488-76-6

Basic information

• Product Name: (-)-VIBO-QUERCITOL
• Synonyms: 1L-1,2,4/3,5-CYCLOHEXANEPENTOL;1-D-3-DEOXY-MYO-INOSITOL;(-)-VIBO-QUERCITOL;VIBURNITOL;L-chiro-Inositol, 1-deoxy-;(-)-1-Deoxy-L-chiro-inositol;1-Deoxy-L-chiro-inositol;L-Quercitol
• CAS NO: 488-76-6
• Molecular Formula: C₆H₁₂O₅
• Molecular Weight: 164.16
• Product Categories: Biochemistry;Sugars
• Mol File: 488-76-6.mol

Chemical Properties

• Melting Point: 180-181 °C
• Boiling Point: 293.6°Cat760mmHg
• Flash Point: 146.2°C
• Appearance: /
• Density: 1.796g/cm³
• Vapor Pressure: 0.00018mmHg at 25°C
• Refractive Index: 1.707
• Storage Temp.: Freezer
• PKA: 13.42±0.70(Predicted)
• CAS DataBase Reference: (-)-VIBO-QUERCITOL(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-VIBO-QUERCITOL(488-76-6)
• EPA Substance Registry System: (-)-VIBO-QUERCITOL(488-76-6)

Safety Data

• Hazardous Substances Data: 488-76-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(-)-VIBO-QUERCITOL is used as a therapeutic agent for its potential in treating various diseases, including cancer and diabetes, due to its antioxidant and anti-inflammatory properties.
Used in Research and Development:
(-)-VIBO-QUERCITOL is used as a subject of study for its potential applications in medicine, given its biological activity and the possibility of isolating it from natural sources or synthesizing it in laboratories.

InChI:InChI=1/C6H12O5/c7-2-1-3(8)5(10)6(11)4(2)9/h2-11H,1H2/t2-,3-,4-,5+,6+/m1/s1

Upstream product

• 97087-18-8 1D-3-deoxy-1,2:5,6-di-O-isopropylidene-4-O-methyl-myo-inositol 
• 152884-27-0 (1R,2R,3R,4S,5R)-1,2:3,4-di-O-cyclohexylidene-5-O-(methyl)cyclohexane-1,2,3,4,5-pentol 
• 863224-34-4 (+)-penta-O-acetyl-1-deoxy-myo-inositol 
• 6848-53-9 L-3,4:5.6-di-O-cyclohexylidene-2-O-methyl-(-)-chiro-inositol 
• 78963-40-3 2L-(2,4/3,5)-2,3,4,5-tetrahydroxycyclohexan-1-one 
• 18376-41-5 Acetic acid (1R,3R,4R,6R)-2,3,4,6-tetraacetoxy-cyclohexyl ester 
• 65173-65-1 (3aR,7aS)-2,2-dimethyl-3a,4,7,7a-tetrahydrobenzo-1,3-dioxole 
• 1165952-92-0 cyclohexa-1,4-diene 
• 406682-04-0 cis-cyclohex-4-ene-1,2-diol 
• 55990-89-1 (1α,2α,3β,4α,5α)-1,2:4,5-dianhydro-1,2,3,4,5-cyclohexane-pentol 
• 62776-30-1 1,2:4,5-cis-Dianhydrodesoxyinosit 
• 125477-54-5 conduritol A terabenzoate 
• 130824-35-0 proto-quercitol tetramethyl ether 
• 18376-41-5 DL-proto-quercitol pentaacetate 

Downstream Products

• 78147-99-6 (-)-1L-Cyclohexane-1,3/2,4-tetrol 
• 527-42-4 1-deoxy-scyllo-inositol 
• 148888-41-9 1D-6-O-benzyl-3-deoxy-1,2-O-isopropylidene-myo-inositol 
• 148888-40-8 1D-4-O-benzyl-3-deoxy-1,2-O-isopropylidene-myo-inositol 
• 148888-38-4 1D-4-O-benzyl-1,2:5,6-di-O-isopropylidene-3-deoxy-myo-inositol 
• 148888-39-5 1D-6-O-benzyl-1,2:4,5-di-O-isopropylidene-3-deoxy-myo-inositol 
• 132662-65-8 1D-4,5-di-O-benzoyl-6-O-benzyl-3-deoxy-1,2-O-isopropylidene-myo-inositol 
• 132662-66-9 1D-5,6-di-O-benzoyl-4-O-benzyl-3-deoxy-1,2-O-isopropylidene-myo-inositol 
• 17230-47-6 (-)-penta-O-benzoyl-ribo-quercitol 
• 229612-85-5 C₃₄H₂₈O₉ 
• 141-82-2 malonic acid 
• 78963-40-3 2L-(2,4/3,5)-2,3,4,5-tetrahydroxycyclohexan-1-one 
• 22144-52-1 (3S)-3r,4t,5c-trihydroxy-cyclohexane-1,2-dione-bis-phenylhydrazone 
• 1350889-90-5 C₁₂H₁₄O₇ 

Relevant articles and documents

1L-2,3:4,5-Bis-O-(tetraisopropyldisiloxane-1,3-diyl)-chiro-inositol: a useful intermediate for the preparation of several novel cyclitols

