methyl (1S,4aR,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

Base Information

• Chemical Name: methyl (1S,4aR,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
• CAS No.: 24512-63-8
• Molecular Formula: C17H24O10
• Molecular Weight: 388.372
• Hs Code.: 29389090
• European Community (EC) Number: 683-175-1
• Wikipedia: Geniposide
• Mol file: 24512-63-8.mol

Synonyms:24512-63-8

Chemical Property of methyl (1S,4aR,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

Chemical Property:

• Melting Point: 161-162 °C
• Boiling Point: 693.7 °C at 760 mmHg
• PKA: 12.80±0.70(Predicted)
• Flash Point: 251.3 °C
• PSA: 155.14000
• Density: 1.59 g/cm³
• LogP: -2.22910
• Storage Temp.: ?20°C
• Solubility.: H2O: ≥5mg/mL
• XLogP3: -2.3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 6
• Exact Mass: 388.13694696
• Heavy Atom Count: 27
• Complexity: 617

Purity/Quality:

99% ^*data from raw suppliers

Geniposide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=COC(C2C1CC=C2CO)OC3C(C(C(C(O3)CO)O)O)O
• Isomeric SMILES: COC(=O)C1=CO[C@H]([C@H]2[C@H]1CC=C2CO)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• Uses: Geniposide is an iridoid glycoside isolated from the fruit of Gardenia jasminoides Ellis. Geniposide is one of the biologically active ingredients of gardenia fruit. Geniposide is widely used in multi-component injection in the treatment of cerebrovascula

Technology Process of methyl (1S,4aR,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate

There total 8 articles about methyl (1S,4aR,7aS)-7-(hydroxymethyl)-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate 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:

6,7-dihydroapodantheroside

(S)-1-((1S,2R,3S)-2,3-Bis-hydroxymethyl-cyclopentyl)-ethane-1,2-diol

((1R,2S,3S)-2,3-Bis-benzyloxymethyl-cyclopentyl)-methanol

C₂₂H₂₄O₅

Refernces

• 1、 Xia, Qing,Dong, Jianyang,Li, Ling,Wang, Qiang,Liu, Yuxiu,Wang, Qingmin. "Discovery of Glycosylated Genipin Derivatives as Novel Antiviral, Insecticidal, and Fungicidal Agents". . p. 1341 - 1348. Retrieved 2018.
• 2、 -. "Hair dyeing by iridoid glycosides and aglycons thereof". . . Retrieved 2008/06/13.