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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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$596.00

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$930.00

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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

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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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Show Differences

1 of 4

This Item
669911152544C102504
Vinylcyclohexene dioxide purum, suitable for electron microscopy, mixture of isomers, ≥96.0% (GC)

Sigma-Aldrich

94956

Vinylcyclohexene dioxide

3,4-Epoxy-1-cyclohexene ≥96.0%

Sigma-Aldrich

669911

3,4-Epoxy-1-cyclohexene

4-Vinyl-1-cyclohexene 1,2-epoxide, mixture of isomers 98%

Sigma-Aldrich

152544

4-Vinyl-1-cyclohexene 1,2-epoxide, mixture of isomers

Cyclohexene oxide 98%

Sigma-Aldrich

C102504

Cyclohexene oxide

form

liquid

form

-

form

liquid

form

liquid

assay

≥96.0% (GC)

assay

≥96.0% (GC)

assay

98%

assay

98%

technique(s)

electron microscopy: suitable

technique(s)

-

technique(s)

-

technique(s)

-

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

grade

purum

grade

-

grade

-

grade

-

refractive index

n20/D 1.477 (lit.)

refractive index

-

refractive index

n20/D 1.469 (lit.)

refractive index

n20/D 1.452 (lit.)

Application

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

related product

Product No.
Description
Pricing

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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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)
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
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
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)
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
View All Related Papers

Questions

1–7 of 7 Questions  

  1. マウスの閉経モデルを作成するのに使いたいのですが、本来使おうとしていた試薬は販売中止でこちらの代替品を勧められました。こちらで閉経モデルを作成するにあたっての用法容量などの注意点はありますか？

    1 answer

    1. This product has not been tested for in vivo or in vitro use. However, it has been used successfully by other researchers to induce menopause in mouse models. Please see the links below to review example publications:

      Loss of ovarian function in the VCD mouse-model of menopause leads to insulin resistance and a rapid progression into the metabolic syndrome
      https://pmc.ncbi.nlm.nih.gov/articles/PMC2739794/

      Accelerated Ovarian Failure: a novel, chemically-induced animal model of menopause
      https://pmc.ncbi.nlm.nih.gov/articles/PMC3078694/

      Helpful?

  2. For the purpose of our study, we will be injecting 4-VCD dissolved in sesame oil for 20 consecutive days. Can the mixture be stored at four degree for a few days to avoid the hustle of freezing and thawing?

    1 answer

    1. Unfortunately, there is no data available on the stability of this mixture when stored at 4 °C.

      Helpful?

  3. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

      Helpful?

  4. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Helpful?

  5. How should VCD be stored, for short term and long term?

    1 answer

    1. This product may be stored at room temperature for both, short and long term periods.

      Helpful?

  6. What is the concentration of VCD #94956 ( mg / ml)?

    1 answer

    1. This product is supplied as a neat or pure liquid with a density of 1.094 g/mL and a molecular weight of 140.18 g/mol. The minimum purity is 96%, thus the molarity will vary slightly from lot to lot. The molarity can range from 7.5 M (96%) to 7.8 M (100%). The lot specific purity is reported on the Certificate of Analysis. Please see the link below to review a sample Certificate: https://www.sigmaaldrich.com/certificates/sapfs/PROD/sap/certificate_pdfs/COFA/Q14/94956-BULKBCCJ4415.pdf

      Helpful?

  7. ¿En qué está disuelto este producto (94956): aceite de sesamo, Alcohol, DMSO? . Tengo que usarlo más diluido para inyectar en ratones. Gracias

    1 answer

    1. Product 94956 is a neat liquid of Vinylcyclohexene dioxide (VCD) at room temperature. According to the following scientific article, https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2703138/, VCD was either prepared for intramuscular injection with cottonseed oil, or prepared with sesame oil for intraperitoneal injection.

      Helpful?

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