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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:14:53 UTC

HMDB ID

HMDB0000500

Secondary Accession Numbers

HMDB00500

Metabolite Identification

Common Name

4-Hydroxybenzoic acid

Description

4-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 is a white crystalline solid that is slightly soluble in water and chloroform but more soluble in polar organic solvents such as alcohols and acetone. It is a nutty and phenolic tasting compound. 4-Hydroxybenzoic acid exists in all living species, ranging from bacteria to plants to humans. 4-Hydroxybenzoic acid can be found naturally in coconut. It is one of the main catechins metabolites found in humans after consumption of green tea infusions. It is also found in wine, in vanilla, in A√ßa√≠ oil, obtained from the fruit of the a√ßa√≠ palm (Euterpe oleracea), at relatively high concetrations (892¬±52 mg/kg). It is also found in cloudy olive oil and in the edible mushroom Russula virescens. It has been detected in red huckleberries, rabbiteye blueberries, and corianders and in a lower concentration in olives, red raspberries, and almonds. In humans, 4-hydroxybenzoic acid is involved in ubiquinone biosynthesis. In particular, the enzyme 4-hydroxybenzoate polyprenyltransferase uses a polyprenyl diphosphate and 4-hydroxybenzoate to produce diphosphate and 4-hydroxy-3-polyprenylbenzoate. This enzyme participates in ubiquinone biosynthesis. 4-Hydroxybenzoic acid can be biosynthesized by the enzyme Chorismate lyase. Chorismate lyase is an enzyme that transforms chorismate into 4-hydroxybenzoate and pyruvate. This enzyme catalyses the first step in ubiquinone biosynthesis in Escherichia coli and other Gram-negative bacteria. 4-Hydroxybenzoate is an intermediate in many enzyme-mediated reactions in microbes. For instance, the enzyme 4-hydroxybenzaldehyde dehydrogenase uses 4-hydroxybenzaldehyde, NAD+ and H2O to produce 4-hydroxybenzoate, NADH and H+. This enzyme participates in toluene and xylene degradation in bacteria such as Pseudomonas mendocina. 4-hydroxybenzaldehyde dehydrogenase is also found in carrots. The enzyme 4-hydroxybenzoate 1-hydroxylase transforms 4-hydroxybenzoate, NAD(P)H, 2 H+ and O2 into hydroquinone, NAD(P)+, H2O and CO2. This enzyme participates in 2,4-dichlorobenzoate degradation and is found in Candida parapsilosis. The enzyme 4-hydroxybenzoate 3-monooxygenase transforms 4-hydroxybenzoate, NADPH, H+ and O2 into protocatechuate, NADP+ and H2O. This enzyme participates in benzoate degradation via hydroxylation and 2,4-dichlorobenzoate degradation and is found in Pseudomonas putida and Pseudomonas fluorescens. 4-Hydroxybenzoic acid is a popular antioxidant in part because of its low toxicity. 4-Hydroxybenzoic acid has estrogenic activity both in vitro and in vivo (PMID 9417843 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Carboxyphenol	ChEBI
p-HYDROXYBENZOIC ACID	ChEBI
p-Salicylic acid	ChEBI
Hydroxybenzoic acid	Kegg
Hydroxybenzenecarboxylic acid	Kegg
p-HYDROXYBENZOate	Generator
p-Salicylate	Generator
Hydroxybenzoate	Generator
Hydroxybenzenecarboxylate	Generator
4-Hydroxybenzoate	Generator
4-Hydroxy-benzoate	HMDB
4-Hydroxy-benzoesaeure	HMDB
4-Hydroxy-benzoic acid	HMDB
p-Carboxyphenol	HMDB
p-Hydroxy-benzoate	HMDB
p-Hydroxy-benzoic acid	HMDB
Paraben-acid	HMDB
4-Hydroxybenzoic acid, calcium salt	HMDB
4-Hydroxybenzoic acid, dilithium salt	HMDB
4-Hydroxybenzoic acid, disodium salt	HMDB
Para-hydroxybenzoic acid	HMDB
Sodium p-hydroxybenzoate tetrahydrate	HMDB
4-Hydroxybenzoic acid, copper(2+)(1:1) salt	HMDB
4-Hydroxybenzoic acid, dipotassium salt	HMDB
4-Hydroxybenzoic acid, monopotassium salt	HMDB
4-Hydroxybenzoic acid, monosodium salt	HMDB
4-Hydroxybenzoic acid, monosodium salt, 11C-labeled	HMDB
4-Hydroxybenzene carboxylic acid	HMDB
p-Hydroxyl benzoic acid	HMDB
4-Hydroxybenzoic acid	HMDB

