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general/4-hydroxyphenyl-compounds

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4-Hydroxybenzaldehyde

4Hydroxy­benzaldehyde (parahydroxy­benzaldehyde) is an organic compound with the formula . Along with 2-hydroxybenzaldehyde and 3-hydroxybenzaldehyde, it is one of the three isomers of hydroxybenzaldehyde.

Synthesis, reactions, uses

4-Hydroxybenzaldehyde is prepared by reaction of phenol with chloroform, which gives isomeric hydroxybenzal chlorides. Hydrolysis of the C-Cl bonds gives the aldehyde.

4-Hydroxybenzaldehyde is a precursor to 4-hydroxyphenylglycine, which is itself a precursor to penicillins. In the Dakin oxidation, 4-hydroxybenzaldehyde reacts with hydrogen peroxide in base to form hydroquinone.

Metabolism and occurrence

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

4-Hydroxybenzaldehyde is found in the orchids Gastrodia elata, Galeola faberi,{{Cite journal | trans-title = Studies on the phenolic derivatives from Galeola faberi Rolfe

References

Cited sources

References

  1. Haynes, p. 3.304
  2. Haynes, p. 5.92
  3. Haynes, p. 5.154
  4. ''Merck Index'', 11th Edition, '''8295'''
  5. (2000). "Kirk-Othmer Encyclopedia of Chemical Technology".
  6. (2008). "Evidence for p-hydroxybenzoate formation involving enzymatic phenylpropanoid side-chain cleavage in hairy roots of Daucus carota". Journal of Plant Physiology.
  7. (2000). "4-Hydroxybenzaldehyde from Gastrodia elata B1. Is active in the antioxidation and GABAergic neuromodulation of the rat brain". Journal of Ethnopharmacology.
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4-hydroxyphenyl-compounds 4-hydroxybenzaldehyde-derivatives
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