Baishouwubenzophenone is a naturally occurring

atropisomer Atropisomers are stereoisomers arising because of hindered rotation about a covalent bond, single bond, where Gibbs free energy, energy differences due to steric strain or other contributors create a barrier to rotation that is high enough to all ...

ic compound with the formula CHO. Classified as a

benzophenone Benzophenone is a naturally occurring organic compound with the formula (C6H5)2CO, generally abbreviated Ph2CO. Benzophenone has been found in some fungi, fruits and plants, including grapes. It is a white solid with a low melting point and ros ...

derivative, it has been isolated from the roots of several species in the genus ''

Cynanchum ''Cynanchum'' is a genus of about 300 species including some swallowworts, belonging to the family Apocynaceae. The taxon name comes from Greek ''kynos'' (meaning "dog") and ''anchein'' ("to choke"), hence the common name for several species is ...

'', including ''Cynanchum wilfordii'', ''Cynanchum auriculatum'' (now ''

Vincetoxicum auriculatum ''Vincetoxicum auriculatum'', synonym ''Cynanchum auriculatum'', is a species of climbing vine. Its Chinese name is ''niu pi xiao'' 牛皮消 (leather eater). ''V. auriculatum'' flowers between June and August; fruiting from August all the ...

''), and ''Cynanchum bungei''.

Structure and properties

Baishouwubenzophenone has the molecular formula CHO. Structurally, it consists of two aromatic rings connected by a central

carbonyl group In organic chemistry, a carbonyl group is a functional group with the formula , composed of a carbon atom double-bonded to an oxygen atom, and it is divalent at the C atom. It is common to several classes of organic compounds (such as aldehydes ...

, characteristic of the benzophenone framework. The molecule contains multiple

hydroxyl groups In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...

, which contribute to its positive reaction with

ferric chloride Iron(III) chloride describes the inorganic compounds with the formula (H2O)x. Also called ferric chloride, these compounds are some of the most important and commonplace compounds of iron. They are available both in anhydrous and in hydrated f ...

(FeCl), indicative of phenolic functionality. Baishouwubenzophenone is an example of a non- biaryl

. 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)-

enantiomer In chemistry, an enantiomer (Help:IPA/English, /ɪˈnænti.əmər, ɛ-, -oʊ-/ Help:Pronunciation respelling key, ''ih-NAN-tee-ə-mər''), also known as an optical isomer, antipode, or optical antipode, is one of a pair of molecular entities whi ...

s have been observed. The absolute configuration and chiroptical properties of the compound have been elucidated using techniques such as experimental electronic circular

dichroism In optics, a dichroic material is either one which causes visible light to be split up into distinct beams of different wavelengths (colours) (not to be confused with Dispersion (optics), dispersion), or one in which light rays having different P ...

(ECD) and

time-dependent density functional theory Time-dependent density-functional theory (TDDFT) is a quantum mechanical theory used in physics and chemistry to investigate the properties and dynamics of many-body systems in the presence of time-dependent potentials, such as electric or magne ...

(TDDFT) calculations.

Applications

Baishouwubenzophenone is thought to contribute to the pharmacological properties of ''

'' species, which have been used in

traditional Chinese medicine Traditional Chinese medicine (TCM) is an alternative medicine, alternative medical practice drawn from traditional medicine in China. A large share of its claims are pseudoscientific, with the majority of treatments having no robust evidence ...

for their tonic agents and exhibit various pharmacological activities like

anti-tumor Chemotherapy (often abbreviated chemo, sometimes CTX and CTx) is the type of cancer treatment that uses one or more anti-cancer drugs ( chemotherapeutic agents or alkylating agents) in a standard regimen. Chemotherapy may be given with a cu ...

antioxidant Antioxidants are Chemical compound, compounds that inhibit Redox, oxidation, a chemical reaction that can produce Radical (chemistry), free radicals. Autoxidation leads to degradation of organic compounds, including living matter. Antioxidants ...

, gastroprotective,

anti-aging The anti-aging movement is a social movement devoted to eliminating or reversing aging, or reducing the effects of it. A substantial portion of the attention of the movement is on the possibilities for life extension, but there is also interest i ...

, and immune regulatory effects. In addition to its role in natural product chemistry, baishouwubenzophenone has been investigated as a potential atropisomeric ligand for use in asymmetric catalysis. Its rigid chiral scaffold and multiple coordination sites make it a candidate for applications in enantioselective synthesis.

References

{{Reflist Benzophenones Natural phenols Tetrols Acetyl compounds