Details
| Stereochemistry | MIXED |
| Molecular Formula | C8H12O2 |
| Molecular Weight | 140.1797 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 0 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C1OC1C2CCC3OC3C2
InChI
InChIKey=OECTYKWYRCHAKR-UHFFFAOYSA-N
InChI=1S/C8H12O2/c1-2-6-7(10-6)3-5(1)8-4-9-8/h5-8H,1-4H2
| Molecular Formula | C8H12O2 |
| Molecular Weight | 140.1797 |
| Charge | 0 |
| Count |
|
| Stereochemistry | MIXED |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Irritant symptoms and immunologic responses to multiple chemicals: importance of clinical and immunologic correlations. | 1988 |
|
| Enhanced expression of bax in small preantral follicles during 4-vinylcyclohexene diepoxide-induced ovotoxicity in the rat. | 1996 Aug |
|
| Mechanisms of ovotoxicity induced by environmental chemicals: 4-vinylcyclohexene diepoxide as a model chemical. | 2001 |
|
| 4-Vinyl-1-cyclohexene diepoxide. | 2002 |
|
| 17beta-estradiol affords protection against 4-vinylcyclohexene diepoxide-induced ovarian follicle loss in Fischer-344 rats. | 2002 Mar |
|
| Long-term effects of ovarian follicular depletion in rats by 4-vinylcyclohexene diepoxide. | 2002 Nov-Dec |
|
| Characterization of a rat in vitro ovarian culture system to study the ovarian toxicant 4-vinylcyclohexene diepoxide. | 2002 Oct 15 |
|
| Activation of mitogen-activated protein kinases and AP-1 transcription factor in ovotoxicity induced by 4-vinylcyclohexene diepoxide in rats. | 2002 Sep |
|
| Ovarian follicle counts--not as simple as 1, 2, 3. | 2003 Feb 6 |
|
| Bax, caspase-2, and caspase-3 are required for ovarian follicle loss caused by 4-vinylcyclohexene diepoxide exposure of female mice in vivo. | 2003 Jan |
|
| In vivo exposure of female rats to toxicants may affect oocyte quality. | 2003 May-Jun |
|
| 4-Vinyl-1-cyclohexene diepoxide. | 2004 |
|
| The follicle-deplete mouse ovary produces androgen. | 2004 Jul |
|
| Initiation of delayed ovotoxicity by in vitro and in vivo exposures of rat ovaries to 4-vinylcyclohexene diepoxide. | 2004 Nov |
|
| Differences between rats and mice in the involvement of the aryl hydrocarbon receptor in 4-vinylcyclohexene diepoxide-induced ovarian follicle loss. | 2005 Mar 1 |
|
| Atherosclerotic lesion development in a novel ovary-intact mouse model of perimenopause. | 2005 Sep |
|
| Recent female mouse models displaying advanced reproductive aging. | 2006 Feb |
|
| Dual modality imaging of a novel rat model of ovarian carcinogenesis. | 2006 Jul-Aug |
|
| Effect of duration of dosing on onset of ovarian failure in a chemical-induced mouse model of perimenopause. | 2006 May-Jun |
|
| Destruction of primordial ovarian follicles in adult cynomolgus macaques after exposure to 4-vinylcyclohexene diepoxide: a nonhuman primate model of the menopausal transition. | 2006 Oct |
|
| Hormonal status affects the progression of STZ-induced diabetes and diabetic renal damage in the VCD mouse model of menopause. | 2007 Jul |
|
| Effects of impending ovarian failure induced by 4-vinylcyclohexene diepoxide on fertility in C57BL/6 female mice. | 2007 Oct |
|
| Involvement of the KIT/KITL signaling pathway in 4-vinylcyclohexene diepoxide-induced ovarian follicle loss in rats. | 2008 Aug |
|
| Comparison of skeletal effects of ovariectomy versus chemically induced ovarian failure in mice. | 2008 Aug |
|
| Correlation of serum anti-Müllerian hormone with accelerated follicle loss following 4-vinylcyclohexene diepoxide-induced follicle loss in mice. | 2008 Oct |
|
| Effect of CYP2E1 gene deletion in mice on expression of microsomal epoxide hydrolase in response to VCD exposure. | 2008 Oct |
|
| Behavioral consequences of ovarian atrophy and estrogen replacement in the APPswe mouse. | 2008 Oct |
|
| Oridonin confers protection against arsenic-induced toxicity through activation of the Nrf2-mediated defensive response. | 2008 Sep |
|
| Collaborative work on evaluation of ovarian toxicity. 4) Effects of fertility study of 4-vinylcyclohexene diepoxide in female rats. | 2009 |
|
