(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
(Z)-Stilbene molecule
Names
IUPAC name
cis-1,2-Diphenylethylene
Preferred IUPAC name
(Z)-1,2-Diphenylethene
Other names
cis-Stilbene
Identifiers
3D model (JSmol)
1616739
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.010.406
EC Number
  • 211-445-7
4380
UNII
  • InChI=1S/C14H12/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-12H/b12-11- checkY
    Key: PJANXHGTPQOBST-QXMHVHEDSA-N checkY
  • InChI=1/C14H12/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-12H/b12-11-
    Key: PJANXHGTPQOBST-QXMHVHEDBW
  • c2(\C=C/c1ccccc1)ccccc2
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:
GHS07: Exclamation mark
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).
checkY verify (what is checkY☒N ?)
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.[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.

Uses

Properties

Natural occurrence

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

References

  1. "cis-Stilbene". pubchem.ncbi.nlm.nih.gov. Retrieved 5 December 2021.
  2. 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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