1.0 2010-04-08 22:09:10 UTC 2025-11-18 23:19:45 UTC FDB010508 4-Hydroxybenzoic acid 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 group. 4-Hydroxybenzoic acid is a neutral compound with a nutty and phenolic taste. 4-Hydroxybenzoic acid exists in all living species, from bacteria to humans. In humans, 4-hydroxybenzoic acid is involved in ubiquinone biosynthesis. 4-Hydroxybenzoic acid is found in highest concentrations in red huckleberries, corianders, and garden onions and in lower concentrations in soybeans, rye bread, and almonds. 4-hydroxybenzoic acid has also been detected in sour cherries, common beans, wild carrots, common oregano, and soft-necked garlics. This could make 4-hydroxybenzoic acid a potential biomarker for the consumption of these foods. 4-Hydroxybenzoic acid esters, known as parabens, are used as preservatives in cosmetics and some ophthalmic solutions. It is isomeric with 2-hydroxybenzoic acid, known as salicylic acid, a precursor to aspirin, and with 3-hydroxybenzoic acid. 4-Hydroxybenzoic acid has estrogenic activity and stimulated the growth of breast cancer cell lines (PMID: 16021681). It can be found in Escherichia coli as part of the ubiquinone pathway. In the first step of this pathway, chorismate lyase transforms chorismate into 4-hydroxybenzoate and pyruvate (PMID 1644758). In Pseudomonas sp., 4-hydroxybenzoate and chloride are produced when the enzyme 4-chlorobenzoate dehalogenase acts on the halide bond of 4-chlorobenzoate with H2O (PMID: 6497878). 4-Carboxyphenol 4-hydroxy-benzoate 4-Hydroxy-benzoesaeure 4-hydroxy-benzoic acid 4-Hydroxybenzoate Benzoic acid, 4-hydroxy Benzoic acid, 4-hydroxy- Benzoic acid, p-hydroxy Benzoic acid, p-hydroxy- Catalpinic acid (obsol.) Hydroxybenzenecarboxylic acid Hydroxybenzoic acid Hydroxybenzoic acid, para P-carboxyphenol P-hydroxy-benzoate P-hydroxy-benzoic acid P-hydroxybenzoate P-hydroxybenzoic acid P-salicyclic acid P-salicylate p-Salicylic acid Para-hydroxybenzoic acid Paraben-acid C7H6O3 138.122 138.031694053 4-hydroxybenzoic acid P-hydroxybenzoic acid 99-96-7 OC(=O)C1=CC=C(O)C=C1 InChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10) FJKROLUGYXJWQN-UHFFFAOYSA-N 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. Hydroxybenzoic acid derivatives Organic compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Aromatic homomonocyclic compounds 1-hydroxy-2-unsubstituted benzenoids Benzoic acids Benzoyl derivatives Carboxylic acids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Organooxygen compounds 1-hydroxy-2-unsubstituted benzenoid Aromatic homomonocyclic compound Benzoic acid Benzoyl Carboxylic acid Carboxylic acid derivative Hydrocarbon derivative Hydroxybenzoic acid Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Phenol monohydroxybenzoic acid Solid logp 1.58 ALOGPS logs -1.06 ALOGPS solubility 1.19e+01 g/l ALOGPS melting_point Mp 213-214° logp 1.33 ChemAxon pka_strongest_acidic 4.38 ChemAxon pka_strongest_basic -6.1 ChemAxon iupac 4-hydroxybenzoic acid ChemAxon average_mass 138.122 ChemAxon mono_mass 138.031694053 ChemAxon smiles OC(=O)C1=CC=C(O)C=C1 ChemAxon formula C7H6O3 ChemAxon inchi InChI=1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10) ChemAxon inchikey FJKROLUGYXJWQN-UHFFFAOYSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 35.3 ChemAxon polarizability 12.94 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Ubiquinone Biosynthesis SMP00065 map00130 Specdb::EiMs 1592 Specdb::MsIr 572 Specdb::MsIr 573 Specdb::MsIr 574 Specdb::NmrTwoD 1021 Specdb::NmrTwoD 1338 Specdb::NmrOneD 