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4-Hydroxybenzaldehyde

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4-Hydroxybenzaldehyde
Names
Preferred IUPAC name 4-Hydroxybenzaldehyde
Other names p-Hydroxybenzaldehyde, 4-formylphenol
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 1.129 g/cm (130 °C)
Melting point 116 °C (241 °F; 389 K)
Boiling point 310 to 311 °C (590 to 592 °F; 583 to 584 K)
Solubility in water 12.9 g/L
Acidity (pKa) 7.61 (25 °C)
Magnetic susceptibility (χ) -78.0·10 cm/mol
Refractive index (nD) 1.57051 (130 °C)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

4‑Hydroxy­benzaldehyde (para‑hydroxy­benzaldehyde) is an organic compound with the formula C6H4OH(CHO). 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, 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, and the Vanilla orchids.

See also

References

  1. ^ Haynes, p. 3.304
  2. Haynes, p. 5.154
  3. Haynes, p. 5.92
  4. Merck Index, 11th Edition, 8295
  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. 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. 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. 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.

Cited sources

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