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비닐 시클로헥센 디옥사이드

Vinyl cyclohexene dioxide

HCID 7833
새 노트새 반응견적 요청하기
인쇄 미리보기
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
106-87-6
표준 SMILES
C1CC2OC2CC1C1CO1
InChIKey
OECTYKWYRCHAKR-UHFFFAOYSA-N
분자식
C8H12O2
평균 분자량
140.18 g/mol
단동위원소 질량
140.08372962

개요

Vinyl cyclohexene dioxide (4-vinyl-1-cyclohexene diepoxide) can cause cancer according to The National Toxicology Program. It can cause female reproductive toxicity according to an independent committee of scientific and health experts. It can cause male reproductive toxicity according to California Labor Code.

이름 및 식별자

우선 이름
Vinyl cyclohexene dioxide
IUPAC
3-(oxiran-2-yl)-7-oxabicyclo[4.1.0]heptane
현지명
비닐 시클로헥센 디옥사이드
영어명
4-Vinylcyclohexene dioxide
분자식
C8H12O2
분자량
140.18

이름 및 동의어

4-Vinylcyclohexene dioxide106-87-64-Vinyl-1-cyclohexene dioxide3-(oxiran-2-yl)-7-oxabicyclo[4.1.0]heptane4-Vinylcyclohexene diepoxide4-Vinyl-1-cyclohexene diepoxideVINYLCYCLOHEXENE DIOXIDEVinyl cyclohexene dioxideVinyl cyclohexene diepoxide1-Vinyl-3-cyclohexene dioxideChissonox 2061-Ethyleneoxy-3,4-epoxycyclohexane
이름 더 보기
비닐시클로헥센디옥사이드비닐시클로헥센디옥사이드비닐사이클로헥센 다이옥사이드VCD7-oxabicyclo[4.1.0]heptane,3-oxiranyl-VCHDep-206ERL 4206
7-Oxabicyclo[4.1.0]heptane, 3-oxiranyl-1-Epoxyethyl-3,4-epoxycyclohexaneUnox epoxide 2064-Vinyl-1,2-cyclohexene diepoxideChissonox 206 monomerVinylcyclohexene DiepoxideErla-2270Erla-2271

데이터베이스 식별자

CAS
106-87-6、25086-25-3
PubChem CID
7833
DTXSID
DTXSID0020604
ChEMBL
CHEMBL1734307
ChEBI
CHEBI:59001
UNII
596C064IG4
EC Number
203-437-7
Nikkaji
J65.676C

물성

구조 계산 물성

XLogP
0.8
극성 표면적
25.1 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
2
회전 가능 결합 수
1
무거운 원자 수
10
형식 전하
0
복잡도
157

실험 및 물리화학적 성질

Chemical ClassesCarcinogens
PolymersPlastics & Rubber -> Epoxides
LogP · 2건

1.3

0.44

Density · 6건

1.0986 at 68 °F (NTP, 1992) - Denser than water; will sink

1.0986 @ 20 °C/20 °C

Relative density (water = 1): 1.10

1.099

1.0966 @ 20°C

1.10

Viscosity7.77 CP @ 20 °C
Color/Form · 2건

COLORLESS LIQUID

Colorless liquid.

Solubility · 4건

50 to 100 mg/mL at 72 °F (NTP, 1992)

SOL IN WATER

Solubility in water, g/100ml at 20 °C: 18.3

High

Flash Point · 5건

230 °F (NTP, 1992)

230 °F

110 °C o.c.

230 °F (open cup)

(oc) 230 °F

Endocrine DisruptorsPotential endocrine disrupting compound
Boiling Point · 6건

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P264, P270, P271, P280, P301+P317, P304+P340, P316, P318, P321, P330, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H301 (95.1%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P318, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

유해성 정보

Regulatory Information · 4건

Chemical: 7-Oxabicyclo[4.1.0]heptane, 3-oxiranyl-

Hazard Traits - Carcinogenicity; Reproductive Toxicity

Vinyl cyclohexene dioxide: HSNO Approval: HSR003101 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - Epoxidised cycloaliphatic olefins: Human health tier II assessment
DOT LabelPoison
Fire Hazards · 2건

This chemical is combustible. (NTP, 1992)

Combustible. Risk of fire and explosion on contact with acids or bases.

