ECMDB: 4-Hydroxybenzoic acid (ECMDB00500) (M2MDB000143)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (3)XML

Proteins (551)

Record Information

Version

2.0

Creation Date

2012-05-31 10:27:02 -0600

Update Date

2015-09-13 12:56:08 -0600

Secondary Accession Numbers

ECMDB00500

Identification

Name:

4-Hydroxybenzoic acid

Description

4-Hydroxybenzoic acid, or p-hydroxybenzoic acid, is a phenolic derivative of benzoic acid. It a white crystalline solid that is slightly soluble in water and chloroform, but well soluble in alcohols, ether, and acetone.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms:

4-Carboxyphenol
4-Hydroxy-benzoate
4-Hydroxy-benzoesaeure
4-Hydroxy-benzoic acid
4-Hydroxybenzoate
4-Hydroxybenzoic acid
p-hydroxybenzoate
P-Carboxyphenol
P-Hydroxy-Benzoate
P-Hydroxy-Benzoic acid
P-Hydroxybenzoate
P-Hydroxybenzoic acid
P-Salicylate
P-Salicylic acid
Paraben-acid
PHBA

Chemical Formula:

C₇H₆O₃

Weight:

Average: 138.1207
Monoisotopic: 138.031694058

InChI Key:

FJKROLUGYXJWQN-UHFFFAOYSA-N

InChI:

InChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10)

CAS number:

99-96-7

IUPAC Name:

4-hydroxybenzoic acid

Traditional IUPAC Name:

P-hydroxybenzoic acid

SMILES:

OC(=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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Hydroxybenzoic 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

monohydroxybenzoic acid (CHEBI:30763 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source
Water Solubility:	5.0 mg/mL [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP:	1.58 [HANSCH,C ET AL. (1995)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	11.9 g/L	ALOGPS
logP	1.58	ALOGPS
logP	1.33	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	4.38	ChemAxon
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	35.3 m³·mol⁻¹	ChemAxon
Polarizability	12.94 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

SMPDB Pathways:

Phenylalanine metabolism	PW000921
Secondary Metabolites: Ubiquinol biosynthesis	PW000981
Secondary Metabolites: Ubiquinol biosynthesis 2	PW002036

KEGG Pathways:

1,4-Dichlorobenzene degradation ec00627
Benzoate degradation via hydroxylation ec00362
Bisphenol degradation ec00363
Metabolic pathways eco01100
Microbial metabolism in diverse environments ec01120
Phenylalanine metabolism ec00360
Toluene degradation ec00623
Ubiquinone and other terpenoid-quinone biosynthesis ec00130

EcoCyc Pathways:

Not Available

Concentrations

Concentration	Strain	Media	Growth Status	Growth System	Temperature	Details
52± 0 uM	K12 NCM3722	Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose	Mid-Log Phase	Shake flask and filter culture	37 oC	PMID: 19561621
787± 0 uM	K12 NCM3722	Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glycerol	Mid-Log Phase	Shake flask and filter culture	37 oC	PMID: 19561621
294± 0 uM	K12 NCM3722	Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L acetate	Mid-Log Phase	Shake flask and filter culture	37 oC	PMID: 19561621

Find out more about how we convert literature concentrations.

