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

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

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

• 35237-02-6 1,2-dihydroxy-3-(pentadec-8-enyl)benzene 
• 102542-25-6 1-(2,5-dimethoxy-tetrahydro-furan-2-yl)-heptadecan-1-one 
• 4827-98-9 α-<2.5-Diaethoxy-tetrahydro>-furfuroyl-α-pentadecyl-essigsaeure-aethylester 
• 64-17-5 ethanol 
• 7461-74-7 2,3-dimethoxy-Δ^1'-pentadecenylbenzene 
• 117788-49-5 2-heptadecanoylfuran 
• 33597-07-8 (+/-)-1-hydroxy-1-(2.3-dimethoxy-phenyl)-pentadecane 
• 91-16-7 1,2-dimethoxybenzene 
• 629-72-1 pentadecyl bromide 
• 7461-75-8 1,2-dimethoxy-3-pentadecyl-benzene 
• 112-71-0 1-Bromotetradecane 
• 24677-78-9 2,3-dihydroxybenzaldehyde 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 86-51-1 2,3-dimethyoxybenzaldehyde 

Downstream Products

• 22693-10-3 2-pentadecylquinone 
• 120-80-9 benzene-1,2-diol 
• 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

Study of two isoforms of lipoxygenase by kinetic assays, docking and molecular dynamics of a specialised metabolite isolated from the aerial portion of Lithrea caustica (Anacardiaceae) and its synthetic analogs

Our investigation focused on the characterization and study of epicuticular leaf extracts (dichloromethane extract) and certain derivatives of Lithrea caustica (Molina) Hook and Arn. (Anacardiaceae) as inhibitors of 15 soybean and 5 human lipoxygenases (1

Inhibition of Soybean 15-Lipoxygenase and Human 5-Lipoxygenase by Extracts of Leaves, Stem Bark, Phenols and Catechols Isolated From Lithraea caustica (Anacardiaceae)

Lithraea caustica (Molina) Hook. and Arn. (Anacardiaceae), common name Litre, is an evergreen endemic plant used in the Mapuche Chilean folk medicine. The stem juice of L. caustica mixed with Rubus ulmifolius (blackberry) is used to treat cough and the in

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.

Nonallergenic urushiol derivatives inhibit the oxidation of unilamellar vesicles and of rat plasma induced by various radical generators

Urushiols consist of an o-dihydroxybenzene (catechol) structure and an alkyl chain of 15 or 17 carbons in the 3-position of a benzene ring and are allergens found in the family Anacardiaceae. We synthesized various veratrole (1,2-dimethoxybenzene)-type an

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.

Synthesis and antiallergenic properties of 3-n-pentadecyl- and 3-n-heptadecylcatechol esters

A synthetic procedure is described for the preparation of 3-n-pentadecyl- and 3-n-heptadecylcatechols and their acetate and alaninate esters. The Wittig reagent prepared from 2,3-dimethoxybenzyltriphenylphosphonium bromide (III) was coupled with 1-tetrade

Long-chain Phenols. Part 18. Conversion of Anacardic Acid into Urushiol

(15:0)-Anacardic acid (6-pentadecylsalicylic acid), prepared by reduction of unsaturated anacardic acid from Anacardium occidentale, has been converted into anacardic alcohol (6-pentadecylsalicylic alcohol) and thence by oxidation at carbon into anacardaldehyde.Phenolic oxidation of anacardic alcohol led to 8-pentadecyl-1-oxaspiroocta-5,7-dien-4-one, itself readily convertible photochemically, but less so thermally, into anacardaldehyde.Reaction of thionyl chloride with anacardic acid led mainly to the anhydride, which by hydride reduction gave anacardaldehyde less satisfactorily.Dakin oxidation of anacardaldehyde furnished (15:0)-urushiol (3-pentadecylcatechol) identical chemically and from argentation t.l.c. with the hydrogenated natural product from Rhus vernicifera. (15:0)-Cardanol (3-pentadecylphenol) has been detected in hydrogenated urushiol.The composition of the unsaturated constituents of urushiol from Rhus vernicifera and Rhus toxicodendron and its mode of formation have been discussed.An improved synthesis of (15:0)-urushiol has been devised based on an organo-lithium route.Aromatic methyl ether and ester formation in this series is greatly facilitated by phase-transfer catalysis.

Vesicant Principles of Poison Ivy and Related Plants: Synthesis of the Urushiols, 1,2-Dihydroxy-3-benzene and 1,2-Dihydroxy-3-pentadecylbenzene

New syntheses of 1,2-dihydroxy-3-benzene (1) and 1,2-dihydroxy-3-pentadecylbenzene (4), vesicant principles of Poison Ivy (Rhus radicans) and other species of Anacardiaceae, are described starting from 1,2-dimethoxybenzene (7).The lithiation of 1,2-dimethoxybenzene (7) has been re-examined and the yield of the product, 2,3-dimethoxyphenyl-lithium (8), re-determined.The reaction of the aryl-lithium with 1,7-dibromoheptane has been studied by g.l.c., using tributyltin chloride as a quenching reagent.The extracts of two plants of the Anacardiaceae family, Semecarpus vitiensis Engl. and Melanorrhoea beccari Engl., have been examined for the presence of urushiols.The bark of the latter has been found to contain gallic acid.