Fire PotentialSlight, when exposed to heat or flame.
Health HazardsExcerpt from NIOSH Pocket Guide for Vinyl cyclohexene dioxide:
Hazards SummaryA potential skin sensitizer; [HSDB] VCD causes male and female reproductive damage in high-dose animal studies. [ACGIH] May cause respiratory tract irritation and pulmonary edema; May cause kidney injury; [ICSC]

화학 및 산업

약리 정보

Metabolism/Metabolites · 4건

In vitro studies with rabbit liver microsomal preparations showed that 4-vinyl-1-cyclohexene diepoxide can be metabolized to monoepoxymonoglycols, 1,2-hydroxy-4-vinylcyclohexane oxide, and 4-(1',2'-dihydroxyethyl)-1-cyclohexane oxide. Formation of these products is catalyzed by epoxide hydrolase. Conjugation with glutathione is another pathway for metabolism of 4-vinyl-1- cyclohexene. Depletion of reduced glutathione /was reported/ in the liver of mice given ip injections of 500 mg/kg 4-vinyl-1-cyclohexene diepoxide.

Carcinogenicity studies have shown that chronic administration of 4-vinylcyclohexene will induce ovarian tumors in B6C3F1 mice but not F-344 rats. This occurs because the blood level of the ovotoxic 4-vinylcyclohexene metabolite, 4-vinylcyclohexene-1,2-epoxide, is dramatically higher in 4-vinylcyclohexene treated female mice compared with rats. This species difference in 4-vinylcyclohexene epoxidation is also reflected in the rate of 4-vinylcyclohexene metabolism by hepatic microsomes (female mouse greater than female rat). The present study assessed the ability of microsomes obtained from human liver to metabolize 4-vinylcyclohexene to epoxides since humans are exposed to 4-vinylcyclohexene in certain occupational settings. The production of 4-vinylcyclohexene-1,2-epoxide and 4-vinylcyclohexene-7,8-epoxide from 4-vinylcyclohexene (1 mM) by human hepatic microsomes was linear with respect to microsomal protein concentration (0.25-1.0 mg/ml) and incubation time (5-20 min). 4-Vinylcyclohexene-1,2-epoxide was the major metabolite, while the rate 4-vinylcyclohexene-7,8-epoxide formation was about 6 fold lower and in some cases was below the limit of detection. There was no dramatic difference in the rate of 4-vinylcyclohexene epoxidation by hepatic microsomes obtained from male and female humans. The rate of 4-vinylcyclohexene-1,2-epoxide formation by female human hepatic microsomes was 0.71 + or - 0.35 nmol/mg microsomal protein/min (n = 4). This is 13 and 2 fold lower than the rate of 4-vinylcyclohexene-1,2-epoxide formation by female mouse and rat hepatic microsomes, respectively.

