1 / 7

Urushiol

Urushiol. Biosynthesis. Urushiol Composition. Urushiol is a mixture of several closely related organic compounds called phenols. It is a catechol . Phenol 1, 2-dihydroxybenzene (benzenediol) Benzene ring, 2 hydroxyl (OH) groups, and substituted alkyl chain of 15 or 17 carbon atoms.

ivana-russo
Download Presentation

Urushiol

An Image/Link below is provided (as is) to download presentation Download Policy: Content on the Website is provided to you AS IS for your information and personal use and may not be sold / licensed / shared on other websites without getting consent from its author. Content is provided to you AS IS for your information and personal use only. Download presentation by click this link. While downloading, if for some reason you are not able to download a presentation, the publisher may have deleted the file from their server. During download, if you can't get a presentation, the file might be deleted by the publisher.

E N D

Presentation Transcript

  1. Urushiol Biosynthesis

  2. Urushiol Composition • Urushiol is a mixture of several closely related organic compounds called phenols. • It is a catechol. • Phenol • 1, 2-dihydroxybenzene (benzenediol) • Benzene ring, 2 hydroxyl (OH) groups, and substituted alkyl chain of 15 or 17 carbon atoms

  3. Structures • Left: catechol • Right: Urushiol with a 15-carbon alkyl group

  4. Variations of Urushiol • Poison oak urushiol is usually composed of catechols with 17-carbon alkyl chains. • Poison ivy urushiol is usually composed of catechols with 15-carbon alkyl chains.

  5. Urushiol • Top: Urushiol of poison ivy • Bottom: Urushiol of poison oak

  6. Urushiol & Allergic Reaction • The alkyl chain can be saturated (with single bonds between all carbons) or unsaturated (with double bonds between all carbons). • The degree of saturation determines the allergic reaction • Fully saturated – less than 50% of the general population is allergic • At least two degrees of unsaturation – over 90% of the general population is allergic

  7. Synthesis of Urushiol • A polyketide family of enzymes called chalcone synthases catalyze the elongation of the alkyl chain of urushiol • This elongation is similar to fatty acid biosynthesis.

More Related