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Revision as of 11:09, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 477164053 of page Protocatechuic_acid for the Chem/Drugbox validation project (updated: '').		Latest revision as of 21:52, 10 September 2024 edit Citation bot (talk | contribs)Bots5,418,152 edits Add: issue, bibcode. | Use this bot. Report bugs. | Suggested by Abductive | Category:Phenol antioxidants | #UCB_Category 10/25
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	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{chembox		{{chembox
	| Verifiedfields = changed
	| Watchedfields = changed		| Watchedfields = changed
	| verifiedrevid = 399906069		| verifiedrevid = 477165260
	| ImageFile=Protocatechusäure.svg		| ImageFile=Protocatechusäure.svg
	| ImageSize=120px		| ImageSize=120px
	| IUPACName=3,4-Dihydroxybenzoic acid		| PIN=3,4-Dihydroxybenzoic acid
	| OtherNames = 3,4-Dihydroxybenzoic acid, PCA		| ImageFile1 = 3,4-Dihydroxybenzoic acid.jpg
			| OtherNames = 3,4-Dihydroxybenzoic acid<br>PCA<br>Protocatechuate
	|Section1={{Chembox Identifiers		|Section1={{Chembox Identifiers
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo=99-50-3		| CASNo=99-50-3
			| UNII_Ref = {{fdacite|correct|FDA}}
	| PubChem=72
			| UNII = 36R5QJ8L4B
	| ChEMBL_Ref = {{ebicite|changed|EBI}}
			| PubChem=72
			| ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 37537		| ChEMBL = 37537
	| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 71		| ChemSpiderID = 71
	| DrugBank_Ref = {{drugbankcite|changed|drugbank}}		| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
	| DrugBank = DB03946		| DrugBank = DB03946
			| EINECS = 202-760-0
	| ChEBI_Ref = {{ebicite|changed|EBI}}
			| KEGG = C00230
			| 3DMet = B00064
			| RTECS = UL0560000
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 36062		| ChEBI = 36062
	| StdInChI_Ref = {{stdinchicite|changed|chemspider}}		| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C7H6O4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H,(H,10,11)		| StdInChI = 1S/C7H6O4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H,(H,10,11)
	| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = YQUVCSBJEUQKSH-UHFFFAOYSA-N		| StdInChIKey = YQUVCSBJEUQKSH-UHFFFAOYSA-N
	| SMILES=C1=CC(=C(C=C1C(=O)O)O)O		| SMILES=C1=CC(=C(C=C1C(=O)O)O)O
	}}		}}
	|Section2={{Chembox Properties		|Section2={{Chembox Properties
	| Formula = C<sub>7</sub>H<sub>6</sub>O<sub>4</sub>		| Formula = C<sub>7</sub>H<sub>6</sub>O<sub>4</sub>
	| MolarMass = 154.12 g/mol		| MolarMass = 154.12 g/mol
			| Appearance= light brown solid
	| ExactMass = 154.026608 u
			| Density=1.524 g/cm<sup>3</sup> (4 °C)<ref name=crc>Haynes, p. 3.190</ref>
	| Appearance=
			| MeltingPtC= 202
	| Density=
			| MeltingPt_ref = <ref name=crc/>
	| MeltingPt=
			| BoilingPtC =
	| BoilingPt=
			| Solubility= 18 g/L (14 °C)<br>271 g/L (80 °C)<ref>Haynes, p. 5.148</ref>
	| Solubility=
			| SolubleOther = soluble in ], ] <br> insoluble in ]
	| pKa = 4.48 <ref> Dawson, R. M. C. et al., ''Data for Biochemical Research'', Oxford, Clarendon Press, 1959. </ref>
			| pKa = 4.48, 8.83, 12.6<ref>Haynes, p. 5.91</ref>
	}}		}}
	|Section3={{Chembox Hazards		|Section3={{Chembox Hazards
			| ExternalSDS =
	| MainHazards=
