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Revision as of 15:40, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 465714095 of page 2,3-Dihydroxybenzoic_acid for the Chem/Drugbox validation project (updated: '').  Latest revision as of 23:30, 9 August 2023 edit Materialscientist (talk | contribs)Edit filter managers, Autopatrolled, Checkusers, Administrators1,994,280 edits tidied 
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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
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 443646723 | verifiedrevid = 477198527
| ImageFile = 2,3-Dihydroxybenzoesäure.svg|150px | ImageFile = 2,3-Dihydroxybenzoesäure.svg
| ImageSize = 150px | ImageSize = 100px
| IUPACName = 2,3-Dihydroxybenzoic acid | PIN = 2,3-Dihydroxybenzoic acid
| OtherNames = 2,3-DHBA<br>2,3-DHB<br>2-pyrocatechuic acid<br>o-pyrocatechuic acid | OtherNames = Hypogallic acid; 2-Pyrocatechuic acid; ''o''-Pyrocatechuic acid
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| Abbreviations = 2,3-DHBA; 2,3-DHB
| ChemSpiderID = 18
| PubChem = 19 | ChemSpiderID = 18
| KEGG_Ref = {{keggcite|correct|kegg}} | PubChem = 19
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C00196 | KEGG = C00196
| InChI = 1/C7H6O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,8-9H,(H,10,11) | InChI = 1/C7H6O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,8-9H,(H,10,11)
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01672 | DrugBank = DB01672
| SMILES = O=C(O)c1cccc(O)c1O | SMILES = O=C(O)c1cccc(O)c1O
| InChIKey = GLDQAMYCGOIJDV-UHFFFAOYAE | InChIKey = GLDQAMYCGOIJDV-UHFFFAOYAE
| SMILES1 = c1cc(c(c(c1)O)O)C(=O)O | SMILES1 = c1cc(c(c(c1)O)O)C(=O)O
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1432 | ChEBI = 18026
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1432
⚫ | StdInChI = 1S/C7H6O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,8-9H,(H,10,11)
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChI = 1S/C7H6O4/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,8-9H,(H,10,11)
⚫ | StdInChIKey = GLDQAMYCGOIJDV-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫ | StdInChIKey = GLDQAMYCGOIJDV-UHFFFAOYSA-N
⚫ | CASNo = 303-38-8 }}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | CASNo_Ref = {{cascite|correct|CAS}}
⚫ | CASNo = 303-38-8
| ChEBI_Ref = {{ebicite|correct|EBI}} | UNII_Ref = {{fdacite|correct|FDA}}
| ChEBI = 18026
| UNII = 70D5FBB392
⚫ | Section2 = {{Chembox Properties
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
}}
⚫ |Section2={{Chembox Properties
| C=7 | H=6 | O=4 | C=7 | H=6 | O=4
⚫ | Appearance = Colorless solid
| ExactMass = 154.026609 u
| Density=1.542 g/cm<sup>3</sup> (20 °C)<ref name=crc/>
⚫ | Appearance = Colorless solid
| MeltingPtC = 205
| MeltingPt = 204–206&nbsp;°C
| MeltingPt_ref=<ref name=crc>{{cite book |ref=Haynes| editor= Haynes, William M. | date = 2016| title = ] | edition = 97th | publisher = ] | isbn = 9781498754293|page=3.190}}</ref>
| BoilingPt =
| Solubility = low | BoilingPt =
| Solubility =
}} }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| NFPA-H = | NFPA-H =
| NFPA-F = | NFPA-F =
| NFPA-R = | NFPA-R =
| NFPA-O = | NFPA-S =
| FlashPt = | FlashPtC=
}} }}
}} }}

'''2,3-Dihydroxybenzoic acid''' is a natural phenol found in '']''<ref>{{cite journal | doi = 10.1124/mol.106.025262 | pmid=17065237 | volume=71 | issue=1 | title=An extract from the medicinal plant Phyllanthus acidus and its isolated compounds induce airway chloride secretion: A potential treatment for cystic fibrosis |date=January 2007 | journal=Mol. Pharmacol. | pages=366–76 |vauthors=Sousa M, Ousingsawat J, Seitz R, etal| s2cid=5793585 }}</ref> and in the aquatic fern '']''.<ref>{{Cite journal| last1 = Choudhary| first1 = M. I. | last2 = Naheed | first2 = N. | last3 = Abbaskhan | first3 = A. | last4 = Musharraf | first4 = S. G. | last5 = Siddiqui | first5 = H. | last6 = Atta-Ur-Rahman | doi = 10.1016/j.phytochem.2007.10.028 | title = Phenolic and other constituents of fresh water fern Salvinia molesta | journal = Phytochemistry | volume = 69 | issue = 4 | pages = 1018–1023 | year = 2008 | pmid = 18177906}}</ref> It is also abundant in the fruits of '']''. It is a ], a type of organic compound.

