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106-87-6,MFCD00022354
Catalog No.:AA00ILIM

106-87-6 | Vinylcyclohexene dioxide

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250mg
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$12.00   $8.00
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5g
95%
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25g
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  • Technical Information
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00ILIM
Chemical Name:
Vinylcyclohexene dioxide
CAS Number:
106-87-6
Molecular Formula:
C8H12O2
Molecular Weight:
140.1797
MDL Number:
MFCD00022354
SMILES:
C1CC2C(O2)CC1C3CO3
UN Number:
2810
Properties
Computed Properties
 
Complexity:
157  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
10  
Hydrogen Bond Acceptor Count:
2  
Rotatable Bond Count:
1  
Undefined Atom Stereocenter Count:
4  
XLogP3:
0.8  

Literature

Title: Depletion of follicles accelerated by combined exposure to phthalates and 4-vinylcyclohexene diepoxide, leading to premature ovarian failure in rats.

Journal: Reproductive toxicology (Elmsford, N.Y.) 20180901

Title: 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.

Journal: Redox biology 20150801

Title: Glutathione S-transferase class μ regulation of apoptosis signal-regulating kinase 1 protein during VCD-induced ovotoxicity in neonatal rat ovaries.

Journal: Toxicology and applied pharmacology 20130215

Title: An update on primary ovarian insufficiency.

Journal: Science China. Life sciences 20120801

Title: Analysis of second-harmonic-generation microscopy in a mouse model of ovarian carcinoma.

Journal: Journal of biomedical optics 20120701

Title: Modeling perimenopause in Sprague-Dawley rats by chemical manipulation of the transition to ovarian failure.

Journal: Comparative medicine 20120601

Title: Decreased bone mineral density in rats rendered follicle-deplete by an ovotoxic chemical correlates with changes in follicle-stimulating hormone and inhibin A.

Journal: Calcified tissue international 20120301

Title: 4-vinylcyclohexene diepoxide: a model chemical for ovotoxicity.

Journal: Systems biology in reproductive medicine 20120201

Title: Ovarian expressed microsomal epoxide hydrolase: role in detoxification of 4-vinylcyclohexene diepoxide and regulation by phosphatidylinositol-3 kinase signaling.

Journal: Toxicology and applied pharmacology 20120101

Title: Inhibition of ovarian KIT phosphorylation by the ovotoxicant 4-vinylcyclohexene diepoxide in rats.

Journal: Biology of reproduction 20111001

Title: Estradiol treatment, physical activity, and muscle function in ovarian-senescent mice.

Journal: Experimental gerontology 20110801

Title: 4-Vinylcyclohexene diepoxide (VCD) inhibits mammary epithelial differentiation and induces fibroadenoma formation in female Sprague Dawley rats.

Journal: Reproductive toxicology (Elmsford, N.Y.) 20110701

Title: Induction of a menopausal state alters the growth and histology of ovarian tumors in a mouse model of ovarian cancer.

Journal: Menopause (New York, N.Y.) 20110501

Title: Inhibition of PIK3 signaling pathway members by the ovotoxicant 4-vinylcyclohexene diepoxide in rats.

Journal: Biology of reproduction 20110401

Title: Accelerated ovarian failure: a novel, chemically induced animal model of menopause.

Journal: Brain research 20110316

Title: Midkine, a heparin-binding protein, is increased in the diabetic mouse kidney postmenopause.

Journal: American journal of physiology. Renal physiology 20110101

Title: Chemotherapy-induced late transgenerational effects in mice.

Journal: PloS one 20110101

Title: 4-Vinyl-1-cyclohexene diepoxide.

Journal: Report on carcinogens : carcinogen profiles 20110101

Title: Strategies and methods to study sex differences in cardiovascular structure and function: a guide for basic scientists.

Journal: Biology of sex differences 20110101

Title: Adding insult to injury: effects of xenobiotic-induced preantral ovotoxicity on ovarian development and oocyte fusibility.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20101201

Title: Distribution and responsiveness of rat anti-Müllerian hormone during ovarian development and VCD-induced ovotoxicity.

Journal: Toxicology and applied pharmacology 20101115

Title: Experimental induction of reduced ovarian reserve in a nonhuman primate model (Macaca fascicularis).

Journal: Comparative medicine 20101001

Title: Dual protective role for glutathione S-transferase class pi against VCD-induced ovotoxicity in the rat ovary.

Journal: Toxicology and applied pharmacology 20100901

Title: Simultaneous optical coherence tomography and laser induced fluorescence imaging in rat model of ovarian carcinogenesis.

Journal: Cancer biology & therapy 20100901

Title: The cognitive effects of conjugated equine estrogens depend on whether menopause etiology is transitional or surgical.

