3-Hydroxybenzaldehyde

Quality 0.50 · 2 views · Updated 2 months ago

title: "3-Hydroxybenzaldehyde" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["3-hydroxyphenyl-compounds", "hydroxybenzaldehydes"] topic_path: "general/3-hydroxyphenyl-compounds" source: "https://en.wikipedia.org/wiki/3-Hydroxybenzaldehyde" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| ImageFile = 3-hydroxybenzaldehyde.svg | ImageSize = 120px | PIN = 3-Hydroxybenzaldehyde | OtherNames = m-Hydroxybenzaldehyde; m-Formylphenol; 3-formylphenol |Section1={{Chembox Identifiers | ChemSpiderID_Ref = | ChemSpiderID = 21105795 | KEGG_Ref = | KEGG = C03067 | InChI = 1/C7H6O2/c8-5-6-2-1-3-7(9)4-6/h1-5,9H | InChIKey = IAVREABSGIHHMO-UHFFFAOYAC | ChEMBL_Ref = | ChEMBL = 243816 | StdInChI_Ref = | StdInChI = 1S/C7H6O2/c8-5-6-2-1-3-7(9)4-6/h1-5,9H | StdInChIKey_Ref = | StdInChIKey = IAVREABSGIHHMO-UHFFFAOYSA-N | CASNo_Ref = | CASNo = 100-83-4 | UNII_Ref = | UNII = 8Z2819J40E | PubChem = 101 | ChEBI_Ref = | ChEBI = 16207 | SMILES = O=Cc1cc(O)ccc1 |Section2={{Chembox Properties | C=7 | H=6 | O=2 | Appearance = colorless solid | Density = 1.1179 g/cm3 (130 °C) | pKa = 8.98 (25 °C) | MeltingPtC = 106 | MeltingPt_ref = | BoilingPtC = 240 | BoilingPt_ref = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt =

3-Hydroxybenzaldehyde is an organic compound with the formula . 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.{{cite journal|title= m-Hydroxybenzaldehyde|journal=Organic Syntheses|volume = 25| page=55|year=1945|author=Woodward, R. B. |doi=10.15227/orgsyn.025.0055}}

3-hydroxybenzyl-alcohol dehydrogenase is an nicotinamide adenine dinucleotide phosphate-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.

References

Cited sources

References

  1. Haynes, p. 3.304
  2. Haynes, p. 5.92
  3. Icke, Roland N.. (1949). "m-Methoxybenzaldehyde". Organic Syntheses.
  4. (1972). "M-Hydroxybenzyl alcohol dehydrogenase from Penicillium urticae". Biochemistry.
  5. {{KEGG enzyme. 1.1.1.97
  6. (22 March 2016). "Vasculoprotective Effects of 3-Hydroxybenzaldehyde against VSMCs Proliferation and ECs Inflammation". PLOS ONE.
  7. (2007). "Rapid preparation of the mitotic kinesin Eg5 inhibitor monastrol using controlled microwave-assisted synthesis". Nature Protocols.
  8. (2002). "Improved synthesis and preparative scale resolution of racemic monastrol". Tetrahedron Letters.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

3-hydroxyphenyl-compoundshydroxybenzaldehydes