β-Cyclodextrin

• CAT Number: R057424
• CAS Number: 7585-39-9
• Molecular Formula: C₄₂H₇₀O₃₅
• Molecular Weight: 1134.98
• Purity: ≥95%
• Storage: -20°C
• InChI: InChI=1S/C42H70O35/c43-1-8-29-15(50)22(57)36(64-8)72-30-9(2-44)66-38(24(59)17(30)52)74-32-11(4-46)68-40(26(61)19(32)54)76-34-13(6-48)70-42(28(63)21(34)56)77-35-14(7-49)69-41(27(62)20(35)55)75-33-12(5-47)67-39(25(60)18(33)53)73-31-10(3-45)65-37(71-29)23(58
• InChIKey: WHGYBXFWUBPSRW-UOFYCTJFSA-N
• SMILES: O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@H](O)[C@@H](O)[C@H](O3)[C@@H](CO)O2)[C@@H](CO)O[C@@H]1O[C@H]4[C@H](O)[C@@H](O)[C@@H](O[C@@H]5[C@@H](O)[C@H](O)[C@H](O[C@@H]6[C@@H](O)[C@H](O)[C@H](O[C@@H]7[C@@H](O)[C@H](O)[C@H](O[C@@H]8[C@@H](O)[C@H](O)[C@H]3O[C@H]8CO)O[

β-Cyclodextrin is a cyclic heptamer composed of seven glucose units joined "head-to-tail" by alpha-1.4 links. It is produced by the action of the enzyme, cyclodextrin glycosyl transferase (CGT)，on hydrolyzed starch syrups. Cyclodextrins are able to form host-guest complexes with hydrophobic molecules given the unique nature imparted by their structure. As a result, these molecules have found a number of applications in a wide range of fields. β-cyclodextrins are used to produce HPLC columns allowing chiral enantiomers separation, and are also the main ingredient in P&G/’s product Febreze which claims that the β-cyclodextrins "trap" odor causing compounds, thereby reducing the odor.

Reference

1:β-cyclodextrin induces the differentiation of resident cardiac stem cells to cardiomyocytes through autophagy. Shi X, Li W, Liu H, Yin D, Zhao J.Biochim Biophys Acta. 2017 May 15. pii: S0167-4889(17)30123-4. doi: 10.1016/j.bbamcr.2017.05.012. [Epub ahead of print] PMID: 28522298 2:Methyl-β-cyclodextrin modulates thapsigargin-induced store-dependent Ca2+ entry in macrophages. Krutetskaya ZI, Milenina LS, Naumova AA, Butov SN, Antonov VG, Nozdrachev AD.Dokl Biochem Biophys. 2017 Mar;473(1):88-90. doi: 10.1134/S1607672917020028. Epub 2017 May 17. PMID: 28510132 3:Application of Partially Substituted 3,5-Dimethylphenylcarbamate-(3-(2-O-β-Cyclodextrin)-2-Hydroxypropoxy)-Propylsilyl-Appended Silica Particles as Chiral Stationary Phase for Multi-mode High-performance Liquid Chromatography. Ma M, Wei Q, Meng M, Yin J, Du L, Zhu X, Min M, Zhou X, Yin X, Gong Y.J Chromatogr Sci. 2017 May 13:1-7. doi: 10.1093/chromsci/bmx044. [Epub ahead of print] PMID: 28505281 4:Inclusion complexes of β-cyclodextrin with tricyclic drugs: an X-ray diffraction, NMR and molecular dynamics study. Castiglione F, Ganazzoli F, Malpezzi L, Mele A, Panzeri W, Raffaini G.Beilstein J Org Chem. 2017 Apr 13;13:714-719. doi: 10.3762/bjoc.13.70. eCollection 2017. PMID: 28503206 Free PMC Article5:A Multifunctional β-Cyclodextrin-Conjugate Photodelivering Nitric Oxide with Fluorescence Reporting. Benkovics G, Perez-Lloret M, Afonso D, Darcsi A, Béni S, Fenyvesi É, Malanga M, Sortino S.Int J Pharm. 2017 May 11. pii: S0378-5173(17)30433-7. doi: 10.1016/j.ijpharm.2017.05.023. [Epub ahead of print] PMID: 28502897 6:Novel molecularly imprinted polymer based on β-cyclodextrin@graphene oxide: Synthesis and application for selective diphenylamine determination. Sedghi R, Heidari B, Yassari M.J Colloid Interface Sci. 2017 May 6;503:47-56. doi: 10.1016/j.jcis.2017.05.013. [Epub ahead of print] PMID: 28500939 7:Magnetic porous β-cyclodextrin polymer for magnetic solid-phase extraction of microcystins from environmental water samples. Zhang W, Lin M, Wang M, Tong P, Lu Q, Zhang L.J Chromatogr A. 2017 May 1. pii: S0021-9673(17)30659-3. doi: 10.1016/j.chroma.2017.04.063. [Epub ahead of print] PMID: 28499596 8:Anti-hyperalgesic effect of Lippia grata leaf essential oil complexed with β-cyclodextrin in a chronic musculoskeletal pain animal model: Complemented with a molecular docking and antioxidant screening. Siqueira-Lima PS, Brito RG, Araújo-Filho HG, Santos PL, Lucchesi A, Araújo AAS, Menezes PP, Scotti L, Scotti MT, Menezes IRA, Coutinho HDM, Zengin G, Aktumsek A, Antoniolli AR, Quintans-Júnior LJ, Quintans JSS.Biomed Pharmacother. 2017 May 9;91:739-747. doi: 10.1016/j.biopha.2017.05.009. [Epub ahead of print] PMID: 28499245 9:Induction of mitophagy-mediated antitumor activity with folate-appended methyl-β-cyclodextrin. Kameyama K, Motoyama K, Tanaka N, Yamashita Y, Higashi T, Arima H.Int J Nanomedicine. 2017 Apr 28;12:3433-3446. doi: 10.2147/IJN.S133482. eCollection 2017. PMID: 28496320 Free PMC Article10:Optimal Solubility of Diclofenac β-Cyclodextrin in Combination with Local Anaesthetics for Mesotherapy Applications. Tringali G, Navarra P.Evid Based Complement Alternat Med. 2017;2017:8321325. doi: 10.1155/2017/8321325. Epub 2017 Apr 10. PMID: 28491114 Free PMC Article