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3-Hydroxybenzaldehyde

January 01, 1970

3-Hydroxybenzaldehyde is an organic compound with the formula HOC6H4CHO. It is a colorless solid although most samples appear tan. Two other isomers of hydroxybenzaldehyde exist.

3-Hydroxybenzaldehyde
Names
Preferred IUPAC name
3-Hydroxybenzaldehyde
Other names
m-Hydroxybenzaldehyde; m-Formylphenol; 3-formylphenol[1]
Identifiers
  • 100-83-4 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:16207 Y
ChEMBL
  • ChEMBL243816 Y
ChemSpider
  • 21105795 Y
ECHA InfoCard 100.002.630
KEGG
  • C03067 Y
  • 101
UNII
  • 8Z2819J40E N
  • DTXSID7059220
  • InChI=1S/C7H6O2/c8-5-6-2-1-3-7(9)4-6/h1-5,9H Y
    Key: IAVREABSGIHHMO-UHFFFAOYSA-N Y
  • InChI=1/C7H6O2/c8-5-6-2-1-3-7(9)4-6/h1-5,9H
    Key: IAVREABSGIHHMO-UHFFFAOYAC
  • O=Cc1cc(O)ccc1
Properties
C7H6O2
Molar mass 122.123 g·mol−1
Appearance colorless solid
Density 1.1179 g/cm3 (130 °C)[1]
Melting point 106 °C (223 °F; 379 K)[1]
Boiling point 240 °C (464 °F; 513 K)[1]
Acidity (pKa) 8.98 (25 °C)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

Preparation edit

It has been prepared from 3-nitrobenzaldehyde in a sequence of nitro group reduction, diazotization of the amine, and hydrolysis.[3][4]

3-hydroxybenzyl-alcohol dehydrogenase is an NADP-dependent enzyme that produces 3-hydroxybenzaldehyde from 3-hydroxybenzyl alcohol.[5]

Biomedical properties edit

3-Hydroxybenzaldehyde exhibits vasculoprotective effects by lowering vascular smooth muscle cell proliferation and endothelial cells inflammation.[6] 3-Hydroxybenzaldehyde is used in the synthesis of monastrol.[7][8]

See also edit

References edit

  1. ^ a b c d Haynes, p. 3.304
  2. ^ Haynes, p. 5.92
  3. ^ Woodward, R. B. (1945). "m-Hydroxybenzaldehyde". Organic Syntheses. 25: 55. doi:10.15227/orgsyn.025.0055.
  4. ^ Icke, Roland N.; Redemann, C. Ernst; Wisegarver, Burnett B.; Alles, Gordon A. (1949). "m-Methoxybenzaldehyde". Organic Syntheses. 29: 63. doi:10.15227/orgsyn.029.0063.
  5. ^ Forrester, P. I.; Gaucher, G. M. (1972). "M-Hydroxybenzyl alcohol dehydrogenase from Penicillium urticae". Biochemistry. 11 (6): 1108–1114. doi:10.1021/bi00756a026. PMID 4335290.
  6. ^ Kong, Byung Soo; Im, Soo Jung; Lee, Yang Jong; Cho, Yoon Hee; Do, Yu Ri; Byun, Jung Woo; Ku, Cheol Ryong; Lee, Eun Jig (22 March 2016). "Vasculoprotective Effects of 3-Hydroxybenzaldehyde against VSMCs Proliferation and ECs Inflammation". PLOS ONE. 11 (3): e0149394. Bibcode:2016PLoSO..1149394K. doi:10.1371/journal.pone.0149394. PMC 4803227. PMID 27002821.
  7. ^ Dallinger, Doris; Kappe, C Oliver (2007). "Rapid preparation of the mitotic kinesin Eg5 inhibitor monastrol using controlled microwave-assisted synthesis". Nature Protocols. 2 (2): 317–321. doi:10.1038/nprot.2006.436. PMID 17406591. S2CID 35508377.
  8. ^ Dondoni, Alessandro; Massi, Alessandro; Sabbatini, Simona (2002). "Improved synthesis and preparative scale resolution of racemic monastrol". Tetrahedron Letters. 43 (34): 5913–5916. doi:10.1016/S0040-4039(02)01269-8.

