Page last updated: 2024-12-05

4-vinylcyclohexene

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

4-vinylcyclohexene is a cyclic hydrocarbon with a vinyl group attached to the cyclohexene ring. It is a colorless liquid with a pungent odor. It is used as a monomer in the production of polymers and as an intermediate in organic synthesis. 4-vinylcyclohexene is also a component of some natural products, such as turpentine. It can be synthesized by the Diels-Alder reaction of cyclopentadiene and butadiene. It has been studied for its potential use in the production of new polymers and materials. It has also been studied for its biological activity, such as its potential to inhibit the growth of certain types of cancer cells. 4-vinylcyclohexene is a reactive compound and should be handled with care.'

4-vinylcyclohexene: structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID7499
CHEMBL ID1330194
CHEBI ID82377
MeSH IDM0061724

Synonyms (65)

Synonym
LS-13442
4-vinyl-cyclohexene
100-40-3
nsc-15760
1,3,4-tetrahydrostyrene
1-vinyl-3-cyclohexene
nsc15760
cyclohexene, 4-vinyl-
4-vinylcyclohexene-1
nci-c54999
4-vinyl-1-cyclohexene
1-cyclohexene, 4-vinyl-
wln: l6utj d1u1
4-ethenyl-1-cyclohexene
4-vinylcyclohexene
1-vinylcyclohex-3-ene
cyclohexenylethylene
butadiene dimer
cyclohexene, 4-ethenyl-
1-vinylcyclohexene-3
4-ethenylcyclohexene
NCGC00091539-01
brn 1901553
4-vinyl cyclohexene
einecs 202-848-9
nsc 15760
ccris 1422
hsdb 2872
1,2,3,4-tetrahydrostyrene
vinylcyclohexene, 4-
ai3-08499
ethenyl-1-cyclohexene
NCGC00091539-02
V0023
NCGC00091539-03
4-05-00-00406 (beilstein handbook reference)
ec 202-848-9
unii-212jqj15ps
212jqj15ps ,
C19310
NCGC00257942-01
tox21_200388
cas-100-40-3
dtxcid601437
dtxsid3021437 ,
FT-0619549
4-vinylcyclohex-1-ene
AKOS015903842
4-vinylcyclohexene [iarc]
4-vch
4-vinylcyclohene
CHEBI:82377 ,
CHEMBL1330194
4-vinylcylohexene
J-000127
4-vinyl-1-cyclohexene, analytical standard
4-vinyl-1-cyclohexene (stabilized with bht)
mfcd00001576
4-vinyl-1-cyclohexene, 99%
4-vinyl-1-cyclohexene 2000 microg/ml in methanol
4-ethenylcyclohex-1-ene
Q4637205
4 vinyl cyclohexene
D92779
EN300-123688

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" In mice, the most notable adverse histopathological effect was ovarian atrophy in females exposed to 1000 ppm VCH or 1000 ppm butadiene."( Subchronic toxicity of 4-vinylcyclohexene in rats and mice by inhalation exposure.
Baldwin, JK; Bevan, C; Elliott, GS; Frame, SR; Leung, HW; Moran, E; Panepinto, AS; Stadler, JC, 1996
)
0.6