4-Vinylcyclohexene is a chemical to which humans are exposed in the rubber industry. A chronic carcinogenicity bioassay conducted by the NTP showed that oral administration of 4-vinylcyclohexene induced tumors in the ovaries of mice but not in those of rats. The hypothesis tested was that the species and organ specificity of 4-vinylcyclohexene toxicity was due to differences in the disposition of 4-vinylcyclohexene between the female rat and mouse. Therefore, the disposition of a single oral dose of 400 mg/kg (14)C 4-vinylcyclohexene was studied in female B6C3F1 mice and Fischer 344 rats. Mice eliminated greater than 95% of the dose in 24 hr, whereas rats required 48 hr to eliminate greater than 95% of the dose. The major routes of excretion of (14)C 4-vinylcyclohexene derived radioactivity were in the urine (50-60%) and expired air (30-40%). No evidence was obtained to indicate that the ovaries of either species retained 4-vinylcyclohexene as a parent cmpd or as radioactive equivalents. A dramatic difference was observed between the rat and mouse in the appearance of a monoepoxide of 4-vinylcyclohexene in blood from 0.5 to 6 hr after 4-vinylcyclohexene administration (800 mg/kg, ip). 4-Vinylcyclohexene-1,2-epoxide was present in the blood of mice with the highest concentration at 2 hr (41 nmol/ml). The blood concentration of 4-vinylcyclohexene-1,2-epoxide in rats was less than 2.5 nmol/ml at all times examined. 4-Vinylcyclohexene-7,8-epoxide was not present in the blood of either species at the level of detection. These findings were supported by in vitro studies of 4-vinylcyclohexene epoxidation by liver microsomes. The rate of epoxidation of 4-vinylcyclohexene (1 mM) to 4-vinylcyclohexene-1,2-epoxide was 6.5 fold greater in mouse liver microsomes than that in rat liver microsomes. The species difference in the rate of epoxide formation by the liver may be an important factor in the species difference in susceptibility to 4-vinylcyclohexene induced ovarian tumors.

관련 반응

3건
반응 기록 만들기
HRID 926344 반응식
HRID 926344반응물로uspto-grants-2016_03
HRID 983361 반응식
HRID 983361반응물로uspto-grants-2005_03
HRID 1627404 반응식
HRID 1627404반응물로uspto-grants-2014_07

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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441 °F at 760 mmHg (NTP, 1992)

227 °C @ 760 MM HG

227 °C

441 °F

227 °C @760 [mm Hg]

441 °F

Melting Point · 4건

less than -67 °F (NTP, 1992)

LESS THAN -55 °C

<-67 °F

-164 °F

Vapor Density · 3건

4.07 (NTP, 1992) - Heavier than air; will sink (Relative to Air)

Relative vapor density (air = 1): 4.8

4.07

물리화학적 성질

녹는점
-55 °C · -55°C
끓는 점
230 · 230-232 °C(lit.)
밀도
1.094 g/mL · 1.094 g/mL at 25 °C(lit.)
굴절률
20 · n20/D 1.477(lit.)
인화점
225 °F · 225 °F
저장 조건
2 · under inert gas (nitrogen or Argon) at 2-8°C
물리적 상태
Colorless or pale yellow liquid
색상
Colorless to light yellow
수용성
154.7 g/L · 154.7g/L(20℃)
BRN
106071 · 106071
안정성
안정적인. 타기 쉬운. 강한 산화제, 알코올, 아민 및 활성 수소를 함유한 기타 화합물과 호환되지 않습니다. 물에서 천천히 가수분해됩니다.
InChI
InChI=1S/C8H12O2/c1-2-6-7(10-6)3-5(1)8-4-9-8/h5-8H,1-4H2
InChIKey
OECTYKWYRCHAKR-UHFFFAOYSA-N
SMILES
C12C(O1)CCC(C1CO1)C2
EPA
4 · 4-Vinylcyclohexene diepoxide (106-87-6)

화학적 성질

colourless liquid. Combustible.

Reactive GroupEpoxides
EC ClassificationSymbol: T; R: 23/24/25-68; S: (1/2)-23-24-45
UN ClassificationUN Hazard Class: 6.1
Special Reports · 2건

National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. 4-Vinyl-1-cyclohexene Diepoxide (106-87-6) is listed as reasonably anticipated to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s187vch.pdf]

NTP TR No 362; Route: skin paint; Species: rats and mice. NTIS No PB90219957/AS.[NTP; Division of Toxicology Research and Testing; Management Status Report; 07/22/92; p.27]

TSCA RequirementsSection 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble of the 51 FR 41329.

안전 및 보호

Fire Fighting · 2건

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)

Use water spray, powder, alcohol-resistant foam, carbon dioxide.

First Aid Measures · 4건

Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Refer for medical attention .

