| Revision as of 17:51, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Saving copy of the {{chembox}} taken from revid 465716104 of page 3-Hydroxybenzaldehyde for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 12:59, 21 October 2024 edit JWBE (talk | contribs)Extended confirmed users10,129 edits added Category:3-Hydroxyphenyl compounds using HotCat |
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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.}} |
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{{Chembox |
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{{Chembox |
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| Watchedfields = changed |
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| verifiedrevid = 443348039 |
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| verifiedrevid = 477218634 |
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| ImageFile = 3-hydroxybenzaldehyde.svg |
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| ImageFile = 3-hydroxybenzaldehyde.svg |
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| ImageSize = 120px |
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| ImageSize = 120px |
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| IUPACName = 3-Hydroxybenzaldehyde |
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| PIN = 3-Hydroxybenzaldehyde |
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| OtherNames = ''m''-Hydroxybenzaldehyde; ''m''-Formylphenol; 3-Formylphenol |
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| OtherNames = ''m''-Hydroxybenzaldehyde; ''m''-Formylphenol; 3-formylphenol<ref name=crc>Haynes, p. 3.304</ref> |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 21105795 |
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| ChemSpiderID = 21105795 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 100-83-4 |
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| CASNo = 100-83-4 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = 8Z2819J40E |
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| PubChem = 101 |
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| PubChem = 101 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| SMILES = O=Cc1cc(O)ccc1 |
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| SMILES = O=Cc1cc(O)ccc1 |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=7|H=6|O=2 |
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| C=7 | H=6 | O=2 |
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| Appearance = light-tan crystals |
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| Appearance = colorless solid |
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| Density = 1.1179 g/cm<sup>3</sup> (130 °C)<ref name=crc/> |
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| Density = |
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| pKa = 8.98 (25 °C)<ref>Haynes, p. 5.92</ref> |
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| MeltingPt = 100–103 °C |
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| MeltingPtC = 106 |
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| BoilingPt = 191 °C (50 mmHg) |
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| MeltingPt_ref = <ref name=crc/> |
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| BoilingPtC = 240 |
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| BoilingPt_ref = <ref name=crc/> |
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| Solubility = }} |
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| Section3 = {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| Autoignition = }} |
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'''3-Hydroxybenzaldehyde''' is an ] with the formula {{chem2|HOC6H4CHO}}. It is a colorless solid although most samples appear tan. Two other ]s of ] exist. |
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==Preparation== |
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It has been prepared from 3-nitrobenzaldehyde in a sequence of ] ], ] of the amine, and ].<ref>{{cite journal|title= m-Hydroxybenzaldehyde|journal=Organic Syntheses|volume = 25| page=55|year=1945|author=Woodward, R. B. |
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|doi=10.15227/orgsyn.025.0055}}</ref><ref>{{cite journal|title= m-Methoxybenzaldehyde|journal=Organic Syntheses|volume= 29|page=63|year=1949|author=Icke, Roland N. |author2= Redemann, C. Ernst |author3=Wisegarver, Burnett B. |author4=Alles, Gordon A. |doi=10.15227/orgsyn.029.0063}}</ref> |
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] is an NADP-dependent enzyme that produces 3-hydroxybenzaldehyde from 3-hydroxybenzyl alcohol.<ref>{{cite journal|doi=10.1021/bi00756a026 |title=M-Hydroxybenzyl alcohol dehydrogenase from Penicillium urticae |date=1972 |last1=Forrester |first1=P. I. |last2=Gaucher |first2=G. M. |journal=Biochemistry |volume=11 |issue=6 |pages=1108–1114 |pmid=4335290 }}</ref> |
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==Biomedical properties== |
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3-Hydroxybenzaldehyde exhibits vasculoprotective effects by lowering vascular smooth muscle cell proliferation and endothelial cells inflammation.<ref>{{cite journal |last1=Kong |first1=Byung Soo |last2=Im |first2=Soo Jung |last3=Lee |first3=Yang Jong |last4=Cho |first4=Yoon Hee |last5=Do |first5=Yu Ri |last6=Byun |first6=Jung Woo |last7=Ku |first7=Cheol Ryong |last8=Lee |first8=Eun Jig |title=Vasculoprotective Effects of 3-Hydroxybenzaldehyde against VSMCs Proliferation and ECs Inflammation |journal=PLOS ONE |date=22 March 2016 |volume=11 |issue=3 |pages=e0149394 |doi=10.1371/journal.pone.0149394 |doi-access=free |pmc=4803227 |pmid=27002821|bibcode=2016PLoSO..1149394K }}</ref> 3-Hydroxybenzaldehyde is used in the synthesis of ].<ref>{{cite journal|doi=10.1038/nprot.2006.436 |title=Rapid preparation of the mitotic kinesin Eg5 inhibitor monastrol using controlled microwave-assisted synthesis |date=2007 |last1=Dallinger |first1=Doris |last2=Kappe |first2=C Oliver |journal=Nature Protocols |volume=2 |issue=2 |pages=317–321 |pmid=17406591 |s2cid=35508377 |doi-access=free }}</ref><ref>{{cite journal|doi=10.1016/S0040-4039(02)01269-8 |title=Improved synthesis and preparative scale resolution of racemic monastrol |date=2002 |last1=Dondoni |first1=Alessandro |last2=Massi |first2=Alessandro |last3=Sabbatini |first3=Simona |journal=Tetrahedron Letters |volume=43 |issue=34 |pages=5913–5916 }}</ref> |
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==See also== |
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* ] (2-hydroxybenzaldehyde) |
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* ] |
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==References== |
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{{reflist}} |
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==Cited sources== |
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*{{cite book |ref=Haynes| editor= Haynes, William M. | date = 2016| title = ] | edition = 97th | publisher = ] | isbn = 9781498754293}} |
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{{DEFAULTSORT:Hydroxybenzaldehyde, 3-}} |
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] |
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] |