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4-Hydroxybenzaldehyde

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4-Hydroxybenzaldehyde
Names
IUPAC name 4-Hydroxybenzaldehyde
Other names p-Hydroxybenzaldehyde
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.004.182 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C7H6O2/c8-5-6-1-3-7(9)4-2-6/h1-5,9HKey: RGHHSNMVTDWUBI-UHFFFAOYSA-N
  • InChI=1/C7H6O2/c8-5-6-1-3-7(9)4-2-6/h1-5,9HKey: RGHHSNMVTDWUBI-UHFFFAOYAN
SMILES
  • O=Cc1ccc(O)cc1
Properties
Chemical formula C7H6O2
Molar mass 122.123 g·mol
Appearance yellow to tan powder
Density 1.226 ± 0.06 g/cm
Melting point 112–116 °C
Boiling point 310–311 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkverify (what is  ?) Infobox references
Chemical compound

4-Hydroxybenzaldehyde is one of the three isomers of hydroxybenzaldehyde. It can be found in the orchid Gastrodia elata.

Chemistry

The Dakin oxidation is an organic redox reaction in which an ortho- or para-hydroxylated phenyl aldehyde (2-hydroxybenzaldehyde or 4-hydroxybenzaldehyde) or ketone reacts with hydrogen peroxide in base to form a benzenediol and a carboxylate. Overall, the carbonyl group is oxidized, and the hydrogen peroxide is reduced.

Metabolism

p-hydroxybenzaldehyde dehydrogenase is an enzyme found in carrots (Daucus carota).

See also

References

  1. 4-Hydroxybenzaldehyde from Gastrodia elata B1. is active in the antioxidation and GABAergic neuromodulation of the rat brain. Jeoung-Hee Ha, Dong-Ung Lee, Jae-Tae Lee, Jin-Sook Kim, Chul-Soon Yong, Jung-Ae Kim, Jung-Sang Ha and Keun- Huh, Journal of Ethnopharmacology, Volume 73, Issues 1-2, November 2000, Pages 329-333, doi:10.1016/S0378-8741(00)00313-5
  2. Evidence for p-hydroxybenzoate formation involving enzymatic phenylpropanoid side-chain cleavage in hairy roots of Daucus carota. Debabrata Sircar and Adinpunya Mitra, Journal of Plant Physiology, Volume 165, Issue 4, 13 March 2008, Pages 407-414, doi:10.1016/j.jplph.2007.05.005


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