3-Hydroxybenzaldehyde

Source: Wikipedia, the free encyclopedia.
3-Hydroxybenzaldehyde
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 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C7H6O2/c8-5-6-2-1-3-7(9)4-6/h1-5,9H checkY
    Key: IAVREABSGIHHMO-UHFFFAOYSA-N checkY
  • 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 checkY☒N ?)

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

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. ^ a b c d Haynes, p. 3.304
  2. ^ Haynes, p. 5.92
  3. doi:10.15227/orgsyn.025.0055
    .
  4. doi:10.15227/orgsyn.029.0063
    .
  5. PMID 4335290
    .
  6. PMID 27002821
    .
  7. S2CID 35508377
    .
  8. doi:10.1016/S0040-4039(02)01269-8
    .

Cited sources
Retrieved from "https://en.wikipedia.org/w/index.php?title=3-Hydroxybenzaldehyde&oldid=1170144236"