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1,2-Cyclohexanediol - CAS 931-17-9

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Category
Main Product
Product Name
1,2-Cyclohexanediol
Catalog Number
931-17-9
Synonyms
1,2-Benzenediol, hexahydro-;1,2-Cyclohexanediol cis-trans;1,2-cyclohexanediol(cis-andtrans-mixture;1,2-Cyclohexanediol,c&t;1,2-cyclohexanediol,mixtureofcisandtrans;2-Hydroxycyclohexanol;Brenzcatechin;Brenzkatechin
CAS Number
931-17-9
Molecular Weight
116.16
Molecular Formula
C6H12O2
COA
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MSDS
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Structure
CAS 931-17-9 1,2-Cyclohexanediol
Specification
Purity
95%
Boiling Point
118-120ºC (10 mmHg)
Melting Point
73-77ºC
Density
1.156 g/cm3
Appearance
beige crystals.
Physical Description
1,2-Cyclohexanediol, mixture of cis and trans 98% (100g)
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Reference Reading
1.On the origins of kinetic resolution of cyclohexane-1,2-diols through stereoselective acylation by chiral tetrapeptides.
Shinisha CB1, Sunoj RB. Org Lett. 2009 Aug 6;11(15):3242-5. doi: 10.1021/ol9011822.
The relative energies of cyclohexane-1,2-diols and chiral tetrapeptide (2 (Boc) or 3 (Moc)) complexes calculated using DFT indicate a thermodynamic preference for chiral recognition toward (1R,2R)(e,e)-alpha isomer. The barrier for stereoselective acyl transfer is identified as lower for trans-(1R,2R)-cyclohexane-1,2-diol, leading to the kinetic resolution (KR) of trans-(1S,2S)-cyclohexane-1,2-diol. The prediction is in concert with the reported experiments for trans-diols, while that for hitherto unknown cis-diol demands experimental verification. It is proposed that desymmetrization would enable the resolution of cis-(1R,2S)-2-hydroxycyclohexyl acetate.
2.From simple diols to carbohydrate derivatives of phenylarsonic acid.
Betz R1, Klüfers P. Inorg Chem. 2009 Feb 2;48(3):925-35. doi: 10.1021/ic8014018.
A series of spiro-arsoranes bearing a phenyl moiety as the fifth substituent were synthesized applying open-chain, as well as cyclic vicinal diols, as chelating molecules by condensation reactions in aprotic solvents. The products synthesized are the spiro compounds of the general formula PhAs(DiolH(-2))(2) derived from the vicinal diols meso-2,3-butanediol, PhAs(meso-2,3-ButdH(-2))(2) (1), exo-cis-2,3-norbornanediol, PhAs{exo-cis-NobdH(-2)}(2) (2), cis-1,2-cyclopentanediol, PhAs(cis-1,2-CptdH(-2))(2) (3), anhydroerythritol, PhAs(AnErytH(-2))(2) (4), cis-1,2-cyclohexanediol, PhAs(cis-1,2-ChxdH(-2))(2) (5), and rac-trans-1,2-cyclohexanediol, rac-{PhAs(trans-1,2-ChxdH(-2))(2)} (6) which were identified as mononuclear compounds. A novel dimeric double-spiro environment for oxyarsoranes was found in the reaction products derived from the sterically demanding diols 1,1'-bicyclohexyl-1,1'-diol {PhAs(BhxdH(-2))O}(2) (7) and perfluorpinacol, {PhAs(FpinH(-2))O}(2) (8).
3.Isolation, characterization, and nuclease activity of biologically relevant chromium(V) complexes with monosaccharides and model diols. Likely intermediates in chromium-induced cancers.
Bartholomäus R1, Irwin JA, Shi L, Smith SM, Levina A, Lay PA. Inorg Chem. 2013 Apr 15;52(8):4282-92. doi: 10.1021/ic3022408. Epub 2013 Mar 26.
The stabilization of Cr(V) by biological 1,2-diolato ligands, including carbohydrates, glycoproteins, and sialic acid derivatives, is likely to play a crucial role in the genotoxicity of Cr(VI) and has also been implicated in the antidiabetic effect of Cr(III). Previously, such complexes have been observed by electron paramagnetic resonance (EPR) spectroscopy in living cells or animals, treated with carcinogenic Cr(VI), as well as in numerous model systems, but attempts to isolate them have been elusive. Recently, the first crystal structure of a Cr(V) complex with cis-1,2-cyclohexanediol (1, a close structural analogue of carbohydrates) has been reported. In this work, Cr(V) complexes of the general formula [Cr(V)OL2](-) [where LH2 = 1, cis-1,2-cyclopentanediol (2), D-glucose (3), D-mannose (4), D-galactose (5), and D-ribose (6)] have been isolated from light-catalyzed reactions of Cr(VI) (anhydrous Na2Cr2O7) with slight molar excesses of the corresponding ligands in N,N-dimethylformamide.
4.Effect of hydroxyl groups and rigid structure in 1,4-cyclohexanediol on percutaneous absorption of metronidazole.
Zhang Y1, Tan F, Jia W, Li N, Zhang J. AAPS PharmSciTech. 2014 Aug;15(4):973-80. doi: 10.1208/s12249-014-0125-8. Epub 2014 May 13.
In a previous study, a synergistic retardation effect of 1,4-cyclohexanediol and 1,2-hexanediol on percutaneous absorption and penetration of metronidazole (MTZ) was discovered. A complex formation between 1,4-cyclohexanediol and 1,2-hexanediol was proposed to be responsible for the observed effect. The objective of this study was to investigate the necessity of hydroxyl group and the ring structure in 1,4-cyclohexanediol on percutaneous absorption and penetration of MTZ. Eleven formulations were studied in an in vitro porcine skin model using glass vertical Frans Diffusion Cell. 1,4-Cyclohexanediol was changed into 1,4-cyclohexanedicarboxylic acid, trans (and cis)-1,2-cyclohexanediol and 1,6-hexanediol, respectively, to study if H-bonding or ring structure would influence the retardation effect. MTZ was applied at infinite dose (100 mg), which corresponded to 750 μg of MTZ. Based on modifier ratios (MR) calculated by the flux values, the retardation effect on percutaneous absorption and penetration of MTZ was found in the formulations containing 1,4-cyclohexanedicarboxylic acid or cis-1,2-cyclohexanediol (MR values were 0.
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