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94956

Sigma-Aldrich

Vinylcyclohexene dioxide

purum, suitable for electron microscopy, mixture of isomers, ≥96.0% (GC)

Synonym(s):

4-vinyl-1-cyclohexene diepoxide, 1,2-Epoxy-4-epoxyethylcyclohexane, 3-Epoxyethyl-7-oxabicyclo[4.1.0]heptane

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About This Item

Empirical Formula (Hill Notation):
C8H12O2
CAS Number:
Molecular Weight:
140.18
Beilstein/REAXYS Number:
106071
EC Number:
MDL number:
UNSPSC Code:
12162002
PubChem Substance ID:
NACRES:
NA.25

grade

purum

assay

≥96.0% (GC)

form

liquid

technique(s)

electron microscopy: suitable

refractive index

n20/D 1.477 (lit.)
n20/D 1.479

bp

230-232 °C (lit.)

density

1.094 g/mL at 25 °C (lit.)

SMILES string

C1CC2OC2CC1C3CO3

InChI

1S/C8H12O2/c1-2-6-7(10-6)3-5(1)8-4-9-8/h5-8H,1-4H2

InChI key

OECTYKWYRCHAKR-UHFFFAOYSA-N

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Application

Vinylcyclohexene dioxide (VCD) may be used to study and understand its effect on ovarian follicles and effects on epithelial differentiation.

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Description
Pricing

pictograms

Skull and crossbonesHealth hazard

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Carc. 1B - Muta. 2 - Repr. 1B

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 1

flash_point_f

224.6 °F - closed cup

flash_point_c

107 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


Certificates of Analysis (COA)

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Melissa J Romero-Aleshire et al.
American journal of physiology. Regulatory, integrative and comparative physiology, 297(3), R587-R592 (2009-05-15)
Factors comprising the metabolic syndrome occur with increased incidence in postmenopausal women. To investigate the effects of ovarian failure on the progression of the metabolic syndrome, female B(6)C(3)F(1) mice were treated with 4-vinylcyclohexene diepoxide (VCD) and fed a high-fat (HF)
Tracey A Van Kempen et al.
Brain research, 1379, 176-187 (2011-01-08)
Current rodent models of menopause fail to adequately recapitulate the menopause transition. The intact aging model fails to achieve very low estrogen levels, and the ovariectomy model lacks a perimenopause phase. A new rodent model of accelerated ovarian failure (AOF)
Lida P Hariri et al.
Cancer biology & therapy, 10(5), 438-447 (2010-11-26)
Determining if an ovarian mass is benign or malignant is an ongoing clinical challenge. The development of reliable animal models provides means to evaluate new diagnostic tools to more accurately determine if an ovary has benign or malignant features. Although
Aileen F Keating et al.
Biology of reproduction, 84(4), 743-751 (2010-11-16)
4-Vinylcyclohexene diepoxide (VCD), an occupational chemical that specifically destroys primordial and small primary follicles in the ovaries of rats and mice, is thought to target an oocyte-expressed tyrosine kinase receptor, Kit. This study compared the temporal effect of VCD on
Aileen F Keating et al.
Toxicology and applied pharmacology, 247(2), 71-75 (2010-06-15)
The occupational chemical 4-vinylcyclohexene diepoxide (VCD) selectively destroys ovarian small pre-antral follicles in rats and mice via apoptosis. Detoxification of VCD can occur through glutathione conjugation, catalyzed by glutathione S-transferase (GST) enzymes. Further, GST class pi (GSTp) can negatively regulate

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