24-Nor-D:A-friedooleana-1(10),5,7-tetraen-29-oic acid, 3-hydroxy-2-oxo-, methyl ester

Base Information

• Chemical Name: 24-Nor-D:A-friedooleana-1(10),5,7-tetraen-29-oic acid, 3-hydroxy-2-oxo-, methyl ester
• CAS No.: 1258-84-0
• Molecular Formula: C30H40 O4
• Molecular Weight: 464.645
• NSC Number: 99281
• Wikidata: Q105126542
• Mol file: 1258-84-0.mol

Synonyms:NSC-99281;jm5b01461, Compound 95;SCHEMBL17328930;BDBM429277;BCP22624;NSC99281;FT-0697494;24-Nor-D:A-friedooleana-1(10),5,7-tetraen-29-oic acid, 3-hydroxy-2-oxo-, methyl ester;(9b,13a,14b,20a)-3-Hydroxy-9,13-dimethyl-2-oxo-24,25,26 -trinoroleana-1(10),3,5,7-tertraen-29-oic acid methyl ester;D:A-Friedo-24-noroleana-1(10),5,7-tetraen-29-oic acid, 3-hydroxy-2-oxo-, methyl ester, (20.alpha.)-

Chemical Property of 24-Nor-D:A-friedooleana-1(10),5,7-tetraen-29-oic acid, 3-hydroxy-2-oxo-, methyl ester

Chemical Property:

• Vapor Pressure: 2.63E-17mmHg at 25°C
• Melting Point: 219.5°C
• Refractive Index: 1.4800 (estimate)
• Boiling Point: 607.7°Cat760mmHg
• PKA: 8.60±0.70(Predicted)
• Flash Point: 195.1°C
• PSA: 63.60000
• Density: 1.16g/cm³
• LogP: 6.78610
• Storage Temp.: Store at -20°C
• Solubility.: DMSO: ≥5mg/mL
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 464.29265975
• Heavy Atom Count: 34
• Complexity: 1120

Purity/Quality:

≥98% ^*data from raw suppliers

Pristimerin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=C(C(=O)C=C2C1=CC=C3C2(CCC4(C3(CCC5(C4CC(CC5)(C)C(=O)OC)C)C)C)C)O
• Description: Monoacylglycerol lipase (MAGL) hydrolyzes the endogenous cannabinoid 2-arachidonoyl glycerol (2-AG), terminating its capacity to activate cannabinoid receptors. Pristimerin is a naturally occurring terpenoid that potently inhibits MAGL (IC50 = 93 nM). Its actions are rapid, reversible, and noncompetitive. Pristimerin (1 μM) significantly increases 2-AG levels in isolated rat neurons, indicating that it inhibits endogenous MAGL in cultured cells. Moreover, it does not increase levels of palmitoyl ethanolamide, suggesting that pristimerin does not affect the activity of fatty acid amide hydrolase (FAAH).
• Uses: Pristimerin is a triterpenoid that inhibits tumor angiogenesis by targeting VEGFR2 activation and is known to exhibit anti-inflammatory properties.

Technology Process of 24-Nor-D:A-friedooleana-1(10),5,7-tetraen-29-oic acid, 3-hydroxy-2-oxo-, methyl ester

There total 5 articles about 24-Nor-D:A-friedooleana-1(10),5,7-tetraen-29-oic acid, 3-hydroxy-2-oxo-, methyl ester 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: 96.8%

celastrol (34157-83-0) + methyl iodide (74-88-4) → pristimerin (1258-84-0)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1016/j.bmc.2016.08.070

Reference yield: 96.0%

celastrol (34157-83-0,80286-51-7) + methyl iodide (74-88-4) → pristimerin (1258-84-0)

Guidance literature:

With Sodium hydrogenocarbonate; In N,N-dimethyl-formamide; at 20 ℃; for 0.166667h;

DOI:10.1016/j.ejmech.2022.114254

Reference yield: 91.0%

celastrol (34157-83-0) → pristimerin (1258-84-0)

Guidance literature:

With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1016/j.bmcl.2017.05.083

upstream raw materials:

diazomethane

celastrol

methyl iodide

dichloromethane

Downstream raw materials:

(2R,4aR,6bR,12bS,14aS)-6b,10,11-Trihydroxy-2,4a,6,9,12b,14a-hexamethyl-1,2,3,4,4a,5,6b,12b,13,14,14a,14b-dodecahydro-picene-2-carboxylic acid methyl ester

netzahualcoyene

C₆₀H₇₈O₉

C₆₀H₇₈O₉

Refernces

NEW EPIMERIC DI-TRITERPENE QUINONE ETHERS. THEIR PARTIAL SYNTHESIS AND THAT OF NETZAHUALCOYENE FROM PRISTIMERIN AND DDQ

10.1016/S0040-4039(01)80637-7

The study focuses on the isolation and partial synthesis of two new di-triterpene quinone ethers (compounds 5 and 6) from the roots of Rzedowskia tolantonguensis. Pristimerin (1) was reacted with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) to produce a mixture of products, including netzahualcoyene (2) and alcohol 4. The structures of the synthesized compounds were determined using NMR data and compared with natural products. The study provides insights into the theorized biogenetic pathway to triterpene quinones with a rearranged netzahualcoyene skeleton.

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