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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 443352062 |
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| verifiedrevid = 477222223 |
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| Name = 4-Hydroxybenzoic acid |
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| ImageFileL1 = 4-Hydroxybenzoic acid.svg |
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| Name = 4-Hydroxybenzoic acid |
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| ImageFile1 = 4-hydroxybenzoic acid 200.svg |
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| ImageSizeL1 = 95px |
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| ImageNameL1 = Skeletal formula |
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| ImageName1 = Skeletal formula |
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| ImageSize1 = 200px |
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| ImageFileR1 = 4-Hydroxybenzoic-acid-3D-balls.png |
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| ImageFile2 = 4-Hydroxybenzoic-acid-3D-balls.png |
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| ImageSizeR1 = 108px |
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| ImageNameR1 = Ball-and-stick model |
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| ImageName2 = Ball-and-stick model |
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| ImageSize2 = 100px |
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| IUPACName = 4-Hydroxybenzoic acid |
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| OtherNames = ''p''-Hydroxybenzoic acid<br />''para''-Hydroxybenzoic acid |
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| PIN = 4-Hydroxybenzoic acid |
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| OtherNames = ''p''-Hydroxybenzoic acid<br>''para''-Hydroxybenzoic acid<br>PHBA<br>4-hydroxybenzoate |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 132 |
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| ChemSpiderID = 132 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 441343 |
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| ChEMBL = 441343 |
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| IUPHAR_ligand = 5783 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10) |
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| StdInChI = 1S/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10) |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 99-96-7 |
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| CASNo = 99-96-7 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = JG8Z55Y12H |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 30763 |
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| ChEBI = 30763 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB04242 |
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| DrugBank = DB04242 |
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| SMILES = O=C(O)c1ccc(O)cc1 |
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| SMILES = O=C(O)c1ccc(O)cc1 |
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| PubChem = 135 |
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| PubChem = 135 |
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| EINECS = 202-804-9 |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=7 | H=6 | O=3 |
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| Formula = C<sub>7</sub>H<sub>6</sub>O<sub>3</sub> |
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| Appearance = White crystalline solid |
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| MolarMass = 138.12074 g/mol |
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| Odor = Odorless |
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| Density = 1.46 g/cm³ |
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| Density = 1.46{{nbsp}}g/cm<sup>3</sup> |
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| MeltingPt = 214-217 °C |
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| MeltingPtC = 214.5 |
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| BoilingPt = N/A, |
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| BoilingPt_notes = decomposes<ref>{{cite web |
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| title = 4-Hydroxybenzoic acid |
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| url = http://www.inchem.org/documents/sids/sids/99967.pdf |
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| website = International Programme on Chemical Safety (IPCS) |
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| access-date = 10 January 2015 |
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| archive-url = https://web.archive.org/web/20150924052013/http://www.inchem.org/documents/sids/sids/99967.pdf |
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| archive-date = 24 September 2015 |
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| url-status = dead |
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}}</ref> |
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| Solubility = 0.5{{nbsp}}g/100{{nnbsp}}mL |
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| SolubleOther = {{ubl |
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| Soluble in ], ], ] |
