Vetivazulene

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Vetivazulene
Vetivazulene.png
Names
Preferred IUPAC name
4,8-Dimethyl-2-(propan-2-yl)azulene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.683 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C15H18/c1-10(2)13-8-14-11(3)6-5-7-12(4)15(14)9-13/h5-10H,1-4H3 Yes check.svgY
    Key: APVKGMMYGFJZHY-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C15H18/c1-10(2)13-8-14-11(3)6-5-7-12(4)15(14)9-13/h5-10H,1-4H3
    Key: APVKGMMYGFJZHY-UHFFFAOYAH
  • c12c(cccc(c1cc(c2)C(C)C)C)C
Properties
C15H18
Molar mass 198.31 g/mol
Melting point 32 to 33 °C (90 to 91 °F; 305 to 306 K)
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

Vetivazulene is an azulene derivate obtained from vetiver oil. [1] It is a bicyclic sesquiterpene and an isomer of guaiazulene.

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In chemistry isomerization or isomerisation is the process in which a molecule, ion or molecular fragment is transformed into an isomer with a different chemical structure. Enolization is an example of isomerization, as is tautomerization. When the isomerization occurs intramolecularly it may be called a rearrangement reaction.

Azulene Chemical compound

Azulene is an organic compound and an isomer of naphthalene. Whereas naphthalene is colourless, azulene is dark blue. Two terpenoids, vetivazulene (4,8-dimethyl-2-isopropylazulene) and guaiazulene (1,4-dimethyl-7-isopropylazulene), that feature the azulene skeleton are found in nature as constituents of pigments in mushrooms, guaiac wood oil, and some marine invertebrates.

Iminium Functional group in organic chemistry

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Guaiazulene Chemical compound

Guaiazulene, also azulon or 1,4-dimethyl-7-isopropylazulene, is a dark blue crystalline hydrocarbon. A derivative of azulene, guaiazulene is a bicyclic sesquiterpene that is a constituent of some essential oils, mainly oil of guaiac and chamomile oil, which also serve as its commercial sources. Various soft corals also contain guaiazulene as a principal pigment. Its low melting point makes guaiazulene difficult to handle, in contrast to the crystalline nature of the parent azulene. The electronic structure of guaiazulene and azulene are very similar.

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Fulvalene Chemical compound

Fulvalene (bicyclopentadienylidene) is the member of the fulvalene family with the molecular formula C10H8. It is of theoretical interest as one of the simplest non-benzenoid conjugated hydrocarbons. Fulvalene is an unstable isomer of the more common benzenoid aromatic compounds naphthalene and azulene. Fulvalene consists of two 5-membered rings, each with two double bonds, joined by yet a fifth double bond. It has D2h symmetry.

The molecular formula C10H8 (molar mass: 128.17 g/mol) may refer to:

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Chamazulene Chemical compound

Chamazulene is an aromatic chemical compound with the molecular formula C14H16 found in a variety of plants including in chamomile (Matricaria chamomilla), wormwood (Artemisia absinthium), and yarrow (Achillea millefolium). It is a blue-violet derivative of azulene which is biosynthesized from the sesquiterpene matricin.

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Thermal rearrangements of aromatic hydrocarbons are considered to be unimolecular reactions that directly involve the atoms of an aromatic ring structure and require no other reagent than heat. These reactions can be categorized in two major types: one that involves a complete and permanent skeletal reorganization (isomerization), and one in which the atoms are scrambled but no net change in the aromatic ring occurs (automerization). The general reaction schemes of the two types are illustrated in Figure 1.

Spathulenol Chemical compound

Spathulenol is a tricyclic sesquiterpene alcohol which has a basic skeleton similar to the azulenes. It occurs in oregano among other plants.

Elassovalene Chemical compound

Elassovalene (2a,8b-dihydro-cyclopent[cd]azulene) is a polycyclic hydrocarbon with chemical formula C12H10, composed of one cycloheptatriene ring and two fused cyclopentene rings.

Matricin Chemical compound

Matricin is a sesquiterpene. It can be extracted from flower of chamomille. Matricin is colorless.

References

  1. Gordon, Maxwell (1 February 1952). "The Azulenes". Chemical Reviews. 50 (1): 127–200. doi:10.1021/cr60155a004.