4-Hydroxybenzaldehyde

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title: "4-Hydroxybenzaldehyde" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["4-hydroxyphenyl-compounds", "4-hydroxybenzaldehyde-derivatives"] topic_path: "general/4-hydroxyphenyl-compounds" source: "https://en.wikipedia.org/wiki/4-Hydroxybenzaldehyde" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Watchedfields = changed | verifiedrevid = 477222206 | ImageFile =4-hydroxybenzaldehyde.svg | ImageSize = 80 | ImageFile1 = 4-Hydroxybenzadehyde sample.jpg | PIN =4-Hydroxybenzaldehyde | OtherNames =p-Hydroxybenzaldehyde, 4-formylphenol |Section1={{Chembox Identifiers | ChemSpiderID_Ref = | ChemSpiderID = 123 | UNII_Ref = | UNII = O1738X3Y38 | KEGG_Ref = | KEGG = C00633 | InChI = 1/C7H6O2/c8-5-6-1-3-7(9)4-2-6/h1-5,9H | InChIKey = RGHHSNMVTDWUBI-UHFFFAOYAN | ChEMBL_Ref = | ChEMBL = 14193 | StdInChI_Ref = | StdInChI = 1S/C7H6O2/c8-5-6-1-3-7(9)4-2-6/h1-5,9H | StdInChIKey_Ref = | StdInChIKey = RGHHSNMVTDWUBI-UHFFFAOYSA-N | CASNo_Ref = | CASNo =123-08-0 | PubChem =126 | ChEBI_Ref = | ChEBI = 17597 | DrugBank_Ref = | DrugBank = DB03560 | SMILES = O=Cc1ccc(O)cc1 |Section2={{Chembox Properties | C=7 | H=6 | O=2 | Appearance =yellow to tan powder | Density =1.129 g/cm3 (130 °C) | RefractIndex =1.57051 (130 °C) | pKa = 7.61 (25 °C) | MeltingPtC = 116 | MeltingPt_ref = | BoilingPtC = 310 to 311 | BoilingPt_notes = | Solubility = 12.9 g/L | MagSus = −78.0·10−6 cm3/mol |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt =

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 | last1 = Li | first1 = Y. M. | last2 = Zhou | first2 = Z. L. | last3 = Hong | first3 = Y. F. | title = (title in Chinese) | trans-title = Studies on the phenolic derivatives from Galeola faberi Rolfe | journal = Yao Xue Xue Bao = Acta Pharmaceutica Sinica | volume = 28 | issue = 10 | pages = 766–771 | year = 1993 | pmid = 8009989 | language=zh

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-compounds4-hydroxybenzaldehyde-derivatives