3-Hydroxybenzaldehyde

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
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.630
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
Melting point 100 to 103 °C (212 to 217 °F; 373 to 376 K)
Boiling point 191 °C (376 °F; 464 K) (50 mmHg)
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 ?)
Infobox references

Preparation

It has been prepared from 3-nitrobenzaldehyde in a sequence of nitro group reduction, diazotization of the amine, and hydrolysis.[1][2]

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

Bio-medical properties

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

See also

References
  1. R. B. Woodward (1945). "m-Hydroxybenzaldehyde". Organic Syntheses. 25: 55. doi:10.15227/orgsyn.025.0055.
  2. Roland N. Icke, C. Ernst Redemann, Burnett B. Wisegarver, Gordon A. Alles (1949). "m-Methoxybenzaldehyde". Organic Syntheses. 29: 63. doi:10.15227/orgsyn.029.0063.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. 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.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.