89103-56-0

Basic information

• Product Name: (2R)-Tetrahydro-4β-methyl-2-[(E)-3-methyl-1,3-butadienyl]furan
• Synonyms: (2R)-Tetrahydro-4β-methyl-2-[(E)-3-methyl-1,3-butadienyl]furan;Marmelo oxide A
• CAS NO: 89103-56-0
• Molecular Formula: C10H16O
• Molecular Weight: 152.23344
• Mol File: 89103-56-0.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2R)-Tetrahydro-4β-methyl-2-[(E)-3-methyl-1,3-butadienyl]furan(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-Tetrahydro-4β-methyl-2-[(E)-3-methyl-1,3-butadienyl]furan(89103-56-0)
• EPA Substance Registry System: (2R)-Tetrahydro-4β-methyl-2-[(E)-3-methyl-1,3-butadienyl]furan(89103-56-0)

Safety Data

• Hazardous Substances Data: 89103-56-0(Hazardous Substances Data)

Upstream product

• 134486-07-0 2-((E)-3-acetoxy-3-methyl-1-buten-1-yl)-4-methyltetrahydrofuran 
• 134486-07-0 2-((E)-3-acetoxy-3-methyl-1-buten-1-yl)-4-methyltetrahydrofuran 
• 134486-12-7 2-((E)-3-acetoxy-3-methyl-1-buten-1-yl)-4-methyltetrahydrofuran 
• 69514-47-2 (E)-2-methyl-3,5-hexadien-2-ol 
• 134486-03-6 (E)-2-methyl-2,5-hexadien-2-yl acetate 
• 134486-06-9 2,7-dimethyl-4,6-octadien-1-ol 
• 134486-05-8 ethyl 2,7-dimethyl-4,6-octadienoate 
• 134486-04-7 diethyl 2-methyl-2-(5-methyl-2,4-hexadien-1-yl)-malonate 
• 27200-84-6 methyl triphenylphosphonium bromide 
• 120943-95-5 (E)-4-(4-methyltetrahydro-2-furyl)but-3-en-2-one 
• 6906-52-1 (4-methyl-tetrahydro-furan-2-yl)-methanol 
• 120943-91-1 2-Allyloxy-3-bromo-propan-1-ol 
• 89102-91-0 (2S,4R,5E)-2,7-Dimethyl-5,7-octadien-1,4-diol 
• 88972-37-6 (2R,4R,5E)-2,7-Dimethyl-5,7-octadien-1,4-diol 

Relevant articles and documents

Synthesis of Furanoid Terpenes via an Efficient Palladium-Catalyzed Cyclization of 4,6-Dienols

The total syntheses of marmelo oxides A and B and a terpene alcohol found in peppermint oil are described.The key steps in these syntheses are the regioselective palladium-catalyzed allylic substitution of 4 and 11 to 6a and 12, respectively, and the regioselective palladium-catalyzed cyclization of 8 and 14 to 9a, 9b, and 15, respectively.The relative stereochemistry of marmelo oxides A and B was established by NOE measurements.

The Enantioselective Synthesis of Marmelo Oxides A and B and the Assignment of the Absolute Configurations of Marmelo Oxides

(+)-Marmelo oxide A and (-)-marmelo oxide B were stereoselectively synthesized form D-glutamic acid via (-)-marmelo lactones A and B.The absolute configurations of marmelo oxides were thus determined to be the (+)-oxide A having the (2R,4R) and (+)-oxide B having (2S,4R) configuration.

Volatile Components of Quince Fruit (Cydonia oblonga Mill.)

Steam distilled oil of quince fruit (Cydonia oblonga Mill.= C. vulgaris Pers., marmelo in Japanese) was analyzed by gas chromatography and gas chromatography-mass spectrometry.Sixty-two compounds, 2 hydrocarbons, 13 esters, 11 alcohols, 11 aldehydes, 11 ketones, 5 lactones and 9 miscellaneous compounds, were indentified.Of them, the chemical structures of two new oxide compounds, trans- and cis-3-methyl-5-tetrahydrofuran, were elucidated by instrumental analyses.