Maslinic acid

Base Information

• Chemical Name: Maslinic acid
• CAS No.: 4373-41-5
• Molecular Formula: C₃₀H₄₈O₄
• Molecular Weight: 472.709
• Hs Code.: 29181990
• European Community (EC) Number: 610-137-3
• UNII: E233J88OHQ
• DSSTox Substance ID: DTXSID30905074
• Nikkaji Number: J22.580K
• Wikipedia: Maslinic_acid
• Wikidata: Q1907191
• Pharos Ligand ID: M1U6NG983FQB
• Metabolomics Workbench ID: 72213
• ChEMBL ID: CHEMBL201515
• Mol file: 4373-41-5.mol

Synonyms:(2alpha, 3beta)-2,3-dihydroxy-olean-12-en-28-oic acid;(2alpha, 3beta)-2,3-dihydroxyolean-12-en-28-oic acid;(2beta, 3alpha)-2,3-dihydroxy-olean-12-en-28-oic acid;(2beta, 3alpha)-2,3-dihydroxyolean-12-en-28-oic acid;2-hydroxyoleanolic acid;2alpha-hydroxyoleanolic acid;bredemolic acid;crataegolic acid;crategolic acid;maslic acid;maslinic acid;olean-12-en-28-oic acid, 2,3-dihydroxy-, (2alpha, 3beta)-

Chemical Property of Maslinic acid

Chemical Property:

• Vapor Pressure: 2.3E-15mmHg at 25°C
• Melting Point: 267～269℃
• Refractive Index: 1.568
• Boiling Point: 570 °C at 760 mmHg
• PKA: 4.63±0.70(Predicted)
• Flash Point: 312.6 °C
• PSA: 77.76000
• Density: 1.15 g/cm³
• LogP: 6.20440
• Storage Temp.: 2-8°C
• Solubility.: acetone: soluble1mg/mL, clear, colorless
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 472.35526001
• Heavy Atom Count: 34
• Complexity: 919

Purity/Quality:

95%-98% ^*data from raw suppliers

Maslinic acid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CC(C(C5(C)C)O)O)C)C)C2C1)C)C(=O)O)C
• Isomeric SMILES: C[C@@]12CC[C@@H]3[C@@]([C@H]1CC=C4[C@]2(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O)C)(C[C@H]([C@@H](C3(C)C)O)O)C
• Recent NIPH Clinical Trials: Development of the tailor-made health program appropriated to the health condition of the elderly : (2) A declining tendency of the knee function
• Description: Maslinic acid (2-α,3-β-dihydroxyolean-12-en-28-oic acid) is a pentacyclic triterpene abundant in the cuticular lipid layer of olive fruits (Bianchi et al.，1994) .It is a compound of 30 carbon atoms grouped in five cycles that have several substitutes. Maslinic acid presents two hydroxyl groups bound to carbons 2 and 3,one carboxyl group bound to carbon 17, and a double bond between carbons 12 and 13.It is a highly hydrophobic compound of low water solubility. Maslinic acid is synthesized in plants via the cytoplasmic acetate/mevalonate pathway that leads to oxidosqualene (Seo et al., 1988).Oxidosqualene is cycled by various oxidosqualene cyclases, among them β-amyrin synthase, which catalyzes the transformation of oxydosqualene into β-amyrin (olean-12-3n-3β-ol). Afterwards,β-amyrin is converted by successive reactions into erythrodiol, oleanolic acid, and finally maslinic acid (Saimaru et al.,2007; Stiti et al.,2007). Maslinic acid is found in a number of natural sources, most notably pomace olive oil (orujo). This pentacyclic triterpene has an antiproliferative effect against Caco-2 cancer cells (EC50 = 15 μM), HT-29 human colon cancer cells (EC50 = 74 μM), 1321N1 astrocytoma cells (IC50 = 25 μM), and human leukemia (CCRF-CEM and CEM/ADR5000) cells (IC50 = 7 μM and 9 μM respectively). Maslinic acid''s antiproliferative activity likely comes from the induction of an oxidative apoptotic pathway, causing cell cycle and cytoskeleton alterations. Maslinic acid has been found to attenuate intracellular oxidative stress via inhibition of NO and H2O2 production and reduction of pro-inflammatory cytokine generation in murine macrophages. Recently maslinic acid has been found to inhibit the spread of the HIV virus by inhibiting the replication of a primary HIV-1 isolate as well as decreased the cytopathic effect and p24 antigen levels in MT2 cells.
• Uses: Maslinic acid may be used as an analytical reference standard for the quantification of the analyte in the leaves of Ziziphus species and fruits using different chromatography techniques. Maslinic Acid is an apoptosis inducer in lung cancer cells, occuring under normoxic and hypoxic conditions.

Technology Process of Maslinic acid

There total 20 articles about Maslinic 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: 100.0%

benzyl (2α,3β)-2,3-dihydroxy-olean-12-en-28-oate (464876-77-5) → maslinic acid (4373-41-5,5957-40-4,26563-68-8,26707-60-8,120707-84-8,125137-38-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.bmcl.2005.10.014

Reference yield: 70.0%

methyl maslinate (22425-82-7) → maslinic acid (4373-41-5,5957-40-4,26563-68-8,26707-60-8,120707-84-8,125137-38-4)

Guidance literature:

With lithium; In ethylenediamine; for 4h; Heating;

Reference yield: 48.0%

(2α)-2-hydroxy-3-oxo-olean-12-en-28-oic acid (73584-62-0) + acetone (67-64-1) → maslinic acid (4373-41-5,5957-40-4,26563-68-8,26707-60-8,120707-84-8,125137-38-4) + (2α,3α)-(isopropylidenedioxy)olean-12-en-28-oic acid

Guidance literature:

(2α)-2-hydroxy-3-oxo-olean-12-en-28-oic acid; With sodium tetrahydroborate; In tetrahydrofuran; methanol; at 0 ℃; for 1h;

acetone; With sulfuric acid; at 0 - 60 ℃; for 0.5h;

DOI:10.1016/j.tet.2015.09.037

upstream raw materials:

methyl maslinate

2α,3β-diacetoxyoleane 12-ene-28-carboxylic acid

3-acetylmaslinic acid (TARB-2)

benzyl (2α,3β)-2,3-dihydroxy-olean-12-en-28-oate

Downstream raw materials:

(2α,3β) methyl 2,3-diacetyl-olean-12-en-28-oate

benzyl (2α,3β)-2,3-dihydroxy-olean-12-en-28-oate

Refernces

• 1、 Sommerwerk, Sven,Heller, Lucie,Serbian, Immo,Csuk, René. "Straightforward partial synthesis of four diastereomeric 2,3-dihydroxy-olean-12-en-28-oic acids from oleanolic acid". . p. 8528 - 8534. Retrieved 2016/02/03.
• 2、 Wang, Hong-Min,Liu, Qun-Fang,Zhao, Yi-Wu,Liu, Shuang-Zhu,Chen, Zhen-Hua,Zhang, Ru-Jun,Wang, Zhen-Zhong,Xiao, Wei,Zhao, Wei-Min. "Four new triterpenoids isolated from the resin of Garcinia hanburyi". . p. 20 - 28. Retrieved 2014/02/14.