4-Hydroxybenzaldehyde
{{chembox
| Watchedfields = changed
| verifiedrevid = 477222206
| ImageFile =4-hydroxybenzaldehyde.svg
| ImageSize = 80
| ImageFile1 = 4-Hydroxybenzadehyde sample.jpg
| PIN =4-Hydroxybenzaldehyde
| OtherNames =p-Hydroxybenzaldehyde, 4-formylphenolHaynes, p. 3.304
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 123
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = O1738X3Y38
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C00633
| InChI = 1/C7H6O2/c8-5-6-1-3-7(9)4-2-6/h1-5,9H
| InChIKey = RGHHSNMVTDWUBI-UHFFFAOYAN
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 14193
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C7H6O2/c8-5-6-1-3-7(9)4-2-6/h1-5,9H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = RGHHSNMVTDWUBI-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo =123-08-0
| PubChem =126
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 17597
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB03560
| SMILES = O=Cc1ccc(O)cc1
}}
|Section2={{Chembox Properties
| C=7 | H=6 | O=2
| Appearance =yellow to tan powder
| Density =1.129 g/cm3 (130 °C)
| RefractIndex =1.57051 (130 °C)
| pKa = 7.61 (25 °C)Haynes, p. 5.92
| MeltingPtC = 116
| BoilingPtC = 310 to 311
| BoilingPt_notes =
| Solubility = 12.9 g/LHaynes, p. 5.154
| MagSus = −78.0·10−6 cm3/mol
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
4{{nbh}}Hydroxybenzaldehyde (para{{nbh}}hydroxybenzaldehyde) is an organic compound with the formula {{chem2|C6H4OH(CHO)}}.Merck Index, 11th Edition, 8295{{cite book |doi=10.1002/0471238961.0825041813011209.a01 |chapter=Hydroxybenzaldehydes |title=Kirk-Othmer Encyclopedia of Chemical Technology |date=2000 |last1=Maliverney |first1=Christian |last2=Mulhauser |first2=Michel |isbn=978-0-471-48494-3 }} Along with 2-hydroxybenzaldehyde and 3-hydroxybenzaldehyde, it is one of the three isomers of hydroxybenzaldehyde.
Synthesis, reactions, uses
4-Hydroxybenzaldehyde is prepared by reaction of phenol with chloroform, which gives isomeric hydroxybenzal chlorides. Hydrolysis of the C-Cl bonds gives the aldehyde.
4-Hydroxybenzaldehyde is a precursor to 4-hydroxyphenylglycine, a precursor to penicillins. In the Dakin oxidation, 4-hydroxybenzaldehyde reacts with hydrogen peroxide in base to form hydroquinone.
Metabolism and occurrence
p-Hydroxybenzaldehyde dehydrogenase is an enzyme found in carrots (Daucus carota).{{Cite journal | last1 = Sircar | first1 = D. | last2 = Mitra | first2 = A. | doi = 10.1016/j.jplph.2007.05.005 | title = Evidence for p-hydroxybenzoate formation involving enzymatic phenylpropanoid side-chain cleavage in hairy roots of Daucus carota | journal = Journal of Plant Physiology | volume = 165 | issue = 4 | pages = 407–414 | year = 2008 | pmid = 17658659}}
4-Hydroxybenzaldehyde is found in the orchids Gastrodia elata,{{Cite journal | last1 = Ha | first1 = J. H. | last2 = Lee | first2 = D. U. | last3 = Lee | first3 = J. T. | last4 = Kim | first4 = J. S. | last5 = Yong | first5 = C. S. | last6 = Kim | first6 = J. A. | last7 = Ha | first7 = J. S. | last8 = Huh | first8 = K. | doi = 10.1016/S0378-8741(00)00313-5 | title = 4-Hydroxybenzaldehyde from Gastrodia elata B1. Is active in the antioxidation and GABAergic neuromodulation of the rat brain | journal = Journal of Ethnopharmacology | volume = 73 | issue = 1–2 | pages = 329–333 | year = 2000 | pmid = 11025174}} Galeola faberi,{{Cite journal
| last1 = Li | first1 = Y. M.
| last2 = Zhou | first2 = Z. L.
| last3 = Hong | first3 = Y. F.
| title = (title in Chinese)
| trans-title = Studies on the phenolic derivatives from Galeola faberi Rolfe
| journal = Yao Xue Xue Bao = Acta Pharmaceutica Sinica
| volume = 28
| issue = 10
| pages = 766–771
| year = 1993
| pmid = 8009989
| language=zh
}} and the Vanilla orchids.
See also
- Salicylaldehyde (2-hydroxybenzaldehyde)
References
{{Reflist}}
Cited sources
- {{cite book |ref=Haynes| editor= Haynes, William M. | date = 2016| title = CRC Handbook of Chemistry and Physics | edition = 97th | publisher = CRC Press | isbn = 9781498754293}}
{{DEFAULTSORT:Hydroxybenzaldehyde, 4-}}