Quebrachitol

Cas：642-38-6

Product Information：

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 Formula: C7H14O6

Exact Mass: 194.079

Molecular Weight: 194.18

Elemental Analysis: C, 43.30; H, 7.27; O, 49.43

Synonym:

Brahol

NSC-26254

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

Technical Data：

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

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

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

References:

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.

Products are for research use only. Not for human use.