492-89-7

Basic information

• Product Name: 3-PENTADECYLCATECHOL
• Synonyms: 3-n-pentadecylcatechol;3-pentadecacatechol;3-pentadecyl-pyrocatecho;dihydrorhengol;hydroureshiol;tetrahydrourushiol;3-PENTADECYLCATECHOL;URUSHIOL II
• CAS NO: 492-89-7
• Molecular Formula: C₂₁H₃₆O₂
• Molecular Weight: 320.51
• Mol File: 492-89-7.mol
• Article Data: 9

Chemical Properties

• Melting Point: 59.5°C
• Boiling Point: 419.39°C (rough estimate)
• Flash Point: 191.7°C
• Appearance: /
• Density: 0.9461 (rough estimate)
• Vapor Pressure: 1.49E-08mmHg at 25°C
• Refractive Index: 1.5100 (estimate)
• PKA: 9.89±0.10(Predicted)
• CAS DataBase Reference: 3-PENTADECYLCATECHOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-PENTADECYLCATECHOL(492-89-7)
• EPA Substance Registry System: 3-PENTADECYLCATECHOL(492-89-7)

Safety Data

• Hazardous Substances Data: 492-89-7(Hazardous Substances Data)

Usage

Description

3-PENTADECYLCATECHOL, also known as Pentadecylcatechol, is an urushiol derivative found in the sap of the lacquer tree (Rhus verniciflua Stokes). It is the main allergen of the Anacardiaceae family, which includes poison ivy (Toxicodendron radicans) and poison oak (Toxicodendron diversiloba, Rhus diversiloba). 3-PENTADECYLCATECHOL is known for its anti-Helicobacter pylori activity in vivo.

Uses

Used in Pharmaceutical Applications:
3-PENTADECYLCATECHOL is used as an active compound for its anti-Helicobacter pylori activity, which is beneficial in treating bacterial infections caused by this pathogen.
Used in Allergen Research:
3-PENTADECYLCATECHOL is used as a key allergen in the study of allergic reactions and dermatitis caused by contact with poison ivy and poison oak. This research helps in understanding the mechanisms of allergic responses and developing potential treatments or preventive measures.
Used in Traditional Medicine:
In traditional medicine, 3-PENTADECYLCATECHOL may be used as a component in the formulation of remedies derived from the lacquer tree, potentially benefiting from its anti-Helicobacter pylori properties.
Used in Chemical Research:
3-PENTADECYLCATECHOL can be used as a starting material or a compound of interest in chemical research, particularly in the study of urushiol derivatives and their potential applications in various fields.

Contact allergens

Pentadecylcatechol belongs to the urushiols and is the main allergen of the Anacardiaceae poison ivy (Toxicodendron radicans) and of Poison oak (Toxicodendron diversiloba, Rhus diversiloba).

Contact allergens

Urushiol is a generic name that indicates a mixture of several close alkylcatechols contained in the sap of the Anacardiaceae family such as Toxicodendron radicans Kuntze (poison ivy) or Anacardium occidentale L. (cashew nut tree). The R-side chain generally includes 13, 15, or 17 carbons. A urushiol with a C15 side chain is named pentadecylcatechol (a term sometimes employed in medical literature for poison ivy urushiol), and a urushiol with a C17 side chain is a heptadecylcatechol (mostly encountered in poison oak urushiol).

InChI:InChI=1/C21H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19-17-15-18-20(22)21(19)23/h15,17-18,22-23H,2-14,16H2,1H3

Upstream product

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• 102542-25-6 1-(2,5-dimethoxy-tetrahydro-furan-2-yl)-heptadecan-1-one 
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• 64-17-5 ethanol 
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• 112-71-0 1-Bromotetradecane 
• 5779-91-9 2,3-bis(benzyloxy)benzaldehyde 
• 123-99-9 azelaic acid 
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Downstream Products

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• 57-10-3 1-hexadecylcarboxylic acid 
• 73881-19-3 1,2-diacethyl-3-pentadecylbenzene 
• 2792-00-9 1,2-bis-benzyloxy-3-pentadecyl-benzene 
• 121233-37-2 2-Benzoyloxy-6-pentadecyl-phenol 
• 121233-38-3 2-Benzoyloxy-3-pentadecyl-phenol 
• 103270-33-3 1,2-bis-benzoyloxy-3-pentadecyl-benzene 
• 16825-58-4 hydrourushiol monomethyl ether 
• 95221-96-8 2-Methoxy-3-pentadecyl-phenol 
• 103099-13-4 (2-hydroxy-3-pentadecyl-phenyl)-β-D-glucopyranoside 
• 7461-75-8 1,2-dimethoxy-3-pentadecyl-benzene 

Relevant articles and documents

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Compositions for prevention/prophylactic treatment of poison ivy dermatitis

The present invention, in one or more embodiments, comprises water-soluble derivatives of 3-n-pentadecylcatechol (poison ivy urushiol saturated congener) and/or 3-n-heptadecylcatechol (poison oak urushiol saturated congener) as compositions for the prevention and/or prophylactic treatment of contact dermatitis caused by poison ivy and poison oak. The present invention is also directed towards processes for making such compounds. Disclosed are compounds which are effective for tolerizing and desensitizing a subject against allergens contained in plants of the Anacardiaceae and Ginkgoaceae families comprising water soluble urushiol esters of general formula (I) tolerizing and desensitizing mammals, including humans, to allergens contained in plants of the Anacardiaceae and Ginkgoaceae families is attained by administering a composition containing at least one water soluble urushiol ester compound.

Synthesis of 3-Alkylcatechols via Intramolecular Cyclization

The intramolecular cyclization of 2-alkanoyl-2,5-dimethoxytetrahydrofurans 4 with aqueous acid is described. 3-Alkylcatechols 7 were prepared in generally good yields by boiling the dioxane solution of compounds 4 in the presence of 1 M hydrochloric acid.In addition, 4,5-dioxoalkanals 6 were obtained in good to high yields when the dioxane solution of compounds 4 was treated with 0.1 M hydrochloric acid.