Keywords: Cyclitols, novel; Inositol, 1L-2,3:4,5-bis-O-(tetraisopropyldisiloxane-1,3-diyl)-chiro-

Identification and characterization of a novel (?)-vibo-quercitol 1-dehydrogenase from Burkholderia terrae suitable for production of (?)-vibo-quercitol from 2-deoxy-scyllo-inosose

(?)-vibo-Quercitol is a deoxyinositol (1l-1,2,4/3,5-cyclohexanepentol) that naturally occurs in oak species, honeydew honey, wines aged in oak barrels, and Gymnema sylvestre and is a potential intermediate for pharmaceuticals. We found that (?)-vibo-quercitol is stereoselectively synthesized from 2-deoxy-scyllo-inosose by the reductive reaction of a novel (?)-vibo-quercitol 1-dehydrogenase found in the proteomes of Burkholderia, Pseudomonas, and Arthrobacter. Among them, Burkholderia terrae sp. AKC-020 (40-1) produced a (?)-vibo-quercitol 1-dehydrogenase appropriate for synthesizing (?)-vibo-quercitol with a high diastereomeric excess. The enzyme was strongly induced in Bu. terrae cells when quercitol or 2-deoxy-scyllo-inosose was used as carbon source in the culture medium. The enzyme is NAD(H)-dependent and shows highly specific activity for (?)-vibo-quercitol and myo-inositol among the substrates tested. The enzyme gene (qudh) was obtained by PCR using degenerate primers based on the N-terminal and internal amino acid sequences of the purified enzyme, followed by thermal asymmetric interlaced PCR. The qudh gene showed homology with inositol 2-dehydrogenase (sharing 49.5% amino acid identity with IdhA from Sinorhizobium meliloti 1021). We successfully produced several recombinant (?)-vibo-quercitol 1-dehydrogenases and related enzymes identified by genome database mining using an Escherichia coli expression system. This revealed that scyllo-inositol dehydrogenase (IolX) in Bacillus subtilis can catalyze the reduction of 2-deoxy-scyllo-inosose to yield scyllo-quercitol, a stereoisomer of (?)-vibo-quercitol. Thus, we successfully identified two enzymes to produce both stereoisomers of deoxyinositols that are rare in nature.

Stereoselective syntheses of racemic quercitols and bromoquercitols starting from cyclohexa-1,4-diene: Gala-, epi-, muco-, and neo-quercitol

The efficient synthesis of gala-, epi-, neo-, and muco-quercitols and some brominated quercitols starting from cyclohexa-1,4-diene is reported. Treatment of the dibromide, obtained by the addition of bromine to cyclohexa-1,4-diene, with m-chloroperbenzoic

Epoxidation of protected (1,4,5)-cyclohex-2-ene-triols and their acid hydrolysis to synthesize quercitols from D-(-)-quinic acid

Highly stereoselective epoxidations have been achieved in both cyclohexylidene acetal and butane 2,3-bisacetal (BBA) protection of (1,4,5)-cyclohex-2-ene-triols. These epoxy derivatives are all derived from D-(-)-quinic acid and can be used for the synthe

An efficient and highly stereoselective synthesis of gala-Quercitol from 1,4-cyclohexadiene

gala-Quercitol was synthesized from 1,4-cyclohexadiene in seven steps and overall yield of 68%. Reaction of 5,6-dibromo-2,2-dimethylhexahydro-1,3-benzodioxole, synthesized from 1,4-cyclohexadiene in three steps, with excess NaOMe gave (3aα,5α,7aα)-5-metho

An Advantageous Synthesis of 1D- and 1L-1,2,3,5/4-Cyclohexanepentol

The title compounds D-10 and L-10 were prepared from 1 in eight steps and in a combined overall yield of 41-49%.

A concise and convenient synthesis of DL-proto-quercitol and DL-gala-quercitol via ene reaction of singlet oxygen combined with [2 + 4] cycloaddition to cyclohexadiene

Photooxygenation of 1,4-cyclohexadiene afforded hydroperoxy endoperoxides 3 and 4 in a ratio of 88:12. Reduction of 3 with LiAlH4 or thiourea followed by acetylation of the hydroxyl group and KMnO4 oxidation of the double bond gave proto-quercitol 10b. Application of the same reaction sequences to 4 resulted in the formation of gala-quercitol 14. Quercitols were easily obtained by ammonolysis of acetate derivatives in MeOH. The outcome of dihydroxylation reactions were supported by conformational analysis.

A novel synthesis of DL-proto-, and DL-vibo- quercitol via 1,4- cyclohexadiene

Photooxygenation of 1,4-cyclohexadiene 3 followed by reduction with LiAIH4 or thiourea gave (25/1)-cyclohex-3-ene-triol 7a. trans-Hydroxylation of triol 7a with three different methods afforded both of proto-quercitol 1a and vibo-quercitol 2a.

Synthesis and evaluation of 3-modified 1D-myo-inositols as inhibitors and substrates of phosphatidylinositol synthase and inhibitors of myo-inositol uptake by cells

A number of 3-substituted 1D-myo-inositols were synthesized and evaluated as substrates for phosphatidylinositol synthase and uptake by intact cells. 1D-3-Amino-, -3-chloro-, and -3-(acetylthio)-3-deoxy-myo-inositols were all synthesized by nucleophilic d