Identification | More | [Name]
(3-HYDROXY-ADAMANTAN-1-YL)-ACETIC ACID | [CAS]
17768-36-4 | [Synonyms]
(3-HYDROXY-1-ADAMANTYL)ACETIC ACID (3-HYDROXY-ADAMANTAN-1-YL)-ACETIC ACID 3-HYDROXYADAMANTANE-1-ACETIC ACID AKOS BC-0174 CHEMBRDG-BB 4013907 IFLAB-BB F3052-0016 LABOTEST-BB LT00077093 (3-Hydroxyadamantanyl)acetic acid | [Molecular Formula]
C12H18O3 | [MDL Number]
MFCD00167797 | [Molecular Weight]
210.27 | [MOL File]
17768-36-4.mol |
Chemical Properties | Back Directory | [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) |
Hazard Information | Back Directory | [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] Chemische Berichte, 1968, vol. 101, p. 564 - 573 [5] Russian Journal of Organic Chemistry, 2017, vol. 53, # 7, p. 971 - 976 |
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