69501-36-6

Basic information

• Product Name: (1S,2S)-trans-1,2-cyclohexanediol-1-O-β-D-glucopyranoside
• Synonyms: (1S,2S)-trans-1,2-cyclohexanediol-1-O-β-D-glucopyranoside
• CAS NO: 69501-36-6
• Molecular Weight: 278.302
• Mol File: 69501-36-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (1S,2S)-trans-1,2-cyclohexanediol-1-O-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-trans-1,2-cyclohexanediol-1-O-β-D-glucopyranoside(69501-36-6)
• EPA Substance Registry System: (1S,2S)-trans-1,2-cyclohexanediol-1-O-β-D-glucopyranoside(69501-36-6)

Safety Data

• Hazardous Substances Data: 69501-36-6(Hazardous Substances Data)

Upstream product

• 931-17-9 1,2-Cyclohexanediol 
• 2818-58-8 phenyl-β-D-galactopyranoside 
• 1460-57-7 trans-1,2-cyclohexandiol 
• 1464-44-4 phenyl-β-D-glucopyranoside 
• 439-03-2 2,3,4,6-tetra-O-acetyl-1-fluoro-α-D-glucopyranose 
• 133-89-1 UDP-glucose 
• 138-52-3 D-(-)-salicin 

Downstream Products

• 2280-44-6 D-Glucose 
• 57794-08-8 (1S,2S)-trans-1,2-Cyclohexanediol 
• 76035-73-9 (1S,2S)-2-hydroxycyclohexyl α-D-glucopyranoside 

Relevant articles and documents

Phenolic glycosides from the twigs of Salix glandulosa

As a part of an ongoing search for bioactive constituents from Korean medicinal plants, the phytochemical investigations of the twigs of Salix glandulosa afforded 12 new phenolic glycosides (1-12) and a known analogue (13). The structures of 1-13 were characterized by a combination of NMR methods (1H and 13C NMR, 1H-1H COSY, HMQC, and HMBC), chemical hydrolysis, and GC/MS. The absolute configuration of 13 [(1R,2S)-2-hydroxycyclohexyl-2′-O-trans-p-coumaroyl-β-d- glucopyranoside] was determined for the first time. Compounds 1-3, 6, and 7 exhibited inhibitory effects on nitric oxide production in lipopolysaccharide- activated murine microglial cells (IC50 values in the range 6.6-20.5 μM).

Stereochemical Studies of Enzymatic Transglycosylation using Sulfolobus solfataricus

Stereochemistry of β-glycosyl transfer from phenyl β-D-galactoside, lactose, and phenyl β-D-glucoside to various 1,2-, 1,3-, and 1,4-diols, a secondary-tertiary diol, a cyclic diol, and a racemic alkohol has been studied using β-glycosidase activity in a crude preparation from the thermophilic archaebacterium Sulfolobus solfataricus.Good enantioselection for the galactosyl transfer to the secondary hydroxy group of different 1,2-diols has been observed.Good yields in comparison with enzymes from other sources, and results concerning the reaction's regioselectivity, have also been reported.

STEREOSPECIFIC PREPARATION OF MONOGLUCOSIDES OF OPTICALY ACTIVE trans-1,2-CYCLOHEXANEDIOLS BY ENZYMIC TRANS-D-GLUCOSYLATION, AND (13)C-N.M.R. SPECTROSCOPY OF THE RESULTING MONO-D-GLUCOPYRANOSIDES

Anomeric mono-D-glucosides of optically active trans-1,2-cyclohexanediols were stereoselectively prepared from the racemic mixture by means of enzymic trans-D-glucosylation using crude enzyme preparations that are commercially available or are utilized for food manufacturing.The (13)C-n.m.r. spectra of these D-glucosides were characterized, and the stereochemical influence, on the glycosylation shifts of cyclohexanol, of the vicinal hydroxyl substitution was discussed in comparison with that of vicinal alkyl substitution reported previously.