488-73-3

Usage

Uses

Used in Food and Beverage Industry:
(+)-PROTO-QUERCITOL is used as a flavoring agent for its natural presence in many plants and its ability to enhance the taste of food and drinks.
Used in Pharmaceutical Industry:
(+)-PROTO-QUERCITOL is used as a precursor in the production of hydroquinone, which is a common ingredient in various skin-lightening products, due to its non-toxic nature and its role in the biosynthesis of aromatic compounds.

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

Upstream product

• 91432-03-0 5-O-galloyl-3,4-(S)-hexahydroxydiphenoyl proto-quercitol 
• 909878-64-4 meso-erythritol 
• 87-69-4 L-Tartaric acid 
• 64-17-5 ethanol 
• 745809-25-0 Acetic acid (3aR,5R,7aS)-2-oxo-3a,4,5,7a-tetrahydro-2λ⁴-benzo[1,3,2]dioxathiol-5-yl ester 
• 1165952-92-0 cyclohexa-1,4-diene 
• 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 
• 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

• 488-31-3 L-arabinaric acid 
• 526-99-8 meso-galactaric acid 
• 33012-71-4 D-xylo-3-deoxy-hexaric acid 
• 141-82-2 malonic acid 
• 130633-22-6 (2R)-O³,O⁴-isopropylidene-1-deoxy-muco-inositol 
• 123-31-9 hydroquinone 
• 106-34-3 quinhydrone 
• 106-51-4 p-benzoquinone 
• 876509-24-9 1,2,3,4,5-pentaacetoxy-cyclohexane 
• 22412-50-6 (+)-penta-O-benzoyl-proto-quercitol 
• 22144-52-1 (3S)-3r,4t,5c-trihydroxy-cyclohexane-1,2-dione-bis-phenylhydrazone 
• 144-62-7 oxalic acid 
• 124-38-9 carbon dioxide 
• 71-43-2 benzene 

Relevant academic research and scientific papers

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

Stereoselective syntheses of (+)-proto, (-)-gala quercitols and carba-l-rhamnose from d-(-)-quinic acid

Efficient syntheses of (+)-proto, (-)-gala quercitols and carba-l-rhamnose from d-(-)-quinic acid are described.

Resolution of (±)-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol via Candida cylindracea lipase: Synthesis of (-)- and (+)-proto-quercitol

Photooxygenation of cyclohexa-1,4-diene afforded anti-2,3-dioxabicyclo[2.2. 2]oct-7-en-5-yl hydroperoxide. The hydroperoxy endoperoxide was reduced with dimethylsulfide-titanium tetraisopropoxide to produce (±)-anti-2,3- dioxabicyclo[2.2.2]oct-7-en-5-ol. The highly efficient enantioselective resolution of the racemic (±)-anti-2,3-dioxabicyclo[2.2.2]oct-7-en-5-ol was accomplished with Candida cylindracea lipase (CCL) to produce the enantiomerically enriched alcohol and the corresponding acetate: The cleavage of the peroxide linkage by thiourea followed by the oxidation of the double bond with OsO4 resulted in the formation of (-)-proto-quercitol and (+)-proto-quercitol, respectively.

A facile synthesis of a new trihydroxy piperidine derivative and (+)-proto-quercitol from D-(-)-quinic acid

We described herein the new synthesis of a trihydroxy piperidine derivative (1,4,5-trideoxy-1,5-imino-D-ribo-hexitol) and (+)-proto-quercitol from D-(-)-quinic acid, both are considered as inhibitors for glycosidases.

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 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.

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 Stereocontrolled Synthesis of proto-Quercitol

Conduritol A tetramethyl ether (2) has been converted by hydroboration-oxidation into proto-quercitol tetramethyl ether (5) which on demethylation afforded a mixture (2:1) of proto-quercitol (4) and vibo-quercitol (11). proto-Quecitol was also obtained (15percent) from conduritol A tetrabenzoate (3) by a similar sequence.