Quebrachitol

• CAT Number: I014659
• CAS Number: 642-38-6
• Molecular Formula: C7H14O6
• Molecular Weight: 194.18
• Purity: ≥95%
• Synonyms: Quebrachitol; Brahol; Quebrachit; NSC-26254; NSC 26254; NSC26254;;(1R,2S,3S,4S,5R,6R)-6-methoxycyclohexane-1,2,3,4,5-pentaol
• Target: Wnt; β-catenin
• Solubility: Soluble in DMSO
• Storage: 2-8°C
• IUPAC Name: (1R,2S,4S,5R)-6-methoxycyclohexane-1,2,3,4,5-pentol
• InChI: InChI=1S/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2?,3-,4-,5+,6+,7?/m0/s1
• InChIKey: DSCFFEYYQKSRSV-MBXCVVGISA-N
• SMILES: COC1C(C(C(C(C1O)O)O)O)O

Quebrachitol (Cat No.:I014659) is a naturally occurring cyclic alcohol derived from the Quebracho tree. It is a white crystalline solid with a sweet taste. Quebrachitol has attracted attention for its potential medicinal properties, including antioxidant, anti-inflammatory, and antiparasitic activities. It has shown inhibitory effects on carbohydrate-metabolizing enzymes and is being investigated for its potential in diabetes treatment. Quebrachitol also finds applications in drug delivery systems and serves as a chiral building block in organic synthesis. Its diverse properties make it a promising compound for various pharmaceutical and chemical applications.

