6286-43-7

Usage

Uses

Used in Pharmaceutical Industry:
1,2,3-Cyclohexanetriol is used as an active pharmaceutical ingredient or an excipient for its versatile properties, contributing to the formulation and effectiveness of various medications.
Used in Fragrance Industry:
1,2,3-Cyclohexanetriol is used as a fragrance ingredient due to its ability to enhance or modify the scent profiles of different perfumes and scented products.
Used in Organic Synthesis:
1,2,3-Cyclohexanetriol is used as a building block in organic chemistry for the preparation of complex compounds, taking advantage of its multiple hydroxyl groups for further reactions and functionalization.
Used in Resin and Plastics Production:
1,2,3-Cyclohexanetriol is used as a component in the synthesis of resins and plastics, leveraging its polyol nature to improve material properties such as flexibility, durability, and stability.
Safety Precautions:
It is important to handle 1,2,3-Cyclohexanetriol with care, as it can be harmful if ingested or inhaled, and may cause irritation to the skin and eyes. Proper safety measures, including the use of personal protective equipment and adherence to material safety data sheets, should be followed during its use in various applications.

InChI:InChI=1/C6H12O3/c7-4-2-1-3-5(8)6(4)9/h4-9H,1-3H2

Upstream product

• 87-66-1 2-hydroxyresorcinol 
• 64-17-5 ethanol 
• 7732-18-5 water 
• 4845-05-0 cyclohex-2-enyl hydroperoxide 
• 7664-93-9 sulfuric acid 
• 930-68-7 cyclohexenone 
• 822-67-3 Cyclohex-2-enol 
• 2699-13-0 3-methoxycyclohexene 
• 4337-36-4 2,3-dihydroxy-cyclohex-2-enone 
• 110-83-8 cyclohexene 
• 124-38-9 carbon dioxide 
• 90399-57-8 C₁₂H₁₄O₆ 
• 1192-78-5 2,3-epoxycyclohexanol 
• 93-59-4 Perbenzoic acid 

Downstream Products

• 20021-58-3 rac-cyclohexane-1,2,3-triyl triacetate 
• 62365-17-7 cyclohexane-1,2,3-triol triacetate 
• 60793-36-4 trans-2,3-dihydroxycyclohexan-1-one 
• 60793-36-4 (+/-)-(2S,3S)-2,3-dihydroxycyclohexanone 

Relevant academic research and scientific papers

Molybdenum-catalyzed diastereoselective anti-dihydroxylation of secondary allylic alcohols

In this protocol, we report a Mo-catalyzed anti-dihydroxylation of secondary allylic alcohols, providing a general method for the preparation of 1,2,3-triols bearing up to three continuous stereocenters with excellent diastereocontrol. The mechanistic studies reveal that this dihydroxylation reaction consists of two steps and up to excellent diastereomeric ratios of the final triol products can be achieved due to the high level of both diastereocontrol in the initial epoxidation and regiocontrol in the following hydrolysis in situ.

Cyclotriol derivative and production method and application thereof

The invention discloses a cyclotriol derivative and a production method and application thereof. The cyclotriol derivative is of a structure as shown in a general formula I, wherein R1, R2 and R3 areOH or AcNH; R1=OH, and R2=R3=AcNH or R2=OH, and R1=R3=AcNH or R3=OH, and R1=R2=AcNH; * stands for R configuration or S configuration; and Ac stands for caffeoyl CAc or derivatives caffesulfonyl SAc and caffe(mono-methyl ester)phosphonyl PAc of the caffeoyl CAc. According to the production method of the cyclotriol derivative, conditions are mild, automatic and industrial production are easy to achieve, operation is simple, convenient and safe, and the obtained cyclotriol derivative can act on anti-respiratory syncytial virus F protein, has high anti-RSV activity, low cell toxicity and high stability, can be used for producing medicines for treating virus infection, and is especially used for producing medicines for treating respiratory syncytial virus infection.

