| Identification | More | [Name]
3-HYDROXYADAMANTANE-1-CARBOXYLIC ACID | [CAS]
42711-75-1 | [Synonyms]
1-HYDROXYADAMANTANE-3-CARBOXYLIC ACID
3-HYDROXYADAMANTANCARBOXYLIC ACID
3-HYDROXYADAMANTANE-1-CARBOXYLIC ACID
3-HYDROXYADAMANTANECARBOXYLIC ACID
AKOS BC-0508
TIMTEC-BB SBB010113
3-Hydroxy-1-Adamantanecarboxylic Acid
3-Hydroxy--1-Amantane Carboxylic Acid | [Molecular Formula]
C11H16O3 | [MDL Number]
MFCD00193929 | [Molecular Weight]
196.24 | [MOL File]
42711-75-1.mol |
| Chemical Properties | Back Directory | [Melting point ]
203 °C | [Boiling point ]
357.2±25.0 °C(Predicted) | [density ]
1.419±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
4.60±0.40(Predicted) | [color ]
Off-White | [InChI]
InChI=1S/C11H16O3/c12-9(13)10-2-7-1-8(3-10)5-11(14,4-7)6-10/h7-8,14H,1-6H2,(H,12,13) | [InChIKey]
CJJMAWPEZKYJAP-UHFFFAOYSA-N | [SMILES]
C12(C(O)=O)CC3CC(CC(O)(C3)C1)C2 | [CAS DataBase Reference]
42711-75-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3 | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT | [HS Code ]
29181990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [Chemical Properties]
White to yellow solid | [Uses]
1-Carboxy-3-adamantanol is used in the synthesis of potent pyridyl amide/sulfonamide inhibitors of 11β-HSD-1 which could be applied to a treatment of ulcers or in hormone therapy treatments relating to cortisol. | [Uses]
3-Hydroxy-1-AdaMantane Carboxylic Acid is used in the synthesis of potent pyridyl amide/sulfonamide inhibitors of 11β-HSD-1 which could be applied to a treatment of ulcers or in hormone therapy treatments relating t o cortisol.
| [Synthesis Reference(s)]
Synthetic Communications, 18, p. 1967, 1988 DOI: 10.1080/00397918808068263 | [Synthesis]
The general procedure for the synthesis of 3-hydroxyadamantane from 1-adamantanecarboxylic acid was as follows: 30.2 g of 1-adamantanol (99% purity) was added to a glass reaction flask equipped with a stirrer, a thermometer, a dropping funnel, and a Dimroth condenser, followed by the addition of 215.2 g of 96% concentrated sulfuric acid. After stirring at room temperature until the ingredients were completely dissolved, 9.3 g of formic acid was slowly added dropwise over a period of 15 minutes and the temperature of the reaction solution was maintained between 10 and 20 °C by external cooling. After the dropwise addition, the reaction temperature was raised to 35 °C for 3 hours. The progress of the reaction was monitored by gas chromatography (GC) and 1-adamantanecarboxylic acid was produced when the conversion of 1-adamantanol reached 100%. Subsequently, 23.1 g of 70% nitric acid was slowly added dropwise over a period of 30 min under continued cooling conditions, maintaining the temperature of the reaction solution in the range of 10 to 20 °C. After completion of the dropwise addition, the reaction temperature was maintained at 35 °C for 3 hours to continue the reaction. After confirming the complete conversion of 1-adamantanecarboxylic acid to 3-hydroxyadamantane-1-carboxylic acid by GC, the subsequent purification step was carried out.
Purification step: in another glass flask equipped with a stirrer and a thermometer, a mixed solution of sodium hydroxide and sodium sulfite was prepared by adding 90.2 g of sodium hydroxide, 35.5 g of sodium sulfite and 812 g of ion-exchanged water, and the flask was cooled. 277.8 g of reaction solution containing 3-hydroxy-1-adamantanecarboxylic acid was slowly added to the above mixed solution, and the temperature of the liquid was controlled not to exceed 40 ℃. The precipitated white crystals were separated by filtration and washed with deionized water. The resulting crystals were dried under reduced pressure at 40 °C for 8 h. Finally, 35.8 g (92.6% yield) of white crystals of 3-hydroxyadamantane-1-carboxylic acid were obtained. The content of high boiling point by-products (high molecular weight by-products) in the crystals was 1.28% as analyzed by gel permeation chromatography-refractive index detector (GPC-RI). | [References]
[1] Journal of Medicinal Chemistry, 2018, vol. 61, # 1, p. 98 - 118
[2] Patent: JP2016/84315, 2016, A. Location in patent: Paragraph 0043-0045
[3] Letters in Organic Chemistry, 2016, vol. 13, # 7, p. 514 - 518
[4] Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 10, p. 1680 - 1683
[5] Zhurnal Organicheskoi Khimii, 1992, vol. 28, # 10, p. 2098 - 2102 |
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