First Aid · 2건

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

(General first aid procedures)

Safe StorageSeparated from food and feedstuffs, alcohols, amines and other active hydrogen compounds. Dry. Ventilation along the floor.
Fire Fighting ProceduresTo fight fire: Water, foam, dry chemical.
Nonfire Spill Response · 1건

SMALL SPILLS AND LEAKAGE: If you should spill this chemical, use absorbent paper to pick up all liquid spill material. Seal the absorbent paper, as well as any of your clothing which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Wash any surfaces you may have contaminated with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Spillage DisposalPersonal protection: complete protective clothing including self-contained breathing apparatus. Ventilation. Collect leaking liquid in sealable containers. Wash away remainder with plenty of water.
Preventive Measures · 2건

The worker should immediately wash the skin when it becomes contaminated.

Work clothing that becomes wet or significantly contaminated should be removed and replaced.

Isolation and EvacuationExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Eye PreventionWear face shield or eye protection in combination with breathing protection.
Fire PreventionNO open flames.
Inhalation RiskA harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C.

독성 정보

Cancer Sites[in animals: skin tumors]
Target OrgansEyes, skin, respiratory system, blood, thymus, reproductive system
Adverse EffectsNephrotoxin - The chemical is potentially toxic to the kidneys in the occupational setting.
Exposure Routes · 2건

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

inhalation, skin absorption, ingestion, skin and/or eye contact

Signs and Symptoms · 5건

Cough. Laboured breathing. Sore throat.

MAY BE ABSORBED! Dry skin. Redness. Pain. Swelling.

Redness. Pain.

See Inhalation.

In Animals: irritation eyes, skin, respiratory system; testicular atrophy; leukopenia (reduced blood leukocytes), necrosis thymus; skin sensitization; [potential occupational carcinogen]

Ongoing Test Status · 1건

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=106-87-6]

Human Toxicity Excerpts · 5건

HUMAN EXPERIENCE INDICATES THAT IT IS MILD TO MODERATE SKIN IRRITANT ... . ONE CASE OF SEVERE VESICULATION OF SKIN OF BOTH FEET WHEN WORKER WORE SHOES PREVIOUSLY CONTAMINATED WITH THIS COMPD.

TOXIC BY INGESTION & SKIN ABSORPTION. STRONG IRRITANT TO SKIN & TISSUE.

EYE INJURY IS CONSIDERED TO BE DEFINITE HAZARD. IF VAPOR PRESSURE OF 0.1 MM HG AT 20 °C IS CORRECT ... RISK BY INHALATION IS CONSIDERED TO BE SLIGHT. BECAUSE OF VERY LIMITED ... DATA & BECAUSE OF DEMONSTRATED CARCINOGENICITY WHEN ... APPLIED TO SKIN OF MOUSE, EXTREME CAUTION SHOULD BE EXERCISED IN USE OF THIS DIEPOXIDE.

Allergic contact dermatitis occurred in an electron microscopist after exposure to the cycloaliphatic epoxy, vinyl cyclohexane diepoxide. Cycloaliphatic epoxies are not based on the diglycidyl ether of bisphenol A, presently the epoxy of greatest commercial usage. Latex or polyvinyl chloride gloves did not protect the reported patient from precutaneous absorption and elicitation of allergic dermatitis.

A study of occupational exposure to sensitizing chemicals was conducted. The study was initiated because of numerous complaints of eye, nasal, skin, and respiratory irritation among workers at an industrial facility. Serum samples were obtained from 31 workers and assayed for immunoglobulin G and immunoglobulin E to an unspecified number of chemicals. An enzyme linked immunosorbent assay technique was used to detect the antibodies. Immunoglobulin G and immunoglobulin E antibodies against four chemicals were found: an aliphatic diisocyanate, 4-vinylcyclohexene-dioxide, trimellitic anhydride, and an unknown substance which was a component of n-octyl-n-decyl-trimellitate. The presence or absence of antibodies could not be correlated with the presence or absence of symptoms; however, the highest incidence of symptoms occurred in workers who were classified as having the highest exposures. It was noted that trimellitic anhydride is not known to be present at the facility. The source of the trimellitic anhydride response is not known. It was concluded that there is no occupational allergic disease in the worker population. The lack of correlation between the antibody responses and symptoms suggests that an immunologic factor is not the cause of the reported symptoms. The symptoms are more likely to be due to irritant nonimmunological reactions.