Cited sources edit

January 01, 1970
hydroxybenzaldehyde, organic, compound, with, formula, hoc6h4cho, colorless, solid, although, most, samples, appear, other, isomers, hydroxybenzaldehyde, exist, names, preferred, iupac, name, other, names, hydroxybenzaldehyde, formylphenol, formylphenol, ident. 3 Hydroxybenzaldehyde is an organic compound with the formula HOC6H4CHO It is a colorless solid although most samples appear tan Two other isomers of hydroxybenzaldehyde exist 3 Hydroxybenzaldehyde Names Preferred IUPAC name 3 Hydroxybenzaldehyde Other names m Hydroxybenzaldehyde m Formylphenol 3 formylphenol 1 Identifiers CAS Number 100 83 4 Y 3D model JSmol Interactive image ChEBI CHEBI 16207 Y ChEMBL ChEMBL243816 Y ChemSpider 21105795 Y ECHA InfoCard 100 002 630 KEGG C03067 Y PubChem CID 101 UNII 8Z2819J40E N CompTox Dashboard EPA DTXSID7059220 InChI InChI 1S C7H6O2 c8 5 6 2 1 3 7 9 4 6 h1 5 9H YKey IAVREABSGIHHMO UHFFFAOYSA N YInChI 1 C7H6O2 c8 5 6 2 1 3 7 9 4 6 h1 5 9HKey IAVREABSGIHHMO UHFFFAOYAC SMILES O Cc1cc O ccc1 Properties Chemical formula C 7H 6O 2 Molar mass 122 123 g mol 1 Appearance colorless solid Density 1 1179 g cm3 130 C 1 Melting point 106 C 223 F 379 K 1 Boiling point 240 C 464 F 513 K 1 Acidity pKa 8 98 25 C 2 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Preparation 2 Biomedical properties 3 See also 4 References 5 Cited sourcesPreparation editIt has been prepared from 3 nitrobenzaldehyde in a sequence of nitro group reduction diazotization of the amine and hydrolysis 3 4 3 hydroxybenzyl alcohol dehydrogenase is an NADP dependent enzyme that produces 3 hydroxybenzaldehyde from 3 hydroxybenzyl alcohol 5 Biomedical properties edit3 Hydroxybenzaldehyde exhibits vasculoprotective effects by lowering vascular smooth muscle cell proliferation and endothelial cells inflammation 6 3 Hydroxybenzaldehyde is used in the synthesis of monastrol 7 8 See also editSalicylaldehyde 2 hydroxybenzaldehyde 4 HydroxybenzaldehydeReferences edit a b c d Haynes p 3 304 Haynes p 5 92 Woodward R B 1945 m Hydroxybenzaldehyde Organic Syntheses 25 55 doi 10 15227 orgsyn 025 0055 Icke Roland N Redemann C Ernst Wisegarver Burnett B Alles Gordon A 1949 m Methoxybenzaldehyde Organic Syntheses 29 63 doi 10 15227 orgsyn 029 0063 Forrester P I Gaucher G M 1972 M Hydroxybenzyl alcohol dehydrogenase from Penicillium urticae Biochemistry 11 6 1108 1114 doi 10 1021 bi00756a026 PMID 4335290 Kong Byung Soo Im Soo Jung Lee Yang Jong Cho Yoon Hee Do Yu Ri Byun Jung Woo Ku Cheol Ryong Lee Eun Jig 22 March 2016 Vasculoprotective Effects of 3 Hydroxybenzaldehyde against VSMCs Proliferation and ECs Inflammation PLOS ONE 11 3 e0149394 Bibcode 2016PLoSO 1149394K doi 10 1371 journal pone 0149394 PMC 4803227 PMID 27002821 Dallinger Doris Kappe C Oliver 2007 Rapid preparation of the mitotic kinesin Eg5 inhibitor monastrol using controlled microwave assisted synthesis Nature Protocols 2 2 317 321 doi 10 1038 nprot 2006 436 PMID 17406591 S2CID 35508377 Dondoni Alessandro Massi Alessandro Sabbatini Simona 2002 Improved synthesis and preparative scale resolution of racemic monastrol Tetrahedron Letters 43 34 5913 5916 doi 10 1016 S0040 4039 02 01269 8 Cited sources editHaynes William M ed 2016 CRC Handbook of Chemistry and Physics 97th ed CRC Press ISBN 9781498754293 Retrieved from https en wikipedia org w index php title 3 Hydroxybenzaldehyde amp oldid 1170144236, wikipedia, wiki, book, books, library,

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