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423807

Sigma-Aldrich

5-Hydroxy-2-adamantanone

98%

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About This Item

Empirical Formula (Hill Notation):
C10H14O2
CAS Number:
20098-14-0
Molecular Weight:
166.22
MDL number:
MFCD00192211
UNSPSC Code:
12352100
PubChem Substance ID:
24866531
NACRES:
NA.22

Assay

98%

form

solid

mp

>300 °C (lit.)

functional group

hydroxyl
ketone

SMILES string

O[C@]12C[C@@H]3C[C@H](C1)C(=O)[C@@H](C3)C2

InChI

1S/C10H14O2/c11-9-7-1-6-2-8(9)5-10(12,3-6)4-7/h6-8,12H,1-5H2/t6-,7-,8+,10-

InChI key

TZBDEVBNMSLVKT-XYYXLIQBSA-N

General description

5-Hydroxy-2-adamantanone is a disubstituted derivative of adamantane.[1] The biocatalyzed synthesis of 5-hydroxy-2-adamantanone from 2-adamantanone has been investigated.[2]

Application

5-Hydroxy-2-adamantanone may be used in the following studies:
  • As a model compound to investigate the application of lanthanide NMR shift reagents for the analysis of disubstituted derivative of adamantane.[1]
  • As a starting material for the synthesis of E-2-amino-5-hydroxyadamantane.[3]
  • As a starting material for the synthesis of 4-(triphenylsilyloxy)adamantan-1-ol.[4]

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCN0955
MKBC8866
MKAA2767
00818AJ
05811JE

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S S Boĭko et al.
Farmakologiia i toksikologiia, 54(1), 57-59 (1991-01-01)
The pharmacokinetics of a new Soviet-made immunostimulant kemantane, a derivative of adamantine, was studied by gas-liquid chromatography in patients with bronchial pathology. It was found that in the blood of the patients kemantane was not practically detected due to a
V M Man'ko et al.
Zhurnal mikrobiologii, epidemiologii, i immunobiologii, (6)(6), 63-65 (1991-06-01)
The in vivo study of the influence of Kemantan on the growth of endogenous colonies in the spleen of sublethally (6 Gy) irradiated (CBA x C57BL/6J) F1 mice (mitostatic action) and on the capacity of transplanted lymphocytes of CBA mice
S S Boĭko et al.
Biulleten' eksperimental'noi biologii i meditsiny, 110(11), 501-503 (1990-11-01)
Pharmacokinetics of novel immunostimulating drug kamantane was studied by using gas-liquid chromatography in experiments on rats. It was found that kemantane biotransformed rapidly after oral administration with the forming of active metabolite. Kemantane and its metabolites are distributed rapidly from
An expeditious preparation of E-2-amino-5-hydroxyadamantane and its Z-isomer.
Jaroskova L, et al.
Tetrahedron Letters, 47(46), 8063-8067 (2006)
Marta L Lage et al.
Tetrahedron, 69(27-28), 5609-5613 (2013-09-03)
A chemoselective method for the hydrosilylation of ketones has been developed, using the combination of triphenylsilane and a catalyst prepared from Ni(COD)
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