1394 Specdb::NmrOneD 4014 Specdb::NmrOneD 4301 Specdb::NmrOneD 4898 Specdb::NmrOneD 4899 Specdb::NmrOneD 6942 Specdb::NmrOneD 6943 Specdb::NmrOneD 6944 Specdb::NmrOneD 6945 Specdb::NmrOneD 6946 Specdb::NmrOneD 6947 Specdb::NmrOneD 6948 Specdb::NmrOneD 6949 Specdb::NmrOneD 6950 Specdb::NmrOneD 6951 Specdb::NmrOneD 6952 Specdb::NmrOneD 6953 Specdb::NmrOneD 6954 Specdb::NmrOneD 6955 Specdb::NmrOneD 6956 Specdb::NmrOneD 6957 Specdb::NmrOneD 6958 Specdb::NmrOneD 6959 Specdb::NmrOneD 6960 Specdb::NmrOneD 6961 Specdb::MsMs 716 Specdb::MsMs 717 Specdb::MsMs 718 Specdb::MsMs 4111 Specdb::MsMs 4112 Specdb::MsMs 4113 Specdb::MsMs 4114 Specdb::MsMs 4115 Specdb::MsMs 4116 Specdb::MsMs 4117 Specdb::MsMs 4118 Specdb::MsMs 4122 Specdb::MsMs 4123 Specdb::MsMs 4124 Specdb::MsMs 179391 Specdb::MsMs 179392 Specdb::MsMs 179393 Specdb::MsMs 181719 Specdb::MsMs 181720 Specdb::MsMs 181721 Specdb::MsMs 374047 Specdb::MsMs 437771 Specdb::MsMs 437772 Specdb::MsMs 437773 Specdb::MsMs 437774 Specdb::CMs 562 Specdb::CMs 563 Specdb::CMs 564 Specdb::CMs 1306 Specdb::CMs 3055 Specdb::CMs 27535 Specdb::CMs 29091 Specdb::CMs 29550 Specdb::CMs 29661 Specdb::CMs 29780 Specdb::CMs 30128 Specdb::CMs 30329 Specdb::CMs 30670 Specdb::CMs 30925 Specdb::CMs 31155 Specdb::CMs 31881 Specdb::CMs 37574 Specdb::CMs 161901 Specdb::CMs 1064187 Specdb::CMs 1064189 Specdb::CMs 1064191 Specdb::CMs 1064192 Specdb::CMs 1064194 HMDB00500 PHB #<Reference:0x000055ce32aab558> #<Reference:0x000055ce32aab350> #<Reference:0x000055ce32aab148> #<Reference:0x000055ce32aaaf68> #<Reference:0x000055ce32aaad38> #<Reference:0x000055ce32aaab80> Alcoholic beverages Unknown generic Almond Type 1 specific Prunus dulcis 3755 0.0041 0.0041 0.0041 mg/100 g American cranberry Type 1 specific Vaccinium macrocarpon 13750 2.68 3.2 2.160000086 mg/100 g Anatidae Type 1 specific Anatidae 8830 Anise Type 1 specific Pimpinella anisum 271192 0.0 0.0 0.0 mg/100 g Apple Type 1 specific Malus pumila 283210 0.0 0.0 0.0 mg/100 g Arabica coffee Type 1 specific Coffea arabica 13443 0.0375 0.075000003 0.0 mg/100 g Arrowroot Type 1 specific Maranta arundinacea 210060 Barley Type 1 specific Hordeum vulgare 4513 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Beer Type 2 specific 1.949405 9.038 0.0 mg/100 g Bilberry Type 1 specific Vaccinium myrtillus 180763 Bison Type 1 specific Bison bison 9901 Black huckleberry Type 1 specific Gaylussacia baccata 128893 0.153333 0.153333329 0.153333329 mg/100 g Black walnut Type 1 specific Juglans nigra 16719 Blackcurrant Type 1 specific Ribes nigrum 78511 0.3 0.3 0.3 mg/100 g Bog bilberry Type 1 specific Vaccinium uliginosum 190548 0.895 0.894999981 0.894999981 mg/100 g Broad bean Type 1 specific Vicia faba 3906 0.0 0.0 0.0 mg/100 g Broccoli Type 1 specific Brassica oleracea var. italica 36774 Buffalo Type 1 specific Bubalus bubalis 89462 Cardamom Type 1 specific Elettaria cardamomum 105181 Carrot Type 1 specific Daucus carota ssp. sativus 79200 2.7795 5.5 0.058999997 mg/100 g Cascade huckleberry Type 1 specific Vaccinium deliciosum 190531 0.695 0.695000023 0.695000023 mg/100 g Cashew nut Type 1 specific Anacardium occidentale 171929 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Chickpea Type 1 specific Cicer arietinum 3827 0.0 0.0 0.0 mg/100 g Chicory Type 1 specific Cichorium intybus 13427 1.1 1.1 1.1 mg/100 g Cocoa bean Type 1 specific Theobroma cacao 3641 Cocoa powder Type 2 specific 0.0 0.0 0.0 mg/100 g Coconut Type 1 specific Cocos nucifera 13894 Coffee Type 1 generic Coffea 13442 0.0375 0.075000003 0.0 mg/100 g Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Common bean Type 1 specific Phaseolus vulgaris 3885 0.0 0.0 0.0 mg/100 g Common buckwheat Type 1 specific Fagopyrum esculentum 3617 Common grape Type 1 specific Vitis vinifera 29760 Common oregano Type 1 specific Origanum vulgare 39352 Common pea Type 1 specific Pisum sativum 3888 0.0 0.0 0.0 mg/100 g Common sage Type 1 specific Salvia officinalis 38868 1.2 1.200000048 1.200000048 mg/100 g Common thyme Type 1 specific Thymus vulgaris 49992 1.4 1.399999976 1.399999976 mg/100 g Common wheat Type 1 specific Triticum aestivum 4565 0.25 0.75 0.0 mg/100 g Coriander Type 1 specific Coriandrum sativum 4047 41.75 96.0 0.0 mg/100 g Corn Type 1 specific Zea mays 4577 0.165144 0.357831674 0.025799999 mg/100 g Cowpea Type 1 specific Vigna unguiculata 3917 0.0 0.0 0.0 mg/100 g Cumin Type 1 specific Cuminum cyminum 52462 0.0 0.0 0.0 mg/100 g Date Type 1 specific Phoenix dactylifera 42345 0.081667 0.163333337 0.0 mg/100 g Deer Type 1 specific Cervidae 9850 Dill Type 1 specific Anethum graveolens 40922 0.0 0.0 0.0 mg/100 g Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Eggplant Type 1 specific Solanum melongena 4111 0.092333 0.092333334 0.092333334 mg/100 g Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European cranberry Type 1 specific Vaccinium oxycoccos 516948 0.78 0.779999971 0.779999971 mg/100 g European rabbit Type 1 specific Oryctolagus 9984 Evening primrose Type 1 specific Oenothera biennis 3942 Evergreen huckleberry Type 1 specific Vaccinium ovatum 84019 1.215 1.215000033 1.215000033 mg/100 g Fennel Type 1 specific Foeniculum vulgare 48038 0.0 0.0 0.0 mg/100 g Flaxseed Type 1 specific Linum usitatissimum 4006 Garden onion Type 1 specific Allium cepa 4679 10.7 10.7 10.7 mg/100 g Garden tomato (var.) Type 1 specific Solanum lycopersicum var. lycopersicum 397755 0.0255 0.050999999 0.0 mg/100 g German camomile Type 1 specific Matricaria recutita 127986 2.0 2.0 2.0 mg/100 g Ginger Type 1 specific Zingiber officinale 94328 Ginkgo nuts Type 1 specific Ginkgo biloba 3311 Grape wine Type 2 specific 0.153318 0.549388227 0.01 mg/100 g Grapefruit Type 1 specific Citrus X paradisi 37656 0.1075 0.209999993 0.005 mg/100 g Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Half-highbush blueberry Type 1 specific Vaccinium angustifolium X Vaccinium corymbosum 934696 0.0 0.0 0.0 mg/100 g Highbush blueberry Type 1 specific Vaccinium corymbosum 69266 4.319583 8.639166938 0.0 mg/100 g Horse Type 1 specific Equus caballus 9796 Horseradish Type 1 specific Armoracia rusticana 3704 1.4 1.4 1.4 mg/100 g Hyssop Type 1 specific Hyssopus officinalis 39324 1.2 1.200000048 1.200000048 mg/100 g Lemon balm Type 1 specific Melissa officinalis 39338 2.3 2.299999952 2.299999952 mg/100 g Lentils Type 1 generic Lens culinaris 3864 0.219375 0.324999988 0.113750001 mg/100 g Lima bean Type 1 specific Phaseolus lunatus 3884 0.0 0.0 0.0 mg/100 g Loquat Type 1 specific Eriobotrya japonica 32224 4.655714 4.655714308 4.655714308 mg/100 g Mallard duck Type 1 specific Anas platyrhynchos 8839 Milk (Cow) Type 2 specific Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Mung bean Type 1 specific Vigna radiata 157791 0.0 0.0 0.0 mg/100 g Muskmelon Type 1 specific Cucumis melo 3656 Oat Type 1 specific Avena sativa 4498 0.213 0.449999996 0.063000001 mg/100 g Olive Type 1 specific Olea europaea 4146 3.699191 8.5 0.003625 mg/100 g Opium poppy Type 1 specific Papaver somniferum 3469 Ostrich Type 1 specific Struthio camelus 8801 Oval-leaf huckleberry Type 1 specific Vaccinium ovalifolium 190544 0.163333 0.163333334 