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-01b9-0490000000-89473836b0071542185e	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00xu-2890000000-dd5367ba838ccd5b29d8	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00di-9540000000-11db590137f79b7a32bf	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-00xu-3890000000-7e553522b6ec5c075e25	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00dr-5900000000-9b1d88421f1e1ded16f9	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00di-9700000000-a9bb4b71d8b23a56ca67	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0079-6900000000-617d58eb059c1e918ca0	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00dr-4900000000-97bfa38b0d6bc152d470	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00dr-7900000000-290af590b1fc44a86969	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-01b9-0490000000-d6001fb50397705d3e0b	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-01b9-0490000000-89473836b0071542185e	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00xu-2890000000-dd5367ba838ccd5b29d8	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9540000000-11db590137f79b7a32bf	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00xu-3890000000-7e553522b6ec5c075e25	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00xu-2980000000-0ba0ea7d63bd7fff3b22	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0079-5900000000-fcde26d72ca8445dff7e	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00xu-7950000000-cc553d409cc2a872749d	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-000f-9400000000-9fb9f8fbd7cf90a88604	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0006-9000000000-f5d09d09184f72ec3bd7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0006-9000000000-d31cea608d0764edf5d0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positive	splash10-00dr-5900000000-9b1d88421f1e1ded16f9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-60) , Positive	splash10-00di-9700000000-3ac766249fee4c68b8f4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80) , Positive	splash10-0079-6900000000-4e15a4102e0b3bc8ddce	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0a4r-9800000000-9e7208bfb79f9cca336b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0a4i-9000000000-1ed6d8123d44d126ed64	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4i-9000000000-63a0e9c65e315bb89281	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a4i-9000000000-a8befcaa45eced4a9a51	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4i-9000000000-26788d399f2b459abc21	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0072-6900000000-ba06f5c422d59cd10cea	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0002-9100000000-193fd4eb0cf324fb3abc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0006-9200000000-c834f7be13341f3e19b8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-00di-0900000000-4f58e660923e896589a3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4r-9800000000-9e7208bfb79f9cca336b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-1ed6d8123d44d126ed64	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-e80d9637393e63e2d07c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-a8befcaa45eced4a9a51	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0079-0900000000-6351b89d53d1742a1fbb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1900000000-bdd873f3d1dc0f2af556	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00fu-9400000000-37262c1edda5dec21a19	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-3900000000-fcd512c9827982e7c9aa	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000f-9600000000-36013030005316a50fab	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-5efa05442f95e2900559	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-00dr-6900000000-71548845dbf99346758d	View in MoNA
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	View in JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. Pubmed: 8087979
Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Sakurai M, Ohsako M, Nagano M, Nakamura C, Tsuzuki O, Ichikawa M, Matsumoto Y: [Effect of human serum albumin on transport of drugs through human erythrocyte membranes] Yakugaku Zasshi. 1996 Aug;116(8):630-8. Pubmed: 8831264
Shibusawa H, Sano Y, Yamamoto T, Kambegawa A, Ohkawa T, Satoh N, Okinaga S, Arai K: A radioimmunoassay of serum 16alpha-hydroxypregnenolone with specific antiserum. Endocrinol Jpn. 1978 Apr;25(2):185-9. Pubmed: 668632
Soni MG, Burdock GA, Taylor SL, Greenberg NA: Safety assessment of propyl paraben: a review of the published literature. Food Chem Toxicol. 2001 Jun;39(6):513-32. Pubmed: 11346481
Soni MG, Taylor SL, Greenberg NA, Burdock GA: Evaluation of the health aspects of methyl paraben: a review of the published literature. Food Chem Toxicol. 2002 Oct;40(10):1335-73. Pubmed: 12387298
van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Wiebe LI, Mercer JR, Ryan AJ: Urinary metabolites of 3,5-di-(1-[13C]methyl-1-methylethyl)4-hydroxytoluene (BHT-13C) in man. Drug Metab Dispos. 1978 May-Jun;6(3):296-302. Pubmed: 26551
Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064

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.

Material Safety Data Sheet (MSDS)

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Links

External Links:

Resource	Link
CHEBI ID	30763
HMDB ID	HMDB00500
Pubchem Compound ID	135
Kegg ID	C00156
ChemSpider ID	132
Wikipedia	4-Hydroxybenzoic acid
BioCyc ID	4-hydroxybenzoate
EcoCyc ID	4-hydroxybenzoate
Ligand Expo	PHB

Enzymes

Protein Details

1. Chorismate--pyruvate lyase

General function:: Involved in chorismate lyase activity
Specific function:: Removes the pyruvyl group from chorismate, with concomitant aromatization of the ring, to provide 4- hydroxybenzoate (4HB) for the ubiquinone pathway
Gene Name:: ubiC
Uniprot ID:: P26602
Molecular weight:: 18777

Reactions

Chorismate = 4-hydroxybenzoate + pyruvate.

Protein Details

2. 4-hydroxybenzoate octaprenyltransferase

General function:: Involved in prenyltransferase activity
Specific function:: Synthesis of 3-octaprenyl-4-hydroxybenzoate
Gene Name:: ubiA
Uniprot ID:: P0AGK1
Molecular weight:: 32511

Reactions

4-hydroxybenzoate + farnesylfarnesylgeraniol = 3-octaprenyl-4-hydroxybenzoate.

Protein Details

3. acetyl esterase (EC:3.1.1.-)

General function:: Not Available
Specific function:: Not Available
Gene Name:: aes
Uniprot ID:: P23872
Molecular weight:: Not Available

4-Hydroxybenzoic acid (ECMDB00500) (M2MDB000143)

Structure for #<Compound:0x9c04cc4c>

Enzymes

Reactions

Reactions