4-hydroxybenzaldehyde

4-Hydroxybenzaldehyde

4-Hydroxybenzaldehyde

Chemical compound

4-Hydroxybenzaldehyde (2-hydroxybenzaldehyde) is an organic compound with the formula C6H4OH(CHO).[4][5] Along with 2-hydroxybenzaldehyde and 3-hydroxybenzaldehyde, it is one of the three isomers of hydroxybenzaldehyde.

Quick Facts Names, Identifiers ...

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.[5]

4-Hydroxybenzaldehyde is a precursor to 4-hydroxyphenylglycine, 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).[6]

4-Hydroxybenzaldehyde is found in the orchids Gastrodia elata,[7] Galeola faberi,[8] and the Vanilla orchids.

See also

References

  1. [1]
    Haynes, p. 3.304
  2. [2]
    Haynes, p. 5.154
  3. [3]
    Haynes, p. 5.92
  4. [4]
    Merck Index, 11th Edition, 8295
  5. [5]
    Maliverney, Christian; Mulhauser, Michel (2000). "Hydroxybenzaldehydes". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.0825041813011209.a01. ISBN 978-0-471-48494-3.
  6. [6]
    Sircar, D.; Mitra, A. (2008). "Evidence for p-hydroxybenzoate formation involving enzymatic phenylpropanoid side-chain cleavage in hairy roots of Daucus carota". Journal of Plant Physiology. 165 (4): 407–414. doi:10.1016/j.jplph.2007.05.005. PMID 17658659.
  7. [7]
    Ha, J. H.; Lee, D. U.; Lee, J. T.; Kim, J. S.; Yong, C. S.; Kim, J. A.; Ha, J. S.; Huh, K. (2000). "4-Hydroxybenzaldehyde from Gastrodia elata B1. Is active in the antioxidation and GABAergic neuromodulation of the rat brain". Journal of Ethnopharmacology. 73 (1–2): 329–333. doi:10.1016/S0378-8741(00)00313-5. PMID 11025174.
  8. [8]
    Li, Y. M.; Zhou, Z. L.; Hong, Y. F. (1993). "(title in Chinese)" [Studies on the phenolic derivatives from Galeola faberi Rolfe]. Yao Xue Xue Bao = Acta Pharmaceutica Sinica (in Chinese). 28 (10): 766–771. PMID 8009989.

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