35237-02-6

Usage

Uses

Used in Fragrance Industry:
1,2-Benzenediol, 3-(8Z)-8-pentadecenylis used as a fragrance ingredient in perfumes and cosmetics for its pleasant, lilac-like scent, enhancing the overall aroma of these products.
Used in Food Industry:
Alpha-terpineol is used as a flavoring agent in food products, imparting a unique taste and improving the sensory experience of consumers.
Used in Pharmaceutical Industry:
1,2-Benzenediol, 3-(8Z)-8-pentadecenylis used as an intermediate in the synthesis of other organic compounds, contributing to the development of various pharmaceuticals.
Used in Chemical Synthesis:
Alpha-terpineol serves as a key intermediate in the production of other organic compounds, facilitating the creation of a wide range of chemical products.
Used in Industrial Processes:
1,2-Benzenediol, 3-(8Z)-8-pentadecenylis utilized as a solvent in various industrial processes, aiding in the manufacturing and processing of different materials.

Upstream product

• 76032-18-3 1,2-bis(trimethylsilyloxy)-3-<(Z)-pentadec-8-enyl>benzene 
• 71-36-3 butan-1-ol 
• 53545-43-0 3-(pentadec-8-ynyl)catechol 
• 2009-83-8 6-chloro-1-hexanol 
• 53545-41-8 7-(2,3-dimethoxyphenyl)heptan-1-ol 
• 59340-54-4 1-(2,3-dimethoxyphenyl)heptane-1,7-diol 
• 76014-93-2 1-bromo-7-(2,3-dimethoxyphenyl)heptane 
• 21433-45-4 1-octynyllithium 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 51732-22-0 acetaldehyde ethyl 6-chlorohexyl acetal 
• 86-51-1 2,3-dimethyoxybenzaldehyde 
• 53545-42-9 7-(2,3-dihydroxyphenyl)heptyl bromide 
• 53545-40-7 1-(2,3-dimethoxy-phenyl)-7-(1-ethoxy-ethoxy)-heptan-1-ol 
• 123-99-9 azelaic acid 

Downstream Products

• 72955-56-7 1,2-diacetoxy-3-pentadec-8-enyl-benzene 
• 73881-19-3 1,2-diacethyl-3-pentadecylbenzene 
• 76035-43-3 1,2-dimethoxy-3-<(Z)-pentadec-8-enyl>benzene 
• 492-89-7 3-pentadecylcatechol 

Relevant academic research and scientific papers

Application of benzyl protecting groups in the synthesis of prenylated aromatic compounds

Benzyl ethers have proven to be useful protecting groups for synthesis of phenols bearing isoprenoid chains because the benzyl groups can tolerate the conditions of halogen-metal exchange used to introduce the side chains yet are cleaved in good yields upon treatment with sodium s-butanol.

A synthesis of the phenolic lipid, 3-[(Z)-pentadec-8-enyl] catechol, (15:1)-urushiol

A synthesis of (15:1)-urushiol, urushiol monoene, 3-[(Z)-pentadec-8-enyl] catechol, 1,2-dihydroxy-3-[(Z)-pentadec-8-enyl] benzene, one of the toxic principles of Rhus toxicodendron and of Rhus vernicifera is described. 6-Chlorohexan-1-ol protected at the OH group with ethyl vinyl ether reacted with 2,3-dimethoxybenzaldehyde in the presence of lithium to give, after removal of the protective group with methanolic 4-toluenesulphonic acid, 1-(2,3-dimethoxyphenyl) heptane-1,7-diol. Catalytic hydrogenolysis in ethanol with palladium-carbon selectively afforded 7-(2,3-dimethoxyphenyl)heptane-1-ol accompanied by a small proportion of the 7-(3-methoxyphenyl)heptane-1-diol, formed by demethoxylation. Reaction of the dimethoxy compound with boron tribromide resulted in both bromination and demethylation to give 7-(2,3-dihydroxyphenyl) heptylbromide. This bromide in tetrahydrofuran (THF) containing hexamethylphosphoric triamide reacted with excess lithium oct-1-yne to give 3-(pentadec-8-enyl)catechol which, by catalytic hydrogenation in ethyl acetate containing quinoline, selectively formed the required cis product, 3-[(Z)-pentadec-8-enyl]catechol which was identical chromatographically and spectroscopically with urushiol monoene separated from the natural product.

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.