白桦脂醇
化合物
白桦脂醇(英语:Betulin,也译作桦木醇)是一种天然的羽扇豆烷型五环三萜化合物,大量存在于桦树的树皮中,比如占到垂枝桦(Betula pendula)树皮干重的30%[2],白桦茸(Inonotus obliquus)[3]和红桤木(Alnus rubra)也有白桦脂醇[4]。
白桦脂醇 | |
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IUPAC名 Lup-20(29)-ene-3β,28-diol | |
系统名 (1R,2R,5S,8R,9R,10R,13R,14R,17S,19R)-5-hydroxymethyl-1,2,14,18,18-hexamethyl-8-(1-methylethenyl)pentacyclo[11.8.0.02,10.05,9.014,19]henicosan-17-ol (1R,2R,5S,8R,9R,10R,13R,14R,17S,19R)-1,2,14,18,18-五甲基-5-羟甲基-8-(1-甲基乙烯基)五环[11.8.0.02,10.05,9.014,19]-17-二十一醇 | |
英文名 | Betulin |
别名 | 桦木醇 |
识别 | |
CAS号 | 473-98-3 ![]() |
PubChem | 72326 |
ChemSpider | 65272 |
SMILES |
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InChI |
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InChIKey | FVWJYYTZTCVBKE-ROUWMTJPBQ |
KEGG | C08618 |
性质 | |
化学式 | C30H50O2 |
摩尔质量 | 442.72 g·mol−1 |
外观 | 针状晶体[1] |
熔点 | 256—257 °C(493—495 °F;529—530 K) |
溶解性(水) | 不溶[1] |
溶解性 | 微溶于乙醇和苯,易溶于二乙醚、乙酸乙酯和石油英[1] |
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。 |
白桦脂醇于1788年由约汉·托比阿斯·洛维茨发现。[5][6]
参考文献
编辑- ^ 1.0 1.1 1.2 Haynes, William M.; Lide, David R.; Bruno, Thomas J. 3. CRC Handbook of Chemistry and Physics 95th. Boca Raton, Florida: CRC Press. 2014: 340. ISBN 9781482208689. OCLC 908078665.
- ^ Green, Brian; Bentley, Michael D.; Chung, Bong Y.; Lynch, Nicholas G.; Jensen, Bruce L. Isolation of Betulin and Rearrangement to Allobetulin. A Biomimetic Natural Product Synthesis. Journal of Chemical Education. 2007-12-01, 84 (12): 1985. Bibcode:2007JChEd..84.1985G. doi:10.1021/ed084p1985 (英语).
- ^ Gao, Yuan; Xu, Hongyu; Lu, Zhenming; Xu, Zhenghong. Quantitative determination of steroids in the fruiting bodies and submerged-cultured mycelia of Inonotus obliquus. Se Pu. November 2009, 27 (6): 745–749. ISSN 1000-8713. PMID 20352924.
- ^ Gregory L., Tilford. Edible and medicinal plants of the West. Missoula, Mont.: Mountain Press Pub. 1997: 12 [2019-12-21]. ISBN 9780878423590. LCCN 97000842. OCLC 36307825. (原始内容存档于2021-04-27).
- ^ Lowitz, J. T. Űber eine neue, fast benzoeartige substanz der briken. Crell's Chem. Ann. 1788, 1: 312–317.
- ^ Król, Sylwia Katarzyna; Kiełbus, Michał; Rivero-Müller, Adolfo; Stepulak, Andrzej. Comprehensive Review on Betulin as a Potent Anticancer Agent. BioMed Research International. 2015, 2015: 584189. PMC 4383233 . PMID 25866796. doi:10.1155/2015/584189 .