Carcinogen Classification · 6건

4-Vinylcyclohexene diepoxide

Group 2B: Possibly carcinogenic to humans

Volume Sup 7: Overall Evaluations of Carcinogenicity: An Updating of IARC Monographs Volumes 1 to 42, 1987; 440 pages; ISBN 92-832-1411-0 (out of print)

1994

1994

4-Vinyl-1-Cyclohexene Diepoxide

Non-Human Toxicity Excerpts · 5건

20 REPEATED SKIN APPLICATIONS TO RABBITS CAUSES SEVERE TO EXTREME IRRITATION.

REPEATED SKIN APPLICATIONS OF 16 MG OF A COMMERCIAL SAMPLE OF /VINYLCYCLOHEXENE DIOXIDE/ ... IN ACETONE 5 TIMES WEEKLY FOR 12 MO ... SKIN TUMORS IN 11/20 MALE ALBINO MICE; 9 ... SQUAMOUS CELL CARCINOMAS &/OR SARCOMAS. ... 1/20 & 4/18 C57B1 OR C3H MICE DEVELOPED SKIN TUMORS AFTER ... 10% SOLN IN ACETONE & TOTAL DOSES OF 70 & 78 MG (CONTROL DATA ... GIVEN FOR NEITHER OF ABOVE STUDIES).

OF 30 8 WK OLD MALE SWISS ICR/HA MICE PAINTED ON CLIPPED DORSAL SKIN WITH 0.1 MLOF A 10% SOLN /OF VINYLCYCLOHEXENEDIOXIDE/ IN BENZENE THRICE WEEKLY, 14 DEVELOPED SKIN TUMORS; 9 ... HAD SQUAMOUS CELL CARCINOMAS; MEAN SURVIVAL TIME WAS 326 DAYS. AMONG 150 BENZENE-TREATED MICE, SKIN TUMORS ... IN 11, 1 ... SQUAMOUS-CELL ... .

/VINYLCYCLOHEXENE DIOXIDE/ CAUSES ACUTE RESP TRACT IRRITATION & CONGESTION OF LUNGS. IT PRODUCES REDNESS & SWELLING COMPATIBLE WITH 1ST DEG BURN ON CLIPPED SKIN OF RABBITS. TREATED RATS SHOWED FOCAL NECROSIS OF THYMUS, & LEUKOCYTE COUNT FELL BY MORE THAN 60% DURING 1ST 4 DAYS. ... TESTICULAR ATROPHY IN SOME ... ANIMALS ... .

For more Non-Human Toxicity Excerpts (Complete) data for VINYLCYCLOHEXENE DIOXIDE (20 total), please visit the HSDB record page.

Evidence for Carcinogenicity · 3건

Evaluation: There is inadequate evidence in humans for the carcinogenicity of 4-vinylcyclohexene diepoxide. There is sufficient evidence in experimental animals for the carcinogenicity of 4-vinylcyclohexene diepoxide. Overall evaluation: 4-Vinylcyclohexene diepoxide is possibly carcinogenic to humans (Group 2B).

A3; Confirmed animal carcinogen with unknown relevance to humans.

4-Vinyl-1-cyclohexene Diepoxide: reasonably anticipated to be a human carcinogen.

