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106399

Sigma-Aldrich

1-Adamantanecarboxylic acid

99%

Synonym(s):

Adamantane carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C11H16O2
CAS Number:
828-51-3
Molecular Weight:
180.24
Beilstein:
1910637
EC Number:
212-584-6
MDL number:
MFCD00074720
UNSPSC Code:
12352100
PubChem Substance ID:
24846732
NACRES:
NA.22
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Quality Level

200

Assay

99%

mp

172-174 °C (lit.)

functional group

carboxylic acid

SMILES string

OC(=O)C12C[C@H]3C[C@H](C[C@H](C3)C1)C2

InChI

1S/C11H16O2/c12-10(13)11-4-7-1-8(5-11)3-9(2-7)6-11/h7-9H,1-6H2,(H,12,13)/t7-,8+,9-,11-

InChI key

JIMXXGFJRDUSRO-KJZNFTALSA-N

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Application

1-Adamantanecarboxylic acid can be used as:
  • A stabilizer in the synthesis of monodisperse, highly crystalline CoPt3 nanoparticles[1] and porous platinum nanoparticles.[2]
  • An additive in polycondensation reactions to yield conjugated polymers as possible optoelectronic materials.[3]
  • An additive in the allylic substitution reaction, which is catalyzed by palladium in an aqueous medium.[4]

Biochem/physiol Actions

1-Adamantanecarboxylic acid undergoes complexation reactions with cyclohexaamylose[5]. It is an inhibitor of phenyl ester hydrolysis of cycloheptaamylose[6].

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
BCCL6381
BCCJ8395
BCCJ1031
BCCD7006
BCCC2722

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Nicolas Taulier et al.
The journal of physical chemistry. B, 112(31), 9546-9549 (2008-07-16)
We report temperature-dependent ultrasonic velocimetric and densimetric data on changes in volume, expansibility, and adiabatic compressibility associated with the binding of 1-adamantanecarboxylic acid (AD) to gamma-cyclodextrin (gamma-CD). We compare these results with our previous data on the binding of AD
D Rozema et al.
Biochemistry, 35(49), 15760-15771 (1996-12-10)
Conditions that promote renaturation of an unfolded protein also promote protein aggregation, in many cases, because these competing intramolecular and intermolecular processes are driven by similar networks of noncovalent interactions. The GroEL/GroES system and related biological chaperones facilitate the renaturation
Synthesis of porous platinum nanoparticles
Teng X, et al.
Small, 2(2), 249-253 (2006)
Ying-Ming Zhang et al.
Bioorganic & medicinal chemistry, 18(4), 1415-1420 (2010-02-05)
A novel beta-cyclodextrin derivative 1 bearing 8-hydroxyquinolino and triazole groups was synthesized in satisfactory yield by 'click chemistry'. With a good water solubility up to 0.03 mol/L, 1 exhibited an effective switch-on fluorescence response to Cd(2+) over other common metal
The complexation chemistry of cyclohexaamyloses: Adducts with 1-adamantanecarboxylic acid and anion.
Gelb RI, et al.
Bioorganic Chemistry, 9(4), 450-461 (1980)
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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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