488-58-4

Basic information

• Product Name: EPI-INOSITOL
• Synonyms: EPI-INOSITOL;Inositol, epi-;L-epi-Inositol;epi-Cyclohexanehexol;(1R,2R,3R,4S,5S,6s)
• CAS NO: 488-58-4
• Molecular Formula: C6H12O6
• Molecular Weight: 180.16
• EINECS: 207-682-0
• Product Categories: Biochemistry;Sugars;Vitamin Related Compounds;Vitamins
• Mol File: 488-58-4.mol
• Article Data: 18

Chemical Properties

• Melting Point: 304°C(dec.)(lit.)
• Boiling Point: 291.3°Cat760mmHg
• Flash Point: 143.4°C
• Appearance: /
• Density: 2.038g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.784
• PKA: 12.63±0.70(Predicted)
• CAS DataBase Reference: EPI-INOSITOL(CAS DataBase Reference)
• NIST Chemistry Reference: EPI-INOSITOL(488-58-4)
• EPA Substance Registry System: EPI-INOSITOL(488-58-4)

Safety Data

• Hazardous Substances Data: 488-58-4(Hazardous Substances Data)

Usage

Uses

epi-Inositol is a stereoisomer of Inositol (I666000). Studies show that epi-inositol effectively prevented lithium-pilocarpine seizures following chronic lithium.

InChI:InChI=1/C6H12O6/c7-1-2(8)4(10)6(12)5(11)3(1)9/h1-12H/t1-,2-,3-,4+,5-,6+

Upstream product

• 81562-21-2 DL-1,2:3,4-di-O-cyclohexylidene-6-O-methylthiomethyl-epi-inositol 
• 7664-93-9 sulfuric acid 
• 1195579-55-5 5,6-anhydro-allo-inositol 
• 20108-71-8 hexa-O-acetyl-epi-inositol 
• 38643-29-7 (+/-)-O¹,O²;O³,O⁴;O⁵,O⁶-triisopropylidene-epi-inositol 
• 60802-59-7 (2R,3R,4S,5S,6S)-2,3,4,5,6-Pentahydroxy-cyclohexanone 
• 283586-00-5 1D-2,6-di-O-benzyl-epi-inositol 
• 64-17-5 ethanol 
• 608-80-0 benzenehexol 
• 1004791-97-2 C₁₀H₁₈O₆ 
• 554433-80-6 2,3,4,5-tetra-O-methyl-D-mannitol 
• 1607827-99-5 C₃₄H₃₆O₆ 
• 1607827-86-0 (2S,3S,4R,5R,6R)-6-hydroxy-2,3,4,5-tetramethoxycyclohexanone 
• 488-73-3 (+)-proto-quercitol 

Downstream Products

• 33471-33-9 1L-epi-2-inosose 
• 38643-30-0 (+/-)-O¹,O²;O³,O⁴-diisopropylidene-epi-inositol 
• 2671-07-0 (+/-)-1r,2c,3c,4c,5t-pentaacetoxy-6t-bromo-cyclohexane 
• 849670-29-7 hexa-O-benzoyl-myo-inositol 
• 89826-95-9 hexa-O-benzoyl-epi-inositol 
• 122596-73-0 (+/-)-O¹,O²;O³,O⁴-diisopropylidene-O⁵,O⁶-bis-(4-nitro-benzenesulfonyl)-epi-inositol 
• 4782-75-6 conduritol D 
• 488-66-4 (2R)-2r,3c,4t,5c,6t-pentahydroxy-cyclohexanone 
• 4099-90-5 myo-inositol hexabenzoate 
• 20108-71-8 hexa-O-acetyl-epi-inositol 
• 551-72-4 inositol 

Relevant articles and documents

Synthesis of allo - And epi -inositol via the NHC-catalyzed carbocyclization of carbohydrate-derived dialdehydes

A synthesis of carbocyclic sugars from carbohydrate-derived dialdehydes using organocatalysis has been developed. Sorbitol, mannitol, and galactitol were converted via 1,6-tritylation, perbenzylation or permethylation, detritylation, and Swern oxidation into 2,3,4,5-tetra-O-alkyl-dialdoses that were cyclized via the benzoin reaction promoted by a triazolium carbene. Manno- and galacto-configured dialdehydes gave predominantly single inosose stereoisomers in up to 75% yield if the mixture was acetylated prior to isolation while the gluco-dialdehyde afforded a mixture of three stereoisomers in 61% overall yield. The inososes were stereospecifically reduced using sodium borohydride and then deprotected to give allo- and epi-inositol in good yield that confirmed the structural and stereochemical assignments.

Protecting group directed stereoselective reduction of an epi-inosose: Efficient synthesis of epi-inositol

A facile and high yielding synthesis of epi-inositol via stereoselective reduction of a pentaprotected epi-inosose is reported. Extent of stereoselectivity during the hydride reduction appears to depend on the ability of the substrate to complex with metal ions in the reducing agent.

Concise chemoenzymatic synthesis of epi-inositol

epi-Inositol was synthesized in six steps in 40% overall yield from a bacterial bromobenzene metabolite. The chemoenzymatic route involved toluene dioxygenase oxidation, substrate-directed catalytic osmylation, m-CPBA epoxidation, radical debromination, and Amberlite-catalized hydrolysis. The route described is amenable to scaleup and could allow access to cis-inositol, and deoxy derivatives of epi-inositol.