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4-Hydroxybenzoic acid (YMDB00495)

Identification
YMDB IDYMDB00495
Name4-Hydroxybenzoic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description4-Hydroxybenzoic acid, also known as p-hydroxybenzoate or 4-carboxyphenol, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 4-Hydroxybenzoic acid exists in all living species, ranging from bacteria to plants to humans. In yeast, 4-hydroxybenzoic acid is involved in the metabolic pathway called the ubiquinone biosynthesis pathway. Based on a literature review a significant number of articles have been published on 4-Hydroxybenzoic acid.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • 4-Carboxyphenol
  • 4-hydroxy-benzoate
  • 4-Hydroxy-benzoesaeure
  • 4-hydroxy-benzoic acid
  • 4-Hydroxybenzoate
  • 4-Hydroxybenzoic acid
  • 4-hydroxybenzoic acid, ion(1-)
  • Benzoic acid, 4-hydroxy
  • Benzoic acid, 4-hydroxy-
  • Benzoic acid, p-hydroxy
  • Benzoic acid, p-hydroxy-
  • hydroxybenzenecarboxylic acid
  • hydroxybenzoic acid
  • Hydroxybenzoic acid, para
  • Kyselina 4-hydroxybenzoova
  • p-Carboxyphenol
  • p-hydroxy-Benzoate
  • p-hydroxy-Benzoic acid
  • p-Hydroxybenzoate
  • p-Hydroxybenzoic acid
  • p-Salicylate
  • p-Salicylic acid
  • para-Hydroxybenzoic acid
  • Paraben
  • Paraben-acid
  • Viminol 4-hydroxybenzoate
  • Hydroxybenzoate
  • Hydroxybenzenecarboxylate
  • 4-Hydroxybenzoic acid, calcium salt
  • 4-Hydroxybenzoic acid, dilithium salt
  • 4-Hydroxybenzoic acid, disodium salt
  • Sodium p-hydroxybenzoate tetrahydrate
  • 4-Hydroxybenzoic acid, copper(2+)(1:1) salt
  • 4-Hydroxybenzoic acid, dipotassium salt
  • 4-Hydroxybenzoic acid, monopotassium salt
  • 4-Hydroxybenzoic acid, monosodium salt
  • 4-Hydroxybenzoic acid, monosodium salt, 11C-labeled
  • 4-Hydroxybenzene carboxylic acid
  • p-Hydroxyl benzoic acid
CAS number99-96-7
WeightAverage: 138.1207
Monoisotopic: 138.031694058
InChI KeyFJKROLUGYXJWQN-UHFFFAOYSA-N
InChIInChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10)
IUPAC Name4-hydroxybenzoic acid
Traditional IUPAC NameP-hydroxybenzoic acid
Chemical FormulaC7H6O3
SMILESOC(=O)C1=CC=C(O)C=C1
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHydroxybenzoic acid derivatives
Alternative Parents
Substituents
  • Hydroxybenzoic acid
  • Benzoic acid
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 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 point214.5 °C
Experimental Properties
PropertyValueReference
Water Solubility5 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP1.58 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility11.9 g/LALOGPS
logP1.58ALOGPS
logP1.33ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)4.38ChemAxon
pKa (Strongest Basic)-6.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.3 m³·mol⁻¹ChemAxon
Polarizability12.94 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondrion
Organoleptic Properties
Flavour/OdourSource
NuttyFDB010508
PhenolicFDB010508
SMPDB Pathways
Phenylalanine metabolismPW002437 ThumbThumb?image type=greyscaleThumb?image type=simple
Ubiquinone BiosynthesisPW002473 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Phenylalanine metabolismec00360 Map00360
Ubiquinone and other terpenoid-quinone biosynthesisec00130 Map00130
SMPDB Reactions
4-Hydroxybenzoic acid + hexaprenyl diphosphate → 3-Hexaprenyl-4-hydroxybenzoic acid + Pyrophosphate
KEGG Reactions
water + 4-hydroxybenzoyl-CoA → 4-Hydroxybenzoic acid + hydron + Coenzyme A
nonaprenyl diphosphate + 4-Hydroxybenzoic acid ↔ Pyrophosphate + hydron + nonaprenyl 4-hydroxybenzoate
Chorismate → Pyruvic acid + 4-Hydroxybenzoic acid
hexaprenyl diphosphate + 4-Hydroxybenzoic acid → Pyrophosphate + 3-Hexaprenyl-4-hydroxybenzoic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-01b9-0490000000-89473836b0071542185eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-00xu-2890000000-dd5367ba838ccd5b29d8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-00di-9540000000-11db590137f79b7a32bfJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-00xu-3890000000-7e553522b6ec5c075e25JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00dr-5900000000-9b1d88421f1e1ded16f9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-9700000000-a9bb4b71d8b23a56ca67JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0079-6900000000-617d58eb059c1e918ca0JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00dr-4900000000-97bfa38b0d6bc152d470JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00dr-7900000000-290af590b1fc44a86969JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01b9-0490000000-d6001fb50397705d3e0bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-01b9-0490000000-89473836b0071542185eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00xu-2890000000-dd5367ba838ccd5b29d8