3-Hydroxyadamantane-1-acetic acid Chemical Properties

Melting point:

125-129 °C

Boiling point:

375.3±15.0 °C(Predicted)

Density 

1.329

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystaline

pka

4.72±0.10(Predicted)

color 

White to Almost white

InChI

InChI=1S/C12H18O3/c13-10(14)6-11-2-8-1-9(3-11)5-12(15,4-8)7-11/h8-9,15H,1-7H2,(H,13,14)

InChIKey

JFMDWSCOQLUOCZ-UHFFFAOYSA-N

SMILES

C12(CC(O)=O)CC3CC(CC(O)(C3)C1)C2

CAS DataBase Reference

17768-36-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29162090

Storage Class

11 - Combustible Solids

3-Hydroxyadamantane-1-acetic acid Usage And Synthesis

Chemical Properties

Light yellow powder

Uses

3-Hydroxyadamantane-1-acetic acid is a derivative of adamantane. Its crystal structure has been analyzed through X-ray diffraction, revealing stabilization through intermolecular O-H...O hydrogen bonds that form a chain. The application of adamantane and its derivatives is widespread in medicine. For example, adamantaneamine has demonstrated efficacy in inhibiting influenza A virus exuviation and in easing Parkinsonian symptoms (Lu et al., 1996).

Synthesis

General procedure for the synthesis of 3-hydroxy-1-adamantaneacetic acid from 1-adamantaneacetic acid: adamantanecarboxylic acid (1a-1s, 3.5 g) was added in batches to a mixture comprising 2.5-3 or 7 equivalents of MnO2 and 2.5-14 mL of 93% H2SO4, pre-cooled to -30 °C, with the reaction maintained at a temperature of less than 25 °C, under vigorous stirring. The reaction mixture was maintained at this temperature for 0.5-24 hours and subsequently treated with cold water under ice bath cooling. The precipitate was collected by filtration and washed with a small amount of water and butan-1-ol. The product was extracted with butan-1-ol (5 x 2 mL). For the isolation of the products 2j-21 and 2q-2s, it was necessary to adjust the mixture to pH 3-4 with 30% aqueous sodium hydroxide solution prior to extraction. all organic phases were combined, washed sequentially with water, sodium bicarbonate solution, and water, and then dried by azeotropic distillation. Finally, the solvent was removed under reduced pressure on a rotary evaporator and the target product 3-hydroxy-1-adamantaneacetic acid was purified by recrystallization.

References

[1] Russian Journal of Organic Chemistry, 2016, vol. 52, # 6, p. 785 - 790
[2] Zh. Org. Khim., 2016, vol. 52, # 6, p. 800 - 805,6
[3] Chemische Berichte, 1968, vol. 101, p. 564 - 573
[4] Russian Journal of Organic Chemistry, 2017, vol. 53, # 7, p. 971 - 976

3-Hydroxyadamantane-1-acetic acid(17768-36-4)Related Product Information

• TARTRONIC ACID
• Acetic acid
• Adamantane
• 4-HYDROXYPHENOXYACETIC ACID
• 3-Hydroxy-1-AdaMantane Carboxylic Acid
• CYCLOOCTANOL
• 3-Hydroxyadamantane-1-acetic acid
• AKOS BB-9052
• 1-METHYLCYCLOOCTANOL