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31481

Sigma-Aldrich

cis-3,5-Diacetoxy-1-cyclopentene

≥98.0% (GC)

Synonym(s):

cis-4-Cyclopentene-1,3-diol diacetate

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About This Item

Empirical Formula (Hill Notation):
C9H12O4
CAS Number:
54664-61-8
Molecular Weight:
184.19
Beilstein/REAXYS Number:
1961566
MDL number:
MFCD03002563
UNSPSC Code:
12352100
PubChem Substance ID:
57648575
NACRES:
NA.22

assay

≥98.0% (GC)

form

solid

refractive index

n20/D 1.460

density

1.127 g/mL at 20 °C (lit.)

Storage temp.

2-8°C

SMILES string

CC(=O)O[C@@H]1C[C@H](OC(C)=O)C=C1

InChI

1S/C9H12O4/c1-6(10)12-8-3-4-9(5-8)13-7(2)11/h3-4,8-9H,5H2,1-2H3/t8-,9+

Inchi Key

UKPIBFMHHUEUQR-DTORHVGOSA-N

General description

cis-3,5-Diacetoxy-1-cyclopentene is an organic building block.

Application

cis-3,5-Diacetoxy-1-cyclopentene may be employed as substrate to investigate the enantioselectivity of esterase EstA3 (obtained from a drinking water metagenome) and esterase EstCE1 (obtained from a soil metagenome).[1]

Other Notes

Versatile building block; synthesis of carba-nucleosides [2]; Enzyme catalyzed hydrolysis to chiral acetoxy alcohol[3][4]

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves

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B.M. Trost et al.
Journal of the American Chemical Society, 114, 8745-8745 (1992)
C.R. Johnson et al.
Tetrahedron Letters, 33, 7287-7287 (1992)
D.R. Deardorff et al.
Tetrahedron Letters, 27, 1255-1255 (1986)
C Elend et al.
Applied and environmental microbiology, 72(5), 3637-3645 (2006-05-05)
The metagenomes of uncultured microbial communities are rich sources for novel biocatalysts. In this study, esterase EstA3 was derived from a drinking water metagenome, and esterase EstCE1 was derived from a soil metagenome. Both esterases are approximately 380 amino acids
Senthil Kumar Rathnasamy et al.
Scientific reports, 10(1), 13356-13356 (2020-08-10)
The present study report for the first time on the one-pot production and purification of fibrinolytic protease from Bacillus cereus by extractive fermentation using natural deep eutectic solvents (NADES). Cheese whey was chosen as a sustainable low-cost production alternative yielding

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