Journal: Endocrinology 20100801

Title: 7,12-dimethylbenz[a]anthracene induces sertoli-leydig-cell tumors in the follicle-depleted ovaries of mice treated with 4-vinylcyclohexene diepoxide.

Journal: Comparative medicine 20100201

Title: Retaining Residual Ovarian Tissue following Ovarian Failure Has Limited Influence on Bone Loss in Aged Mice.

Journal: Journal of osteoporosis 20100101

Title: A longitudinal study of the effect of genistein on bone in two different murine models of diminished estrogen-producing capacity.

Journal: Journal of osteoporosis 20100101

Title: Effect of phosphatidylinositol-3 kinase inhibition on ovotoxicity caused by 4-vinylcyclohexene diepoxide and 7, 12-dimethylbenz[a]anthracene in neonatal rat ovaries.

Journal: Toxicology and applied pharmacology 20091201

Title: Loss of ovarian function in the VCD mouse-model of menopause leads to insulin resistance and a rapid progression into the metabolic syndrome.

Journal: American journal of physiology. Regulatory, integrative and comparative physiology 20090901

Title: Transitional versus surgical menopause in a rodent model: etiology of ovarian hormone loss impacts memory and the acetylcholine system.

Journal: Endocrinology 20090901

Title: Using basic science to design a clinical trial: baseline characteristics of women enrolled in the Kronos Early Estrogen Prevention Study (KEEPS).

Journal: Journal of cardiovascular translational research 20090901

Title: Lactational coumestrol exposure increases ovarian apoptosis in adult rats.

Journal: Archives of toxicology 20090601

Title: Neuroprotection against excitotoxic brain injury in mice after ovarian steroid depletion.

Journal: Brain research 20090410

Title: Ovarian neoplasm development by 7,12-dimethylbenz[a]anthracene (DMBA) in a chemically-induced rat model of ovarian failure.

Journal: Gynecologic oncology 20090301

Title: Steroidogenic capacity of residual ovarian tissue in 4-vinylcyclohexene diepoxide-treated mice.

Journal: Biology of reproduction 20090201

Title: Effects of 4-vinylcyclohexene diepoxide on peripubertal and adult Sprague-Dawley rats: ovarian, clinical, and pathologic outcomes.

Journal: Comparative medicine 20090201

Title: Collaborative work on evaluation of ovarian toxicity. 4) Two- or four-week repeated dose study of 4-vinylcyclohexene diepoxide in female rats.

Journal: The Journal of toxicological sciences 20090101

Title: Collaborative work on evaluation of ovarian toxicity. 4) Effects of fertility study of 4-vinylcyclohexene diepoxide in female rats.

Journal: The Journal of toxicological sciences 20090101

Title: Behavioral consequences of ovarian atrophy and estrogen replacement in the APPswe mouse.

Journal: Neurobiology of aging 20081001

Title: Effect of CYP2E1 gene deletion in mice on expression of microsomal epoxide hydrolase in response to VCD exposure.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20081001

Title: Correlation of serum anti-Müllerian hormone with accelerated follicle loss following 4-vinylcyclohexene diepoxide-induced follicle loss in mice.

Journal: Reproductive toxicology (Elmsford, N.Y.) 20081001

Title: Oridonin confers protection against arsenic-induced toxicity through activation of the Nrf2-mediated defensive response.

Journal: Environmental health perspectives 20080901

Title: Comparison of skeletal effects of ovariectomy versus chemically induced ovarian failure in mice.

Journal: Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20080801

Title: Involvement of the KIT/KITL signaling pathway in 4-vinylcyclohexene diepoxide-induced ovarian follicle loss in rats.

Journal: Biology of reproduction 20080801

Title: Expression of ovarian microsomal epoxide hydrolase and glutathione S-transferase during onset of VCD-induced ovotoxicity in B6C3F(1) mice.

Journal: Toxicology and applied pharmacology 20080701

Title: Peer review and reflection continues forever.

Journal: Fertility and sterility 20080401

Title: Development of a sampling and analysis method for 4-vinyl-1-cyclohexene in air.

Journal: Journal of occupational health 20080101

Title: Effects of impending ovarian failure induced by 4-vinylcyclohexene diepoxide on fertility in C57BL/6 female mice.

Journal: Comparative medicine 20071001

Title: Hormonal status affects the progression of STZ-induced diabetes and diabetic renal damage in the VCD mouse model of menopause.

Journal: American journal of physiology. Renal physiology 20070701

Title: Destruction of primordial ovarian follicles in adult cynomolgus macaques after exposure to 4-vinylcyclohexene diepoxide: a nonhuman primate model of the menopausal transition.

Journal: Fertility and sterility 20061001

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Recent female mouse models displaying advanced reproductive aging.

Journal: Experimental gerontology 20060201

Title: Effect of duration of dosing on onset of ovarian failure in a chemical-induced mouse model of perimenopause.

