伞形花内酯

化合物
(重定向自伞形酮

伞形花内酯也译为伞形酮(英語:Umbelliferone,也称为7-羟基香豆素7-hydroxycoumarin)是一种天然的香豆素类化合物,最早发现于伞形科植物,因而得名,有抗氧化活性[1][2],可用作防曬油[3]

Umbelliferone
Unbelliferone, or 7-hydroxycoumarin, is a yellowish white crystalline powder lacking the odor of coumarin, or any strong odor.
IUPAC名
7-Hydroxychromen-2-one
别名 7-羟基-2H-1-苯并吡喃-2-酮
识别
CAS号 93-35-6  checkY
PubChem 5281426
ChemSpider 4444774
SMILES
 
  • c1cc(cc2c1ccc(=O)o2)O
InChI
 
  • 1/C9H6O3/c10-7-3-1-6-2-4-9(11)12-8(6)5-7/h1-5,10H
InChIKey ORHBXUUXSCNDEV-UHFFFAOYAL
ChEBI 27510
性质
化学式 C9H6O3
摩尔质量 162.14 g/mol g·mol⁻¹
外观 浅黄色晶体
熔点 230 °C(503 K)(分解)
磁化率 -88.22·10−6 cm3/mol
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

它可由2,4-二羟基苯甲醛丙二酸为原料反应制得。[4]乙酰基间苯二酚丙烯酸甲酯乙酸钠甲酸的存在下(乙酸亚铑催化)反应,也可得到产物。[5]它和乙酸酐反应,可以得到乙酰基伞形花内酯。[6]

参考文献

  1. ^ UMBELLIFERONE. www.chemicalland21.com. [21 November 2011]. (原始内容存档于2020-09-19). 
  2. ^ Sim MO, Lee HI, Ham JR, Seo KI, Kim MJ, Lee MK. Anti-inflammatory and antioxidant effects of umbelliferone in chronic alcohol-fed rats. Nutr Res Pract. 2015, 9 (4): 364–369. PMC 4523479 . PMID 26244074. doi:10.4162/nrp.2015.9.4.364. 
  3. ^ Du, Lupei. Rational design of a fluorescent hydrogen peroxide probe based on the umbelliferone fluorophore. Tetrahedron Letters. 2008, 49 (19): 3045–3048. PMC 2490821 . PMID 19081820. doi:10.1016/j.tetlet.2008.03.063. 
  4. ^ Jack van Schijndel, Dennis Molendijk, Luiz Alberto Canalle, Erik Theodorus Rump, Jan Meuldijk. Temperature Dependent Green Synthesis of 3-Carboxycoumarins and 3,4-unsubstituted Coumarins. Current Organic Synthesis. 2019-02-04, 16 (1): 130–135 [2021-02-01]. doi:10.2174/1570179415666180924124134 (英语). 
  5. ^ Sunita K. Gadakh, Soumen Dey, Arumugam Sudalai. Rh-Catalyzed Synthesis of Coumarin Derivatives from Phenolic Acetates and Acrylates via C–H Bond Activation. The Journal of Organic Chemistry. 2015-11-20, 80 (22): 11544–11550 [2021-02-01]. ISSN 0022-3263. doi:10.1021/acs.joc.5b01713. (原始内容存档于2017-05-25) (英语). 
  6. ^ Pierre Stocker, Mathieu Cassien, Nicolas Vidal, Sophie Thétiot-Laurent, Sylvia Pietri. A fluorescent homogeneous assay for myeloperoxidase measurement in biological samples. A positive correlation between myeloperoxidase-generated HOCl level and oxidative status in STZ-diabetic rats. Talanta. 2017-08, 170: 119–127 [2021-02-01]. doi:10.1016/j.talanta.2017.03.102. (原始内容存档于2018-06-15) (英语). 

外部链接

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