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| Slightly soluble in ] |
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| Negligibly in ] |
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| pKa = 4.54 |
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| LogP = 1.58 |
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}} |
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|Section5={{Chembox Hazards |
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| MainHazards = Irritant |
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| ExternalSDS = |
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| AutoignitionPtC = 250 |
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| NFPA-H = 2 | NFPA-F = 0 | NFPA-R = 0 |
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| LD50 = 2200{{nbsp}}mg/kg (oral, mouse) |
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}} |
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'''4-Hydroxybenzoic acid''' is a ], a phenolic derivative of benzoic acid. It is a white crystalline solid that is slightly soluble in water and ] but more soluble in polar organic solvents such as ]s and ]. 4-Hydroxybenzoic acid is primarily known as the basis for the preparation of its ]s, known as ]s, which are used as preservatives in cosmetics. It is ]ic with 2-hydroxybenzoic acid, known as ], a precursor to ]. |
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'''4-Hydroxybenzoic acid''', also known as '''''p''-hydroxybenzoic acid''' ('''PHBA'''), is a ], a phenolic derivative of benzoic acid. It is a white crystalline solid that is slightly soluble in water and ] but more soluble in polar organic solvents such as ]s and ]. 4-Hydroxybenzoic acid is primarily known as the basis for the preparation of its ]s, known as ]s, which are used as preservatives in cosmetics and some ophthalmic solutions. It is ]ic with 2-hydroxybenzoic acid, known as ], a precursor to ], and with ]. |
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== Natural occurrences == |
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4-Hydroxybenzoic acid can be found naturally in '']''<ref>Profiling C6–C3 and C6–C1 phenolic metabolites in Cocos nucifera. Gargi Dey, Moumita Chakraborty and Adinpunya Mitra, Journal of Plant Physiology, Volume 162, Issue 4, 22 April 2005, Pages 375-381 {{doi:10.1016/j.jplph.2004.08.006}}</ref>. |
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It is found in plants of the genus ''Vitex'' such as '']'' or '']'', and in '']'' (St John's wort). It is also found in '']'', a freshwater green alga. |
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The compound is also found in '']'', a ] with the longest record of use. |
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==Production== |
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4-Hydroxybenzoic acid is produced commercially from potassium ] and ] in the ].<ref>Edwin Ritzer and Rudolf Sundermann “Hydroxycarboxylic Acids, Aromatic” in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. {{DOI| 10.1002/14356007.a13_519}}</ref> |
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'']'' is a bacterium species that produces ] from ] via 4-hydroxybenzoate.<ref name=Juteau>{{cite journal|title=''Cryptanaerobacter phenolicus'' gen. nov., sp. nov., an anaerobe that transforms phenol into benzoate via 4-hydroxybenzoate |first1=P. |last1=Juteau |first2=V. |last2=Côté |first3=M.-F. |last3=Duckett |first4=R. |last4=Beaudet |first5=F. |last5=Lépine |first6=R. |last6=Villemur |first7=J.-G. |last7=Bisaillon |journal=International Journal of Systematic and Evolutionary Microbiology |date=January 2005 |volume=55 |issue=1 |pages=245–250 |doi=10.1099/ijs.0.02914-0|pmid=15653882 |doi-access=free }}</ref> |
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4-Hydroxybenzoic acid can also be produced in the laboratory by heating ] with ] to 240 °C, followed by treating with acid.<ref>{{OrgSynth | prep = CV2P0341 | author = C. A. Buehler and W. E. Cate | title = ''p''-Hydroxybenzoic acid | collvol = 2 | collvolpages = 341 | year = 1943 }}</ref> |
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=== Occurrences in food === |
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==Reactions== |
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4-Hydroxybenzoic acid can be found naturally in ].<ref>{{cite journal|title=Profiling C6–C3 and C6–C1 phenolic metabolites in ''Cocos nucifera'' |first1=G. |last1=Dey |first2=M. |last2=Chakraborty |first3=A. |last3=Mitra |journal=Journal of Plant Physiology |volume=162 |issue=4 |date=April 2005 |pages=375–381 |doi=10.1016/j.jplph.2004.08.006|pmid=15900879 }}</ref> It is one of the main catechins ]s found in humans after consumption of ] infusions.<ref>{{cite journal|title=Catechin metabolites after intake of green tea infusions |first1=P. G. |last1=Pietta |first2=P. |last2=Simonetti |first3=C. |last3=Gardana |first4=A. |last4=Brusamolino |first5=P. |last5=Morazzoni |first6=E. |last6=Bombardelli |journal=BioFactors |date=1998 |volume=8 |issue=1–2 |pages=111–118 |doi=10.1002/biof.5520080119|pmid=9699018 |s2cid=37684286 }}</ref> It is also found in ],<ref>{{cite journal|title=Comparison of phenolic acids and flavan-3-ols during wine fermentation of grapes with different harvest times |first1=R.