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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:
106-87-6
Molecular Weight:
140.18
Beilstein:
106071
EC Number:
203-437-7
MDL number:
MFCD00022354
UNSPSC Code:
12162002
PubChem Substance ID:
57653591
NACRES:
NA.25

Quality Level

100

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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Product No.
Description
Pricing

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Classifications

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

Storage Class Code

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

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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Cyclohexene oxide 98%

Sigma-Aldrich

C102504

Cyclohexene oxide

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
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
P B Hoyer et al.
Toxicologic pathology, 29(1), 91-99 (2001-02-24)
Female mammals are born with a finite number of ovarian primordial follicles that cannot be regenerated; thus, chemicals that destroy oocytes contained in these follicles can produce premature ovarian failure (early menopuase in women). Exposure of women to known ovotoxicants
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)
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.
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