Baishouwubenzophenone

Last updated
Baishouwubenzophenone
Baishouwubenzophenone.svg
Names
Preferred IUPAC name
1-[3-(3,6-dihydroxy-2-methylbenzoyl)-2,4-dihydroxyphenyl]ethanone
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C16H14O6/c1-7-10(18)5-6-11(19)13(7)16(22)14-12(20)4-3-9(8(2)17)15(14)21/h3-6,18-21H,1-2H3
  • CC1=C(C=CC(=C1C(=O)C2=C(C=CC(=C2O)C(=O)C)O)O)O
Properties
C16H14O6
Molar mass 302.282 g·mol−1
AppearanceColorless needles
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Baishouwubenzophenone is a naturally occurring atropisomeric compound with the formula C16H14O6. Classified as a benzophenone derivative, [1] it has been isolated from the roots of several species in the genus Cynanchum , including Cynanchum wilfordii, [1] Cynanchum auriculatum (now Vincetoxicum auriculatum ), [2] and Cynanchum bungei. [3]

Contents

Structure and properties

Baishouwubenzophenone has the molecular formula C16H14O6. Structurally, it consists of two aromatic rings connected by a central carbonyl group, characteristic of the benzophenone framework. [1] The molecule contains multiple hydroxyl groups, which contribute to its positive reaction with ferric chloride (FeCl3), indicative of phenolic functionality. [2]

Baishouwubenzophenone is an example of a non-biaryl atropisomer. [1] The presence of bulky substituents ortho to the carbonyl bridge on both aromatic rings results in restricted rotation around the Ar–CO–Ar axis, giving rise to stable atropisomers. Both (R)- and (S)-enantiomers have been observed. [1] The absolute configuration and chiroptical properties of the compound have been elucidated using techniques such as experimental electronic circular dichroism (ECD) and time-dependent density functional theory (TDDFT) calculations. [1]

Applications

Baishouwubenzophenone is thought to contribute to the pharmacological properties of Cynanchum species, which have been used in traditional Chinese medicine for their tonic agents and exhibit various pharmacological activities like anti-tumor, antioxidant, gastroprotective, anti-aging, and immune regulatory effects. [2] In addition to its role in natural product chemistry, baishouwubenzophenone has been investigated as a potential atropisomeric ligand for use in asymmetric catalysis. [1] Its rigid chiral scaffold and multiple coordination sites make it a candidate for applications in enantioselective synthesis. [1]

References

  1. 1 2 3 4 5 6 7 8 Zhou, Zhixu; Wang, Zhiqiang; Li, Linwei; Zhang, Ke; Peng, Qing; Wang, Shuyun; Wang, Jinhui; Huang, Jian; Sun, Tiemin (2016). "The stereochemistry of baishouwubenzophenone, a unique atropisomer from C. wilfordii". Journal of Molecular Structure. 1125: 370–373. Bibcode:2016JMoSt1125..370Z. doi:10.1016/j.molstruc.2016.07.008.
  2. 1 2 3 Sun, Yinshi; Liu, Zhengbo; Wang, Jianhua; Xiang, Lan; Zhu, Lixiang (2009). "Separation and Purification of Baishouwubenzophenone, 4-Hydroxyacetophenone and 2,4-Dihydroxyacetophenone from Cynanchum auriculatum Royle ex Wight by HSCCC" . Chromatographia. 70 (1–2): 1–6. doi:10.1365/s10337-009-1107-y. ISSN   0009-5893.
  3. ↑ Sun, Yinshi; Lin, Hongmei; Wang, Jianhua; Hu, Jiangning; Liu, Zhengbo; Gao, Aidong (2011). "An Application of High-speed Counter-current Chromatography for Separation and Purification of Bungeiside-A, Bungeiside-B and Baishouwubenzophenone from Cynanchum bungei Decne" . Phytochemical Analysis. 22 (6): 526–531. Bibcode:2011PChAn..22..526S. doi:10.1002/pca.1313. ISSN   0958-0344. PMID   21465600.
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