Chemical Formula

C₇H₆O₃

Average Molecular Weight

138.122

Monoisotopic Molecular Weight

138.031694053

IUPAC Name

4-hydroxybenzoic acid

Traditional Name

P-hydroxybenzoic acid

CAS Registry Number

99-96-7

SMILES

OC(=O)C1=CC=C(O)C=C1

InChI Identifier

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

InChI Key

FJKROLUGYXJWQN-UHFFFAOYSA-N

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 )

Ontology

Physiological effect

Health effect

Respiratory system disorder

Supradiaphragmatic malignancy (HMDB: HMDB0000500)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 12771321)
Cerebrospinal Fluid (CSF) (PMID: 10553836)
Saliva (HMDB: HMDB0000500)
Cerebrospinal fluid (HMDB: HMDB0000500)

Excreta

Biofluid or Excreta

Urine (PMID: 8087979)
Feces (PMID: 24010549)
Sweat (PMID: 26755145)

Cellular substructure

Cytoplasm (HMDB: HMDB0000500)

Organelle

Mitochondrion (HMDB: HMDB0000500)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0000500)

Source

Exogenous

Exogenous (HMDB: HMDB0000500)

Food

Food (HMDB: HMDB0000500)
Legumes (HMDB: HMDB0000500)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)
Grape wine (FooDB: FOOD00612)

Fortified wines

Port wine (FooDB: FOOD00630)
Sherry (FooDB: FOOD00632)

Alcoholic beverage

Red wine (HMDB: HMDB0000500)
Alcoholic beverages (FooDB: FOOD00854)

Nut

Fruit

Pome

Apple (FooDB: FOOD00105)
Pear (FooDB: FOOD00152)

Fruits (HMDB: HMDB0000500)

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Strawberry (FooDB: FOOD00083)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Red raspberry (FooDB: FOOD00162)
Salmonberry (FooDB: FOOD00456)
Sea-buckthornberry (FooDB: FOOD00087)
Black huckleberry (FooDB: FOOD00084)
Highbush blueberry (FooDB: FOOD00191)
Bog bilberry (FooDB: FOOD00212)
European cranberry (FooDB: FOOD00217)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Half-highbush blueberry (FooDB: FOOD00248)
Rabbiteye blueberry (FooDB: FOOD00898)

Tropical fruit

Coconut (FooDB: FOOD00336)
Loquat (FooDB: FOOD00076)

Other fruit

Date (FooDB: FOOD00135)

Citrus

Grapefruit (FooDB: FOOD00256)

Drupe

Sour cherry (FooDB: FOOD00146)

Vegetable

Fruit vegetable

Vegetables (HMDB: HMDB0000500)

Root vegetable

Cabbage

Broccoli (FooDB: FOOD00034)

Leaf vegetable

Swiss chard (FooDB: FOOD00237)

Tuber

Arrowroot (FooDB: FOOD00290)

Onion-family vegetable

Garden onion (FooDB: FOOD00006)

Cereal and cereal product

Cereal

Barley (FooDB: FOOD00088)
Common buckwheat (FooDB: FOOD00079)
Corn (FooDB: FOOD00205)
Oat (FooDB: FOOD00022)
Rice (FooDB: FOOD00125)
Rye (FooDB: FOOD00169)
Common wheat (FooDB: FOOD00187)

Cereal product

Whole grain cereal products (HMDB: HMDB0000500)

