threo-Guaiacylglycerol

Base Information

• Chemical Name: threo-Guaiacylglycerol
• CAS No.: 84799-27-9
• Molecular Formula: C₁₀H₁₄O₅
• Molecular Weight: 214.218
• DSSTox Substance ID: DTXSID00453870
• Nikkaji Number: J455.325J
• Wikidata: Q82275147

Synonyms:threo-Guaiacylglycerol;27391-16-8;84799-27-9;(1R,2R)-1-(4-HYDROXY-3-METHOXYPHENYL)PROPANE-1,2,3-TRIOL;D-threo-Guaiacylglycerol;DTXSID00453870;1,2,3-Propanetriol, 1-(4-hydroxy-3-methoxyphenyl)-, (1R,2R)-;AKOS032962378;FS-9699

Chemical Property of threo-Guaiacylglycerol

Chemical Property:

• PSA: 90.15000
• LogP: -0.21260
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 214.08412354
• Heavy Atom Count: 15
• Complexity: 187

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C(C(CO)O)O)O
• Isomeric SMILES: COC1=C(C=CC(=C1)[C@H]([C@@H](CO)O)O)O

Technology Process of threo-Guaiacylglycerol

There total 16 articles about threo-Guaiacylglycerol 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:

9-(6-O-[(2E,6S)-2,6-dimethyl-6-hydroxy-2,7-octadienoyl]-β-D-glucopyranosyloxy)guaiacylglycerol (1370004-83-3) → guaiacyl glycerol (7095-33-2,27391-16-8,27431-21-6,38916-91-5,62078-66-4,84799-27-9,84822-99-1,1208-42-0) + (+)-2,6-dimethyl-6(S)-hydroxy-2-trans-2,7-octadecanoic acid (26187-81-5,28420-25-9,34935-27-8,67711-07-3,83945-54-4,98168-60-6,121843-29-6,124753-77-1,75979-26-9)

Guidance literature:

With water; sodium hydroxide;

DOI:10.1016/j.carres.2012.01.012

Reference yield:

1-(4-hydroxy-3-methoxy)-phenyl-2-[4-(1,2,3- trihydroxypropyl)-2-methoxy]-phenoxy-1, 3-propandiol (14070-76-9,79171-60-1) → guaiacyl glycerol (7095-33-2,27391-16-8,27431-21-6,38916-91-5,62078-66-4,84799-27-9,84822-99-1,1208-42-0)

Guidance literature:

Multistep reaction; (i) aq. NaOH, (heating), (ii) H₂, PtO₂, AcOEt;

Reference yield:

(2RS,3RS)-2,3-diacetoxy-3-(4-acetoxy-3-methoxy-phenyl)-propionic acid methyl ester (93722-55-5) → threo-guaiacylglycerol (1208-42-0,7095-33-2,27391-16-8,27431-21-6,38916-91-5,62078-66-4,84799-27-9,84822-99-1)

Guidance literature:

With lithium aluminium tetrahydride;

upstream raw materials:

D-threo-guaiacylglycerol 8-O-β-D-glucopyranoside

3-(4-hydroxy-3-methoxyphenyl)acrylic acid

1-(4-hydroxy-3-methoxy)-phenyl-2-[4-(1,2,3- trihydroxypropyl)-2-methoxy]-phenoxy-1, 3-propandiol

9-(6-O-[(2E,6S)-2,6-dimethyl-6-hydroxy-2,7-octadienoyl]-β-D-glucopyranosyloxy)guaiacylglycerol

Downstream raw materials:

2-propanone,1-hydroxy-3-(4-hydroxy-3-methoxyphenyl)-

(1RS,2SR)-1-(3,4-dimethoxy-phenyl)-propane-1,2,3-triol

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