4-Hydroxybenzaldehyde

4-Hydroxybenzaldehyde
Names
Preferred IUPAC name
4-Hydroxybenzaldehyde
Other names
p-Hydroxybenzaldehyde, 4-formylphenol[1]
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.004.182 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C7H6O2/c8-5-6-1-3-7(9)4-2-6/h1-5,9H checkY
    Key: RGHHSNMVTDWUBI-UHFFFAOYSA-N checkY
  • InChI=1/C7H6O2/c8-5-6-1-3-7(9)4-2-6/h1-5,9H
    Key: RGHHSNMVTDWUBI-UHFFFAOYAN
  • O=Cc1ccc(O)cc1
Properties
C7H6O2
Molar mass 122.123 g·mol−1
Appearance yellow to tan powder
Density 1.129 g/cm3 (130 °C)[1]
Melting point 116 °C (241 °F; 389 K)[1]
Boiling point 310 to 311 °C (590 to 592 °F; 583 to 584 K)
12.9 g/L[2]
Acidity (pKa) 7.61 (25 °C)[3]
−78.0·10−6 cm3/mol
1.57051 (130 °C)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

4‑Hydroxy­benzaldehyde (para‑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.

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, 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).[6]

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

See also

References

  1. ^ a b c d Haynes, p. 3.304
  2. ^ Haynes, p. 5.154
  3. ^ Haynes, p. 5.92
  4. ^ Merck Index, 11th Edition, 8295
  5. ^ a b 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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