| Revision as of 18:15, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 473879052 of page 4-Hydroxybenzaldehyde for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 10:05, 21 October 2024 edit JWBE (talk | contribs)Extended confirmed users10,127 edits added Category:4-Hydroxyphenyl compounds using HotCat |
| Line 1: |
Line 1: |
|
{{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 = 443654703 |
|
| verifiedrevid = 477222206 |
|
|ImageFile=4-hydroxybenzaldehyde.svg |
|
| ImageFile =4-hydroxybenzaldehyde.svg |
|
|ImageSize=80px |
|
| ImageSize = 80 |
|
|
| ImageFile1 = 4-Hydroxybenzadehyde sample.jpg |
|
|IUPACName=4-Hydroxybenzaldehyde |
|
|
|OtherNames=''p''-Hydroxybenzaldehyde |
|
| PIN =4-Hydroxybenzaldehyde |
|
|
| OtherNames =''p''-Hydroxybenzaldehyde, 4-formylphenol<ref name=crc>Haynes, p. 3.304</ref> |
|
|Section1={{Chembox Identifiers |
|
|Section1={{Chembox Identifiers |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| ChemSpiderID = 123 |
|
| ChemSpiderID = 123 |
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
| UNII_Ref = {{fdacite|correct|FDA}} |
| Line 23: |
Line 23: |
|
| StdInChIKey = RGHHSNMVTDWUBI-UHFFFAOYSA-N |
|
| StdInChIKey = RGHHSNMVTDWUBI-UHFFFAOYSA-N |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| CASNo=123-08-0 |
|
| CASNo =123-08-0 |
|
| PubChem=126 |
|
| PubChem =126 |
|
| ChEBI_Ref = {{ebicite|correct|EBI}} |
|
| ChEBI_Ref = {{ebicite|correct|EBI}} |
|
| ChEBI = 17597 |
|
| ChEBI = 17597 |
|
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
|
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
| Line 32: |
Line 32: |
|
}} |
|
}} |
|
|Section2={{Chembox Properties |
|
|Section2={{Chembox Properties |
|
| C=7|H=6|O=2 |
|
| C=7 | H=6 | O=2 |
|
| Appearance=yellow to tan powder |
|
| Appearance =yellow to tan powder |
|
| Density=1.226 ± 0.06 g/cm<sup>3</sup> |
|
| Density =1.129 g/cm<sup>3</sup> (130 °C)<ref name=crc/> |
|
|
| RefractIndex =1.57051 (130 °C)<ref name=crc/> |
|
| MeltingPt=112–116 °C |
|
|
|
| pKa = 7.61 (25 °C)<ref>Haynes, p. 5.92</ref> |
|
| BoilingPt=310–311 °C |
|
|
|
| MeltingPtC = 116 |
|
| Solubility= |
|
|
|
| MeltingPt_ref = <ref name=crc/> |
|
|
| BoilingPtC = 310 to 311 |
|
|
| BoilingPt_notes = |
|
|
| Solubility = 12.9 g/L<ref>Haynes, p. 5.154</ref> |
|
|
| MagSus = -78.0·10<sup>−6</sup> cm<sup>3</sup>/mol |
|
}} |
|
}} |
|
|Section3={{Chembox Hazards |
|
|Section3={{Chembox Hazards |
|
| MainHazards= |
|
| MainHazards = |
|
| FlashPt= |
|
| FlashPt = |
|
|
| AutoignitionPt = |
|
| Autoignition= |
|
|
}} |
|
}} |
|
}} |
|
}} |
|
|
|
|
|
'''4{{nbh}}Hydroxy­benzaldehyde''' (''para''{{nbh}}hydroxy­benzaldehyde) is an ] with the formula {{chem2|C6H4OH(CHO)}}.<ref>''Merck Index'', 11th Edition, '''8295'''</ref><ref name=KO>{{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 }}</ref> Along with ] and ], it is one of the three ]s of ]. |
|
|
|
|
|
== Synthesis, reactions, uses == |
|
|
4-Hydroxybenzaldehyde is prepared by reaction of ] with ], which gives isomeric hydroxy]s. Hydrolysis of the C-Cl bonds gives the aldehyde.<ref name=KO/> |
|
|
|
|
|
4-Hydroxybenzaldehyde is a precursor to ], a precursor to ]s. In the ], 4-hydroxybenzaldehyde reacts with hydrogen peroxide in base to form ]. |
|
|
|
|
|
== Metabolism and occurrence == |
|
|
] is an enzyme found in carrots ('']'').<ref>{{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}}</ref> |
|
|
|
|
|
4-Hydroxybenzaldehyde is found in the orchids '']'',<ref>{{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}}</ref> '']'',<ref>{{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 '']'' Rolfe |
|
|
| journal = Yao Xue Xue Bao = Acta Pharmaceutica Sinica |
|
|
| volume = 28 |
|
|
| issue = 10 |
|
|
| pages = 766–771 |
|
|
| year = 1993 |
|
|
| pmid = 8009989 |
|
|
| language=zh |
|
|
}}</ref> and the '']'' orchids. |
|
|
|
|
|
== See also == |
|
|
* ] (2-hydroxybenzaldehyde) |
|
|
|
|
|
== References == |
|
|
{{Reflist}} |
|
|
|
|
|
==Cited sources== |
|
|
*{{cite book |ref=Haynes| editor= Haynes, William M. | date = 2016| title = ] | edition = 97th | publisher = ] | isbn = 9781498754293}} |
|
|
|
|
|
{{DEFAULTSORT:Hydroxybenzaldehyde, 4-}} |
|
|
] |
|
|
] |
|
|
] |