Quebrachitol | CAS#642-38-6 | optically active cyclitol

Quebrachitol
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 596449

CAS#: 642-38-6

Description: Quebrachitol is a naturally occurring optically active cyclitol, a cyclic polyol. It can be found in Allophylus edulis and in the serum left after the coagulation of the Hevea brasiliensis latex in the operation of rubber tapping. It is also found in Cannabis sativa, in Paullinia pinnata and in seabuckthorn. Quebrachitol is a versatile building block in the construction of naturally occurring bioactive materials. For example, its conversion into antifungal (E)-β-methoxyacrylate, oudemansin X has been made.

Chemical Structure

Quebrachitol

CAS# 642-38-6

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 596449
Name: Quebrachitol
CAS#: 642-38-6
Chemical Formula: C7H14O6
Exact Mass: 194.08
Molecular Weight: 194.183
Elemental Analysis: C, 43.30; H, 7.27; O, 49.43

Price and Availability

Size	Price	Availability	Quantity
1g	USD 320
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Quebrachitol; Brahol; Quebrachit; NSC-26254; NSC 26254; NSC26254;

IUPAC/Chemical Name: (1R,2S,3S,4S,5R,6R)-6-methoxycyclohexane-1,2,3,4,5-pentaol

InChi Key: DSCFFEYYQKSRSV-FIZWYUIZSA-N

InChi Code: 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

SMILES Code: O[C@H]1[C@H]([C@@H]([C@H]([C@@H]([C@@H]1O)O)O)O)OC

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO and water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO and water

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

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Biological target:	Quebrachitol promotes osteoblastogenesis by uppregulation of BMP-2, runt-related transcription factor-2 (Runx2), MAPK (ERK, JNK, p38α), and Wnt/β-catenin signaling pathway.
In vitro activity:	Findings from this study indicate that quebrachitol may promote osteoblastogenesis by triggering the BMP-2-response as well as the Runx2, MAPK, and Wnt/β-catenin signaling pathway. Quebrachitol significantly promotes proliferation and cell DNA synthesis. It also enhances mineralization accompanied by increases in mRNA expression of bone matrix proteins. Quebrachitol upregulates the mRNA and protein expression of bone morphogenetic protein-2 and runt-related transcription factor-2, while down-regulating the receptor activator of the nuclear factor-κB ligand mRNA level. The expression of regulatory genes associated with the mitogen-activated protein kinase and wingless-type MMTV integration site/β-catenin signaling pathways are also upregulated. Reference: .Molecules. 2018 Nov 26;23(12):3086. https://pubmed.ncbi.nlm.nih.gov/30486330/
In vivo activity:	Quebrachitol was investigated against gastric damage induced by absolute ethanol and indomethacin, in mice. Quebrachitol at oral doses of 12.5, 25, and 50mg/kg markedly attenuated the gastric lesions induced by ethanol to the extent of 69%, 64%, and 53% and against indomethacin by 55%, 59%, and 26%, respectively. Quebrachitol’s effect was significantly reduced in mice pretreated with L-NAME, the respective inhibitors of nitric oxide synthase, and K(+)(ATP) channel activation. Quebrachitol reduces the gastric damage induced by ethanol and indomethacin by mechanisms that involve endogenous prostaglandins, nitric oxide release, and or the activation of K(+)(ATP) channels. Reference: Phytomedicine. 2008 May;15(5):327-33. https://pubmed.ncbi.nlm.nih.gov/17976970/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	125.0	643.73
	Water	100.0	514.99

Preparing Stock Solutions

The following data is based on the product molecular weight 194.18 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Nobre Júnior HV, Cunha GM, Moraes MO, Luciana MF, Oliveira RA, Maia FD, Nogueira MA, Lemos TL, Rao VS. Quebrachitol (2-O-methyl-L-inositol) attenuates 6-hydroxydopamine-induced cytotoxicity in rat fetal mesencephalic cell cultures. Food Chem Toxicol. 2006 Sep;44(9):1544-51. doi: 10.1016/j.fct.2006.04.002. Epub 2006 Apr 26. PMID: 16797817. 2. Yodthong T, Kedjarune-Leggat U, Smythe C, Wititsuwannakul R, Pitakpornpreecha T. l-Quebrachitol Promotes the Proliferation, Differentiation, and Mineralization of MC3T3-E1 Cells: Involvement of the BMP-2/Runx2/MAPK/Wnt/β-Catenin Signaling Pathway. Molecules. 2018 Nov 26;23(12):3086. doi: 10.3390/molecules23123086. PMID: 30486330; PMCID: PMC6321399. 3. 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. PMID: 18343146. 4. 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. doi: 10.1016/j.phymed.2007.09.002. Epub 2007 Oct 31. PMID: 17976970.
In vitro protocol:	1. Nobre Júnior HV, Cunha GM, Moraes MO, Luciana MF, Oliveira RA, Maia FD, Nogueira MA, Lemos TL, Rao VS. Quebrachitol (2-O-methyl-L-inositol) attenuates 6-hydroxydopamine-induced cytotoxicity in rat fetal mesencephalic cell cultures. Food Chem Toxicol. 2006 Sep;44(9):1544-51. doi: 10.1016/j.fct.2006.04.002. Epub 2006 Apr 26. PMID: 16797817. 2. Yodthong T, Kedjarune-Leggat U, Smythe C, Wititsuwannakul R, Pitakpornpreecha T. l-Quebrachitol Promotes the Proliferation, Differentiation, and Mineralization of MC3T3-E1 Cells: Involvement of the BMP-2/Runx2/MAPK/Wnt/β-Catenin Signaling Pathway. Molecules. 2018 Nov 26;23(12):3086. doi: 10.3390/molecules23123086. PMID: 30486330; PMCID: PMC6321399. 3. 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. PMID: 18343146.
In vivo protocol:	1. 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. doi: 10.1016/j.phymed.2007.09.002. Epub 2007 Oct 31. PMID: 17976970.

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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.

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Quebrachitol featured