10,11-Dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

Base Information

• Chemical Name: 10,11-Dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• CAS No.: 465-00-9
• Molecular Formula: C₃₀H₄₈O₅
• Molecular Weight: 488.708
• Wikidata: Q104197007
• Mol file: 465-00-9.mol

Synonyms:2,3,23-trihydroxyolean-12-en-28-oic acid;arjunolic acid

Chemical Property of 10,11-Dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

Chemical Property:

• Vapor Pressure: 3.26E-17mmHg at 25°C
• Melting Point: 332-334 °C
• Refractive Index: 1.58
• Boiling Point: 606°C at 760mmHg
• PKA: 4.62±0.70(Predicted)
• Flash Point: 334.3°C
• PSA: 97.99000
• Density: 1.19g/cm³
• LogP: 5.17680
• Storage Temp.: ?20°C
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 488.35017463
• Heavy Atom Count: 35
• Complexity: 941

Purity/Quality:

99% ^*data from raw suppliers

Arjunolic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CC(C(C5(C)CO)O)O)C)C)C2C1)C)C(=O)O)C
• Description: Arjunolic acid is a triterpene that has been found in T. arjuna and has diverse biological activities, including antioxidant, anticancer, and anti-inflammatory properties. It scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH; ) radicals in a cell-free assay when used at a concentration of 0.8 mM. Arjunolic acid (20 mg/kg for four days) prevents arsenic-induced decreases in the activity of superoxide dismutase (SOD1), catalase, GST, and glutathione reductase in mouse brain. It reduces tumor growth in an Ehrlich murine spontaneous adenocarcinoma model when administered at doses of 100 and 250 mg/kg for 20 days. Arjunolic acid reduces renal fibrosis and increases in kidney TNF-α and IL-1β levels induced by cisplatin in mice when administered at doses of 100 and 250 mg/kg per day for 10 days.
• Uses: Arjunolic Acid is a naturally occurring terpenoid which displays anti-inflammatory activity as well as protective effects during chemical induced organ pathophysiology.

Technology Process of 10,11-Dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid

There total 55 articles about 10,11-Dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic 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: 71.7%

bayogenin {28-O-α-L-rhamnopyranosyl-(1->2)-[β-D-galactopyranosyl(1->3)]-[β-D-glucopyranosyl-(1->6)]-β-D-glucopyranosyl} ester → D-quionovose (7658-08-4,478518-52-4) + D-glucose (50-99-7) + D-Galactose (59-23-4) + bayogenin (465-00-9,6989-24-8,87392-68-5,102519-34-6,106293-97-4,118711-55-0,150821-16-2)

Guidance literature:

bayogenin {28-O-α-L-rhamnopyranosyl-(1->2)-[β-D-galactopyranosyl(1->3)]-[β-D-glucopyranosyl-(1->6)]-β-D-glucopyranosyl} ester; With sulfuric acid; In 1,4-dioxane; for 1h; Reflux;

In 1,4-dioxane;

DOI:10.1248/cpb.59.889

Reference yield: 61.4%

desacylperennisoside XI → D-quionovose (7658-08-4,478518-52-4) + D-glucose (50-99-7) + D-Galactose (59-23-4) + bayogenin (465-00-9,6989-24-8,87392-68-5,102519-34-6,106293-97-4,118711-55-0,150821-16-2)

Guidance literature:

desacylperennisoside XI; With sulfuric acid; In 1,4-dioxane; for 1h; Reflux;

In 1,4-dioxane;

DOI:10.1248/cpb.59.889

Reference yield: 52.2%

desacyl-perennisoside VIII → D-quionovose (7658-08-4,478518-52-4) + D-Fucose (3615-37-0,478518-52-4) + D-glucose (50-99-7) + bayogenin (465-00-9,6989-24-8,87392-68-5,102519-34-6,106293-97-4,118711-55-0,150821-16-2)

Guidance literature:

desacyl-perennisoside VIII; With sulfuric acid; In 1,4-dioxane; for 1h; Reflux;

In 1,4-dioxane;

DOI:10.1248/cpb.59.889

upstream raw materials:

3-O-<α-L-arabinopyranosyl(1->2)-β-D-glucopyranosyl>-bayogenin

lobatoside C

undeca-acetate of medicoside J

3-O-β-D-glucopyranosyl-2β,3β,23-trihydroxyolean-12-en-28-oic acid-28-O-β-D-xylopyranosyl-(1→6)-[β-D-glucopyranosyl-(1→2)]-[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranoside

Downstream raw materials:

Methyl 2β,3β-dihydroxy-23α-hydroxymethyl-Δ¹²-oleanene-28β-carboxylate

C₃₂H₄₈O₆

C₃₀H₄₆O₅

olean-12-ene-2β,3β,23,28-tetraol

Refernces

• 1、 Tava, Aldo,Biazzi, Elisa,Mella, Mariella,Quadrelli, Paolo,Avato, Pinarosa. "Artefact formation during acid hydrolysis of saponins from Medicago spp.". . p. 116 - 127. Retrieved 2017/04/13.
• 2、 Scognamiglio, Monica,D'Abrosca, Brigida,Fiumano, Vittorio,Chambery, Angela,Severino, Valeria,Tsafantakis, Nikolaos,Pacifico, Severina,Esposito, Assunta,Fiorentino, Antonio. "Oleanane saponins from Bellis sylvestris Cyr. and evaluation of their phytotoxicity on Aegilops geniculata Roth". . p. 125 - 134,10. Retrieved 2012/12/12.