National Toxicology Program Studies · 3건

Two-year studies were conducted by administrating 4-vinyl-1- cyclohexene diepoxide in acetone by dermal application, 5 days per week to groups of 60 rats of each sex at 0, 15, or 30 mg/animal. Groups of 60 mice of each sex were administered 0, 2.5, 5, or 10 mg/animal on the same schedule for 103 weeks. None of the doses selected had produced ulceration of skin in 13 week studies. ... In general, the body weights and survival were lower in mid and high dose groups than in vehicle controls. The survival was lower in exposed groups, primarily because of neoplasms (survival at week 105 male rats: vehicle control, 7/50; low dose, 8/50; high dose, 4/50; female rats: 27/50; 23/50; 15/50; male mice; vehicle control 38/50; low dose, 35/50; mid dose, 4/50; high dose, 0/50; female mice; 30/50; 15/50; 0/50). All high dose male mice died by week 83; the 10 surviving high dose female mice were killed during week 85. ... Acanthosis and sebaceous gland hypertrophy of skin from the scapula or back were observed at substantially increased incidences in exposed male and female rats. Squamous cell papillomas in male rats and squamous cell carcinomas in male and female rats were observed only in exposed rats (squamous cell carcinomas--male: vehicle control 0/50; low dose 33/50; high dose, 36/50; female: 0/50; 16/50). The incidences of basal celladenomas or carcinomas (combined) were increased (male: 0/50; 1/50; 6/50; female: 0/50; 3/50; 4/50). ... For exposed mice, acanthosis, hyperkeratosis, and necrotizing inflammation of the skin were observed over the scapula or back. Squamous cell carcinomas were found only in exposed mice (male: vehicle control, 0/50; low dose, 14/50; mid dose, 39/50; high dose, 42/50; female: 0/50; 6/50; 37/50; 41/50). ... Follicular atrophy and tubular hyperplasia of the ovary in female mice were increased (atrophy: 12/50; 43/49; 42/49; 47/50; tubular hyperplasia: 5/50; 35/49; 34/50). Mid and high dose females had benign or malignant granulosa cell tumors (0/50; 0/49; 7/49; 12/50) and benign mixed tumors (0/50; 0/49; 11/49; 6/50). The combined incidences of luteomas, granulosa cell tumors benign mixed tumors, or malignant granulosa cell tumors in mid and high dose female mice were increased (1/50; 0/49; 17/49; 18/50). The incidences of alveolar/bronchiolar adenomas or carcinomas (combined) in exposed female mice were marginally increased (4/50; 9/50; 11/50; 7/50). ... Under the conditions of these 2 year dermal studies, there was clear evidence of carcinogenic activity of 4-vinyl-1-cyclohexene diepoxide for male and female F344/N rats as shown by squamous cell and basal cell neoplasms of the skin. There was clear evidence of carcinogenic activity of 4-vinyl-1- cyclohexene diepoxide for male and female B6C3F1 mice, as shown by squamous cell carcinomas of the skin in males and squamous cell carcinomas of the skin and ovarian neoplasms in females; increased incidences of lung neoplasms in females may also have been related to chemical application.

Toxicity DataLC50 (rat) = 800 ppm/4h

규제 정보

TSCA RequirementsSection 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble of the 51 FR 41329.

안전 데이터

OEB
A
OEL
TWA: 10 ppm (60 mg/m3) [skin]
wgk
1
tsca
TSCA listed
rtecs
RN8640000
ridadr
UN 2810 6.1/PG 3
risk_code
23/24/25-68/20/21/22-68
hazard_code
T
safety_code
23-24-45
포장분류
III
위험 등급
6.1(b)
기존화학 물질
KE-27558
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 4 OralCarc. 1BMuta. 2Repr. 1B
스토리지 클래스
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
유해 물질 데이터
106-87-6(Hazardous Substances Data)

VCH-diepoxide is a known human metabolite of 1,2-Epoxy-4-vinylcyclohexane and Epoxy-4-vinylcyclohexene.

MeSH Pharmacological ClassificationSubstances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included.
Absorption, Distribution and Excretion · 1건

4-Vinyl-1-cyclohexene diepoxide is absorbed by rodents exposed dermally orally, or by inhalation. ... Rats and mice received 0.1 ml and 0.01 ml, respectively, of dose mixtures containing 500 mg/ml (200 uc/ml) [ethylene-(14)C] 4-vinyl-1-cyclohexene diepoxide in acetone. The preliminary results indicate that 30% of the dose applied to the skin is absorbed over a 24 hr period for both rats and mice; only 1%-3% of the dose remained on the skin at the site of application. By 24 hr, 70%-80% of the absorbed dose had been eliminated from the body, virtually all in the urine. The radioactivity remaining in the body was distributed over a number of tissues, with no tissue containing more than 1% of the applied dose. The liver, muscle, and adipose tissue, however, contained 0.5%-1.6% and 1.2%-2.9% of the absorbed dose in rat and mouse tissue, respectively. Tissue to blood ratios ranged from 0.3 to 1.5 in rats and from 0.8 to 2.8 in mice.

