cis-4-Hydroxycyclohexanecarboxylic acid Chemical Properties

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+

InChIKey

HCFRWBBJISAZNK-OLQVQODUSA-N

SMILES

[C@@H]1(C(O)=O)CC[C@H](O)CC1

CAS DataBase Reference

3685-22-1

Safety Information

Hazard Codes 

T

Risk Statements 

36/37/38-25

Safety Statements 

26-36/37/39-45

RIDADR 

UN 2811 6.1 / PGIII

HS Code 

2918199890

cis-4-Hydroxycyclohexanecarboxylic acid Usage And Synthesis

Chemical Properties

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

Uses

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.

cis-4-Hydroxycyclohexanecarboxylic acid(3685-22-1)Related Product Information

• CIS-4-CYCLOHEXENE-1,2-DICARBOXYLIC ACID
• H-CIS-HYP-OME HCL
• cis-4-Hydroxy-D-proline
• cis-4-Hydroxy-L-proline
• Cyclohexanecarboxylic acid, 4-hydroxy-, Methyl ester, cis-
• CIS-3-AMINOCYCLOHEXANECARBOXYLICACID
• Bicyclo[1.1.1]pentane-1,3-dicarboxylic acid, MonoMethyl ester
• Tetrahydro-5-oxo-2- furancarboxyli
• 4-Hydroxycyclohexanecarboxylic acid
• ETHYL 4-HYDROXYCYCLOHEXANECARBOXYLATE
• 1-AMINO-4-OXOCYCLOHEXANECARBOXYLIC ACID ETHYLENE KETAL
• METHYL 4-HYDROXYCYCLOHEXANECARBOXYLATE
• 4-METHOXYCYCLOHEXANECARBOXYLIC ACID
• cis-4-Hydroxycyclohexanecarboxylic acid
• PICROTIN
• ethyl 1,4-dioxaspiro[4.5]decane-8-carboxylate
• TRANS-4-HYDROXYCYCLOHEXANECARBOXYLIC ACID
• 8-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-1,4-DIOXA-SPIRO[4.5]DECANE-8-CARBOXYLIC ACID