-R. |last1=Tian |first2=Q.-H. |last2=Pan |first3=J.-C. |last3=Zhan |first4=J.-M. |last4=Li |first5=S.-B. |last5=Wan |first6=Q.-H. |last6=Zhang |first7=W.-D. |last7=Huang |journal=Molecules |date=2009 |volume=14 |issue=2 |pages=827–838 |pmc=6253884 |doi=10.3390/molecules14020827|pmid=19255542 |doi-access=free }}</ref> in ], in '']'' (horse gram), ]<ref>{{Cite journal | title=Functional Components of Carob Fruit: Linking the Chemical and Biological Space |pmc = 5133875|year = 2016|last1 = Goulas|first1 = V.|last2 = Stylos|first2 = E.|last3 = Chatziathanasiadou|first3 = M. V.|last4 = Mavromoustakos|first4 = T.|last5 = Tzakos|first5 = A. G.|journal = International Journal of Molecular Sciences|volume = 17|issue = 11|pages = 1875|pmid = 27834921|doi = 10.3390/ijms17111875| doi-access=free }}</ref> and in '']'' (Otaheite gooseberry). |
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It is about 10x less acidic than ], ''K<sub>a</sub>'' = 3.3 x 10<sup>−5</sup> M at 19 °C: |
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:HOC<sub>6</sub>H<sub>4</sub>CO<sub>2</sub>H <math>\overrightarrow{\leftarrow}</math> HOC<sub>6</sub>H<sub>4</sub>CO<sub>2</sub><sup>-</sup> + H<sup>+</sup> |
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], obtained from the fruit of the ] (''Euterpe oleracea''), is rich in ''p''-hydroxybenzoic acid ({{val|892|52|u=mg/kg}}).<ref>{{cite journal |journal = Journal of Agricultural and Food Chemistry |date=June 2008 | volume = 56 | issue = 12 | pages = 4631–4636 | title = Chemical composition, antioxidant properties, and thermal stability of a phytochemical enriched oil from Açaí (''Euterpe oleracea'' Mart.) | last1 = Pacheco Palencia | first1 = L. A. | last2 = Mertens-Talcott | first2 = S. | last3 = Talcott | first3 = S. T. |pmid = 18522407| doi = 10.1021/jf800161u}}</ref> It is also found in ]{{citation needed|date=February 2019}} and in the edible mushroom '']'' (green-cracking russula).{{citation needed|date=February 2019}} |
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==Safety== |
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4-Hydroxybenzoic acid is popular antioxidant in part because of its low toxicity. The {{LD50}} is 2200 mg/kg in mice (oral). |
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== Related compounds == |
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==References== |
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] can be found in mycorrhizal and non-mycorrhizal roots of Norway spruces ('']'').<ref>{{cite journal|title=Phenolics of mycorrhizas and non-mycorrhizal roots of Norway spruce |first1=B. |last1=Münzenberger |first2=J. |last2=Heilemann |first3=D. |last3=Strack |first4=I. |last4=Kottke |first5=F. |last5=Oberwinkler |journal=Planta |year=1990 |volume=182 |issue=1 |pages=142–148 |doi=10.1007/BF00239996|pmid=24197010 |s2cid=43504838 }}</ref> |
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] is an anthocyanin, a type of plant pigments, found in blue flowers and incorporating two ''p''-hydroxybenzoic acid residues, one ] and two ] associated with a ]. |
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] is the ester of ] and ''p''-hydroxybenzoic acid.<ref>{{cite journal | title = An analytical high performance liquid chromatographic method for the determination of agnuside and ''p''-hydroxybenzoic acid contents in Agni-casti fructose | first1 = E. | last1 = Hoberg | first2 = B. | last2 = Meier | first3 = O. | last3 = Sticher | journal = Phytochemical Analysis | volume = 11 | issue = 5 | pages = 327–329 | date = September 2000 | doi = 10.1002/1099-1565(200009/10)11:5<327::AID-PCA523>3.0.CO;2-0| bibcode = 2000PChAn..11..327H }}</ref> |
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== Biosynthesis == |
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] is an enzyme that transforms ] into 4-hydroxybenzoate and pyruvate. This enzyme catalyses the first step in ] biosynthesis in '']'' and other Gram-negative bacteria. |
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] is an enzyme that utilizes ], NADPH, H<sup>+</sup> and O<sub>2</sub> to produce 4-hydroxybenzoate, NADP<sup>+</sup> and H<sub>2</sub>O. This enzyme can be found in '']''. |
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4-Hydroxybenzoate also arises from tyrosine.<ref>{{cite journal |doi=10.1016/j.bbabio.2016.03.036 |title=Coenzyme Q biosynthesis in health and disease |date=2016 |last1=Acosta |first1=Manuel Jesús |last2=Vazquez Fonseca |first2=Luis |last3=Desbats |first3=Maria Andrea |last4=Cerqua |first4=Cristina |last5=Zordan |first5=Roberta |last6=Trevisson |first6=Eva |last7=Salviati |first7=Leonardo |journal=Biochimica et Biophysica Acta (BBA) - Bioenergetics |volume=1857 |issue=8 |pages=1079–1085 |pmid=27060254 |doi-access=free }}</ref> |
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== Metabolism == |
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=== As an intermediate === |
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The enzyme ] transforms ], an electron acceptor AH<sub>2</sub> and O<sub>2</sub> into 4-hydroxybenzoate, formaldehyde, the reduction product A and H<sub>2</sub>O. This enzyme participates in ] degradation in '']''. |
