488-73-3

Basic information

• Product Name: (+)-PROTO-QUERCITOL
• Synonyms: (+)-PROTO-QUERCITOL;1L-1,3,4/2,5-CYCLOHEXANEPENTOL;D-chiro-Inositol, 2-deoxy-;CYCLOHEXANE-1,2,3,4,5-PENTOL;(+)-proto-Quericitol;1-L-1,3/2,5-Cyclohexanepentol;Acorn sugar;D-Quercitol
• CAS NO: 488-73-3
• Molecular Formula: C₆H₁₂O₅
• Molecular Weight: 164.16
• Product Categories: Biochemistry;Sugars
• Mol File: 488-73-3.mol
• Article Data: 14

Chemical Properties

• Melting Point: 237 °C
• Boiling Point: 211.61°C (rough estimate)
• Flash Point: 146.2oC
• Appearance: /
• Density: 1.5845
• Vapor Pressure: 0.00018mmHg at 25°C
• Refractive Index: 1.4230 (estimate)
• Storage Temp.: Freezer
• PKA: 13.42±0.70(Predicted)
• Water Solubility: 110g/L(20 oC)
• Merck: 14,8036
• CAS DataBase Reference: (+)-PROTO-QUERCITOL(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-PROTO-QUERCITOL(488-73-3)
• EPA Substance Registry System: (+)-PROTO-QUERCITOL(488-73-3)

Safety Data

• Hazardous Substances Data: 488-73-3(Hazardous Substances Data)

Usage

General Description

(+)-Proto-quercitol, also known as quinic acid, is an organic compound, naturally present in many plants, including fruits, vegetables, and grains. It is a cyclohexanecarboxylic acid derived from cyclitol, a sugar alcohol. It is particularly known for being an essential precursor in the biosynthesis of aromatic compounds in plants. It is non-toxic, has antioxidant properties, and is used in food and drinks as a flavoring agent. In pharmaceutical industries, it is used in the production of hydroquinone, a common ingredient in various skin-lightening products.

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

• 909878-64-4 meso-erythritol 
• 87-69-4 L-Tartaric acid 
• 866334-21-6 C₁₆H₂₂O₆ 
• 18376-41-5 Acetic acid (1R,3R,4R,6R)-2,3,4,6-tetraacetoxy-cyclohexyl ester 
• 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 
• 18376-41-5 DL-gala-quercitol pentaacetate 
• 81562-21-2 DL-1,2:3,4-di-O-cyclohexylidene-6-O-methylthiomethyl-epi-inositol 
• 60504-84-9 DL-1-O-benzoyl-2,3:4,5-di-O-cyclohexylidene-6-O-methylthiomethyl-epi-enositol 
• 34361-62-1 1-O-benzoyl-2,3:4,5-di-O-cyclohexylidene-epi-enositol 
• 130824-35-0 proto-quercitol tetramethyl ether 
• 1165952-92-0 cyclohexa-1,4-diene 
• 72598-62-0 2-bromo-7-oxabicyclo<4.1.0>hept-3-ene 

Downstream Products

• 33012-71-4 D-xylo-3-deoxy-hexaric acid 
• 488-31-3 L-arabinaric acid 
• 526-99-8 meso-galactaric acid 
• 144-62-7 oxalic acid 
• 141-82-2 malonic acid 
• 124-38-9 carbon dioxide 
• 106-51-4 p-benzoquinone 
• 123-31-9 hydroquinone 
• 71-43-2 benzene 
• 108-95-2 phenol 
• 7732-18-5 water 

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

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.

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