Reference

1: Zhu J, Qi J, Fang Y, Xiao X, Li J, Lan J, Tang C. Characterization of Sugar Contents and Sucrose Metabolizing Enzymes in Developing Leaves of Hevea brasiliensis. Front Plant Sci. 2018 Feb 1;9:58. doi: 10.3389/fpls.2018.00058. eCollection 2018. PubMed PMID: 29449852; PubMed Central PMCID: PMC5799706.2: Wu ZC, Zhang JQ, Zhao JT, Li JG, Huang XM, Wang HC. Biosynthesis of quebrachitol, a transportable photosynthate, in Litchi chinensis. J Exp Bot. 2018 Mar 24;69(7):1649-1661. doi: 10.1093/jxb/erx483. PubMed PMID: 29281092.3: Liu Y, Fan G, Zhang J, Zhang Y, Li J, Xiong C, Zhang Q, Li X, Lai X. Metabolic discrimination of sea buckthorn from different Hippophaë species by (1)H NMR based metabolomics. Sci Rep. 2017 May 8;7(1):1585. doi: 10.1038/s41598-017-01722-3. PubMed PMID: 28484246; PubMed Central PMCID: PMC5431470.4: Dos Santos HF, Chagas MA, De Souza LA, Rocha WR, De Almeida MV, Anconi CP, De Almeida WB. Water Solvent Effect on Theoretical Evaluation of (1)H NMR Chemical Shifts: o-Methyl-Inositol Isomer. J Phys Chem A. 2017 Apr 13;121(14):2839-2846. doi: 10.1021/acs.jpca.7b01067. Epub 2017 Mar 30. PubMed PMID: 28328211.5: Wang D, Zhang S, Chang Z, Kong DX, Zuo Z. Quebrachitol: Global Status and Basic Research. Nat Prod Bioprospect. 2017 Feb;7(1):113-122. doi: 10.1007/s13659-017-0120-3. Epub 2017 Jan 28. Review. PubMed PMID: 28132388; PubMed Central PMCID: PMC5315676.6: Kortesniemi M, Sinkkonen J, Yang B, Kallio H. NMR metabolomics demonstrates phenotypic plasticity of sea buckthorn (Hippophaë rhamnoides) berries with respect to growth conditions in Finland and Canada. Food Chem. 2017 Mar 15;219:139-147. doi: 10.1016/j.foodchem.2016.09.125. Epub 2016 Sep 20. PubMed PMID: 27765210.7: Wu ZC, Yang ZY, Li JG, Chen HB, Huang XM, Wang HC. Methyl-inositol, γ-aminobutyric acid and other health benefit compounds in the aril of litchi. Int J Food Sci Nutr. 2016 Nov;67(7):762-72. doi: 10.1080/09637486.2016.1198888. Epub 2016 Jun 17. PubMed PMID: 27314889.8: Shu B, Li W, Liu L, Wei Y, Shi S. Transcriptomes of Arbuscular Mycorrhizal Fungi and Litchi Host Interaction after Tree Girdling. Front Microbiol. 2016 Mar 30;7:408. doi: 10.3389/fmicb.2016.00408. eCollection 2016. PubMed PMID: 27065972; PubMed Central PMCID: PMC4811939.9: Su YW, Tan E, Zhang J, You JL, Liu Y, Liu C, Zhou XD, Zhang Y. [Study on three different species tibetan medicine sea buckthorn by 1H-NMR-based metabonomics]. Zhongguo Zhong Yao Za Zhi. 2014 Nov;39(21):4234-9. Chinese. PubMed PMID: 25775800.10: Seebaluck R, Gurib-Fakim A, Mahomoodally F. Medicinal plants from the genus Acalypha (Euphorbiaceae)–a review of their ethnopharmacology and phytochemistry. J Ethnopharmacol. 2015 Jan 15;159:137-57. doi: 10.1016/j.jep.2014.10.040. Epub 2014 Oct 30. Review. PubMed PMID: 25446604.11: De Almeida MV, Couri MR, De Assis JV, Anconi CP, Dos Santos HF, De Almeida WB. (1) H NMR analysis of O-methyl-inositol isomers: a joint experimental and theoretical study. Magn Reson Chem. 2012 Sep;50(9):608-14. doi: 10.1002/mrc.3848. Epub 2012 Aug 3. PubMed PMID: 22865668.12: Moharam BA, Jantan I, Jalil J, Shaari K. Inhibitory effects of phylligenin and quebrachitol isolated from Mitrephora vulpina on platelet activating factor receptor binding and platelet aggregation. Molecules. 2010 Nov 3;15(11):7840-8. doi: 10.3390/molecules15117840. Erratum in: Molecules. 2014;19(3):3848-9. PubMed PMID: 21060292.13: De Almeida MV, De Assis JV, Couri MR, Anconi CP, Guerreiro MC, Dos Santos HF, De Almeida WB. Experimental and theoretical investigation of epoxide quebrachitol derivatives through spectroscopic analysis. Org Lett. 2010 Dec 3;12(23):5458-61. doi: 10.1021/ol102305x. Epub 2010 Nov 2. PubMed PMID: 21043479.14: Dusotoit-Coucaud A, Porcheron B, Brunel N, Kongsawadworakul P, Franchel J, Viboonjun U, Chrestin H, Lemoine R, Sakr S. Cloning and characterization of a new polyol transporter (HbPLT2) in Hevea brasiliensis. Plant Cell Physiol. 2010 Nov;51(11):1878-88. doi: 10.1093/pcp/pcq151. Epub 2010 Oct 6. PubMed PMID: 20929914.15: Lv Z, Huang L, Chen R, Yu D. [Chemical constituents of Uvaria kurzii]. Zhongguo Zhong Yao Za Zhi. 2009 Sep;34(17):2203-5. Chinese. PubMed PMID: 19943486.16: Kallio H, Lassila M, Järvenpää E, Haraldsson GG, Jonsdottir S, Yang B. Inositols and methylinositols in sea buckthorn (Hippophaë rhamnoides) berries. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 May 15;877(14-15):1426-32. doi: 10.1016/j.jchromb.2009.03.027. Epub 2009 Mar 25. PubMed PMID: 19345619.17: Díaz M, González A, Castro-Gamboa I, Gonzalez D, Rossini C. First record of L-quebrachitol in Allophylus edulis (Sapindaceae). Carbohydr Res. 2008 Oct 13;343(15):2699-700. doi: 10.1016/j.carres.2008.07.014. Epub 2008 Jul 29. PubMed PMID: 18715552.18: Ortbauer M, Popp M. Functional role of polyhydroxy compounds on protein structure and thermal stability studied by circular dichroism spectroscopy. Plant Physiol Biochem. 2008 Apr;46(4):428-34. doi: 10.1016/j.plaphy.2008.02.002. Epub 2008 Feb 8. PubMed PMID: 18343146.19: Liu X, Moody EC, Hecht SS, Sturla SJ. Deoxygenated phosphorothioate inositol phosphate analogs: synthesis, phosphatase stability, and binding affinity. Bioorg Med Chem. 2008 Mar 15;16(6):3419-27. Epub 2007 Oct 14. PubMed PMID: 17981044.20: de Olinda TM, Lemos TL, Machado LL, Rao VS, Santos FA. Quebrachitol-induced gastroprotection against acute gastric lesions: role of prostaglandins, nitric oxide and K+ ATP channels. Phytomedicine. 2008 May;15(5):327-33. Epub 2007 Oct 31. PubMed PMID: 17976970.