巨大戟醇

巨大戟醇(英語:ingenol)是一種巨大戟烷型四環二萜有機化合物,分子式C20H28O5,存在於南歐大戟Euphorbia peplus[1]續隨子Euphorbia lathyris[2]乳漿大戟Euphorbia esula[3]大戟屬植物中。巨大戟醇可由相對便宜的(+)-3-蒈烯為起始原料經14步合成得到,相比於傳統從植物中獲取,效率更高[4]

巨大戟醇
識別
CAS號 30220-46-3
PubChem 442042
ChemSpider 10282511
SMILES
 
  • C[C@@H]1C[C@@H]2[C@@H](C2(C)C)[C@@H]3C=C([C@H]([C@]4([C@@]1(C3=O)C=C([C@@H]4O)C)O)O)CO
ChEBI 5922
KEGG C09112
性質
化學式 C20H28O5
摩爾質量 348.43 g·mol−1
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

參見

參考文獻

  1. ^ Rizk, A.M.; Hammouda, F.M.; El-Missiry, M.M.; Radwan, H.M.; Evans, F.J. Biologically active diterpene esters from euphorbia peplus. Phytochemistry. 1985-01, 24 (7): 1605–1606. doi:10.1016/S0031-9422(00)81076-6. 
  2. ^ Bicchi, C; Appendino, G; Cordero, C; Rubiolo, P; Ortelli, D; Veuthey, JL. HPLC-UV and HPLC-positive-ESI-MS analysis of the diterpenoid fraction from caper spurge (Euphorbia lathyris) seed oil.. Phytochemical analysis : PCA. 2001-07, 12 (4): 255–62. PMID 11705332. doi:10.1002/pca.592. 
  3. ^ Schmoldt, A; Benthe, HF; Haberland, G. Digitoxin metabolism by rat liver microsomes.. Biochemical pharmacology. 1975-09-01, 24 (17): 1639–41. doi:10.1016/0021-9673(93)83215-E. 
  4. ^ Jørgensen L, McKerrall SJ, Kuttruff CA, Ungeheuer F, Felding J, Baran PS. 14-step synthesis of (+)-ingenol from (+)-3-carene. Science. August 2013, 341 (6148): 878–882. Bibcode:2013Sci...341..878J. PMID 23907534. S2CID 26998997. doi:10.1126/science.1241606.