2-Hydroxy-4-methoxybenzaldehyde

2-Hydroxy-4-methoxybenzaldehyde
Chemical structure of 2-hydroxy-4-methoxybenzaldehyde
Names
Preferred IUPAC name
2-Hydroxy-4-methoxybenzaldehyde
Other names
4-Methoxysalicylaldehyde
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.010.550
UNII
  • InChI=1S/C8H8O3/c1-11-7-3-2-6(5-9)8(10)4-7/h2-5,10H,1H3
    Key: WZUODJNEIXSNEU-UHFFFAOYSA-N
  • COC1=CC(=C(C=C1)C=O)O
Properties
C8H8O3
Molar mass 152.149 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

2-Hydroxy-4-methoxybenzaldehyde is a chemical compound and a positional isomer of vanillin.

A fragrant phenolic compound[1] found as a major constituent of the essential oils of the root bark and stem bark of some members of the subfamily Periplocoideae of the plant family Apocynaceae. These include the roots of Decalepis hamiltonii,[2][3] Decalepis salicifolia,[1] Hemidesmus indicus,[4][5] Mondia whitei,[6] Periploca angustifolia,[7] Periploca sepium[7] and Zygostelma benthamii[8] and the stem bark of Periploca graeca.[9] Some of these plants also contain toxic cardenolides.[9]

Urolithin M7, one of the urolithins, has also been synthesized from 2-hydroxy-4-methoxybenzaldehyde using the inverse electron-demand Diels–Alder reaction.[10]

See also

References

  1. 1 2 RODRIGUES, VEREENA; KUMAR, AMIT; GOKUL, SIVARAMAN; SHUKLA, ASHUTOSH K.; RAVIKUMAR, KALIAMOORTHY; SUNDARESAN, VELUSAMY (2021). "Decalepis salicifolia (Bedd. ex Hook. f.) Venter: A steno-endemic and critically endangered medicinal and aromatic plant from Western Ghats, India". Journal of Biosciences. 46 (2) 44. doi:10.1007/s12038-021-00162-6. Retrieved 1 May 2026.
  2. ↑ Thangadurai, Devarajan; Anitha, Sreeyapureddy; Pullaiah, Thammineni; Reddy, Ponnathota Narasimha; Ramachandraiah, Oleti Siva (2002). "Essential Oil Constituents and in Vitro Antimicrobial Activity of Decalepis hamiltonii Roots against Foodborne Pathogens". Journal of Agricultural and Food Chemistry. 50 (11): 3147–3149. Bibcode:2002JAFC...50.3147T. doi:10.1021/jf011541q. PMID 12009977. Retrieved 1 May 2026.
  3. ↑ Nagarajan, S.; Jagan Mohan Rao, L.; Gurudutt, K.N. (2001). "Chemical composition of the volatiles of Decalepis hamiltonii (Wight & Arn)". Flavour and Fragrance Journal. 16 (1): 27–29. doi:10.1002/1099-1026(200101/02)16:1<27::aid-ffj937>3.0.co;2-f. Retrieved 1 May 2026.
  4. ↑ Nagarajan, S.; Jagan Mohan Rao, L.; Gurudutt, K.N. (2001). "Chemical composition of the volatiles of Hemidesmus indicus R. Br". Flavour and Fragrance Journal. 16 (3): 212–214. doi:10.1002/ffj.985. Retrieved 1 May 2026.
  5. ↑ Sreekumar, S.; Seeni, S.; Pushpangadan, P. (1998). "Production of 2-hydroxy 4-methoxy benzaldehyde using root cultures of Hemidesmus indicus". Biotechnology Letters. 20 (7): 631–635. doi:10.1023/A:1005354003727. Retrieved 1 May 2026.
  6. ↑ Mukonyi, Kavaka W.; Ndiege, Isaiah O. (2001). "2-Hydroxy-4-methoxybenzaldehyde: Aromatic taste-modifying compound from Mondia whytei Skeels". Bulletin of the Chemical Society of Ethiopia. 15 (2): 137–142. Retrieved 1 May 2026.
  7. 1 2 Lee, N-H; Lee, H-S (2026). "Periploca root oils as potent, diphenolase-selective tyrosinase inhibitors: chemotype profiling and non-competitive mechanism of 4-methoxy-2-hydroxybenzaldehyde". Journal of the Science of Food and Agriculture. 106 (2): 1185–1194. Bibcode:2026JSFA..106.1185L. doi:10.1002/jsfa.70241. PMID 41048180. Retrieved 2 May 2026.
  8. ↑ Pongpan, N.; Kaewnoi, A.; Vallisuta, O. (2023). "Antiviral activity on selective bitter plants against Influenza A (H1N1) virus" (PDF). The 8th International Conference on Natural Products, Asian Society for Natural Products. 2 (1): P-7. doi:10.23177/NATPRO8.2023.06.22.012. Retrieved 2 May 2026.
  9. 1 2 Huang, Mingjin; Shen, Shoumao; Luo, Chunli; Ren, Yan (2019). "Genus Periploca (Apocynaceae): A Review of Its Classification, Phytochemistry, Biological Activities and Toxicology". Molecules. 24 (15): 2749. doi:10.3390/molecules24152749. PMC 6696197. PMID 31362394.
  10. ↑ Bodwell, Graham; Pottie, Ian; Nandaluru, Penchal (2011). "An Inverse Electron-Demand Diels-Alder-Based Total Synthesis of Urolithin M7". Synlett. 2011 (15): 2245. doi:10.1055/s-0030-1261203.


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