	| FlashPt=		| MainHazards=
			| FlashPt=
	| Autoignition=
			| AutoignitionPt =
			| NFPA-H = 2 | NFPA-F = 0 | NFPA-R = 0
	}}		}}
	}}		}}
			]
			'''Protocatechuic acid''' ('''PCA''') is a ], a type of phenolic acid. It is a major metabolite of antioxidant polyphenols found in green tea. It has mixed effects on normal and cancer cells in '']'' and '']'' studies.<ref>{{cite journal |last1=Lin |first1=H.-H. |last2=Chen |first2=J.-H. |last3=Huang |first3=C.-C. |last4=Wang |first4=C.-J. |title=Apoptotic effect of 3,4-dihydroxybenzoic acid on human gastric carcinoma cells involving JNK/p38 MAPK signaling activation |journal= International Journal of Cancer |volume=120 |issue=11 |pages=2306–2316 |date=June 2007 |pmid=17304508 |doi=10.1002/ijc.22571 |doi-access=free }}</ref> It is produced commercially from ].<ref>{{Ullmann| doi=10.1002/14356007.a13_519| chapter=Hydroxycarboxylic Acids, Aromatic|year=2000| last1=Ritzer| first1=Edwin| last2=Sundermann| first2=Rudolf| isbn=3527306730}}</ref>
			== Biological effects ==
			Protocatechuic acid (PCA) is antioxidant and anti-inflammatory. PCA extracted from ''Hibiscus sabdariffa'' protected against chemically induced liver toxicity ''in vivo''. ''In vitro'' testing documented antioxidant and anti-inflammatory activity of PCA, while liver protection ''in vivo'' was measured by chemical markers and histological assessment.<ref name="hibo">{{cite journal |last1=Liu |first1=C.-L. |last2=Wang |first2=J.-M. |last3=Chu |first3=C.-Y. |title=In vivo protective effect of protocatechuic acid on ''tert''-butyl hydroperoxide-induced rat hepatotoxicity |journal=Food and Chemical Toxicology |volume=40 |pages=635–41 |year=2002 |pmid=11955669 |last4=Cheng |first4=M.-T. |last5=Tseng |first5=T.-H. |issue=5 |doi=10.1016/s0278-6915(02)00002-9}}</ref>
			PCA has been reported to induce ] of human ] cells, as well as malignant HSG1 cells taken from human oral cavities,<ref>{{cite journal |last1=Babich |first1=H. |last2=Sedletcaia |first2=A. |last3=Kenigsberg |first3=B. |title=''In vitro'' cytotoxicity of protocatechuic acid to cultured human cells from oral tissue: involvement in oxidative stress |journal=Pharmacology & Toxicology |volume=91 |issue=5 |pages=245–253 |date=November 2002 |pmid=12570031 |doi=10.1034/j.1600-0773.2002.910505.x |doi-access=free }}</ref> but PCA was found to have mixed effects on ]-induced mouse skin tumours. Depending on the amount of PCA and the time before application, PCA could reduce or enhance tumour growth.<ref>{{cite journal |last1=Nakamura |first1=Y. |last2=Torikai |first2=K. |last3=Ohto |first3=Y. |last4=Murakami |first4=A. |last5=Tanaka |first5=T. |last6=Ohigashi |first6=H. |title=A simple phenolic antioxidant protocatechuic acid enhances tumor promotion and oxidative stress in female ICR mouse skin: dose- and timing-dependent enhancement and involvement of bioactivation by tyrosinase |journal=Carcinogenesis |volume=21 |issue=10 |pages=1899–1907 |date=October 2000 |pmid=11023549 |doi= 10.1093/carcin/21.10.1899|doi-access=free }}</ref> Similarly, PCA was reported to increase proliferation and inhibit apoptosis of neural ]s.<ref>{{cite journal |last1=Guan |first1=S. |last2=Ge |first2=D. |last3=Liu |first3=T. Q. |last4=Ma |first4=X.