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Sigma-Aldrich

2-Adamantanol

97%

Synonym(s):

2-Hydroxyadamantane

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About This Item

Empirical Formula (Hill Notation):
C10H16O
CAS Number:
700-57-2
Molecular Weight:
152.23
Beilstein:
2498536
EC Number:
211-846-7
MDL number:
MFCD00074744
UNSPSC Code:
12352100
PubChem Substance ID:
24849378
NACRES:
NA.22

Assay

97%

form

solid

mp

258-262 °C (lit.)

SMILES string

OC1[C@H]2C[C@@H]3C[C@H](C2)C[C@H]1C3

InChI

1S/C10H16O/c11-10-8-2-6-1-7(4-8)5-9(10)3-6/h6-11H,1-5H2/t6-,7+,8-,9+,10?

InChI key

FOWDOWQYRZXQDP-MGPGSJOLSA-N

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General description

The low-temperature X-ray structure of 2-adamantanol ester has been studied.

Application

2-Adamantanol was used to synthesize ester imides.

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

Certificates of Analysis (COA)

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T Mavromoustakos et al.
Life sciences, 62(20), 1901-1910 (1998-05-26)
Differential Scanning Calorimetry (DSC) has been applied to study the thermal properties of the membrane perturbing antibacterial octyl- and dodecyl-bromide salts of quaternary dimethylamino adamantanol (ADM-8 and ADM-12 correspondingly) incorporated in free or complexed form with beta-cyclodextrin (beta-CD) into dipalmitoylphosphatidylcholine
Koichi Mitsukura et al.
Applied microbiology and biotechnology, 71(4), 502-504 (2005-09-28)
Hydroxylation of adamantane using whole cells of bacteria, actinomyces, and molds was examined. The structure of the product was determined using gas chromatography (GC), nuclear magnetic resonance (NMR), and mass spectroscopy (MS). Among 470 strains tested, Streptomyces griseoplanus was highly
Marisa Spiniello et al.
Organic & biomolecular chemistry, 1(17), 3094-3101 (2003-10-02)
Results of low-temperature X-ray structural studies for five cis-, and three trans-4-tert-butyl cyclohexanol, and six 2-adamantanol ester and ether derivatives are reported. Plots of C-OR bond distance against pKa(ROH) for derivatives of axial alcohol (5), equatorial alcohol (6) and 2-adamantanol
J P Miller et al.
Biochemistry, 33(3), 807-817 (1994-01-25)
Spiro[adamantane-2,2'-diazirine], which produces adamantyl carbene upon photolysis, binds tightly to P450 2B4 (KS = 3.2 microM), giving a normal substrate binding difference spectrum. Irradiation of 2-[3H]adamantane diazirine at 365 nm in the presence of native, ferric P450 2B4 resulted in
Andrzej Orzeszko et al.
Farmaco (Societa chimica italiana : 1989), 57(8), 619-624 (2002-10-04)
Some novel ester imides synthesised from trimellitic acid anhydride and 1-adamantanol or 2-adamantanol, were tested as antimicrobial compounds. Unfortunately, these agents showed a modest antibacterial activity (MIC > 6 microg/ml). However, a comparison of these N-substituted adamantylester imides with the
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