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The enzyme ] uses ], NAD<sup>+</sup> and H<sub>2</sub>O to produce 4-hydroxybenzoate, NADH and H<sup>+</sup>. This enzyme participates in ] and ] degradation in bacteria such as '']''. It is also found in carrots ('']''). |
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The enzyme that ] transforms ] and O<sub>2</sub> into 4-hydroxybenzoate and ]. This enzyme participates in ] degradation. It can be found in '']'' species. |
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The enzyme ] uses ] and H<sub>2</sub>O to produce 4-hydroxybenzoate and ]. It can be found in '']'' species. |
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The enzyme ] utilizes ] and H<sub>2</sub>O to produce 4-hydroxybenzoate and CoA. This enzyme participates in ] degradation. It can be found in '']'' species. |
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The enzyme ] uses a polyprenyl diphosphate and 4-hydroxybenzoate to produce diphosphate and ]. This enzyme participates in ] biosynthesis. |
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The enzyme ] utilizes ] and 4-hydroxybenzoate to produce ] and diphosphate. Biosynthetically, ] is produced in plants from the intermediates 4-hydroxybenzoic acid and ]. This enzyme is involved in ] biosynthesis. It can be found in '']''. |
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The enzyme ] uses ATP, ] and CoA to produce AMP, diphosphate and ]. The enzyme works equally well with 4-hydroxybenzoate. It can be found in '']''. |
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=== Biodegradation === |
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The enzyme ] transforms 4-hydroxybenzoate, NAD(P)H, 2 H<sup>+</sup> and O<sub>2</sub> into ], NAD(P)<sup>+</sup>, H<sub>2</sub>O and CO<sub>2</sub>. This enzyme participates in ] degradation. It can be found in '']''. |
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The enzyme ] transforms 4-hydroxybenzoate, NADPH, H<sup>+</sup> and O<sub>2</sub> into ], NADP<sup>+</sup> and H<sub>2</sub>O. This enzyme participates in ] degradation via hydroxylation and ] degradation. It can be found in '']'' and '']''. |
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The enzyme ] utilizes 4-hydroxybenzoate, NADH, NADPH, H<sup>+</sup> and O<sub>2</sub> to produce 3,4-dihydroxybenzoate (]), NAD<sup>+</sup>, NADP<sup>+</sup> and H<sub>2</sub>O. This enzyme participates in ] degradation via hydroxylation and ] degradation. It can be found in '']'' and in ''] sp''. |
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The enzyme ] uses 4-hydroxybenzoate to produce ] and CO<sub>2</sub>. This enzyme participates in ] degradation via ] (CoA) ligation. It can be found in '']'' (''Aerobacter aerogenes''). |
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The enzyme ] transforms ATP, 4-hydroxybenzoate and CoA to produce AMP, diphosphate and ]. This enzyme participates in ] degradation via CoA ligation. It can be found in '']''. |
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'']'' is a plant pathogen that commonly inhabits fertile soil. It is known to metabolize aromatic compounds of low molecular weight, such as ''p''-hydroxybenzoic acid. |
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=== Glycosylation === |
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The enzyme ] transforms ] and 4-hydroxybenzoate into UDP and ]. It can be found in the pollen of '']''. |
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== Chemistry == |
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The ] describes a linear free-energy relationship relating reaction rates and equilibrium constants for many reactions involving benzoic acid derivatives with meta- and para-substituents. |
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=== Chemical production === |
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4-Hydroxybenzoic acid is produced commercially from potassium ] and ] in the ].<ref>Edwin Ritzer and Rudolf Sundermann "Hydroxycarboxylic Acids, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. {{doi| 10.1002/14356007.a13_519}}</ref> It can also be produced in the laboratory by heating ] with ] to 240 °C, followed by treating with acid.<ref>{{OrgSynth | prep = CV2P0341 | first1 = C. A. | last1 = Buehler | first2 = W. E. | last2 = Cate | title = ''p''-Hydroxybenzoic acid | collvol = 2 | collvolpages = 341 | year = 1943 }}</ref> |
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=== Chemical reactions === |
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4-Hydroxybenzoic acid has about one tenth the acidity of ], having an ] ''K<sub>a</sub>'' = {{val|3.3e-5|u=M}} at 19 °C.{{citation needed|date=August 2012}} Its acid dissociation follows this equation: |
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:{{chem2|HOC6H4CO2H}} ⇌ {{chem2|HOC6H4CO2-}} + {{chem2|H+}} |
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=== Chemical use === |
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] is a manufactured fiber, spun from a ]. Chemically it is an aromatic polyester produced by the polycondensation of 4-hydroxybenzoic acid and ]. The fiber has been shown to exhibit strong radiation shielding used by ] and produced by ].<ref>{{cite web | last=Charles Fishman | first=Dan Winters | title=This Expandable Structure Could Become the Future of Living in Space | website=Smithsonian Magazine | date=2016-04-11 | url=https://www.smithsonianmag.com/science-nature/robert-bigelow-visio-future-living-space-180958698/ | access-date=2020-12-07}}</ref> |