Leavened bread

Rye bread (FooDB: FOOD00809)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Soy

Soy bean (FooDB: FOOD00085)

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0000500)

Cocoa product

Cocoa powder (FooDB: FOOD00685)

Cocoa

Cocoa bean (FooDB: FOOD00182)

Coffee and coffee product

Coffee product

Coffee products (HMDB: HMDB0000500)

Coffee

Tea

Tea products (HMDB: HMDB0000500)

Fat and oil

Olive oil (HMDB: HMDB0000500)

Ginkgo nuts (FooDB: FOOD00367)

Gourd

Muskmelon (FooDB: FOOD00064)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Baking good

Seasoning

Vinegar (FooDB: FOOD00628)

Endogenous

Endogenous (HMDB: HMDB0000500)

Plant

Microbe

Microbe (HMDB: HMDB0000500)
Bifidobacterium (HMDB: HMDB0000500)
Escherichia coli (HMDB: HMDB0000500)
Arthrobacter (HMDB: HMDB0000500)
Corynebacterium glutamicum (HMDB: HMDB0000500)
Clostridium saccharogumia (HMDB: HMDB0000500)
Eubacterium ramulus (HMDB: HMDB0000500)
Microbulbifer (HMDB: HMDB0000500)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Ubiquinone Biosynthesis (HMDB: HMDB0000500)
Ubiquinone Biosynthesis (PathBank: SMP0087215)
Secondary Metabolites: Ubiquinol Biosynthesis 2 (PathBank: SMP0122225)
Ubiquinone Biosynthesis (PathBank: SMP0002372)
Secondary Metabolites: Ubiquinol Biosynthesis (PathBank: SMP0121333)

Role

Industrial applicationBiological role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	213.00 to 215.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	334.00 to 335.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	5 mg/mL	Not Available
LogP	1.58	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	121.1	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000292

