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

Pentadecykatechol is the main allergen of the Anacardiaceae poison ivy (Toxicodendron radicans) and of poison oak (Toxicodendron diversiloba, Rhus diversiloba).

Uses

3-Pentadecylcatechol is an urushiol derivative that displays anti-Helicobacter pylori activity in vivo. Found in the sap of the lacquer tree (Rhus verniciflua Stokes).

Contact allergens

Different sources of media describe the Contact allergens of 492-89-7 differently. You can refer to the following data:
1. 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).
2. 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

• 4549-31-9 1,7-dibromoheptane 
• 629-72-1 pentadecyl bromide 
• 112-71-0 1-Bromotetradecane 
• 24677-78-9 2,3-dihydroxybenzaldehyde 
• 91-16-7 1,2-dimethoxybenzene 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 33597-07-8 (+/-)-1-hydroxy-1-(2.3-dimethoxy-phenyl)-pentadecane 
• 7461-74-7 2,3-dimethoxy-Δ^1'-pentadecenylbenzene 
• 57-10-3 1-hexadecylcarboxylic acid 
• 76014-94-3 3-(pentadec-8-ynyl)veratrole 
• 76014-93-2 1-bromo-7-(2,3-dimethoxyphenyl)heptane 
• 123-99-9 azelaic acid 
• 5779-91-9 2,3-bis(benzyloxy)benzaldehyde 

Downstream Products

• 120334-23-8 (2-benzoyloxy-3-pentadecyl-phenyl)-(tetra-O-acetyl-β-D-glucopyranoside) 
• 95221-96-8 2-Methoxy-3-pentadecyl-phenol 
• 16825-58-4 hydrourushiol monomethyl ether 
• 144-62-7 oxalic acid 
• 57-10-3 1-hexadecylcarboxylic acid 
• 87328-81-2 (S)-2-tert-Butoxycarbonylamino-propionic acid 2-((S)-2-tert-butoxycarbonylamino-propionyloxy)-6-pentadecyl-phenyl ester 
• 7461-75-8 1,2-dimethoxy-3-pentadecyl-benzene 
• 103099-13-4 (2-hydroxy-3-pentadecyl-phenyl)-β-D-glucopyranoside 
• 103270-33-3 1,2-bis-benzoyloxy-3-pentadecyl-benzene 
• 121233-37-2 2-Benzoyloxy-6-pentadecyl-phenol 
• 121233-38-3 2-Benzoyloxy-3-pentadecyl-phenol 
• 2792-00-9 1,2-bis-benzyloxy-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.