trans-stilbene
benzene, 1,1'-(1,2-ethenediyl)bis-, (E)- (9CI)
Identification
| Name | trans-stilbene |
| IUPAC | (E)-stilbene |
| CAS Number | 103-30-0 |
| EINECS | 203-098-5 |
| FDA UNII | 3FA7NW80A0 |
| Molecular Formula | C14 H12 |
| Molecular Weight | 180.24964000 |
| MDL Number | MFCD00064300 |
| Nikkaji Number | J46.982C |
| Beilstein | 1616740 |
| XlogP3 | 4.80 (est) |
Regulatory
Physical Properties
| Appearance | white crystals (est) |
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Specific Gravity | 0.97000 @ 25.00 °C. |
| Melting Point | 123.00 °C. @ 760.00 mm Hg |
| Boiling Point | 307.00 °C. @ 760.00 mm Hg |
| Flash Point | 263.00 °F. TCC ( 128.50 °C. ) (est) |
| logP (o/w) | 4.810 |
| Soluble in | water, 0.29 mg/L @ 25 °C (exp) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | intraperitoneal-mouse LD50 6500 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for trans-stilbene usage levels up to | not for fragrance use. |
| Recommendation for trans-stilbene flavor usage levels up to | not for flavor use. |
Potential Uses
Natural Occurrence
Synonyms
benzene, 1,1'- (1,2-ethenediyl)bis-, (E)-
benzene, 1,1'-(1,2-ethenediyl)bis-, (E)- (9CI)
benzene, 1,1'-(1E)-1,2-ethenediylbis-
benzene, 1,1'-[(E)-1,2-ethenediyl]bis-
trans-
bibenzylidene
dibenzal, (E)-
dibenzylidne, (E)-
(E)-1,2-
diphenyl ethylene
trans-1,2-
diphenyl ethylene
(E)-1,2-
diphenylethene
1,trans-2-
diphenylethene
trans-
diphenylethene
trans-1,2-
diphenylethene
1,2-
diphenylethene, (E)-
(E)-1,2-
diphenylethylene
1,trans-2-
diphenylethylene
trans-1,2-
diphenylethylene
trans-a,b-
diphenylethylene
1,2-
diphenylethylene (trans)
1,2-
diphenylethylene, trans
1,1'-(1,2-
ethanediyl)bis(benzene), (E)-
1,1'-(1,2-
ethanediyl)bis[benzene], trans
1,1'-(E)-
ethen-1,2-diyldibenzol
1,1'-[(E)-1,2-
ethendiyl]dibenzol
(E)-1,1'-(1,2-
ethene diyl) bisbenzene
1,1'-[(1E)-
ethene-1,2-diyl]dibenzene
1,1'-(E)-
ethene-1,2-diyldibenzene
(1,2-
ethenediyl)-1,1'-bisbenzene, (E)-
(E)-1,1'-(1,2-
ethenediyl)bisbenzene
1,1'-[(E)-1,2-
ethenediyl]dibenzene
((E)-2-
phenylethenyl)benzene
[(E)-2-
phenylethenyl]benzene
((1E)-2-
phenylvinyl)benzene
(E)-
stilbene
stilbene, (E)-
PubMed:
Toward an understanding of the role of a catechol moiety in cancer chemoprevention: The case of copper- and o-quinone-dependent Nrf2 activation by a catechol-type resveratrol analog.
PubMed:
Resveratrol and cardiovascular health--promising therapeutic or hopeless illusion?
PubMed:
Preparation of chitosan-TPP microspheres as resveratrol carriers.
PubMed:
Resveratrol down-regulates a glutamate-induced tissue plasminogen activator via Erk and AMPK/mTOR pathways in rat primary cortical neurons.
PubMed:
Stilbene analogs of resveratrol improve insulin resistance through activation of AMPK.
PubMed:
In vivo and in vitro metabolism of trans-resveratrol by human gut microbiota.
PubMed:
Resveratrol affects differently rat liver and brain mitochondrial bioenergetics and oxidative stress in vitro: investigation of the role of gender.
PubMed:
Anti-obesity effect of resveratrol-amplified grape skin extracts on 3T3-L1 adipocytes differentiation.
PubMed:
Piceatannol suppresses breast cancer cell invasion through the inhibition of MMP-9: involvement of PI3K/AKT and NF-κB pathways.
