trans-stilbene

benzene, 1,1'-(1,2-ethenediyl)bis-, (E)- (9CI)

CAS: 103-30-0 C14 H12 MW: 180.24964000

Identification

Nametrans-stilbene
IUPAC(E)-stilbene
CAS Number103-30-0
EINECS203-098-5
FDA UNII3FA7NW80A0
Molecular FormulaC14 H12
Molecular Weight180.24964000
MDL NumberMFCD00064300
Nikkaji NumberJ46.982C
Beilstein1616740
XlogP34.80 (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 SDSView
Oral/Parenteral Toxicityintraperitoneal-mouse LD50 6500 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for trans-stilbene usage levels up tonot for fragrance use.
Recommendation for trans-stilbene flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

petiveria alliacea root

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.