2,4-二羥基-6-甲基苯甲醛

化合物

2,4-二羥基-6-甲基苯甲醛也稱為苔色醛(英語:Orsellinaldehyde)是一種有機化合物,化學式為C8H8O3,它是一些真菌的天然產物,如灰樹花[2]Aspergillus cleistominutus英語Aspergillus cleistominutus[3]小巢狀麴菌[4]田頭菇英語Agrocybe praecox[5]等。

2,4-二羥基-6-甲基苯甲醛
IUPAC名
2,4-Dihydroxy-6-methylbenzaldehyde
別名
  • 苔色醛
    • Orcylaldehyde
    • Orcinaldehyde
    • Orcylic aldehyde
    • 6-Methyl-β-resorcyladehyde
識別
CAS號 487-69-4
PubChem 251690
ChemSpider 220511
SMILES
 
  • CC1=CC(=CC(=C1C=O)O)O
InChI
 
  • 1S/C8H8O3/c1-5-2-6(10)3-8(11)7(5)4-9/h2-4,10-11H,1H3
InChIKey LJFQTUKKYWDRAT-UHFFFAOYSA-N
ChEBI 155863
性質
化學式 C8H8O3
摩爾質量 152.15 g·mol−1
外觀 無色
熔點 181—183 °C(454—456 K)[1]
沸點 321.9 °C(595 K)
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

它可由苔黑酚氰化鋅氯化氫下進行加特曼反應[1],再經水解得到。[1][6]

參考文獻

編輯
  1. ^ 1.0 1.1 1.2 Rao, K Ranganatha; Seshadri, T. R. Synthesis of 7-hydroxy-5-methylcoumarin. Proceeding of the Indian Academy of Sciences. April 1941, 13 (4): 255 [2022-12-25]. S2CID 81699243. doi:10.1007/BF03048997. (原始內容存檔於2022-05-16). 
  2. ^ Lin, Jiun-Tsai; Liu, Wen-Hsiung. 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. 1 October 2006, 54 (20): 7564–7569 [2022-12-25]. PMID 17002422. doi:10.1021/jf0616762. (原始內容存檔 (PDF)於2022-12-25). 
  3. ^ 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. Aspergillus section Nidulantes (formerly Emericella ): Polyphasic taxonomy, chemistry and biology. Studies in Mycology. 1 June 2016, 84 (1): 1–118. PMC 5198626 . PMID 28050053. doi:10.1016/j.simyco.2016.10.001. 
  4. ^ 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. Illuminating the Diversity of Aromatic Polyketide Synthases in Aspergillus nidulans. Journal of the American Chemical Society. 16 May 2012, 134 (19): 8212–8221. PMC 3357392 . PMID 22510154. doi:10.1021/ja3016395 (英語). 
  5. ^ Fushimi, Keiji; Anzai, Kota; Tokuyama, Shinji; Kiriiwa, Yoshikazu; Matsumoto, Noriyuki; Sekiya, Atsushi; Hashizume, Daisuke; Nagasawa, Kazuo; Hirai, Hirofumi; Kawagishi, Hirokazu. Agrocybynes A–E from the culture broth of Agrocybe praecox. Tetrahedron. January 2012, 68 (4): 1262–1265. S2CID 51767920. doi:10.1016/J.TET.2011.11.049. hdl:10297/6698. 
  6. ^ Gattermann, L.; Köbner, M. Synthese von Oxyaldehyden der Benzolreihe. Berichte der Deutschen Chemischen Gesellschaft. January 1899, 32 (1): 278–283. doi:10.1002/cber.18990320144 (德語).