Also known as rosefuran, rose furan
Rosefuran (3-methyl-2-prenylfuran) is an organic compound, classified as a terpenoid. It is a minor constituent of the aroma of the rose (Rosa damascene). Rosefuran is a 2,3-disubstituted furan (3-methyl-2-(3-methyl-2-buten-1-yl)furan). It has an odor threshold of 200 ppb and constitutes 0.16% of Bulgarian rose oil. Rosefuran has been established as a female sex pheromone of an acarid mite, Caloglyphus sp. Concentrations of less than 100 ng of synthetic rosefuran caused sexual excitation in males of the species.
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Rosefuran (3-methyl-2-prenylfuran) is an organic compound, classified as a terpenoid. It is a minor constituent of the aroma of the rose (Rosa damascene). Rosefuran is a 2,3-disubstituted furan (3-methyl-2-(3-methyl-2-buten-1-yl)furan). It has an odor threshold of 200 ppb and constitutes 0.16% of Bulgarian rose oil. Rosefuran has been established as a female sex pheromone of an acarid mite, Caloglyphus sp. Concentrations of less than 100 ng of synthetic rosefuran caused sexual excitation in males of the species.
== Synthesis == Rosefuran was synthesized in 1968 by George Büchi via the organomercury compound bis(3-methyl-2-furyl)mercury. Rosefuran has been synthesized in many steps from common starting materials starting with prenyl chloride (3-methyl-but-2-en-1-yl chloride). Rosefuran has also been synthesized via cyclization of suitable acyclic precursors, such as, 5-oxogeraniol and 5-hydroxycitral (4-hydoxy-3,7-dimethyl-(E)-2,6-octadienol). Rosefuran has also been prepared via palladium catalyzed cross coupling of the methyl ester of 4-bromo-5-methyl-2-furancarboxylic acid followed by decarboxylation.
Discovered by embedding cosine similarity (sentence-transformers MiniLM, 384-dim).