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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.

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Urushiol

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  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.

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