| 词条 | 2,3-Dihydroxybenzoic acid |
| 释义 |
| Watchedfields = changed | verifiedrevid = 477198527 | ImageFile = 2,3-Dihydroxybenzoesäure.svg | ImageSize = 100px | IUPACName = 2,3-Dihydroxybenzoic acid | OtherNames = Hypogallic acid; 2-Pyrocatechuic acid; o-Pyrocatechuic acid |Section1={{Chembox Identifiers | Abbreviations = 2,3-DHBA; 2,3-DHB | ChemSpiderID = 18 | PubChem = 19 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C00196 | 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 = DB01672 | SMILES = O=C(O)c1cccc(O)c1O | InChIKey = GLDQAMYCGOIJDV-UHFFFAOYAE | SMILES1 = c1cc(c(c(c1)O)O)C(=O)O | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 18026 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 1432 | 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_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = GLDQAMYCGOIJDV-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 303-38-8 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} }} |Section2={{Chembox Properties | C=7 | H=6 | O=4 | Appearance = Colorless solid | MeltingPtC = 204 to 206 | BoilingPt = | Solubility = 26 g/L at 22C |Section7={{Chembox Hazards | NFPA-H = | NFPA-F = | NFPA-R = | NFPA-S = | FlashPtC= }} 2,3-Dihydroxybenzoic acid is a natural phenol found in Phyllanthus acidus[1] and in the aquatic fern Salvinia molesta.[2] It is also abundant in the fruits of Flacourtia inermis. It is a dihydroxybenzoic acid, a type of organic compound. The colorless solid occurs naturally, being formed via the shikimate pathway. It is incorporated into various siderophores, which are molecules that strongly complex iron ions for absorption into bacteria. 2,3-DHB consists of a catechol group, which upon deprotonation binds iron centers very strongly, and the carboxylic acid group by which the ring attaches to various scaffolds through amide bonds. A famous high affinity siderophore is enterochelin, which contains three dihydroxybenzoyl substituents linked to the depsipeptide of serine.[3][4] It is a potentially useful iron-chelating drug[5] and has antimicrobial properties.[6][7][8] 2,3-Dihydroxybenzoic acid is also a product of human aspirin metabolism.[9] References1. ^{{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}} {{Phenolic acid}}{{DEFAULTSORT:Dihydroxybenzoic acid, 2,3-}}2. ^{{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| pmc =}} 3. ^{{cite journal |author1=I. G. O'Brien |author2=G. B. Cox |author3=F. Gibson | title = Biologically active compounds containing 2,3-dihydroxybenzoic acid and serine formed by Escherichia coli | journal = Biochimica et Biophysica Acta | year = 1970 | volume = 201 | pages = 453–60 | pmid = 4908639 | issue = 3 | doi=10.1016/0304-4165(70)90165-0}} 4. ^{{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| pmc=}} 5. ^{{cite journal | title = The identification of 2,3-dihroxybenzoic acid as a potentially useful iron-chelating drug |author1=J. H. Graziano |author2=R. W. Grady |author3=A. Cerami | journal = JPET |year = 1974 | volume= 190 | issue = 3| pages =570–575 | url = http://jpet.aspetjournals.org/content/190/3/570.short}} 6. ^{{cite journal |author1=Shibumon George |author2=Benny PJ |author3=Sunny Kuriakose |author4=Cincy George | 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}} 7. ^{{cite journal |author1=Benny PJ |author2=George Shibumon |author3=Kuriakose Sunny |author4=George Cincy | title = 2, 3-Dihydroxybenzoic Acid: An Effective Antifungal Agent Isolated from Flacourtia inermis Fruit | journal = International Journal of Pharmaceutical and Clinical Research | date = 2010 | volume = 2 | issue = 3 | pages = 101–105}} 8. ^{{cite journal |author1=George Shibumon |author2=Benny PJ |author3=Kuriakose Sunny |author4=George Cincy |author5=Gopalakrishnan Sarala | 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}} 9. ^{{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| pmc =}} 3 : Dihydroxybenzoic acids|Salicylic acids|Chelating agents |
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