(E)-Stilbene

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For the class of antioxidant compounds that share the same chemical skeleton see stilbenoids.

(E)-Stilbene


IUPAC name (E)-1,2-Diphenylethene
Other names (E)-Stilbene, trans-Stilbene, trans-1,2-Diphenylethylene
Identifiers
CAS number	103-30-0^Y
PubChem	638088
ChemSpider	553649^Y
ChEBI	CHEBI:36007^Y
ChEMBL	CHEMBL113028^Y
Jmol-3D images	Image 1 Image 2
SMILES c2(\C=C\c1ccccc1)ccccc2 c1ccc(cc1)/C=C/c2ccccc2
InChI InChI=1S/C14H12/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-12H/b12-11+^Y Key: PJANXHGTPQOBST-VAWYXSNFSA-N^Y 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-VAWYXSNFBV
Properties
Molecular formula	C₁₄H₁₂
Molar mass	180.25 g mol⁻¹
Appearance	Solid
Density	0.9707 g/cm³
Melting point	122-125 °C
Boiling point	305-307 °C
Solubility in water	Practically insoluble
Hazards
MSDS	External MSDS
NFPA 704	1 1 0
Flash point	>112 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

(E)-Stilbene, is a diarylethene, i.e., a hydrocarbon consisting of a trans ethene double bond substituted with a phenyl group on both carbon atoms of the double bond. The name stilbene is derived from the Greek word stilbos, which means shining.

Isomers

Stilbene exists as two possible isomers. The first is trans-1,2-diphenylethylene, called (E)-stilbene or trans-stilbene. The second is cis-1,2-diphenylethylene, called (Z)-stilbene or cis-stilbene, and 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, while (E)-stilbene melts around 125 °C, illustrating the two compounds are quite different in their physical properties.

Table 1. Vapor pressures^[1]

Isomer	Temperature, °C	Vapor pressure, kPa
cis-stilbene	100	0.199
cis-stilbene	125	0.765
cis-stilbene	150	2.51
trans-stilbene	150	0.784

Uses

Stilbene is used in manufacture of dyes and optical brighteners, and also as a phosphor and a scintillator.

Stilbene is one of the gain mediums used in dye lasers.

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

Stilbene derivatives especially E(trans) isomer have estrogenic activity so used in making non-steroidal synthetic estrogens such as Diethylstilbestrol, Fosfestrol, Dienestrol.

Chemistry

Stilbene will typically have the chemistry of a conjugated alkene, i.e., a diarylethene.

Trans- and cis-stilbene can interconvert under the influence of light.

References

↑ Lide, David (1995). CRC Handbook of Chemistry and Physics, 76th edition. USA: CRC Press, Inc. pp. 6–107. ISBN 0-8493-0476-8.

External links

(E)-Stilbene on ChemExper

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