(Z)-Stilbene

(Redirected from Cis-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 Edit this at Wikidata
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).
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Isomers

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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.

Uses

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Properties

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Natural occurrence

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

References

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  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.