0.163333334 mg/100 g Parsley Type 1 specific Petroselinum crispum 4043 1.3 1.299999952 1.299999952 mg/100 g Peanut Type 1 specific Arachis hypogaea 3818 1.4 1.4 1.4 mg/100 g Pear Type 1 specific Pyrus communis 23211 0.0 0.0 0.0 mg/100 g Pheasant Type 1 specific Phasianus colchicus 9054 Pigeon pea Type 1 specific Cajanus cajan 3821 0.0 0.0 0.0 mg/100 g Port wine Type 2 specific 0.0 0.0 0.0 mg/100 g Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rabbiteye blueberry Type 1 specific Vaccinium virgatum 51.835 51.835 51.835 mg/100 g Red beetroot Type 1 specific Beta vulgaris var. rubra Red huckleberry Type 1 specific Vaccinium parvifolium 180766 55.299999 55.299999237 55.299999237 mg/100 g Red raspberry Type 1 specific Rubus idaeus 32247 1.566667 2.599999905 0.0 mg/100 g Redcurrant Type 1 specific Ribes rubrum 175228 Rice Type 1 specific Oryza sativa 4530 0.195875 0.449999988 0.0755 mg/100 g Robusta coffee Type 1 specific Coffea canephora 49390 0.0375 0.075000003 0.0 mg/100 g Rock ptarmigan Type 1 specific Lagopus muta 64668 Rosemary Type 1 specific Rosmarinus officinalis 39367 0.7 1.399999976 0.0 mg/100 g Rubus (Blackberry, Raspberry) Type 1 specific Rubus 23216 0.0 0.0 0.0 mg/100 g Rye Type 1 specific Secale cereale 4550 0.087 0.086999997 0.086999997 mg/100 g Rye bread Type 2 specific 0.425 0.850000024 0.0 mg/100 g Salmonberry Type 1 specific Rubus spectabilis 59499 Sea-buckthornberry Type 1 specific Hippophae rhamnoides 193516 0.0 0.0 0.0 mg/100 g Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Sherry Type 2 specific 0.029412 0.029411765 0.029411765 mg/100 g Silver linden Type 1 specific Tilia argentea 0.0 0.0 0.0 mg/100 g Soft-necked garlic Type 1 specific Allium sativum L. var. sativum 4682 Sour cherry Type 1 specific Prunus cerasus 140311 Soy bean Type 1 specific Glycine max 3847 0.0854 0.17 0.0008 mg/100 g Spearmint Type 1 specific Mentha spicata 29719 0.0 0.0 0.0 mg/100 g Squab Type 1 specific Columba 8931 Strawberry Type 1 specific Fragaria X ananassa 3747 3.266667 7.5 0.0 mg/100 g Sunflower Type 1 specific Helianthus annuus 4232 Sweet basil Type 1 specific Ocimum basilicum 39350 1.3 1.299999952 1.299999952 mg/100 g Sweet marjoram Type 1 specific Origanum majorana 268884 0.6 1.200000048 0.0 mg/100 g Swiss chard Type 1 specific Beta vulgaris ssp. cicla 1527200 3.225 4.699999809 1.899999976 mg/100 g Tarragon Type 1 specific Artemisia dracunculus 72341 1.4 1.4 1.4 mg/100 g Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Vinegar Type 2 specific 0.198308 0.198308022 0.198308022 mg/100 g Wild boar Type 1 specific Sus scrofa 9823 Wild carrot Type 1 specific Daucus carota 4039 nutty phenolic 4-hydroxybenzoate polyprenyltransferase, mitochondrial Q96H96 COQ2 Anti bacterial 145 A substance that kills or slows the growth of bacteria. Anti radicular 572 Anti-mutagenic 451 Anti-oxidant 502 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. Anti-sickling 614 Cancer preventive 754 A substance that inhibits or prevents the proliferation of neoplasms. Fungistat 942 Immunosuppressant 1033 An agent that suppresses immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-cells or by inhibiting the activation of helper cells. In addition, an immunosuppressive agent is a role played by a compound which is exhibited by a capability to diminish the extent and/or voracity of an immune response. Pesticide 1210 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. Phytoalexin 1223 A toxin made by a plant that acts against an organism attacking it. Prostaglandigenic 1254 Secretogogue 1308 Ubiquiot 1391