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4-Vinylphenol

Names

[ CAS No. ]:
2628-17-3

[ Name ]:
4-Vinylphenol

[Synonym ]:
EINECS 220-103-6
4-ethenylphenol
MFCD00017593
p-Hydroxystyrene
4-vinyl phenol
para-hydroxystyrene
Phenol, 4-ethenyl-
4-Vinylphenol
p-vinylphenol
1-hydroxy-4-vinylbenzene
Phenol,4-ethenyl
4-Hydroxystyrene
Phenol,P-vinyl

Biological Activity

[Description]:

4-Vinylphenol is found in the medicinal herb Hedyotis diffusa Willd, wild rice and is also the metabolite of p-coumaric and ferulic acid by lactic acid bacteria in wine. 4-Vinylphenol induces apoptosis and inhibits blood vessels formation and suppresses invasive breast tumor growth in vivo[1].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis
Research Areas >> Cancer

[In Vitro]

4-Vinylphenol (12.5-200 µg/mL) significantly reduces cell viability in parental MDA-MB-231 cells, and the IC50 value is 109 µg/mL[1]. 4-Vinylphenol (0.15 or 0.3 µg/mL; 3 days) reduces sphere‑formation and vimentin expression on CSCs in breast cancer[1]. 4-Vinylphenol (50, 100 µg/mL; 72 hours) significantly suppresses cell proliferation in CSC-enriched MDA-MB-231 cells. 4-Vinylphenol significantly reduces ALDH1A1 expression by 50% in CSC-enriched MDA-MB-231 cells[1]. 4-Vinylphenol (100 µg/mL) significantly increases the expressions of caspase 3, likely sensitizing CSC-enriched MDAMB-231 cells to apoptosis[1].

[References]

[1]. Leung HW, et al. The natural agent 4-vinylphenol targets metastasis and stemness features in breast cancer stem-like cells. Cancer Chemother Pharmacol. 2018 Aug;82(2):185-197.

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
206.2±9.0 °C at 760 mmHg

[ Melting Point ]:
73 °C

[ Molecular Formula ]:
C8H8O

[ Molecular Weight ]:
120.148

[ Flash Point ]:
92.3±8.4 °C

[ Exact Mass ]:
120.057518

[ PSA ]:
20.23000

[ LogP ]:
2.16

[ Vapour Pressure ]:
0.2±0.4 mmHg at 25°C

[ Index of Refraction ]:
1.602

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
SN3800000
CHEMICAL NAME :
Phenol, p-vinyl-
CAS REGISTRY NUMBER :
2628-17-3
BEILSTEIN REFERENCE NO. :
0506844
LAST UPDATED :
199710
DATA ITEMS CITED :
5
MOLECULAR FORMULA :
C8-H8-O
MOLECULAR WEIGHT :
120.16
WISWESSER LINE NOTATION :
QR D1U1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration into the eye
SPECIES OBSERVED :
Rodent - rabbit
REFERENCE :
EPASR* United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. (U.S. Environmental Protection Agency, 401 M St., SW, Washington, DC 20460) History unknown. Volume(issue)/page/year: 8EHQ-1285-0579S ** ACUTE TOXICITY DATA **
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
200 mg/kg
TOXIC EFFECTS :
Skin and Appendages - corrosive (after topical exposure)
REFERENCE :
EPASR* United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. (U.S. Environmental Protection Agency, 401 M St., SW, Washington, DC 20460) History unknown. Volume(issue)/page/year: 8EHQ-1285-0579S
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Ocular
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
50 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
EPASR* United States Environmental Protection Agency, Office of Pesticides and Toxic Substances. (U.S. Environmental Protection Agency, 401 M St., SW, Washington, DC 20460) History unknown. Volume(issue)/page/year: 8EHQ-1285-0579S ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1400 mg/kg
SEX/DURATION :
female 7 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - uterus, cervix, vagina
REFERENCE :
SCIEAS Science. (American Assoc. for the Advancement of Science, 1333 H St., NW, Washington, DC 20005) V.1- 1895- Volume(issue)/page/year: 195,575,1977

Safety Information

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R36/38

[ Safety Phrases ]:
S26-S39

[ WGK Germany ]:
2

[ RTECS ]:
SN3800000

[ HS Code ]:
2907199090

Customs

[ HS Code ]: 2907199090

[ Summary ]:
2907199090 other monophenols VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%


Related Compounds