Predicted Molecular 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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	129.091	31661259
DarkChem	[M-H]-	127.315	31661259
AllCCS	[M+H]+	128.981	32859911
AllCCS	[M-H]-	124.456	32859911
DeepCCS	[M+H]+	129.657	30932474
DeepCCS	[M-H]-	126.226	30932474
DeepCCS	[M-2H]-	163.503	30932474
DeepCCS	[M+Na]+	139.041	30932474
AllCCS	[M+H]+	129.0	32859911
AllCCS	[M+H-H2O]+	124.3	32859911
AllCCS	[M+NH4]+	133.3	32859911
AllCCS	[M+Na]+	134.6	32859911
AllCCS	[M-H]-	124.5	32859911
AllCCS	[M+Na-2H]-	126.1	32859911
AllCCS	[M+HCOO]-	127.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxybenzoic acid	OC(=O)C1=CC=C(O)C=C1	2781.8	Standard polar	33892256
4-Hydroxybenzoic acid	OC(=O)C1=CC=C(O)C=C1	1399.3	Standard non polar	33892256
4-Hydroxybenzoic acid	OC(=O)C1=CC=C(O)C=C1	1409.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxybenzoic acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=C(O)C=C1	1590.9	Semi standard non polar	33892256
4-Hydroxybenzoic acid,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C(=O)O)C=C1	1623.4	Semi standard non polar	33892256
4-Hydroxybenzoic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC=C(O[Si](C)(C)C)C=C1	1642.4	Semi standard non polar	33892256
4-Hydroxybenzoic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(O)C=C1	1848.1	Semi standard non polar	33892256
4-Hydroxybenzoic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C(=O)O)C=C1	1867.2	Semi standard non polar	33892256
4-Hydroxybenzoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	2141.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxybenzoic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-01b9-0490000000-89473836b0071542185e	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxybenzoic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00xu-2890000000-dd5367ba838ccd5b29d8	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxybenzoic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-00di-9540000000-11db590137f79b7a32bf	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxybenzoic acid GC-MS (2 TMS)	splash10-00xu-3890000000-7e553522b6ec5c075e25	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxybenzoic acid EI-B (Non-derivatized)	splash10-00dr-5900000000-9b1d88421f1e1ded16f9	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxybenzoic acid EI-B (Non-derivatized)	splash10-00di-9700000000-a9bb4b71d8b23a56ca67	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxybenzoic acid EI-B (Non-derivatized)	splash10-0079-6900000000-617d58eb059c1e918ca0	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxybenzoic acid EI-B (Non-derivatized)	splash10-00dr-4900000000-97bfa38b0d6bc152d470	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxybenzoic acid EI-B (Non-derivatized)	splash10-00dr-7900000000-290af590b1fc44a86969	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxybenzoic acid EI-B (Non-derivatized)	splash10-01b9-0490000000-d6001fb50397705d3e0b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxybenzoic acid GC-EI-TOF (Non-derivatized)	splash10-01b9-0490000000-89473836b0071542185e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxybenzoic acid GC-EI-TOF (Non-derivatized)	splash10-00xu-2890000000-dd5367ba838ccd5b29d8	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxybenzoic acid GC-EI-TOF (Non-derivatized)	splash10-00di-9540000000-11db590137f79b7a32bf	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxybenzoic acid GC-MS (Non-derivatized)	splash10-00xu-3890000000-7e553522b6ec5c075e25	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 4-Hydroxybenzoic acid GC-EI-TOF (Non-derivatized)	splash10-00xu-2980000000-0ba0ea7d63bd7fff3b22	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxybenzoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0079-5900000000-fcde26d72ca8445dff7e	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxybenzoic acid GC-MS (2 TMS) - 70eV, Positive	splash10-00xu-7950000000-cc553d409cc2a872749d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxybenzoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxybenzoic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxybenzoic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxybenzoic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxybenzoic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxybenzoic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-00dr-6900000000-71548845dbf99346758d	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxybenzoic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)	splash10-000f-9400000000-9fb9f8fbd7cf90a88604	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxybenzoic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)	splash10-0006-9000000000-f5d09d09184f72ec3bd7	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxybenzoic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)	splash10-0006-9000000000-d31cea608d0764edf5d0	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxybenzoic acid EI-B (HITACHI M-68) , Positive-QTOF	splash10-00dr-5900000000-9b1d88421f1e1ded16f9	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxybenzoic acid EI-B (HITACHI M-60) , Positive-QTOF	splash10-00di-9700000000-3ac766249fee4c68b8f4	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxybenzoic acid EI-B (HITACHI M-80) , Positive-QTOF	splash10-0079-6900000000-4e15a4102e0b3bc8ddce	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxybenzoic acid LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-0a4r-9800000000-9e7208bfb79f9cca336b	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxybenzoic acid LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-0a4i-9000000000-1ed6d8123d44d126ed64	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxybenzoic acid LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-0a4i-9000000000-63a0e9c65e315bb89281	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxybenzoic acid LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-0a4i-9000000000-a8befcaa45eced4a9a51	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxybenzoic acid LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-0a4i-9000000000-26788d399f2b459abc21	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxybenzoic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-0072-6900000000-ba06f5c422d59cd10cea	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxybenzoic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-0002-9100000000-193fd4eb0cf324fb3abc	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxybenzoic acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-0006-9200000000-c834f7be13341f3e19b8	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxybenzoic acid DI-ESI-qTof , Positive-QTOF	splash10-00di-0900000000-4f58e660923e896589a3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxybenzoic acid LC-ESI-QQ , negative-QTOF	splash10-0a4r-9800000000-9e7208bfb79f9cca336b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxybenzoic acid LC-ESI-QQ , negative-QTOF	splash10-0a4i-9000000000-1ed6d8123d44d126ed64	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxybenzoic acid LC-ESI-QQ , negative-QTOF	splash10-0a4i-9000000000-e80d9637393e63e2d07c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 4-Hydroxybenzoic acid LC-ESI-QQ , negative-QTOF	splash10-0a4i-9000000000-a8befcaa45eced4a9a51	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzoic acid 10V, Positive-QTOF	splash10-0079-0900000000-6351b89d53d1742a1fbb	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzoic acid 20V, Positive-QTOF	splash10-00di-1900000000-bdd873f3d1dc0f2af556	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzoic acid 40V, Positive-QTOF	splash10-00fu-9400000000-37262c1edda5dec21a19	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzoic acid 10V, Negative-QTOF	splash10-000i-3900000000-fcd512c9827982e7c9aa	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzoic acid 20V, Negative-QTOF	splash10-000f-9600000000-36013030005316a50fab	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybenzoic acid 40V, Negative-QTOF	splash10-0006-9100000000-5efa05442f95e2900559	2016-09-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Sweat
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Ubiquinone Biosynthesis