The colorless solid occurs naturally, being formed via the ]. It is incorporated into various ]s, which are molecules that strongly complex iron ions for absorption into bacteria. 2,3-DHB consists of a ] group, which upon deprotonation binds iron centers very strongly, and the ] group by which the ring attaches to various scaffolds through amide bonds. A famous high affinity siderophore is ], which contains three dihydroxybenzoyl substituents linked to the depsipeptide of ].<ref>{{cite journal |author1=O'Brien, I. G. |author2=Cox, G. B. |author3=Gibson, F. | title = Biologically active compounds containing 2,3-dihydroxybenzoic acid and serine formed by ''Escherichia coli'' | journal = ] | year = 1970 | volume = 201 | pages = 453–60 | pmid = 4908639 | issue = 3 | doi=10.1016/0304-4165(70)90165-0}}</ref><ref>{{Cite journal | last1 = Young | first1 = I. G. | last2 = Gibson | first2 = F. | doi = 10.1016/0304-4165(69)90302-X | title = Regulation of the enzymes involved in the biosynthesis of 2,3-dihydroxybenzoic acid in ''Aerobacter aerogenes'' and ''Escherichia coli'' | journal = Biochimica et Biophysica Acta (BBA) - General Subjects | volume = 177 | issue = 3 | pages = 401–11 | year = 1969 | pmid = 4306838}}</ref>

It is a potentially useful ]<ref>{{cite journal | title = The identification of 2,3-dihroxybenzoic acid as a potentially useful iron-chelating drug |author1=Graziano, J. H. |author2=Grady, R. W. |author3=Cerami, A. | journal = Journal of Pharmacology and Experimental Therapeutics |year = 1974 | volume= 190 | issue = 3| pages =570–575 |pmid=4416298 | url = http://jpet.aspetjournals.org/content/190/3/570.short}}</ref> and has ] properties.<ref>{{cite journal |author1=George, Shibumon |author2=PJ, Benny |author3=Kuriakose, Sunny |author4=George, Cincy |url=https://innovareacademics.in/journal/ajpcr/Vol4Issue1/227.pdf| title = Antibiotic activity of 2, 3-dihydroxybenzoic acid isolated from ''Flacourtia inermis'' fruit against multidrug resistant bacteria | journal = Asian Journal of Pharmaceutical and Clinical Research| volume=4 | issue = 1 | date = 2011}}</ref><ref>{{cite journal |author1=PJ, Benny |author2=Shibumon, George |author3=Sunny, Kuriakose |author4=Cincy, George | title = 2, 3-Dihydroxybenzoic Acid: An Effective Antifungal Agent Isolated from ''Flacourtia inermis'' Fruit |url=https://www.researchgate.net/publication/210252724| journal = International Journal of Pharmaceutical and Clinical Research | date = 2010 | volume = 2 | issue = 3 | pages = 101–105}}</ref><ref>{{cite journal |author1=George, Shibumon |author2=PJ, Benny |author3=Kuriakose, Sunny |author4=George, Cincy |author5=Sarala, Gopalakrishnan | title = Antiprotozoal activity of 2, 3-dihydroxybenzoic acid isolated from the fruit extracts of ''Flacourtia inermis'' Roxb | journal = Medicinal Plants - International Journal of Phytomedicines and Related Industries |date=2011 | volume = 3 | issue = 3 | pages = 237–241| doi=10.5958/j.0975-4261.3.3.038}}</ref>

2,3-Dihydroxybenzoic acid is also a product of human ] metabolism.<ref>{{Cite journal | last1 = Grootveld | first1 = M. | last2 = Halliwell | first2 = B. | doi = 10.1016/0006-2952(88)90729-0 | title = 2,3-Dihydroxybenzoic acid is a product of human aspirin metabolism | journal = Biochemical Pharmacology | volume = 37 | issue = 2 | pages = 271–280 | year = 1988 | pmid = 3342084}}</ref>

== References ==
{{reflist}}

{{Phenolic acid}}

{{DEFAULTSORT:Dihydroxybenzoic acid, 2,3-}}
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