131435-06-8

Basic information

• Product Name: (+)-EPI-QUERCITOL
• Synonyms: (+)-EPI-QUERCITOL;1D-1,2,3,5/4-CYCLOHEXANEPENTOL;(+)-epi-Quercitol
• CAS NO: 131435-06-8
• Molecular Formula: C₆H₁₂O₅
• Molecular Weight: 164.16
• Product Categories: Biochemistry;Sugars
• Mol File: 131435-06-8.mol

Chemical Properties

• Melting Point: 192.0 to 197.0 °C
• Boiling Point: 293.641oC at 760 mmHg
• Flash Point: 146.216oC
• Appearance: /
• Density: 1.796g/cm3
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.708
• Storage Temp.: Freezer
• CAS DataBase Reference: (+)-EPI-QUERCITOL(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-EPI-QUERCITOL(131435-06-8)
• EPA Substance Registry System: (+)-EPI-QUERCITOL(131435-06-8)

Safety Data

• Hazardous Substances Data: 131435-06-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
(+)-EPI-QUERCITOL is utilized as a subject of interest in pharmaceutical research and development due to its unique chemical properties and potential therapeutic applications. Its presence in natural sources and plants makes it a valuable compound for exploring new avenues in medicine and healthcare.
Used in the Study of Natural Products and Biological Activities:
(+)-EPI-QUERCITOL serves as a key component in the study of natural products and their biological activities. Its multiple hydroxyl groups and specific chemical structure contribute to its potential role in various scientific and technological applications, warranting further research to uncover its full range of benefits and uses.

InChI:InChI=1/C6H12O5/c7-2-1-3(8)5(10)6(11)4(2)9/h2-11H,1H2/t2-,3+,4-,5-,6-/m0/s1

Upstream product

• 125477-54-5 conduritol A terabenzoate 
• 18376-41-5 DL-proto-quercitol pentaacetate 
• 18376-41-5 DL-gala-quercitol pentaacetate 
• 608-80-0 benzenehexol 
• 18376-41-5 rac-(1R,2S,3R,4S,5S)-cyclohexane-1,2,3,4,5-pentayl pentaacetate 
• 81562-21-2 DL-1,2:3,4-di-O-cyclohexylidene-6-O-methylthiomethyl-epi-inositol 
• 130824-35-0 proto-quercitol tetramethyl ether 
• 62776-30-1 1,2:4,5-cis-Dianhydrodesoxyinosit 
• 55990-89-1 (1α,2α,3β,4α,5α)-1,2:4,5-dianhydro-1,2,3,4,5-cyclohexane-pentol 
• 406682-04-0 cis-cyclohex-4-ene-1,2-diol 
• 1165952-92-0 cyclohexa-1,4-diene 
• 65173-65-1 (3aR,7aS)-2,2-dimethyl-3a,4,7,7a-tetrahydrobenzo-1,3-dioxole 
• 18376-41-5 Acetic acid (1R,3R,4R,6R)-2,3,4,6-tetraacetoxy-cyclohexyl ester 
• 229612-81-1 1,2:3,4-di-O-isopropylidene-5S-(+)-proto-quercitol 

Downstream Products

• 18376-41-5 rac-(1R,2S,3R,4S,5S)-cyclohexane-1,2,3,4,5-pentayl pentaacetate 
• 20021-56-1 DL-(1,3/2,4)-1,2,3,4-Tetra-O-acetylcyclohexanetetrol 
• 6216-28-0 DL-(1,3,5/2,4)-1-Acetamido-2,3,4,5-tetra-O-acetylcyclohexanetetrol 
• 2975-92-0 (+/-)-1L-cyclohexane-1,3/2,4-tetrol 
• 22144-52-1 (+/-)-3r,4t,5c-trihydroxy-cyclohexane-1,2-dione-bis-phenylhydrazone 
• 18376-41-5 Acetic acid (1R,3R,4R,6R)-2,3,4,6-tetraacetoxy-cyclohexyl ester 
• 415726-95-3 3-(acetamidomethyl)-6-deoxy-D-myo-inositol 
• 415726-97-5 1-(acetamidomethyl)-2-deoxy-D-chiro-inositol 
• 415726-94-2 2-(acetamidomethyl)-3-deoxy-L-neo-inositol 

Relevant articles and documents

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

(+)-proto-Quercitol, a natural versatile chiral building block for the synthesis of the α-glucosidase inhibitors, 5-amino-1,2,3,4-cyclohexanetetrols

An efficient synthesis of diastereomerically pure 5-amino-1,2,3,4-cyclohexanetetrols (6 and 11) and quercitol derivatives from naturally available (+)-proto-quercitol (1) is described. The stereochemistry of 1 is perfectly set up for regioselective protec

Highly stereoselective and stereospecific syntheses of a variety of quercitols from d-(-)-quinic acid

The highly stereoselective synthesis of (-)-epi-, (-)-allo- and neo-quercitols as well as stereospecific synthesis of (-)-talo- and (+)-gala-quercitols have been achieved. The general strategy is employing dihydroxylation of the isolated double bond of various kinds of protected chiral (1,4,5)-cyclohex-2-ene-triols, which are derived from d-(-)-quinic acid. The choosing of protecting groups from either BBA (butane 2,3-bisacetal) or acetyl groups will result in the various degrees of stereoselectivity of dihydroxylation. On the other hand, the cyclohexylidene acetal moiety is attributed to the stereospecificity during dihydroxylation to afford the request molecules.

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

Synthesis of the enantiomers of 6-deoxy-myo-inositol 1,3,4,5-Tetrakisphosphate, structural analogues of myo-inositol 1,3,4,5-Tetrakisphosphate

D-myo-Inositol 1,3,4,5-tetrakisphosphate [Ins(1,3,4,5)P4] is produced rapidly from the established second messenger D-myo-inositol 1,4,5trisphosphate [Ins(1,4,5)P4] in stimulated cells. Despite extensive investigations, in particular

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.

Stereoselective synthesis of 6-deoxy and 3,6-dideoxy-D-myo-inositol precursors of deoxy-myo-inositol phosphate analogues from D-galactose

The synthesis of chiral protected D-6-deoxy-myo-inositol derivatives from D-galactose is described. Ferrier rearrangement of hexenogalactopyranosides has been employed to produce the corresponding 6- deoxy-cyclohexanone polyols. The stereoselectivity of the carbocyclic transformation was discussed on the basis of the experimental data and a mechanism has been proposed. From deoxy-inososes, the access to a variety of 6-deoxy and 3,6-dideoxy-myo-inositol was performed to prepare suitable monool, diol and triol precursors for the synthesis of D-deoxy-myo-inositol phosphate analogues.

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.