threo-Guaiacylglycerol

Base Information

• Chemical Name: threo-Guaiacylglycerol
• CAS No.: 27391-16-8
• Molecular Formula: C₁₀H₁₄O₅
• Molecular Weight: 214.218
• Mol file: 27391-16-8.mol

Synonyms:threo-Guaiacylglycerol

Chemical Property of threo-Guaiacylglycerol

Chemical Property:

• PSA: 90.15000
• LogP: -0.21260

Purity/Quality:

98%min ^*data from raw suppliers

threo-Guaiacylglycerol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: threo-Guaiacylglycerol is a component of Viticis Fructus (Vitex rotundifolia) with analgesic effects.

Technology Process of threo-Guaiacylglycerol

There total 12 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:

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

(2RS,3RS)-2,3-diacetoxy-3-(4-acetoxy-3-methoxy-phenyl)-propionic acid methyl ester

(1RS,2SR)-1,2,3-triacetoxy-1-(4-acetoxy-3-methoxy-phenyl)-propane

Downstream raw materials:

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

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

Refernces

• 1、 Sugiyama,Kikuchi. "Studies on the constituents of Osmanthus species. X. Structures of phenolic glucosides from the leaves of Osmanthus asiaticus NAKAI". . p. 325 - 326. Retrieved 2007/10/02.