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 418	12771321	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 418	19671472	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 418	19333587	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 418	20222713	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 418	12663291	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 418	20080030	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 418	19415668	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Blood	Detected and Quantified	2.447 +/- 0.192 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	2.423 +/- 0.19 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	2.599 +/- 0.232 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	2.73 +/- 0.226 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	2.676 +/- 0.168 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	2.387 +/- 0.158 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	2.326 +/- 0.221 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected and Quantified	20.885 +/- 18.445 uM	Adult (>18 years old)	Male	Normal	19812218	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	20809621	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	20809621	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected and Quantified	4.996 +/- 4.923 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Feces	Detected and Quantified	5.358 +/- 5.575 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Feces	Detected and Quantified	6.516 +/- 5.647 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Feces	Detected and Quantified	8.326 +/- 10.136 nmol/g wet feces	Adult (>18 years old)	Both	Normal	24010549	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24029555	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	18502705	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	19573517	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Both	Normal	25486321	details
Feces	Detected and Quantified	5.430 +/- 4.416 nmol/g wet feces	Not Specified	Not Specified	Normal	19573517	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	18085514	details
Feces	Detected and Quantified	1.441 (0.203-12.0690) nmol/g wet feces	Adult (>18 years old)	Both	Normal	28029051	details
Feces	Detected and Quantified	29.684 +/- 31.132 nmol/g wet feces	Not Specified	Not Specified	Normal	20669995	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27065191	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	20669995	details
Saliva	Detected and Quantified	30.23 +/- 31.32 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Sweat	Detected but not Quantified	Not Quantified	Adult	Both	Normal	26755145	details
Urine	Detected and Quantified	1.346 +/- 1.104 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 418	12771321	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 418	19671472	details
Urine	Detected and Quantified	1.7 (0.9-3.0) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 418	19333587	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 418	20222713	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 418	12663291	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 418	20080030	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 418	19415668	details
Urine	Detected and Quantified	0.39-0.75 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	2.751 +/- 2.414 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	1.8 (0.7-29) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	2702744	details
Urine	Detected and Quantified	4.66+/- 1.18 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	12663291	details
Urine	Detected and Quantified	1.8 +/- 1.8 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	15992788	details
Urine	Detected and Quantified	0.36-0.57 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details
Urine	Detected and Quantified	1.291 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	27273479	details
Urine	Detected and Quantified	0.230-5.900 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	26814424	details
Urine	Detected and Quantified	3.0 (0.1-13.5) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	8087979	details
Urine	Detected and Quantified	1.5 (0.1-2.8) umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	8087979	details
Urine	Detected and Quantified	2.5 (0.7-13.7) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	2.6 (0.1-11.1) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	2.0 (0.6-4.2) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	1.717 +/- 0.196 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	19812218	details
Urine	Detected and Quantified	2.4(1.3-3.6) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.5 +/- 0.22 uM	Adult (>18 years old)	Both	Supradiaphragmatic malignancy	10553836	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	2.988 +/- 2.795 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	3.158 +/- 2.557 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Analysis of 30 no...	details
Urine	Detected and Quantified	8.201 +/- 12.712 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Hypertension (mild)	20013882	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Hypertension (mild)	20013882	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

Supradiaphragmatic malignancy
Goudas LC, Langlade A, Serrie A, Matson W, Milbury P, Thurel C, Sandouk P, Carr DB: Acute decreases in cerebrospinal fluid glutathione levels after intracerebroventricular morphine for cancer pain. Anesth Analg. 1999 Nov;89(5):1209-15. [PubMed:10553836 ]
Colorectal cancer
Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

