Geniposide

Base Information

• Chemical Name: Geniposide
• CAS No.: 27745-20-6
• Molecular Formula: C₁₇H₂₄O₁₀
• Molecular Weight: 388.372
• Mol file: 27745-20-6.mol

Synonyms:Cyclopenta[c]pyran-4-carboxylicacid, 1-(b-D-glucopyranosyloxy)-1,4a,5,7a-tetrahydro-7-(hydroxymethyl)-,methyl ester, [1S-(1a,4aa,7aa)]-; Geniposide (8CI)

Chemical Property of Geniposide

Chemical Property:

• Boiling Point: 641.4°Cat760mmHg
• Flash Point: 231.5°C
• PSA: 155.14000
• Density: 1.54g/cm³
• LogP: -2.22910

Purity/Quality:

≥98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Geniposide

There total 8 articles about Geniposide 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:

geniposidic acid (27741-01-1) + diazomethyl-trimethyl-silane (18107-18-1) → geniposide (24512-63-8,27745-20-6)

Guidance literature:

In methanol; hexane; chloroform; at 20 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/ol900360h

Reference yield:

7-(2,2-dimethyl-propionyloxymethyl)-1-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester (1141938-70-6) → geniposide (24512-63-8,27745-20-6)

Guidance literature:

With sodium methylate; In methanol; at 50 ℃; for 3h;

DOI:10.1021/acs.jafc.7b05861

Reference yield:

10-O-(5-phenyl-2,4-pentadienoyl)-geniposide → geniposide (24512-63-8,27745-20-6) + (2E,4E)-methyl 5-phenylpenta-2,4-dienoate (38447-05-1,38448-84-9,101934-35-4,121411-05-0,1516-24-1,24196-39-2)

Guidance literature:

With water; In methanol; for 1h; Ambient temperature;

DOI:10.1016/S0031-9422(00)81110-3

upstream raw materials:

diazomethane

geniposidic acid

diazomethyl-trimethyl-silane

7-(2,2-dimethyl-propionyloxymethyl)-1-(3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-4-carboxylic acid methyl ester

Downstream raw materials:

geniposide penta-acetate

4',6'-O-benzylidene-geniposide

4',6'-O-benzylidene-2',3',10-tri-O-benzyl-geniposide

(2aR,3R,4aS,7aS,7bS)-3-Hydroxy-2a,3,4,4a,7a,7b-hexahydro-2H-1,7-dioxa-cyclopenta[cd]indene-5-carboxylic acid methyl ester

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