Glucoside,6-dimethoxyphenyl, D

Base Information

• Chemical Name: Glucoside,6-dimethoxyphenyl, D
• CAS No.: 118-34-3
• Molecular Formula: C₁₇H₂₄O₉
• Molecular Weight: 372.372
• Hs Code.: 29329990
• NSC Number: 287441
• Mol file: 118-34-3.mol

Synonyms:NSC287441;Glucoside,6-dimethoxyphenyl, D;.beta.-D-Glucopyranoside,6-dimethoxyphenyl;(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[4-(3-hydroxyprop-1-enyl)-2,6-dimethoxyphenoxy]oxane-3,4,5-triol

Chemical Property of Glucoside,6-dimethoxyphenyl, D

Chemical Property:

• Vapor Pressure: 2.17E-17mmHg at 25°C
• Melting Point: 192°C
• Refractive Index: 1.622
• Boiling Point: 642.6 °C at 760 mmHg
• PKA: 12.75±0.70(Predicted)
• Flash Point: 342.4 °C
• PSA: 138.07000
• Density: 1.415 g/cm³
• LogP: -1.11200
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly, Sonicated), Water (Slightly)
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 7
• Exact Mass: 372.14203234
• Heavy Atom Count: 26
• Complexity: 432

Purity/Quality:

98% ^*data from raw suppliers

Syringin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1OC2C(C(C(C(O2)CO)O)O)O)OC)C=CCO
• Isomeric SMILES: COC1=CC(=CC(=C1OC2C(C(C(C(O2)CO)O)O)O)OC)/C=C/CO
• Description: Syringin is a phenylpropanoid glycoside first isolated from A. senticosus that enhances acetylcholine release in pancreatic cells leading to an increase in insulin release through the muscarinic M3 receptor. Syringin dose-dependently (50, 75, and 100 μg/kg, i.v.) decreases plasma glucose levels and increases insulin-like immunoreactivity and C-peptide in rats, and these effects last at least 60 minutes. In a rat model of type 1 diabetes, it decreases plasma glucose and increases β-endorphin release from the adrenal medulla. Syringin increases autophagy through AMP-activated protein kinase α (AMPKα) activation concomitant with preventing the progression of cardiac hypertrophy in mice following aortic banding. It also has immunomodulatory effects, likely due to its metabolite sinapyl alcohol.
• Uses: Syringin is a chemical that is found naturally in various plants such as Araliaceae, a adaptogenic agent with Syringin as the active componet. Syringin have exhibited the ability to enhance glucose ut ilization and the lowering of plasma glucose level in rats suffering from insulin deficiency, suggesting that this chemical may be useful in the treatment of human diabetes. Syringin is a chemical that is found naturally in various plants such as Araliaceae, a adaptogenic agent with Syringin as the active componet. Syringin have exhibited the ability to enhance glucose utilization and the lowering of plasma glucose level in rats suffering from insulin deficiency, suggesting that this chemical may be useful in the treatment of human diabetes.

Technology Process of Glucoside,6-dimethoxyphenyl, D

There total 18 articles about Glucoside,6-dimethoxyphenyl, D 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: 100.0%

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(4-((E)-3-hydroxyprop-1-en-1 -yl)-2,6-dimethoxyphenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (203179-64-0) → syringin (118-34-3,116965-45-8,133815-42-6)

Guidance literature:

With sodium methylate; In methanol; for 3h;

DOI:10.1055/s-1998-2009

Reference yield:

dilatioside B → Oleoside dimethyl ester (30164-95-5) + syringin (118-34-3,116965-45-8,133815-42-6)

Guidance literature:

With methanol; water; potassium hydroxide; at 20 ℃; for 1h; Overall yield = 0.6 mg;

DOI:10.1248/cpb.c16-00804

Reference yield:

UDP-glucose (133-89-1) + trans-sinapyl alcohol (20675-96-1) → syringin (118-34-3,116965-45-8,133815-42-6)

Guidance literature:

With glycosyltransferase 72E₃ derived from Arabidopsis thaliana; 2-hydroxyethanethiol; In aq. buffer; at 22 ℃; for 1h; Enzymatic reaction;

DOI:10.1016/j.phytochem.2014.03.003

upstream raw materials:

3,5-dimethoxy-4-(tetra-O-acetyl-β-D-glucopyranosyloxy)-trans-cinnamaldehyde

trans-sinapyl alcohol

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

tangshenoside I

Downstream raw materials:

syringin penta-acetate

Syringenin

trans-sinapyl alcohol

D-glucose

Refernces

• 1、 Suh, Kyoung Jin,Suh, Won Se,Subedi, Lalita,Kim, Sun Yeou,Choi, Sang Un,Lee, Kang Ro. "Secoiridoid Glucosides from the Twigs of Syringa oblata var. dilatata and Their Neuroprotective and Cytotoxic Activities". . p. 359 - 364. Retrieved 2017/04/14.
• 2、 Chu, Yang,Kwon, Tackmin,Nam, Jaesung. "Enzymatic and metabolic engineering for efficient production of syringin, sinapyl alcohol 4-O-glucoside, in Arabidopsis thaliana". . p. 55 - 63. Retrieved 2014/05/06.