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Merck
CN

94956

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:
106-87-6
Molecular Weight:
140.18
UNSPSC Code:
12162002
NACRES:
NA.25
PubChem Substance ID:
57653591
EC Number:
203-437-7
Beilstein/REAXYS Number:
106071
MDL number:
MFCD00022354
Assay:
≥96.0% (GC)
Form:
liquid
Quality level:
100

Key Documents

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Product Name

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

InChI key

OECTYKWYRCHAKR-UHFFFAOYSA-N

InChI

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

SMILES string

C1CC2OC2CC1C3CO3

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.)

Quality Level

100

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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.

pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

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

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCP2522
BCCN3434
BCCM3213
BCCM5102
BCCJ4415

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Carmen Terren et al.
Scientific reports, 9(1), 19668-19668 (2019-12-25)
Slow freezing (SF) is the reference method for ovarian tissue cryopreservation. Vitrification (VT) constitutes an alternative but controversial method. This study compares SF and VT (open [VTo] and closed [VTc] systems) in terms of freezing damage and fertility restoration ability.
Connie J Kappeler et al.
Systems biology in reproductive medicine, 58(1), 57-62 (2012-01-14)
The occupational chemical 4-vinylcyclohexene diepoxide (VCD) has been shown to cause selective destruction of ovarian small pre-antral (primordial and primary) follicles in rats and mice by accelerating the natural, apoptotic process of atresia. Chemicals that destroy primordial follicles are of
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
Laura A Laviolette et al.
Menopause (New York, N.Y.), 18(5), 549-557 (2011-01-12)
Ovarian cancer is often diagnosed in women after menopause when the levels of the serum gonadotropins follicle-stimulating hormone (FSH) and luteinizing hormone (LH) are increased because of the depletion of growing follicles within the ovary. The ability of FSH and
Poulomi Bhattacharya et al.
Toxicology and applied pharmacology, 267(1), 49-56 (2013-01-01)
4-Vinylcyclohexene diepoxide (VCD) destroys ovarian primordial and small primary follicles via apoptosis. In mice, VCD exposure induces ovarian mRNA expression of glutathione S-transferase (GST) family members, including isoform mu (Gstm). Extra-ovarian GSTM negatively regulates pro-apoptotic apoptosis signal-regulating kinase 1 (ASK1)
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