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Salicylic acid (YMDB01322)

Identification
YMDB IDYMDB01322
NameSalicylic acid
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionSalicylic acid, also known as ionil or 2-carboxyphenol, belongs to the class of organic compounds known as salicylic acids. These are ortho-hydroxylated benzoic acids. Salicylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Salicylic acid exists in all living species, ranging from bacteria to humans. Salicylic acid is a potentially toxic compound.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 2-Carboxyphenol
  • 2-Hydroxybenzenecarboxylate
  • 2-Hydroxybenzenecarboxylic acid
  • 2-Hydroxybenzoate
  • 2-Hydroxybenzoic acid
  • Benzoic acid, 2-hydroxy-
  • Benzoic acid, o-hydroxy-
  • o-Carboxyphenol
  • o-Hydroxybenzoate
  • o-Hydroxybenzoic acid
  • Orthohydroxybenzoic acid
  • Phenol-2-carboxylate
  • Phenol-2-carboxylic acid
  • Psoriacid-S-Stift
  • Salicyclic acid
  • Salicylate
  • Salicylic acid
  • Saligel
  • Salonil
  • Trans-Ver-Sal
  • 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
  • Ionil plus
  • K 537
  • K 557
  • Retarder W
  • Rutranex
  • Salicylic acid collodion
  • Salicylic acid soap
  • Stri-dex
  • 2 Hydroxybenzoic acid
  • Acid, O-hydroxybenzoic
  • O Hydroxybenzoic acid
  • Acid, 2-hydroxybenzoic
  • Ortho hydroxybenzoic acid
  • Acid, salicylic
  • Acid, ortho-hydroxybenzoic
  • Ortho-hydroxybenzoic acid
CAS number69-72-7
WeightAverage: 138.1207
Monoisotopic: 138.031694058
InChI KeyYGSDEFSMJLZEOE-UHFFFAOYSA-N
InChIInChI=1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)
IUPAC Name2-hydroxybenzoic acid
Traditional IUPAC Namesalicylic
Chemical FormulaC7H6O3
SMILESOC(=O)C1=CC=CC=C1O
Chemical Taxonomy
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
Physical Properties
StateSolid
Charge0
Melting point158 °C
Experimental Properties
PropertyValueReference
Water Solubility2.24 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP2.26 [HANSCH,C ET AL. (1995)]PhysProp
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • extracellular
Organoleptic Properties
Flavour/OdourSource
FaintFDB000882
NuttyFDB000882
PhenolicFDB000882
SMPDB Pathways
Phenylalanine metabolismPW002437 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Phenylalanine metabolismec00360 Map00360
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot 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
References
References:
  • Okabe, Y., Katayama, N., Iwama, M., Watanabe, H., Ohgi, K., Irie, M., Nitta, K., Kawauchi, H., Takayanagi, Y., Oyama, F., et, a. l. .. (1991). "Comparative base specificity, stability, and lectin activity of two lectins from eggs of Rana catesbeiana and R. japonica and liver ribonuclease from R. catesbeiana." J Biochem 109:786-790.1917903
Synthesis Reference:Yin, Yingwu; Guo, Qingbin. Preparation of salicylic acid from phenol. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 7pp.
External Links:
ResourceLink
CHEBI ID16914
HMDB IDHMDB01895
Pubchem Compound ID338
Kegg IDC00805
ChemSpider ID331
FOODB IDFDB000882
WikipediaSalicylic acid
BioCyc IDCPD-110