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550485

Sigma-Aldrich

3-Oxo-1-cyclopentanecarboxylic acid

97%

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About This Item

Empirical Formula (Hill Notation):
C6H8O3
CAS Number:
98-78-2
Molecular Weight:
128.13
MDL number:
MFCD01320173
UNSPSC Code:
12352100
PubChem Substance ID:
24879119
NACRES:
NA.22

Assay

97%

mp

59-62 °C (lit.)

SMILES string

OC(=O)C1CCC(=O)C1

InChI

1S/C6H8O3/c7-5-2-1-4(3-5)6(8)9/h4H,1-3H2,(H,8,9)

InChI key

RDSNBKRWKBMPOP-UHFFFAOYSA-N

Related Categories

General description

3-Oxo-1-cyclopentanecarboxylic acid , also known as 3-oxocyclopentanecarboxylic acid, is a keto acid derivative. It undergoes Curtius rearrangement with diphenyl phosphoryl azide and triethylamine in tert-butanol to form the corresponding boc-protected 1-(3-oxo)urea derivative.

Application

3-Oxo-1-cyclopentanecarboxylic acid may be used in the preparation of 3-hydroxycyclopentanecarboxylic acid via hydrogenation.
Substrate used in a study of biohydroxylation with mutants of cytochrome P450 BM-3.

Legal Information

Product of Rieke Metals, Inc.
Rieke is a registered trademark of Rieke Metals, Inc.

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Dieter F Münzer et al.
Chemical communications (Cambridge, England), (20), 2597-2599 (2005-05-19)
Substrate engineered, achiral carboxylic acid derivative was biohydroxylated with various mutants of cytochrome P450 BM-3 to give two out of the four possible diastereoisomers in high de and ee. The BM-3 mutants exhibit up to 9200 total turnovers for hydroxylation
Studies of Configuration. V. The Preparation and Configuration of cis-3-Methoxycyclopentanecarboxylic Acid.
Noyce D and Fessenden J.
The Journal of Organic Chemistry, 24(5), 715-717 (1959)
Boc-protected 1-(3-oxocycloalkyl) ureas via a one-step Curtius rearrangement: mechanism and scope.
Sun X, et al.
Tetrahedron Letters, 55(4), 842-844 (2014)

Articles

Phase I Drug Metabolism

Phase I biotransformation reactions introduce or expose functional groups on the drug with the goal of increasing the polarity of the compound. Although Phase I drug metabolism occurs in most tissues, the primary and first pass site of metabolism occurs during hepatic circulation.

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