-H. |last5=Cui |first5=Z.-F. |date=March 2009 |title= Protocatechuic acid promotes cell proliferation and reduces basal apoptosis in cultured neural stem cells|journal= Toxicology in Vitro|volume= 23|issue= 2|pages=201–208 |pmid= 19095056 |doi= 10.1016/j.tiv.2008.11.008|bibcode=2009ToxVi..23..201G }}</ref> In an ''in vitro'' model using ] ] cells, protocatechuic acid showed an antigenotoxic effect and tumoricidal activity.<ref>{{cite journal|last1=Anter |first1=J. |last2=Romero Jiménez |first2=M. |last3=Fernández Bedmar |first3=Z. |last4=Villatoro Pulido |first4=M. |last5=Analla |first5=M. |last6=Alonso Moraga |first6=A. |last7=Muñoz Serrano |first7=A. |title=Antigenotoxicity, cytotoxicity, and apoptosis induction by apigenin, bisabolol, and protocatechuic acid |journal=Journal of Medicinal Food |date=March 2011 |volume=14 |issue=3 |pages=276–283|doi=10.1089/jmf.2010.0139 |pmid=21182433 }}</ref> In two preclinical investigations, protocatechuic acid from '']'' showed an excellent ability to effectively inhibit the replication of ]<ref>{{cite journal|last1=Hassan |first1=S. T. S. |last2=Švajdlenka |first2=E. |last3=Berchová-Bímová |first3=K. |title=''Hibiscus sabdariffa'' L. and its bioactive constituents exhibit antiviral activity against HSV-2 and anti-enzymatic properties against urease by an ESI–MS based assay |journal=Molecules |date=April 2017 |volume=22 |issue=5 |page=722|doi=10.3390/molecules22050722 |pmid=28468298 |pmc=6154344 |doi-access=free }}</ref> and to potently deactivate the catalytic activity of ].<ref>{{cite journal|last1=Hassan |first1=S. T. S. |last2=Švajdlenka |first2=E. |title=Biological evaluation and molecular docking of protocatechuic acid from ''Hibiscus sabdariffa'' L. as a potent urease inhibitor by an ESI–MS based method|journal=Molecules|date=October 2017 |volume=22 |issue=10 |page=1696|doi=10.3390/molecules22101696 |pmid=29019930 |pmc=6151788 |doi-access=free }}</ref>
			== Occurrence in nature ==
			Protocatechuic acid can be isolated from the stem bark of '']''.<ref>{{cite journal|title=Antibacterial phenolics from ''Boswellia dalzielii'' |last1=Alemika |first1=T. E. |last2=Onawunmi |first2=G. O. |last3=Olugbade |first3=T. O. |journal=Nigerian Journal of Natural Products and Medicines |date=2006 |volume=10 |pages=108–110 |url=http://dspace.unijos.edu.ng/handle/10485/1174 |archive-url=https://web.archive.org/web/20130730080304/http://dspace.unijos.edu.ng/handle/10485/1174 |url-status=dead |archive-date=2013-07-30 |access-date=2013-07-30 }}</ref> and from leaves of '']''.<ref>{{cite journal|last1=Mallavadhani |first1=U. V. |last2=Mahapatra |first2=A. |title=A new aurone and two rare metabolites from the leaves of ''Diospyros melanoxylon'' |journal=Natural Product Research |date=2005 |volume=19 |issue=1 |pages=91–97|doi=10.1080/14786410410001704705 |pmid=15700652 |s2cid=35200920 }}</ref>
			The hardening of the protein component of ] has been shown to be due to the tanning action of an agent produced by oxidation of a phenolic substance. In the analogous hardening of the cockroach ], the phenolic substance concerned is protocatechuic acid.<ref>{{Cite journal
			| last1 = Hackman | first1 = R. H.
			| last2 = Pryor | first2 = M. G.
			| last3 = Todd | first3 = A. R.