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9540000000-11db590137f79b7a32bfJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-00xu-3890000000-7e553522b6ec5c075e25JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00xu-2980000000-0ba0ea7d63bd7fff3b22JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0079-5900000000-fcde26d72ca8445dff7eJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00xu-7950000000-cc553d409cc2a872749dJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000f-9400000000-9fb9f8fbd7cf90a88604JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0006-9000000000-f5d09d09184f72ec3bd7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0006-9000000000-d31cea608d0764edf5d0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positivesplash10-00dr-5900000000-9b1d88421f1e1ded16f9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positivesplash10-00di-9700000000-3ac766249fee4c68b8f4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positivesplash10-0079-6900000000-4e15a4102e0b3bc8ddceJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0a4r-9800000000-9e7208bfb79f9cca336bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4i-9000000000-1ed6d8123d44d126ed64JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9000000000-63a0e9c65e315bb89281JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-9000000000-a8befcaa45eced4a9a51JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9000000000-26788d399f2b459abc21JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0072-6900000000-ba06f5c422d59cd10ceaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0002-9100000000-193fd4eb0cf324fb3abcJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0006-9200000000-c834f7be13341f3e19b8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-00di-0900000000-4f58e660923e896589a3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4r-9800000000-9e7208bfb79f9cca336bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-1ed6d8123d44d126ed64JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-e80d9637393e63e2d07cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-a8befcaa45eced4a9a51JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0900000000-6351b89d53d1742a1fbbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-bdd873f3d1dc0f2af556JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00fu-9400000000-37262c1edda5dec21a19JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-3900000000-fcd512c9827982e7c9aaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000f-9600000000-36013030005316a50fabJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-5efa05442f95e2900559JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-00dr-6900000000-71548845dbf99346758dJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C 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:
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Hsu, A. Y., Do, T. Q., Lee, P. T., Clarke, C. F. (2000). "Genetic evidence for a multi-subunit complex in the O-methyltransferase steps of coenzyme Q biosynthesis." Biochim Biophys Acta 1484:287-297.10760477
  • He, B., Chen, P., Chen, S. Y., Vancura, K. L., Michaelis, S., Powers, S. (1991). "RAM2, an essential gene of yeast, and RAM1 encode the two polypeptide components of the farnesyltransferase that prenylates a-factor and Ras proteins." Proc Natl Acad Sci U S A 88:11373-11377.1763050
Synthesis Reference:Ivanov, G. E.; Slavcheva, L. Preparation, properties, and applications of p-hydroxy-benzoic acid. Khimiya i Industriya (1922-1988) (1966), 38(10), 458-63.
External Links:
ResourceLink
CHEBI ID30763
HMDB IDHMDB00500
Pubchem Compound ID135
Kegg IDC00156
ChemSpider ID132
FOODB IDFDB010508
Wikipedia4-Hydroxybenzoic_acid
BioCyc ID4-hydroxybenzoate

Enzymes

Protein Details
1. Para-hydroxybenzoate--polyprenyltransferase, mitochondrial
General function:
Involved in prenyltransferase activity
Specific function:
Catalyzes the prenylation of para-hydroxybenzoate (PHB) with an all-trans polyprenyl group. Mediates the second step in the final reaction sequence of coenzyme Q (CoQ) biosynthesis, which is the condensation of the polyisoprenoid side chain with PHB
Gene Name:
COQ2
Uniprot ID:
P32378
Molecular weight:
41001.0
Reactions
A polyprenyl diphosphate + 4-hydroxybenzoate → diphosphate + a 4-hydroxy-3-polyprenylbenzoate.
Protein Details
2. Protein farnesyltransferase subunit beta
General function:
Involved in catalytic activity
Specific function:
Catalyzes the transfer of a farnesyl moiety from farnesyl pyrophosphate to a cysteine at the fourth position from the C-terminus of several proteins such as a-factor and RAS. The beta subunit is responsible for peptide-binding
Gene Name:
RAM1
Uniprot ID:
P22007
Molecular weight:
48189.39844
Reactions
Farnesyl diphosphate + protein-cysteine → S-farnesyl protein + diphosphate.