Geniposidic acid

Base Information

• Chemical Name: Geniposidic acid
• CAS No.: 27741-01-1
• Molecular Formula: C16H22O10
• Molecular Weight: 374.345
• Hs Code.: 29389090
• European Community (EC) Number: 683-161-5
• DSSTox Substance ID: DTXSID40182091
• Nikkaji Number: J17.202B
• Wikipedia: Geniposidic_acid
• Wikidata: Q5533206
• Metabolomics Workbench ID: 156495
• ChEMBL ID: CHEMBL460031
• Mol file: 27741-01-1.mol

Synonyms:geniposidic acid

Chemical Property of Geniposidic acid

Chemical Property:

• Melting Point: 138-140 °C(Solv: methanol (67-56-1))
• Refractive Index: 1.659
• Boiling Point: 684.1 °C at 760 mmHg
• PKA: 4.49±0.60(Predicted)
• Flash Point: 250.9 °C
• PSA: 166.14000
• Density: 1.64 g/cm³
• LogP: -2.31750
• Storage Temp.: 2-8°C
• XLogP3: -2.7
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 5
• Exact Mass: 374.12129689
• Heavy Atom Count: 26
• Complexity: 602

Purity/Quality:

98%,99%, ^*data from raw suppliers

Geniposidic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C=C(C2C1C(=COC2OC3C(C(C(C(O3)CO)O)O)O)C(=O)O)CO
• Isomeric SMILES: C1C=C([C@@H]2[C@H]1C(=CO[C@H]2O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)C(=O)O)CO
• Uses: Geniposidic acid is an effective anticancer and radioprotection agent. Geniposidic acid might be a more potent tumor growth inhibitor than geniposide (GP) when combined with the X-irradiation, though there was no significant synergetic effect on their com

Technology Process of Geniposidic acid

There total 5 articles about Geniposidic acid 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: 90.0%

geniposide (24512-63-8,27745-20-6) → geniposidic acid (27741-01-1)

Guidance literature:

With lithium hydroxide; In methanol; at 50 ℃;

DOI:10.1016/j.ejmech.2020.112508

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) → geniposidic acid (27741-01-1)

Guidance literature:

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; With lithium hydroxide monohydrate; water; In acetonitrile; at 40 ℃; for 16.5h; Inert atmosphere;

With acetic acid; In water; acetonitrile; Inert atmosphere;

DOI:10.1021/ol900360h

Reference yield:

daphcalycinosidine C → de-N-oxide-calyciphylline A (750649-07-1) + geniposidic acid (27741-01-1)

Guidance literature:

With potassium hydroxide; at 20 ℃; for 2h;

DOI:10.1021/np040038f

upstream raw materials:

geniposide

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

geniposide

Downstream raw materials:

geniposide

Refernces

• 1、 Touyama,Inoue,Takeda,Yatsuzuka,Ikumoto,Moritome,Shingu,Yokoi,Inouye. "Studies on the blue pigments produced from genipin and methylamine. II. On the formation mechanisms of brownish-red intermediates leading to the blue pigment formation". . p. 1571 - 1578. Retrieved 1994.
• 2、 -. "Pentacetylgardenoside cyclohexanamide capable of reducing uric acid activity and preparation method and application of pentacetylgardenoside cyclohexanamide". Paragraph 0020. . Retrieved 2019/11/21.
• 3、 Jones, Regan A.,Krische, Michael J.. "Asymmetric total synthesis of the iridoid β-glucoside (+)-geniposide via phosphine organocatalysis". supporting information; experimental part. p. 1849 - 1851. Retrieved 2009/09/06.