			| title = The occurrence of phenolic substances in arthropods
			| journal = The Biochemical Journal
			| volume = 43
			| issue = 3
			| pages = 474–477
			| year = 1948
			| pmid = 16748434
			| pmc = 1274717
			| doi=10.1042/bj0430474
			}}</ref>
			=== In foods ===
			], obtained from the fruit of the ] (''Euterpe oleracea''), is rich in protocatechuic acid ({{val|630|36|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.) |pmid = 18522407| doi = 10.1021/jf800161u |last1=Pacheco Palencia |first1=L. A. |last2=Mertens-Talcott |first2=S |last3=Talcott |first3=S. T. }}</ref> Protocatechuic acid also exists in the skins of some strains of onion as an antifungal mechanism, increasing endogenous resistance against smudge fungus. It is also found in '']'' (17,540&nbsp;ppm).<ref>{{Cite web |url=http://www.ars-grin.gov/cgi-bin/duke/highchem.pl |title=Chemical Query |access-date=2011-09-25 |archive-url=https://web.archive.org/web/20130616093128/http://www.ars-grin.gov/cgi-bin/duke/highchem.pl |archive-date=2013-06-16 |url-status=dead }}</ref>
			PCA occurs in ] (''Hibiscus sabdariffa''), which is used worldwide as a food and beverage.<ref name="hibo" />
			Protocatechuic acid is also found in mushrooms such as '']''<ref>{{cite journal |last1=Delsignore |first1=A |last2=Romeo. |first2=F. |last3=Giaccio |first3=M. |title=Content of phenolic substances in basidiomycetes |journal=Mycological Research |volume=101 |pages=552–556 |year=1997 |doi=10.1017/S0953756296003206 |issue=5}}</ref> or '']''.<ref name="pmid18827365">{{cite journal |doi=10.1248/bpb.31.1968 |last1=Lee |first1=Y.-S. |last2=Kang |first2=Y. H. |last3=Jung |first3=J. Y. |display-authors=etal |title=Protein glycation inhibitors from the fruiting body of ''Phellinus linteus'' |journal=Biological & Pharmaceutical Bulletin |volume=31 |issue=10 |pages=1968–72 |date=October 2008 |pmid=18827365 |doi-access=free }}</ref>
			PCA is regarded as an active component in traditional Chinese herbal medicine such as Stenoloma chusanum (L.) Ching, Ilex chinensis Sims, Cibotium barometz (L.) J.Sm.<ref>{{Cite journal|last1=Li|first1=Xican|last2=Wang|first2=Xiaozhen|last3=Chen|first3=Dongfeng|last4=Chen|first4=Shuzhi|date=2011-07-31|title=Antioxidant Activity and Mechanism of Protocatechuic Acid in vitro|url=https://ffhdj.com/index.php/ffhd/article/view/127|journal=Functional Foods in Health and Disease|volume=1|issue=7|pages=232|doi=10.31989/ffhd.v1i7.127|issn=2160-3855|doi-access=free}}</ref>
			== Metabolism ==
			Protocatechuic acid is one of the main catechins ]s found in humans after consumption of ] infusions.<ref>{{cite journal | last1 = Pietta | first1 = P. G. | last2 = Simonetti | first2 = P. | last3 = Gardana | first3 = C. | last4 = Brusamolino | first4 = A. | last5 = Morazzoni | first5 = P. | last6 = Bombardelli | first6 = E. | year = 1998 | title = Catechin metabolites after intake of green tea infusions | journal = BioFactors | volume = 8 | issue = 1–2| pages = 111–118 | doi = 10.1002/biof.5520080119 | pmid=9699018| s2cid = 37684286 }}</ref>
			=== Enzymes ===
			;Biosynthesis enzymes
			* ]
			* ]
			* ]
			* ]
			* ]
			* ]
			* ]
			* ]
			* ]
			]
			; Degradation enzymes
			* The enzyme ] uses 3,4-dihydroxybenzoate to produce ] and ].
			* The enzyme ] uses 3,4-dihydroxybenzoate and ] to produce ].
			== See also ==
			* ]
			== References ==
			{{reflist}}
			==Cited sources==
			*{{cite book |ref=Haynes| editor= Haynes, William M. | date = 2016| title = ] | edition = 97th | publisher = ] | isbn = 9781498754293}}
			{{Phenolic acid}}
			]
			]
			]