3-Hydroxybenzaldehyde is an organic compound with the formula HOC6H4CHO. It is a colorless solid although most samples appear tan. Two other isomers of hydroxybenzaldehyde exist.

Preparation

It has been prepared from 3-nitrobenzaldehyde in a sequence of nitro group reduction, diazotization of the amine, and hydrolysis.[3][4]

3-hydroxybenzyl-alcohol dehydrogenase is an NADP-dependent enzyme that produces 3-hydroxybenzaldehyde from 3-hydroxybenzyl alcohol.[5]

Biomedical properties

3-Hydroxybenzaldehyde exhibits vasculoprotective effects by lowering vascular smooth muscle cell proliferation and endothelial cells inflammation.[6] 3-Hydroxybenzaldehyde is used in the synthesis of monastrol.[7][8]

See also

References

  1. ^ a b c d Haynes, p. 3.304
  2. ^ Haynes, p. 5.92
  3. ^ Woodward, R. B. (1945). "m-Hydroxybenzaldehyde". Organic Syntheses. 25: 55. doi:10.15227/orgsyn.025.0055.
  4. ^ Icke, Roland N.; Redemann, C. Ernst; Wisegarver, Burnett B.; Alles, Gordon A. (1949). "m-Methoxybenzaldehyde". Organic Syntheses. 29: 63. doi:10.15227/orgsyn.029.0063.
  5. ^ Forrester, P. I.; Gaucher, G. M. (1972). "M-Hydroxybenzyl alcohol dehydrogenase from Penicillium urticae". Biochemistry. 11 (6): 1108–1114. doi:10.1021/bi00756a026. PMID 4335290.
  6. ^ Kong, Byung Soo; Im, Soo Jung; Lee, Yang Jong; Cho, Yoon Hee; Do, Yu Ri; Byun, Jung Woo; Ku, Cheol Ryong; Lee, Eun Jig (22 March 2016). "Vasculoprotective Effects of 3-Hydroxybenzaldehyde against VSMCs Proliferation and ECs Inflammation". PLOS ONE. 11 (3): e0149394. Bibcode:2016PLoSO..1149394K. doi:10.1371/journal.pone.0149394. PMC 4803227. PMID 27002821.
  7. ^ Dallinger, Doris; Kappe, C Oliver (2007). "Rapid preparation of the mitotic kinesin Eg5 inhibitor monastrol using controlled microwave-assisted synthesis". Nature Protocols. 2 (2): 317–321. doi:10.1038/nprot.2006.436. PMID 17406591. S2CID 35508377.
  8. ^ Dondoni, Alessandro; Massi, Alessandro; Sabbatini, Simona (2002). "Improved synthesis and preparative scale resolution of racemic monastrol". Tetrahedron Letters. 43 (34): 5913–5916. doi:10.1016/S0040-4039(02)01269-8.

Cited sources

Allikas: http://en.wikipedia.org/wiki/3-Hydroxybenzaldehyde
No tags for this post.