용도 및 제조

Uses · 4건

Used in the plastics industry to manufacture polymers and other organic chemicals; [ACGIH]

POLYMERS; ORGANIC SYNTHESIS

CHEM INT FOR CONDENSATION WITH DICARBOXYLIC ACIDS.

... IS USED AS REACTIVE DILUENT FOR OTHER DIEPOXIDES & FOR EPOXY RESINS DERIVED FROM BISPHENOL-A & EPICHLOROHYDRIN.

Methods of ManufacturingONE GRADE OF 1-EPOXYETHYL-3,4-EPOXYCYCLOHEXENE AVAIL IN US HAS EPOXY EQUIV OF 74-78. ... CAN BE PREPARED BY PERACETIC ACID EPOXIDIZATION OF 4-VINYLCYCLOHEXANE.
General Manufacturing Information · 2건

7-Oxabicyclo[4.1.0]heptane, 3-(2-oxiranyl)-: ACTIVE

IT HAS BEEN PROPOSED FOR USE AS CHEM INTERMEDIATE (EG, FOR CONDENSATION WITH DICARBOXYLIC ACIDS) & AS MONOMER (EG, FOR PREPN OF POLYGLYCOLS CONTAINING UNREACTED EPOXY GROUPS OR FOR HOMO-POLYMERIZATION TO 3-DIMENSIONAL RESIN).

응용 분야

용도Vinylcyclohexene dioxide (VCD) is used to study toxicity as an ovotoxin,and it's also used to understand its mechanisms of toxicity towards ovarian follicles and effects on epithelial differentiation.

일반 설명Clear colorless liquid. Sets to glass at -67°F. Faint olefinic odor.

제조 방법

생산 방법VCHD is manufactured by epoxidation of 4-vinylcyclohexene with peroxyacetic acid .

상·하류 제품 정보

상류 원료

과벤조산아세토나이트릴IRON(III) PERCHLORATE HYDRATE1,3-부타디엔사이클로헥세인톨루엔과산화아세트산클로로포름부탄1,10-페난트롤린(1수화물)4-비닐시클로헥센도데실벤젠설포닉산산화구리(Ⅰ)탄산나트륨(경회)

추가 설명

정의ChEBI: The diepoxide of 4-vinylcyclohexene.

The immunotoxic effects of 4-vinyl-1-cyclohexene diepoxide were studied in male B6C3F1 mice after a 5 day dermal exposure at doses ranging from 2.5 to 10 mg/mouse/day. 4-Vinyl-1-cyclohexene diepoxide was immunosuppressive at 10 mg/mouse and, to a lesser extent, at 5 mg/mouse, as indicated by a decrease in peripheral lymphocytes and the in vitro lymphoproliferative response to phytohemagglutinin and concanavalin A in the high dose group and suppression of the antibody plaque-forming-cell response in the 5 and 10 mg/mouse groups.

4-Vinyl-1-cyclohexene diepoxide was mutagenic in Salmonella typhimurium strains TA98, TA100, and TA1535 with and without exogenous metabolic activation; the compound was equivocally mutagenic in strain TA1537 without S9 but gave a positive response in the presence of activation. 4-Vinyl-1-cyclohexene diepoxide induced resistance to trifluorothymidine in mouse L5178Y/TK cells without exogenous metabolic activation; it was not tested with activation. 4-Vinyl-1-cyclohexene diepoxide induced sister chromatid exchanges and chromosomal aberrations in Chinese hamster ovary cells in the presence and absence of exogenous metabolic activation.