69809-25-2

Upstream product

• 69809-22-9 agarotetrol 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 69809-27-4 Acetic acid (3aR,4S,9S,9aR)-9-acetoxy-2,2-dimethyl-8-oxo-6-phenethyl-4,8,9,9a-tetrahydro-3aH-[1,3]dioxolo[4,5-g]chromen-4-yl ester 
• 69809-26-3 Agarotetrol-5,8-diacetat 
• 69809-28-5 C₃₇H₃₄O₁₂ 

Relevant academic research and scientific papers

Three new 5,6,7,8-tetrahydroxy-5,6,7,8-tetrahydrochromone derivatives enantiomeric to agarotetrol from agarwood

Agarwood (jinkoh in Japanese) is a resinous wood from Aquilaria species of the family Thymelaeaceae and has been used as incense and in traditional medicines. Characteristic chromone derivatives such as agarotetrol have been isolated from agarwood. In previous study, we isolated two new 2-(2-phenylethyl)chromones together with six known compounds from MeOH extract of agarwood. Further chemical investigation of the MeOH extract led to isolation of eighteen 2-(2-phenylethyl)chromones, including three new 5,6,7,8-tetrahydroxy-5,6,7,8-tetrahydrochromones with stereochemistry enantiomeric to agarotetrol-type, viz. (5R,6S,7S,8R)-2-[2-(3′-hydroxy-4′-methoxyphenyl)ethyl]-5,6,7,8-tetrahydroxy-5,6,7,8-tetrahydrochromone (2), (5R,6S,7S,8R)-2-[2-(4′-methoxyphenyl)ethyl]-5,6,7,8-tetrahydroxy-5,6,7,8-tetrahydrochromone (6), and (5R,6S,7S,8R)-2-[2-(4′-hydroxy-3′- methoxyphenyl)ethyl]-5,6,7,8-tetrahydroxy-5,6,7,8-tetrahydrochromone (13). The absolute configurations of the new compounds were determined by exciton chirality method. All isolated compounds were tested for their phosphodiesterase (PDE)?3A inhibitory activity by fluorescence polarization method. Compounds 8, 12–15, 21–24 showed moderate PDE?3A inhibitory activity.

STUDIES ON THE AGALWOOD (JINKOE). IV. STRUCTURES OF 2-(2-PHENYLETHYL)CHROMONE DERIVATIVES, AGAROTETROL AND ISOAGAROTETROL

The structures of two compounds, AH1 and AH2, isolated from agalwood "Jinkoe" were studied.AH1 was obtained as needles having a melting point different from that of agarotetrol (powder) isolated and characterized by Yoshii et al.However, the carbon-13 nuclear magnetic resonance (13C-NMR) data and D values of the two compounds were identical, and AH1 was concluded to have the same structure, including stereochemistry, as agarotetrol.The half-chair conformation of the hexenyl ring moiety assumed by Yoshii et al. was confirmed by detailed analyses of the proton nuclear magnetic resonance (1H-NMR) and 2D-COSY spectra.AH2 was assigned the structure (5S,6R,7R,8S)-2-(2-phenylethyl)-5e',6e,7e,8e'-tetrahydroxy-5,6,7,8-tetrahydrochromone, a stereo-isomer of agarotetrol (7S,8R), on the basis of the 1H-NMR, X-ray analysis and circular dichroism (CD) spectral data.It was named isoagarotetrol.The hexenyl ring moiety of isoagarotetrol was found to have a half-chair conformation identical to that of agarotetrol in the crystalline state as well as in solution.Keywords-2-(2-phenylethyl)chromone; agalwood; Aquilariaceae; agarotetrol; isoagarotetrol; 1H-NMR; 2D-COSY; CD; X-ray analysis