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3-Hydroxybenzaldehyde

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3-Hydroxybenzaldehyde
Names
Preferred IUPAC name 3-Hydroxybenzaldehyde
Other names m-Hydroxybenzaldehyde; m-Formylphenol; 3-formylphenol
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.630 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H6O2/c8-5-6-2-1-3-7(9)4-6/h1-5,9HKey: IAVREABSGIHHMO-UHFFFAOYSA-N
  • InChI=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 C7H6O2
Molar mass 122.123 g·mol
Appearance colorless solid
Density 1.1179 g/cm (130 °C)
Melting point 106 °C (223 °F; 379 K)
Boiling point 240 °C (464 °F; 513 K)
Acidity (pKa) 8.98 (25 °C)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

Preparation

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

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

Biomedical properties

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

See also

References

  1. ^ 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

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