巨大戟醇

巨大戟醇
识别
CAS号	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
性质
化学式	C20H28O5
摩尔质量	348.43 g·mol−1
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

巨大戟醇（英语：ingenol）是一种巨大戟烷型四环二萜类有机化合物，分子式C₂₀H₂₈O₅，存在于南欧大戟（Euphorbia peplus）^[1]、续随子（Euphorbia lathyris）^[2]、乳浆大戟（Euphorbia esula）^[3]等大戟属植物中。巨大戟醇可由相对便宜的(+)-3-蒈烯为起始原料经14步合成得到，相比于传统从植物中获取，效率更高^[4]。

参见

巨大戟醇甲基丁烯酸酯

参考文献

^ 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.
^ 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.
^ 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.
^ 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.

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[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.

[synthesis-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.

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