Chemistry:Orsellinaldehyde
From HandWiki
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| IUPAC name
2,4-Dihydroxy-6-methylbenzaldehyde
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Other names
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3D model (JSmol)
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| Properties | |
| C8H8O3 | |
| Molar mass | 152.149 g·mol−1 |
| Appearance | colourless |
| Melting point | 181–183 °C (358–361 °F; 454–456 K) |
| Boiling point | 321.9 °C (611.4 °F; 595.0 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Orsellinaldehyde is a dihydroxybenzaldehyde with a methyl side group. It can be classified as a resorcinol, benzaldehyde or toluene derivative. It is a natural product of several fungi. Fungi that contain it include Grifola frondosa,[1] Aspergillus cleistominutus,[2] Aspergillus nidulans,[3] and Agrocybe praecox.[4]
Production
Orsellinaldehyde can be produced by a Gattermann reaction of orcinol, using zinc cyanide under a hydrogen chloride atmosphere, which adds an aldimine (-CH=NH) group to the ring,[5] followed by hydrolysis to give the aldehyde.[5][6]
Properties
The melting point is between 181 and 183 °C.[5]
References
- ↑ Lin, Jiun-Tsai; Liu, Wen-Hsiung (1 October 2006). "ο-Orsellinaldehyde from the Submerged Culture of the Edible Mushroom Grifola frondosa Exhibits Selective Cytotoxic Effect Against Hep 3B Cells Through Apoptosis". Journal of Agricultural and Food Chemistry 54 (20): 7564–7569. doi:10.1021/jf0616762. PMID 17002422. http://ntur.lib.ntu.edu.tw/bitstream/246246/201543/-1/09.pdf.
- ↑ Chen, A.J.; Frisvad, J.C.; Sun, B.D.; Varga, J.; Kocsubé, S.; Dijksterhuis, J.; Kim, D.H.; Hong, S.-B. et al. (1 June 2016). "Aspergillus section Nidulantes (formerly Emericella ): Polyphasic taxonomy, chemistry and biology". Studies in Mycology 84 (1): 1–118. doi:10.1016/j.simyco.2016.10.001. PMID 28050053.
- ↑ Ahuja, Manmeet; Chiang, Yi-Ming; Chang, Shu-Lin; Praseuth, Mike B.; Entwistle, Ruth; Sanchez, James F.; Lo, Hsien-Chun; Yeh, Hsu-Hua et al. (16 May 2012). "Illuminating the Diversity of Aromatic Polyketide Synthases in Aspergillus nidulans" (in en). Journal of the American Chemical Society 134 (19): 8212–8221. doi:10.1021/ja3016395. PMID 22510154.
- ↑ Fushimi, Keiji; Anzai, Kota; Tokuyama, Shinji; Kiriiwa, Yoshikazu; Matsumoto, Noriyuki; Sekiya, Atsushi; Hashizume, Daisuke; Nagasawa, Kazuo et al. (January 2012). "Agrocybynes A–E from the culture broth of Agrocybe praecox". Tetrahedron 68 (4): 1262–1265. doi:10.1016/J.TET.2011.11.049.
- ↑ 5.0 5.1 5.2 Rao, K Ranganatha; Seshadri, T. R. (April 1941). "Synthesis of 7-hydroxy-5-methylcoumarin". Proceedings of the Indian Academy of Sciences 13 (4): 255. doi:10.1007/BF03048997. https://www.ias.ac.in/article/fulltext/seca/013/04/0255-0258.
- ↑ Gattermann, L.; Köbner, M. (January 1899). "Synthese von Oxyaldehyden der Benzolreihe" (in de). Berichte der Deutschen Chemischen Gesellschaft 32 (1): 278–283. doi:10.1002/cber.18990320144.
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