PubMed:
A combination of resveratrol and melatonin exerts chemopreventive effects in N-methyl-N-nitrosourea-induced rat mammary carcinogenesis.
PubMed:
3,4,4'-Trihydroxy-trans-stilbene, an analogue of resveratrol, is a potent antioxidant and cytotoxic agent.
PubMed:
Resveratrol derivatives as promising chemopreventive agents with improved potency and selectivity.
PubMed:
Structure-activity relationship of resveratrol and its analogue, 4,4'-dihydroxy-trans-stilbene, toward the endothelin axis in human endothelial cells.
PubMed:
Extract of passion fruit (Passiflora edulis) seed containing high amounts of piceatannol inhibits melanogenesis and promotes collagen synthesis.
PubMed:
Evaluation of anti-invasion effect of resveratrol and related methoxy analogues on human hepatocarcinoma cells.
PubMed:
Physicochemical study of the complexation of pterostilbene by natural and modified cyclodextrins.
PubMed:
Mechanisms of apoptotic effects induced by resveratrol, dibenzoylmethane, and their analogues on human lung carcinoma cells.
PubMed:
Resveratrol analog-3,5,4'-trimethoxy-trans-stilbene inhibits invasion of human lung adenocarcinoma cells by suppressing the MAPK pathway and decreasing matrix metalloproteinase-2 expression.
PubMed:
Structure-activity relationship and mechanism of the tocopherol-regenerating activity of resveratrol and its analogues.
PubMed:
Thiomethylstilbenes as inhibitors of CYP1A1, CYP1A2 and CYP1B1 activities.
PubMed:
The grape and wine constituent piceatannol inhibits proliferation of human bladder cancer cells via blocking cell cycle progression and inducing Fas/membrane bound Fas ligand-mediated apoptotic pathway.
PubMed:
Antidiabetic properties of 2,5-dihydroxy-4,3'-di(beta-D-glucopyranosyloxy)-trans-stilbene from mulberry (Morus bombycis koidzumi) root in streptozotocin-induced diabetic rats.
PubMed:
A pilot study of evaluation of the antioxidative activity of resveratrol and its analogue in a 6-month feeding test in young adult mice.
PubMed:
Myricetin down-regulates phorbol ester-induced cyclooxygenase-2 expression in mouse epidermal cells by blocking activation of nuclear factor kappa B.
PubMed:
Oncogenicity evaluation of resveratrol in p53(+/-) (p53 knockout) mice.
PubMed:
Antioxidant activity and inhibition of alpha-glucosidase by trans-resveratrol, piceid, and a novel trans-stilbene from the roots of Israeli Rumex bucephalophorus L.
PubMed:
Structural basis for DNA-cleaving activity of resveratrol in the presence of Cu(II).
PubMed:
Molecular mechanisms of the chemopreventive effects of resveratrol and its analogs in carcinogenesis.
PubMed:
Metabolism and bioavailability of trans-resveratrol.
PubMed:
A methoxy derivative of resveratrol analogue selectively induced activation of the mitochondrial apoptotic pathway in transformed fibroblasts.
PubMed:
Structural basis for antioxidant activity of trans-resveratrol: ab initio calculations and crystal and molecular structure.
PubMed:
The grape and wine polyphenol piceatannol is a potent inducer of apoptosis in human SK-Mel-28 melanoma cells.
PubMed:
Grape polyphenol resveratrol and the related molecule 4-hydroxystilbene induce growth inhibition, apoptosis, S-phase arrest, and upregulation of cyclins A, E, and B1 in human SK-Mel-28 melanoma cells.
PubMed:
Synthesis and biological evaluation of resveratrol and analogues as apoptosis-inducing agents.
PubMed:
Resveratrol, a natural product derived from grapes, is a new inducer of differentiation in human myeloid leukemias.
PubMed:
Mechanism of cardioprotection by resveratrol, a phenolic antioxidant present in red wine (Review).
PubMed:
Evaluation of resveratrol derivatives as potential antioxidants and identification of a reaction product of resveratrol and 2, 2-diphenyl-1-picryhydrazyl radical.
PubMed:
Fungitoxicity of chemical analogs with heartwood toxins.
PubMed:
Epoxide-metabolizing enzymes in mammary gland and liver from BALB/c mice and effects of inducers on enzyme activity.