(Z)-Stilbene is a diarylethene, that is, a hydrocarbon consisting of a cis ethene double bond substituted with a phenyl group on both carbon atoms of the double bond. The name stilbene was derived from the Greek word stilbos, which means shining.
Names | |
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IUPAC name
cis-1,2-Diphenylethylene
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Preferred IUPAC name
(Z)-1,2-Diphenylethene | |
Other names
cis-Stilbene
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Identifiers | |
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3D model (JSmol)
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1616739 | |
ChEBI |
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ChEMBL |
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ChemSpider |
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ECHA InfoCard | 100.010.406 |
EC Number |
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4380 | |
PubChem CID
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UNII |
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CompTox Dashboard (EPA)
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Properties | |
C14H12 | |
Molar mass | 180.250 g·mol−1 |
Appearance | Liquid |
Melting point | 5 to 6 °C (41 to 43 °F; 278 to 279 K) |
Boiling point | 307 °C (585 °F; 580 K) at 1 atm (82°C to 84°C at 0.4 mmHg) |
Practically insoluble | |
Hazards[1] | |
GHS labelling: | |
Warning | |
H315, H319 | |
P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362 | |
Safety data sheet (SDS) | Oxford MSDS |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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Stilbene exists as two possible isomers known as (E)-stilbene and (Z)-stilbene. (Z)-Stilbene is sterically hindered and less stable because the steric interactions force the aromatic rings 43° out-of-plane and prevent conjugation.[2] (Z)-Stilbene has a melting point of 5–6 °C (41–43 °F), while (E)-stilbene melts around 125 °C (257 °F), illustrating that the two compounds are quite different.
Many stilbene derivatives (stilbenoids) are present naturally in plants. An example is resveratrol and its cousin, pterostilbene.