Umbellulone
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IUPAC name
4-Methyl-1-(propan-2-yl)bicyclo[3.1.0]hex-3-en-2-one
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| Other names
Thujenone; Thujen-2-one; Umbellulon
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3D model (JSmol)
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PubChem CID
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| Properties | |
| C10H14O | |
| Molar mass | 150.22 g·mol−1 |
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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 | |
Umbellulone is a headache-inducing monoterpene ketone found in the leaves of the tree Umbellularia californica, sometimes known as the "headache tree".
It is hypothesized to cause headaches by influencing the trigeminovascular system via TRPA1.
The Umbellularia californica is a tree native to the coastal forest of California.
Menzies was the first to collect the oil at the end of the 18th century. In 1826 this tree was classified as a laurel, Laurus regia, by Douglass. He probably intended to indicate the beauty and splendor of the tree.
In 1833 the tree got another classification by Hooker and Arnott, Tetranthera californica. Shortly after that the present name was given by Nuttal, Umbellularia californica. In 1875 Heaney obtained a colorless liquid (Oreodaphenol) via fractionation under reduced pressure. This oil of the California laural possess a pungent odor.
Stillman (1880) did a fractionation at 215-216 °C. He discovered that inhalation of its fumes can lead to painful cold sensation and severe headaches. In earlier times the leaves of the tree were used for cures for headaches or stomachaches and even toothaches.
Powers and Lee did in 1904 another fractionation on the oil of the tree at 217-222 °C. The yielded different compounds: pinene, cineol, eugenol, methyl eugenol and a ketone called umbellulone. Umbellulone is the chemical responsible for the headaches induced by the tree. They gave umbellulone the following structural formula (Fig. 1).
In 1908 the structural formula was adapted by Tutin (Fig. 2A).
This was correct later that year by Semmller, he gave the structural formula which is accepted today (Fig. 2B).
Umbellulone is a monoterpene ketone that is found in the leaves of the Umbellularia californica. The formula of umbellulone is C10H14O, containing a cyclopropane and cyclopentane ring. There is only one isomer of umbellulone known. Umbellulone is a lipophilic, it's a liquid (oil) at room temperature. The boiling point of umbellulone is 220 °C and the vapor pressure is 0.159 mm/Hg. Due to this extremely low vapor pressure, umbellulone fumes are easily created. This makes the substance easily inhaled. Umbellulone has a high-affinity binding for thiols. The molecule is reactive with most of the thiols, but not with all. The reaction between the thiol cysteamine and umbellulone, is given in figure 3. A European registered medicine called Cystagon® or Procysbi® contains cysteamine, which can interact with umbellulone.
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