反式肉桂酰基β-D-葡萄糖苷

化合物

反式肉桂酰基β-D-葡萄糖苷是一种有机化合物,化学式C15H18O7,可见于蛇菰[1]珍珠绣线菊[2]番石榴[3]等物种。

反式肉桂酰基β-D-葡萄糖苷
英文名 1-O-trans-cinnamoyl-beta-D-glucopyranose
识别
CAS号 40004-96-4  checkY
PubChem 5280653
ChemSpider 4444252
SMILES
 
  • C1=CC=C(C=C1)C=CC(=O)OC2C(C(C(C(O2)CO)O)O)O
InChI
 
  • InChI=1S/C15H18O7/c16-8-10-12(18)13(19)14(20)15(21-10)22-11(17)7-6-9-4-2-1-3-5-9/h1-7,10,12-16,18-20H,8H2/b7-6+/t10-,12-,13+,14-,15+/m1/s1
InChIKey CJGRGYBLAHPYOM-HOLMNUNMSA-N
ChEBI 16279
性质
化学式 C15H18O7
摩尔质量 310.3 g·mol−1
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

它可由α-D-葡萄糖和反式肉桂酸三苯基膦偶氮二甲酸二异丙酯英语Diisopropyl azodicarboxylate存在下反应制得。[4]

参考资料

  1. ^ Natcha Panthama; Somdej Kanokmedhakul; Kwanjai Kanokmedhakul. Galloyl and hexahydroxydiphenoyl esters of phenylpropanoid glucosides, phenylpropanoids and phenylpropanoid glucosides from rhizome of Balanophora fungosa. Chemical & Pharmaceutical Bulletin. 2009, 57 (12). doi:10.1248/CPB.57.1352 (英语). 
  2. ^ Syuntaro Hiradate; Sayaka Morita; Hajime Sugie; Jiro Harada. Phytotoxic cis-cinnamoyl glucosides from Spiraea thunbergii. Phytochemistry. 2004-03, 65 (6). doi:10.1016/J.PHYTOCHEM.2004.01.010. 
  3. ^ Stefan Latza; Dietmar Ganßer; Ralf G. Berger. Carbohydrate esters of cinnamic acid from fruits of Physalis peruviana, Psidium guajava and Vaccinium vitis-idaea. Phytochemistry. 1996-09, 43 (2). doi:10.1016/0031-9422(96)00303-2. 
  4. ^ Hironori Takeuchi; et al. Solvent-Dependent Mechanism and Stereochemistry of Mitsunobu Glycosylation with Unprotected Pyranoses. Org. Lett. 2020, 22, 12, 4754–4759. doi:10.1021/acs.orglett.0c01549.