Orsellinaldehyde

Orsellinaldehyde
Names
	IUPAC name 2,4-Dihydroxy-6-methylbenzaldehyde
	Other names Orcylaldehyde; Orcinaldehyde; Orcylic aldehyde; 6-Methyl-β-resorcyladehyde; ;
Identifiers
CAS Number	487-69-4;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:155863;
ChemSpider	220511;
ECHA InfoCard	100.153.049
EC Number	624-460-2;
PubChem CID	251690;
UNII	15U7JE2JVK;
CompTox Dashboard (EPA)	DTXSID70291004 ;
	InChI InChI=1S/C8H8O3/c1-5-2-6(10)3-8(11)7(5)4-9/h2-4,10-11H,1H3 Key: LJFQTUKKYWDRAT-UHFFFAOYSA-N;
	SMILES CC1=CC(=CC(=C1C=O)O)O;
Properties
Chemical formula	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" (PDF). Journal of Agricultural and Food Chemistry. 54 (20): 7564–7569. doi:10.1021/jf0616762. PMID 17002422.
^ Chen, A.J.; Frisvad, J.C.; Sun, B.D.; Varga, J.; Kocsubé, S.; Dijksterhuis, J.; Kim, D.H.; Hong, S.-B.; Houbraken, J.; Samson, R.A. (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. PMC 5198626. PMID 28050053.
^ Ahuja, Manmeet; Chiang, Yi-Ming; Chang, Shu-Lin; Praseuth, Mike B.; Entwistle, Ruth; Sanchez, James F.; Lo, Hsien-Chun; Yeh, Hsu-Hua; Oakley, Berl R.; Wang, Clay C. C. (16 May 2012). "Illuminating the Diversity of Aromatic Polyketide Synthases in Aspergillus nidulans". Journal of the American Chemical Society. 134 (19): 8212–8221. doi:10.1021/ja3016395. PMC 3357392. PMID 22510154.
^ Fushimi, Keiji; Anzai, Kota; Tokuyama, Shinji; Kiriiwa, Yoshikazu; Matsumoto, Noriyuki; Sekiya, Atsushi; Hashizume, Daisuke; Nagasawa, Kazuo; Hirai, Hirofumi; Kawagishi, Hirokazu (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. hdl:10297/6698. S2CID 51767920.
^ ^a ^b ^c 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. S2CID 81699243.
^ Gattermann, L.; Köbner, M. (January 1899). "Synthese von Oxyaldehyden der Benzolreihe". Berichte der Deutschen Chemischen Gesellschaft (in German). 32 (1): 278–283. doi:10.1002/cber.18990320144.

[1] 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" (PDF). Journal of Agricultural and Food Chemistry. 54 (20): 7564–7569. doi:10.1021/jf0616762. PMID 17002422.

[2] Chen, A.J.; Frisvad, J.C.; Sun, B.D.; Varga, J.; Kocsubé, S.; Dijksterhuis, J.; Kim, D.H.; Hong, S.-B.; Houbraken, J.; Samson, R.A. (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. PMC 5198626. PMID 28050053.

[3] Ahuja, Manmeet; Chiang, Yi-Ming; Chang, Shu-Lin; Praseuth, Mike B.; Entwistle, Ruth; Sanchez, James F.; Lo, Hsien-Chun; Yeh, Hsu-Hua; Oakley, Berl R.; Wang, Clay C. C. (16 May 2012). "Illuminating the Diversity of Aromatic Polyketide Synthases in Aspergillus nidulans". Journal of the American Chemical Society. 134 (19): 8212–8221. doi:10.1021/ja3016395. PMC 3357392. PMID 22510154.

[4] Fushimi, Keiji; Anzai, Kota; Tokuyama, Shinji; Kiriiwa, Yoshikazu; Matsumoto, Noriyuki; Sekiya, Atsushi; Hashizume, Daisuke; Nagasawa, Kazuo; Hirai, Hirofumi; Kawagishi, Hirokazu (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. hdl:10297/6698. S2CID 51767920.

[rao-5] 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. S2CID 81699243.

[6] Gattermann, L.; Köbner, M. (January 1899). "Synthese von Oxyaldehyden der Benzolreihe". Berichte der Deutschen Chemischen Gesellschaft (in German). 32 (1): 278–283. doi:10.1002/cber.18990320144.

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