3-Hydroxybenzaldehyde

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3-Hydroxybenzaldehyde
3-hydroxybenzaldehyde.svg
Names
Preferred IUPAC name
3-Hydroxybenzaldehyde
Other names
m-Hydroxybenzaldehyde; m-Formylphenol; 3-formylphenol [1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.630 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C7H6O2/c8-5-6-2-1-3-7(9)4-6/h1-5,9H Yes check.svgY
    Key: IAVREABSGIHHMO-UHFFFAOYSA-N Yes check.svgY
  • 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
Appearancecolorless 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).
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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.

Contents

Preparation

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

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

References

  1. 1 2 3 4 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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