(Z)-Stilbene

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(Z)-Stilbene
Stilbene cis structure.svg
(Z)-Stilbene molecule
Names
IUPAC names
cis-1,2-Diphenylethylene
(Z)-1,2-Diphenylethene
Other names
cis-Stilbene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.010.406
EC Number 211-445-7
Properties
C14H12
Molar mass 180.25 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
Safety data sheet Oxford MSDS
R-phrases (outdated) R36 R38
S-phrases (outdated) S26 S36
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

(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.

Isomers[edit]

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 out-of-plane and prevent conjugation.[citation needed] (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.

Uses[edit]

Properties[edit]

Natural Occurrence[edit]

Many stilbene derivatives (stilbenoids) are present naturally in plants. An example is resveratrol and its cousin, pterostilbene.