| Collaborative work on evaluation of ovarian toxicity. 4) Two- or four-week repeated dose study of 4-vinylcyclohexene diepoxide in female rats. | 2009 |
|
| Effect of phosphatidylinositol-3 kinase inhibition on ovotoxicity caused by 4-vinylcyclohexene diepoxide and 7, 12-dimethylbenz[a]anthracene in neonatal rat ovaries. | 2009 Dec 1 |
|
| Effects of 4-vinylcyclohexene diepoxide on peripubertal and adult Sprague-Dawley rats: ovarian, clinical, and pathologic outcomes. | 2009 Feb |
|
| Steroidogenic capacity of residual ovarian tissue in 4-vinylcyclohexene diepoxide-treated mice. | 2009 Feb |
|
| Lactational coumestrol exposure increases ovarian apoptosis in adult rats. | 2009 Jun |
|
| Ovarian neoplasm development by 7,12-dimethylbenz[a]anthracene (DMBA) in a chemically-induced rat model of ovarian failure. | 2009 Mar |
|
| Using basic science to design a clinical trial: baseline characteristics of women enrolled in the Kronos Early Estrogen Prevention Study (KEEPS). | 2009 Sep |
|
| Transitional versus surgical menopause in a rodent model: etiology of ovarian hormone loss impacts memory and the acetylcholine system. | 2009 Sep |
|
| Loss of ovarian function in the VCD mouse-model of menopause leads to insulin resistance and a rapid progression into the metabolic syndrome. | 2009 Sep |
|
| A longitudinal study of the effect of genistein on bone in two different murine models of diminished estrogen-producing capacity. | 2010 |
|
| The cognitive effects of conjugated equine estrogens depend on whether menopause etiology is transitional or surgical. | 2010 Aug |
|
| Adding insult to injury: effects of xenobiotic-induced preantral ovotoxicity on ovarian development and oocyte fusibility. | 2010 Dec |
|
| 7,12-dimethylbenz[a]anthracene induces sertoli-leydig-cell tumors in the follicle-depleted ovaries of mice treated with 4-vinylcyclohexene diepoxide. | 2010 Feb |
|
| Retaining Residual Ovarian Tissue following Ovarian Failure Has Limited Influence on Bone Loss in Aged Mice. | 2010 Jun 29 |
|
| Distribution and responsiveness of rat anti-Müllerian hormone during ovarian development and VCD-induced ovotoxicity. | 2010 Nov 15 |
|
| Simultaneous optical coherence tomography and laser induced fluorescence imaging in rat model of ovarian carcinogenesis. | 2010 Sep 1 |
|
| Dual protective role for glutathione S-transferase class pi against VCD-induced ovotoxicity in the rat ovary. | 2010 Sep 1 |
|
| 4-Vinylcyclohexene diepoxide (VCD) inhibits mammary epithelial differentiation and induces fibroadenoma formation in female Sprague Dawley rats. | 2011 Jul |
|
| Ovarian expressed microsomal epoxide hydrolase: role in detoxification of 4-vinylcyclohexene diepoxide and regulation by phosphatidylinositol-3 kinase signaling. | 2012 Jan 1 |
|
| Glutathione S-transferase class μ regulation of apoptosis signal-regulating kinase 1 protein during VCD-induced ovotoxicity in neonatal rat ovaries. | 2013 Feb 15 |
|
| Ovotoxicants 4-vinylcyclohexene 1,2-monoepoxide and 4-vinylcyclohexene diepoxide disrupt redox status and modify different electrophile sensitive target enzymes and genes in Drosophila melanogaster. | 2015 Aug |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 08:59:56 GMT 2023
by
admin
on
Sat Dec 16 08:59:56 GMT 2023
|
| Record UNII |
596C064IG4
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
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4332
Created by
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Vinylcyclohexene dioxide
Created by
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596C064IG4
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59001
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7833
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203-437-7
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106-87-6
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DTXSID0020604
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54752
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7583
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61281
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