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

| MeltingPt_ref =

| 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

References

{{Reflist}}

Cited sources

{{DEFAULTSORT:Hydroxybenzaldehyde, 4-}}

Category:Orchids

Category:4-Hydroxyphenyl compounds