(3R,4S)-4-ethenyl-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,4-c]pyran-8-one

Base Information

• Chemical Name: (3R,4S)-4-ethenyl-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,4-c]pyran-8-one
• CAS No.: 20831-76-9
• Molecular Formula: C16H20O9
• Molecular Weight: 356.329
• Hs Code.: 29389090
• NSC Number: 606402
• Mol file: 20831-76-9.mol

Synonyms:(3R,4S)-4-ethenyl-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,4-c]pyran-8-one;NSC606402

Chemical Property of (3R,4S)-4-ethenyl-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,4-c]pyran-8-one

Chemical Property:

• Appearance/Colour: Yellowish-white hygroscopic powder
• Melting Point: 191 °C
• Refractive Index: 1.5940 (estimate)
• Boiling Point: 667.784 °C at 760 mmHg
• PKA: 12.79±0.70(Predicted)
• Flash Point: 247.129 °C
• PSA: 134.91000
• Density: 1.529 g/cm³
• LogP: -1.67150
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: DMSO (Slightly), Ethanol (Slightly, Sonicated)
• Water Solubility.: <10mg/L(25 oC)
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 4
• Exact Mass: 356.11073221
• Heavy Atom Count: 25
• Complexity: 598

Purity/Quality:

90%-98% ^*data from raw suppliers

Gentiopicroside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: 22-36/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CC1C(OC=C2C1=CCOC2=O)OC3C(C(C(C(O3)CO)O)O)O
• Isomeric SMILES: C=C[C@@H]1[C@H](OC=C2C1=CCOC2=O)OC3C(C(C(C(O3)CO)O)O)O
• Uses: Gentiopicroside is an anticonvulsant agent present in plant extracts.

Technology Process of (3R,4S)-4-ethenyl-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,4-c]pyran-8-one

There total 2 articles about (3R,4S)-4-ethenyl-3-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,4-c]pyran-8-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2'-(2,3-dihydroxybenzoyl)gentiopicroside → methyl-2,3-dihydroxybenzoate (2411-83-8) + gentiopicrin (20831-76-9)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 3h;

DOI:10.1016/j.fitote.2013.08.006

Reference yield:

2'-O-p-coumaroylgentiopicroside → gentiopicrin (20831-76-9)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 2h;

DOI:10.1248/cpb.47.1338

Reference yield: 11.0%

gentiopicrin (20831-76-9) → gentianol + gentioflavine (18058-50-9)

Guidance literature:

With β-glucosidase from Oriental yeast; In aq. phosphate buffer; at 38 ℃; pH=5.5; Enzymatic reaction;

DOI:10.1016/j.tetlet.2019.01.061

Downstream raw materials:

gentiopicroside tetraacetate

D-Glucose

gentiopicral

Refernces

Monoterpene biosynthesis. I. Occurrence and mevalonoid origin of gentiopicroside and loganic acid in Swertia caroliniensis

10.1021/bi00840a054

The research investigates the biosynthesis of gentiopicroside and loganic acid, two monoterpene glucosides found in the plant Swertia caroliniensis. The study aims to elucidate their biosynthetic pathways and confirm their mevalonoid origin. Key chemicals used include acetate-2-14C, mevalonate-2-14C, and mevalonate-2-3H-2-14C as labeled precursors. Through tracer experiments and various chemical transformations such as methylation, acetylation, and oxidation, the researchers demonstrated that both compounds originate from mevalonate. They also revised the structure of gentiopicroside based on chemical and spectral data, including double-resonance nuclear magnetic resonance studies. The results support a biogenetic scheme where mevalonate is converted to geranyl pyrophosphate, then to loganic acid, which undergoes ring cleavage to form gentiopicroside. The study concludes that loganic acid and its derivatives play a significant role as precursors for various iridoids and secoiridoids, and potentially for indole alkaloids, highlighting the interconnected biosynthetic pathways of these plant metabolites.