Molybdenum-Catalyzed Hydroxyl-Directed Anti-Dihydroxylation of Allylic and Homoallylic Alcohols

A catalytic hydroxyl-directed anti-dihydroxylation of allylic and homoallylic alcohols has been developed. This operationally simple method was successfully applied to the direct anti-monodihydroxylation of allylic alcohols containing at least one distal olefinic unit. Under the catalysis of commercially available MoO2(acac)2, an array of hydroxylated dienes were successfully converted into various 1,2,3-triols using hydrogen peroxide as an environmentally benign oxidant under aerobic conditions, notably, in complete regioselectivities and in the most cases in diastereospecific pathway.

One-pot synthesis of 1,2/3-triols from the allylic hydroperoxides catalyzed by zeolite-confined osmium(0) nanoclusters

A facile, efficient and eco-friendly method for the one-pot synthesis of 1,2/3-triols from the allylic hydroperoxides were developed by using zeolite-confined osmium(0) nanoclusters as reusable catalyst and without using any co-oxidant (H2Osub

One-pot synthesis of 1,2,3-triols from allylic hydroperoxides and a catalytic amount of OsO4 in aqueous acetone

Allylic hydroperoxides were converted into the corresponding triols in the presence of a catalytic amount of OsO4. The present reaction involves regeneration of active osmium species by the hydroperoxide functionality and occurs in a diastereoselective manner to form triols in high yields. A plausible mechanism for the formation of 1,2,3-triols from allylic hydroperoxide is presented.

Directed dihydroxylation of cyclic allylic alcohols and trichloroacetamides using OsO4/TMEDA

The oxidation of a range of cyclic allylic alcohols and amides with OsO4/TMEDA is presented. Under these conditions, hydrogen bonding control leads to the (contrasteric) formation of the syn isomer in almost every example that was examined. Evidence for the bidentate binding of TMEDA to OsO4 is presented and a plausible mechanism described.

Synthesis of α-trinositol related analogues. Structure-activity (analgesic and anti-inflammatory) relationships

α-Trinositol analogues, including methyl ethers, deoxy, oxa and aza derivatives were prepared. The parent compound possesses weak analgesic and anti-inflammatory properties. Removal of the non-phosphorylated hydroxyls generates a compound devoid of analgesic activity but which retains the anti-inflammatory property of the parent compound. The protection of these hydroxyls as methyl ethers lends to compounds which keep their anti-inflammatory activity, whereas the replacement of the cyclohexane carbone backbone by a tetrahydropyrane or a piperidine ring leads to compounds which increase the pain.

Optically active phenoxypropionic esters

Optically active compounds of the formula I STR1 where R is C1 -C12 -alkyl or -perfluoroalkyl in which one or two non-adjacent CH2 or CF2 groups can also be replaced by --O-- and/or --CO-- and/or --CO--O-- and/or --CH=CH-- and/or --CH-halogen-- and/or --CHCN-- and/or --0--CO--CH-halogen-- and/or --O--CO--CHCN--, or is C1 -C12 -alkyl which can have a terminal chemically reactive group and in which a CH2 group can be replaced by --O--, A1 and A2 are each, independently of one another, 1,4-phenylene which is unsubstituted or substituted by one or two F and/or Cl and/or Br atoms and/or CH3 groups and/or CN groups and in which one or two CH groups can also be replaced by N, 1,4-cyclohexylene in which one or two non-adjacent CH2 groups can also be replaced by --O-- and/or --S--, 1,4-piperidinediyl, 1,4-bicyclo[2.2.2]octylene, 2,6-naphthalenediyl, decahydro-2,6-naphthalenediyl or 1,2,3,4-tetrahydro-2,6-naphthalenediyl, A3 is unsubstituted or substituted phenyl, Z is --CO--O--, --O--CO--, --CH2 CH2 --, --OCH2 --, --CH2 O--, --C C-- or a single bond and m is 0, 1, 2 or 3.

THE SYNTHESIS OF CHIRAL ISOPROPYLIDENE DERIVATIVES OF 1,2,3-CYCLOHEXANETRIOLS BY ENZYMATIC DIFFERENTIATION

2,3-O-Isopropylidene-1-cyclohexanol chiral building blocks have been prepared with high enantiomeric purities by enzymatic hydrolysis of their racemic acetates or n.butyrates.