DB04242

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

4-Hydroxybenzoic_acid

METLIN ID

5486

PubChem Compound

135

PDB ID

Not Available

ChEBI ID

30763

Food Biomarker Ontology

Not Available

VMH ID

4HBZ

MarkerDB ID

Not Available

Good Scents ID

rw1040201

References

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)

Download (PDF)

General References

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
Rowland I, Gibson G, Heinken A, Scott K, Swann J, Thiele I, Tuohy K: Gut microbiota functions: metabolism of nutrients and other food components. Eur J Nutr. 2018 Feb;57(1):1-24. doi: 10.1007/s00394-017-1445-8. Epub 2017 Apr 9. [PubMed:28393285 ]
Peng X, Adachi K, Chen C, Kasai H, Kanoh K, Shizuri Y, Misawa N: Discovery of a marine bacterium producing 4-hydroxybenzoate and its alkyl esters, parabens. Appl Environ Microbiol. 2006 Aug;72(8):5556-61. doi: 10.1128/AEM.00494-06. [PubMed:16885309 ]
Kallscheuer N, Marienhagen J: Corynebacterium glutamicum as platform for the production of hydroxybenzoic acids. Microb Cell Fact. 2018 May 12;17(1):70. doi: 10.1186/s12934-018-0923-x. [PubMed:29753327 ]
Koistinen VM (2019). Effects of Food Processing and Gut Microbial Metabolism on Whole Grain Phytochemicals: A Metabolomics Approach. In Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510 (pp. 26-58). University of Eastern Finland. [ISBN:978-952-61-3088-0 ]

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

4-Hydroxybenzoic acid → 6-(4-carboxyphenoxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details
4-Hydroxybenzoic acid → 3,4,5-trihydroxy-6-(4-hydroxybenzoyloxy)oxane-2-carboxylic acid	details

Enzyme Details

2. 4-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:: Q96H96
Molecular weight:: 45593.67

Reactions

A polyprenyl diphosphate + 4-Hydroxybenzoic acid → Pyrophosphate + a 4-hydroxy-3-polyprenylbenzoate	details
Geranyl-PP + 4-Hydroxybenzoic acid → 4-Hydroxy-3-polyprenylbenzoate + Pyrophosphate	details
all-trans-Hexaprenyl diphosphate + 4-Hydroxybenzoic acid → 3-Hexaprenyl-4-hydroxybenzoic acid + Pyrophosphate	details
Solanesyl-PP + 4-Hydroxybenzoic acid → Pyrophosphate + Prenyl benzoate	details

Enzyme Details

3. Glycine N-acyltransferase

General function:: Involved in glycine N-acyltransferase activity
Specific function:: Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:: GLYAT
Uniprot ID:: Q6IB77
Molecular weight:: 18506.33

Reactions

4-Hydroxybenzoic acid → p-Hydroxyhippuric acid	details

Enzyme Details

4. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Reactions

4-Hydroxybenzoic acid → 4-hydroxybenzoic acid-4-O-sulphate	details

Showing metabocard for 4-Hydroxybenzoic acid (HMDB0000500)

MOL for HMDB0000500 (4-Hydroxybenzoic acid)

3D MOL for HMDB0000500 (4-Hydroxybenzoic acid)

3D SDF for HMDB0000500 (4-Hydroxybenzoic acid)

3D-SDF for HMDB0000500 (4-Hydroxybenzoic acid)

PDB for HMDB0000500 (4-Hydroxybenzoic acid)

3D PDB for HMDB0000500 (4-Hydroxybenzoic acid)

SMILES for HMDB0000500 (4-Hydroxybenzoic acid)

INCHI for HMDB0000500 (4-Hydroxybenzoic acid)

Structure for HMDB0000500 (4-Hydroxybenzoic acid)

3D Structure for HMDB0000500 (4-Hydroxybenzoic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions

Reactions

Reactions