Madecassicside,(S)

Base Information

• Chemical Name: Madecassicside,(S)
• CAS No.: 18449-41-7
• Molecular Formula: C₃₀H₄₈O₆
• Molecular Weight: 504.708
• Hs Code.: 29389090
• European Community (EC) Number: 606-031-1
• ChEMBL ID: CHEMBL19097
• Wikidata: Q105213585
• Mol file: 18449-41-7.mol

Synonyms:18449-41-7;Madecassicside,(S);UPCMLD-DP049;CHEMBL19097;trihydroxy-9-(hydroxymethyl)-;SCHEMBL24756829;UPCMLD-DP049:001;icosahydropicene-4a-carboxylic acid;MFCD29048539;NCGC00161617-01;Q-100219;,7,8,8a,9,10,11,12,12a,12b,13,14b-;1,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b;(1S,2R,4aS,6aS,6bR,8R,9R,10R,11R,12aR)-8,10,11-;(1S,2R,4aS,6aS,6bR,8R,9R,10R,11R,12aR)-8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

Chemical Property of Madecassicside,(S)

Chemical Property:

• Vapor Pressure: 3.61E-19mmHg at 25°C
• Melting Point: 270 °C (dec.)
• Refractive Index: 1.59
• Boiling Point: 641.7 °C at 760 mmHg
• PKA: 4.63±0.70(Predicted)
• Flash Point: 355.9 °C
• PSA: 118.22000
• Density: 1.23 g/cm³
• LogP: 4.00350
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Sparingly), Methanol (Slightly, Heated)
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 504.34508925
• Heavy Atom Count: 36
• Complexity: 963

Purity/Quality:

98%, ^*data from raw suppliers

Madecassic acid ^*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: CC1CCC2(CCC3(C(=CCC4C3(CC(C5C4(CC(C(C5(C)CO)O)O)C)O)C)C2C1C)C)C(=O)O
• Isomeric SMILES: C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CCC4[C@]3(C[C@H](C5[C@@]4(C[C@H]([C@@H]([C@@]5(C)CO)O)O)C)O)C)C2[C@H]1C)C)C(=O)O
• Description: Madecassic acid is a triterpenoid that has been found in C. asiatica and has diverse biological activities. It inhibits LPS-induced production of nitric oxide (NO), prostaglandin E2 (PGE2; ), TNF-α, IL-1β, and IL-6 in RAW 264.7 macrophages when used at a concentration of 150 μg/ml. Madecassic acid (0.05 and 0.1% in the diet) decreases plasma levels of fibrinogenin and triglycerides, as well as heart and kidney levels of reactive oxygen species (ROS), in a mouse model of diabetes induced by streptozotocin (STZ; ). It decreases tumor growth in a CT26 murine colon cancer model in a dose-dependent manner.
• Uses: wound healing Madecassic Acid is a terpenoid with an ursane skeleton isolated from Centella asiatica. Madecassic Acid displays anti-inflammatory properties as a result of iNOS, COX-2, TNF-alpha, IL-1beta, and IL-6 inhibition via the downregulation of NF-kappaB activation in RAW 264.7 macrophage cells. Madecassic Acid is found in cosmetic products due to its skin-protective activities. Madecassic Acid is a terpenoid with an ursane skeleton isolated from Centella asiatica. Madecassic Acid displays anti-inflammatory properties as a result of iNOS, COX-2, TNF-alpha, IL-1beta, and IL-6 inhibition via the downregulation of NF-kappaB activation in RAW 264.7 macrophage cells. Madecassic Acid is found in cosmetic products due to its skin-protective activities.

Technology Process of Madecassicside,(S)

There total 3 articles about Madecassicside,(S) 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:

methyl 2α,3β,6β,23-tetrahydroxyurs-12-en-28-oate (23140-81-0) → Madecassic acid (18449-41-7)

Guidance literature:

With sodium hydroxide; In ethylene glycol;

DOI:10.1016/S0031-9422(00)85642-3

Reference yield:

→ Madecassic acid (18449-41-7)

Guidance literature:

(yield);

DOI:10.1016/S0031-9422(00)85884-7

Reference yield:

→ Brahminsaeure (18449-41-7)

Guidance literature:

Brahmosid, wss. H2SO4, A., Δ;

upstream raw materials:

methyl 2α,3β,6β,23-tetrahydroxyurs-12-en-28-oate