Journal: Menopause (New York, N.Y.) 20060101

Title: Dual modality imaging of a novel rat model of ovarian carcinogenesis.

Journal: Journal of biomedical optics 20060101

Title: Characterization of cyclicity and hormonal profile with impending ovarian failure in a novel chemical-induced mouse model of perimenopause.

Journal: Comparative medicine 20051201

Title: Atherosclerotic lesion development in a novel ovary-intact mouse model of perimenopause.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20050901

Title: Differences between rats and mice in the involvement of the aryl hydrocarbon receptor in 4-vinylcyclohexene diepoxide-induced ovarian follicle loss.

Journal: Toxicology and applied pharmacology 20050301

Title: Initiation of delayed ovotoxicity by in vitro and in vivo exposures of rat ovaries to 4-vinylcyclohexene diepoxide.

Journal: Reproductive toxicology (Elmsford, N.Y.) 20041101

Title: The follicle-deplete mouse ovary produces androgen.

Journal: Biology of reproduction 20040701

Title: 4-Vinyl-1-cyclohexene diepoxide.

Journal: Report on carcinogens : carcinogen profiles 20040101

Title: Expression and activity of cytochromes P450 2E1, 2A, and 2B in the mouse ovary: the effect of 4-vinylcyclohexene and its diepoxide metabolite.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20030601

Title: Bax, caspase-2, and caspase-3 are required for ovarian follicle loss caused by 4-vinylcyclohexene diepoxide exposure of female mice in vivo.

Journal: Endocrinology 20030101

Title: Ovarian follicle counts--not as simple as 1, 2, 3.

Journal: Reproductive biology and endocrinology : RB&E 20030101

Title: In vivo exposure of female rats to toxicants may affect oocyte quality.

Journal: Reproductive toxicology (Elmsford, N.Y.) 20030101

Title: Characterization of a rat in vitro ovarian culture system to study the ovarian toxicant 4-vinylcyclohexene diepoxide.

Journal: Toxicology and applied pharmacology 20021015

Title: Activation of mitogen-activated protein kinases and AP-1 transcription factor in ovotoxicity induced by 4-vinylcyclohexene diepoxide in rats.

Journal: Biology of reproduction 20020901

Title: Expression and activity of microsomal epoxide hydrolase in follicles isolated from mouse ovaries.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20020701

Title: 17beta-estradiol affords protection against 4-vinylcyclohexene diepoxide-induced ovarian follicle loss in Fischer-344 rats.

Journal: Endocrinology 20020301

Title: Long-term effects of ovarian follicular depletion in rats by 4-vinylcyclohexene diepoxide.

Journal: Reproductive toxicology (Elmsford, N.Y.) 20020101

Title: 4-Vinyl-1-cyclohexene diepoxide.

Journal: Report on carcinogens : carcinogen profiles 20020101

Title: Expression and redistribution of cellular Bad, Bax, and Bcl-X(L) protein is associated with VCD-induced ovotoxicity in rats.

Journal: Biology of reproduction 20011101

Title: Effect of 4-vinylcyclohexene diepoxide dosing in rats on GSH levels in liver and ovaries.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20010801

Title: Evaluation of hepatic cytochrome P4502E1 in the species-dependent bioactivation of 4-vinylcyclohexene.

Journal: Life sciences 20010713

Title: Apoptosis induced in rats by 4-vinylcyclohexene diepoxide is associated with activation of the caspase cascades.

Journal: Biology of reproduction 20010701

Title: Stereochemical aspects in the 4-vinylcyclohexene biotransformation with rat liver microsomes and purified p450s. monoepoxides and diols.

Journal: Chemical research in toxicology 20010501

Title: Ovarian toxicity of 4-vinylcyclohexene diepoxide: a mechanistic model.

Journal: Toxicologic pathology 20010101

Title: Mechanisms of ovotoxicity induced by environmental chemicals: 4-vinylcyclohexene diepoxide as a model chemical.

Journal: Advances in experimental medicine and biology 20010101

Title: Induction of cytochrome P-450 enzymes after repeated exposure to 4-vinylcyclohexene in B6C3F1 mice.

Journal: Drug metabolism and disposition: the biological fate of chemicals 19990201

Title: Enhanced expression of bax in small preantral follicles during 4-vinylcyclohexene diepoxide-induced ovotoxicity in the rat.

Journal: Toxicology and applied pharmacology 19960801

Title: Irritant symptoms and immunologic responses to multiple chemicals: importance of clinical and immunologic correlations.

Journal: International archives of allergy and applied immunology 19880101

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Tags:106-87-6 Molecular Formula|106-87-6 MDL|106-87-6 SMILES|106-87-6 Vinylcyclohexene dioxide |Heterocyclic_Building_Blocks