-65f3f297188dc07b53be2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-2b17aea4ee0ddd6321cf2017-09-14View Spectrum
    MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-320b7cd879b61439cf422017-09-14View Spectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
    1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
    1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
    1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
    1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
    1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
    2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
    2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
    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.