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] is generally prepared by the rearrangement of ''p''-hydroxyphenylbenzoate. Alternatively, ''p''-hydroxybenzoic acid can be converted to ]. This acid chloride reacts with phenol to give, after deacetylation, 4,4′-dihydroxybenzophenone. |
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Examples of drugs made from PHBA include ], ], ] and ]. |
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== Bioactivity and safety == |
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4-Hydroxybenzoic acid is a popular antioxidant in part because of its low toxicity. The {{LD50}} is 2200 mg/kg in mice (oral).<ref>{{cite book | editor-last = Lewis | editor-first = R. J. | title = Sax's Dangerous Properties of Industrial Materials | edition = 9th | volume= 1–3 | location = New York, NY | publisher = Van Nostrand Reinhold | date = 1996 | pages = 2897}}</ref> |
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4-Hydroxybenzoic acid has ]ic activity both ''in vitro'' and ''in vivo'',<ref name="Khetan2014">{{cite book|first=S. K.|last=Khetan|title=Endocrine Disruptors in the Environment|url=https://books.google.com/books?id=s2ajAwAAQBAJ&pg=PT109|date=23 May 2014|publisher=Wiley|isbn=978-1-118-89115-5|page=109}}</ref> and stimulates the growth of human ] cell lines.<ref name="pmid16021681">{{cite journal | last1 = Pugazhendhi |first1=D. |last2=Pope |first2=G. S. |last3=Darbre |first3=P. D. | title = Oestrogenic activity of ''p''-hydroxybenzoic acid (common metabolite of paraben esters) and methylparaben in human breast cancer cell lines | journal = Journal of Applied Toxicology | volume = 25 | issue = 4 | pages = 301–309 | year = 2005 | pmid = 16021681 | doi = 10.1002/jat.1066 |s2cid=12342018 }}</ref><ref name="Gabriel2013">{{cite book|first=J.|last=Gabriel|title=Holistic Beauty from the Inside Out: Your Complete Guide to Natural Health, Nutrition, and Skincare|url=https://books.google.com/books?id=7BLtbCCwR74C&pg=PT31|date=April 2013|publisher=Seven Stories Press|isbn=978-1-60980-462-6|page=31}}</ref> It is a common metabolite of ] ]s, such as ].<ref name="Khetan2014" /><ref name="pmid16021681" /><ref name="Gabriel2013" /> The compound is a relatively weak estrogen, but can produce ] with sufficient doses to an equivalent extent relative to ], which is unusual for a weakly estrogenic compound and indicates that it may be a ] of the ] with relatively low ] for the receptor.<ref name="pmid16021681" /><ref name="pmid9417843">{{cite journal | last1 = Lemini |first1=C. |last2=Silva |first2=G. |last3=Timossi |first3=C. |last4=Luque |first4=D. |last5=Valverde |first5=A. |last6=González Martínez |first6=M. |last7=Hernández |first7=A. |last8=Rubio Póo |first8=C. |last9=Chávez Lara |first9=B. |last10=Valenzuela |first10=F. | title = Estrogenic effects of ''p''-hydroxybenzoic acid in CD1 mice | journal = Environmental Research | volume = 75 | issue = 2 | pages = 130–134 | year = 1997 | pmid = 9417843 | doi = 10.1006/enrs.1997.3782 | bibcode = 1997ER.....75..130L }}</ref><ref name="OECD2004">{{cite book|author=OECD|title=OECD Guidelines for the Testing of Chemicals / OECD Series on Testing and Assessment Detailed Background Review of the Uterotrophic Bioassay|url=https://books.google.com/books?id=nzfqBkSdgXgC&pg=PA183|date=November 2004|publisher=OECD Publishing|isbn=978-92-64-07885-7|page=183}}</ref> It is about 0.2% to 1% as potent as an estrogen as estradiol.<ref name="pmid9417843" /> |
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== See also == |
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* ] |
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* ] |
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== References == |
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{{reflist}} |
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{{reflist}} |
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== External links == |
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{{phenolExplorer|418}} |
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{{Phenolic acid}} |
|
{{Phenolic acid}} |
|
|
{{Xenoestrogens}} |
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|
{{Estrogenics}} |
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|
{{DEFAULTSORT:Hydroxybenzoic acid, 4-}} |
|
{{DEFAULTSORT:Hydroxybenzoic acid, 4-}} |
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] |
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] |
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] |
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] |
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] |
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] |
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] |
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] |
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] |
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] |
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] |
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] |
|