伞形花内酯

Umbelliferone
	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
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。

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]。

它可由2,4-二羟基苯甲醛和丙二酸为原料反应制得。^[4]乙酰基间苯二酚和丙烯酸甲酯在乙酸钠和甲酸的存在下（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[编辑]

^ UMBELLIFERONE. www.chemicalland21.com. [21 November 2011]. （原始内容存档于2020-09-19）.
^ 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.
^ 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.
^ 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）.
^ 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）.
^ 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[编辑]

USDA ARS info on uses

Template:Coumarin

[1] UMBELLIFERONE. www.chemicalland21.com. [21 November 2011]. （原始内容存档于2020-09-19）.

[pmc-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）.

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