Dosage Studied

ExcerptRelevanceReference
" In the 13-wk studies, extensive mortality was observed only in mice dosed at 1200 mg/kg."( Toxicological evaluation of 4-vinylcyclohexene. I. Prechronic (14-day) and subchronic (13-week) gavage studies in Fischer 344 rats and B6C3F1 mice.
Collins, JJ; Manus, AG, 1987
)
0.57
"01) incidences of uncommon ovarian neoplasms, including mixed benign tumors, granulosa-cell tumors, and granulosa-cell tumors or carcinomas (combined), in both groups of dosed female mice."( Toxicological evaluation of 4-vinylcyclohexene. II. Induction of ovarian tumors in female B6C3F1 mice by chronic oral administration of 4-vinylcyclohexene.
Collins, JJ; Manus, AG; Montali, RJ, 1987
)
0.57
" Female B6C3F1 mice were dosed with VCH (6 mmol/kg/day, ip) or 4PC (3 or 6 mmol/kg/day, ip) daily for 30 days."( Differential ovotoxicity of 4-vinylcyclohexene and its analog, 4-phenylcyclohexene.
Hooser, SB; Parola, LR; Sipes, IG; Van Ert, MD, 1993
)
0.58
" Because ovotoxicity requires repeated dosing of VCH, the effect of consecutive daily doses of VCH (7."( Induction of cytochrome P-450 enzymes after repeated exposure to 4-vinylcyclohexene in B6C3F1 mice.
Doerr-Stevens, JK; Fontaine, SM; Halpert, JR; Kraner, JC; Liu, J; Sipes, IG; Stevens, GJ, 1999
)
0.54
" Primordial follicle destruction is known to result from dosing of mice and rats with three polycyclic aromatic hydrocarbons (PAHs), contaminants commonly found in cigarette smoke."( Ovotoxicity in female Fischer rats and B6 mice induced by low-dose exposure to three polycyclic aromatic hydrocarbons: comparison through calculation of an ovotoxic index.
Borman, SM; Christian, PJ; Hoyer, PB; Sipes, IG, 2000
)
0.31
" Since repeated exposure to VCH is required for VCH-induced ovotoxicity, rodents were dosed with VCH for 5 or 10 d to observe effects on the hepatic concentration of CYP2E1 and/or associated activities."( Evaluation of hepatic cytochrome P4502E1 in the species-dependent bioactivation of 4-vinylcyclohexene.
Fontaine, SM; Hoyer, PB; Sipes, IG, 2001
)
0.54
" Mice and rats were then dosed with VCH, VCH-1,2-epoxide, or VCD for 10 days and measured for increases in hepatic microsomal CYP levels or activities."( Role of induction of specific hepatic cytochrome P450 isoforms in epoxidation of 4-vinylcyclohexene.
Fontaine, SM; Halpert, JR; Hoyer, PB; Sipes, IG, 2001
)
0.54
" Expression of mRNA encoding mEH was increased in F1 (410 +/- 5% VCH; 292 +/- 5% VCD) and F2 (1379 +/- 4% VCH; 381 +/- 11% VCD) follicles following repeated dosing with VCH or VCD."( Expression and activity of microsomal epoxide hydrolase in follicles isolated from mouse ovaries.
Cannady, EA; Christian, PJ; Dyer, CA; Hoyer, PB; Sipes, IG, 2002
)
0.31
" This study investigated expression of these isoforms in isolated ovarian fractions (F1, 25-100 microm; F2, 100-250 microm; F3, >250 microm; interstitial cells, Int) from B6C3F1 mice dosed daily (15 days; ip) with vehicle, VCH (7."( Expression and activity of cytochromes P450 2E1, 2A, and 2B in the mouse ovary: the effect of 4-vinylcyclohexene and its diepoxide metabolite.
Cannady, EA; Christian, PJ; Dyer, CA; Hoyer, PB; Sipes, IG, 2003
)
0.54
" Pregnant bcl-2 OE or WT mice were dosed (p."( Effect of bcl-2 overexpression in mice on ovotoxicity caused by 4-vinylcyclohexene.
Babus, JK; Christian, PJ; Flaws, JA; Hoyer, PB; Marion, SL; Miller, KP, 2006
)
0.57
" Twenty-eight days female CYP 2E1 +/+ and -/- mice were dosed daily (15 days; ip) with VCH, 1,2-VCM, VCD or vehicle."( Involvement of CYP 2E1 enzyme in ovotoxicity caused by 4-vinylcyclohexene and its metabolites.
Cannady, EA; Hoyer, PB; Rajapaksa, KS; Sipes, IG, 2007
)
0.59
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
cyclic olefinThe inclusive term for any cyclic hydrocarbon having any number of double bonds.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (6)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
15-lipoxygenase, partialHomo sapiens (human)Potency31.62280.012610.691788.5700AID887
AR proteinHomo sapiens (human)Potency25.11890.000221.22318,912.5098AID588515
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency22.38720.011212.4002100.0000AID1030
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency77.03710.003041.611522,387.1992AID1159552
pregnane X nuclear receptorHomo sapiens (human)Potency34.41120.005428.02631,258.9301AID1346982
thyroid hormone receptor beta isoform aHomo sapiens (human)Potency0.17780.010039.53711,122.0200AID588545
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (45)

TimeframeStudies, This Drug (%)All Drugs %
pre-19909 (20.00)18.7374
1990's14 (31.11)18.2507
2000's16 (35.56)29.6817
2010's6 (13.33)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 39.92

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index39.92 (24.57)
Research Supply Index3.89 (2.92)
Research Growth Index4.47 (4.65)
Search Engine Demand Index55.48 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (39.92)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews7 (14.58%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other41 (85.42%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]