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词条 4-Hydroxybenzaldehyde
释义

  1. Chemistry

     Derivatives 

  2. Metabolism

  3. See also

  4. References

{{chembox
| Watchedfields = changed
| verifiedrevid = 477222206
| ImageFile =4-hydroxybenzaldehyde.svg
| ImageSize =80px
| IUPACName =4-Hydroxybenzaldehyde
| OtherNames =p-Hydroxybenzaldehyde
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 123
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = O1738X3Y38
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C00633
| InChI = 1/C7H6O2/c8-5-6-1-3-7(9)4-2-6/h1-5,9H
| InChIKey = RGHHSNMVTDWUBI-UHFFFAOYAN
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 14193
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C7H6O2/c8-5-6-1-3-7(9)4-2-6/h1-5,9H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = RGHHSNMVTDWUBI-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo =123-08-0
| PubChem =126
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 17597
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB03560
| SMILES = O=Cc1ccc(O)cc1
}}
|Section2={{Chembox Properties
| C=7 | H=6 | O=2
| Appearance =yellow to tan powder
| Density =1.226 ± 0.06 g/cm3
| MeltingPtC = 112 to 116
| MeltingPt_notes =
| BoilingPtC = 310 to 311
| BoilingPt_notes =
| Solubility =
| MagSus = -78.0·10−6 cm3/mol
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}

4-Hydroxybenzaldehyde is one of the three isomers of hydroxybenzaldehyde. It can be found in the orchids Gastrodia elata[1] and Galeola faberi.[2] It is also found in vanilla.

Chemistry

The Dakin oxidation is an organic redox reaction in which an ortho- or para-hydroxylated phenyl aldehyde (2-hydroxybenzaldehyde or 4-hydroxybenzaldehyde) or ketone reacts with hydrogen peroxide in base to form a benzenediol and a carboxylate. Overall, the carbonyl group is oxidized, and the hydrogen peroxide is reduced.

Derivatives

  • Claisen-Schmidt reaction with acetone can have afforded raspberry ketone in an 80% overall yield.
  • Vanillin

Metabolism

p-Hydroxybenzaldehyde dehydrogenase is an enzyme found in carrots (Daucus carota).[3]

See also

  • Salicylaldehyde (2-hydroxybenzaldehyde)
  • 3-Hydroxybenzaldehyde

References

1. ^{{Cite journal | last1 = Ha | first1 = J. H. | last2 = Lee | first2 = D. U. | last3 = Lee | first3 = J. T. | last4 = Kim | first4 = J. S. | last5 = Yong | first5 = C. S. | last6 = Kim | first6 = J. A. | last7 = Ha | first7 = J. S. | last8 = Huh | first8 = K. | doi = 10.1016/S0378-8741(00)00313-5 | title = 4-Hydroxybenzaldehyde from Gastrodia elata B1. Is active in the antioxidation and GABAergic neuromodulation of the rat brain | journal = Journal of Ethnopharmacology | volume = 73 | issue = 1–2 | pages = 329–333 | year = 2000 | pmid = 11025174| pmc = }}
2. ^{{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=Chinese}}
3. ^{{Cite journal | last1 = Sircar | first1 = D. | last2 = Mitra | first2 = A. | doi = 10.1016/j.jplph.2007.05.005 | title = Evidence for p-hydroxybenzoate formation involving enzymatic phenylpropanoid side-chain cleavage in hairy roots of Daucus carota | journal = Journal of Plant Physiology | volume = 165 | issue = 4 | pages = 407–414 | year = 2008 | pmid = 17658659| pmc = }}
{{DEFAULTSORT:Hydroxybenzaldehyde, 4-}}

2 : Hydroxybenzaldehydes|Orchids

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