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HomeProduct name listcis-4-Hydroxycyclohexanecarboxylic acid

cis-4-Hydroxycyclohexanecarboxylic acid

cis-4-Hydroxycyclohexanecarboxylic acid Structural

What is cis-4-Hydroxycyclohexanecarboxylic acid?

Chemical properties

White to Almost white powder to crystal. Melting point: 148.0 to 152.0 °C.

The Uses of cis-4-Hydroxycyclohexanecarboxylic acid

Cis-4-Hydroxycyclohexanecarboxylic acid is a metabolite of p-hydroxybenzoic acid. It is the major metabolite in the urine of rats treated with exogenous p-hydroxybenzoic acid. It has been found to have immunosuppressive activities in rat hepatocytes, as well as metabolic disorders that are related to hyperglycemia or diabetes mellitus.

Definition

ChEBI: 4-Hydroxycyclohexylcarboxylic acid is a hydroxy monocarboxylic acid.

Synthesis

cis-4-Hydroxycyclohexanecarboxylic acid can be synthesized through the following steps:
1. In an argon glove box, dissolve ligands L1-(S,R)-f-ambinol (7.5mg, 0.0105mmol) and [Ir(COD)Cl]2 (3.4mg, 0.005mmol) in 1 mL of iPrOH in a 2mL vial and stir at room temperature for 2 h.
2. Put 1 mmol of raw material 4-substituted cyclohexanone into a 4 mL hydrogenation flask.
3. Add 0.1 mL of the in-situ complexed catalyst solution and 1.6 mg of tBuOLi solid powder to the hydrogenation flask.
4. Add 1 mL of EtOH to dissolve the reactants in the hydrogenation flask.
5. Put the reaction flask into the hydrogenation kettle and replace the kettle body with hydrogen three times.
6. Fill the kettle with 5bar H2 and react at room temperature for 12h.
7. After the reaction is completed, carefully release the hydrogen and spin-dry the solvent under reduced pressure.
8. Purify the hydrogenated product cis-4-substituted cyclohexanol by silica gel column.
9. Obtain the final product cis-4-Hydroxycyclohexanecarboxylic acid.

Properties of cis-4-Hydroxycyclohexanecarboxylic acid

Melting point: 150°C
Boiling point: 115 °C(Press: 8 Torr)
Density  1.246
storage temp.  2-8°C
solubility  almost transparency in Methanol
form  powder to crystal
pka pK1:4.836 (25°C)
color  White to Almost white
InChI InChI=1S/C7H12O3/c8-6-3-1-5(2-4-6)7(9)10/h5-6,8H,1-4H2,(H,9,10)/t5-,6+
CAS DataBase Reference 3685-22-1

Safety information for cis-4-Hydroxycyclohexanecarboxylic acid

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.

Computed Descriptors for cis-4-Hydroxycyclohexanecarboxylic acid

InChIKey HCFRWBBJISAZNK-OLQVQODUSA-N
SMILES [C@@H]1(C(O)=O)CC[C@H](O)CC1

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