(Z)-Stilbene

(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.

(Z)-Stilbene
Names
IUPAC names
cis-1,2-Diphenylethylene
(Z)-1,2-Diphenylethene
Other names
cis-Stilbene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.010.406
EC Number
  • 211-445-7
UNII
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
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R-phrases (outdated) R36 R38
S-phrases (outdated) S26 S36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

Isomers

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.[1] (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

Properties

Natural Occurrence

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

References

  1. Eliel, Ernest L.; Wilen, Samuel H. (1994). Stereochemistry of Organic Compounds. John Wiley and Sons. pp. 566–567. ISBN 0-471-01670-5.
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