Pachymic acid

Base Information

• Chemical Name: Pachymic acid
• CAS No.: 29070-92-6
• Molecular Formula: C33H52O5
• Molecular Weight: 528.773
• UNII: X2FCK16QAH
• Nikkaji Number: J126.682I
• Wikipedia: Pachymic_acid
• Wikidata: Q21099637
• Metabolomics Workbench ID: 94505
• ChEMBL ID: CHEMBL468034
• Mol file: 29070-92-6.mol

Synonyms:Eburica-8,24(28)-dien-21-oicacid, 3b,16a-dihydroxy-, 3-acetate (6CI);Lanost-8-en-21-oic acid,3b,16a-dihydroxy-24-methylene-, 3-acetate (8CI);3-O-Acetyltumulosic acid;NSC 244427;Pachymic acid;

Chemical Property of Pachymic acid

Chemical Property:

• Appearance/Colour: White Powder
• Vapor Pressure: 1.51E-17mmHg at 25°C
• Melting Point: 300 °C(Solv: methanol (67-56-1); acetone (67-64-1))
• Refractive Index: 1.539
• Boiling Point: 612.2 °C at 760 mmHg
• PKA: 4.65±0.10(Predicted)
• Flash Point: 184.7 °C
• PSA: 83.83000
• Density: 1.1 g/cm³
• LogP: 7.33140
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Methanol (Slightly), Pyridine (Slightly)
• XLogP3: 7.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 528.38147475
• Heavy Atom Count: 38
• Complexity: 1020

Purity/Quality:

95%-98% ^*data from raw suppliers

Pachymic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(=C)CCC(C1C(CC2(C1(CCC3=C2CCC4C3(CCC(C4(C)C)OC(=O)C)C)C)C)O)C(=O)O
• Isomeric SMILES: CC(C)C(=C)CC[C@H]([C@H]1[C@@H](C[C@@]2([C@@]1(CCC3=C2CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)OC(=O)C)C)C)C)O)C(=O)O
• Description: Pachymic acid (PA) is a lanostane-type triterpenoid from Poriacocos, which is an important component in traditional Chinese medicine. Previous studies have shown that PA possesses anti-emetic, anti-inflammatory and anticancer properties. It has been demonstrated that PA is able to inhibit the proliferation and invasion of pancreatic cancer cells by decreasing MMP-7 expression. PA was able to activate reactive oxygen species (ROS)-dependent JUN N-terminal kinase mitochondrial and endoplasmic reticulum stress pathways following cell cycle arrest at G2/M phase and cell apoptosis occurred in lung cancer cells. PA reduced proliferation and induced apoptosis through inactivation of AKT signaling and downregulation of AKT downstream protein expression in prostate cancer cells. Another study demonstrated that PA is able to stimulate glucose uptake by enhancing the expression and translocation of glucose transporter type 4. However, the therapeutic effects and potential mechanisms of PA on gastric cancer are poorly understood and therefore remain to be evaluated.
• Uses: Pachymic acid (PA) is a natural triterpenoid known to inhibit the phospholipase A2 (PLA(2)) family of arachidonic acid (AA)-producing enzymes, PA-treatment decreases bad phosphorylation, increases Bcl-2 phosphorylation, and activates caspases-9 and -3, it also decreases the expression and activation of proteins within the AKT signal pathway. suggests that PA initiates apoptosis through mitochondria dysfunction and influences apoptosis by reducing prostaglandin. Pachymic acid can exhibit antiinflammatory and anticancer properties, it can inhibit cell growth and modulate arachidonic acid metabolism in nonsmall cell lung cancer A549 cells by its inhibition of MAPKs and NF-kappaB signaling pathways; it can impair breast cancer cell invasion by suppressing nuclear factor-κB-dependent matrix metalloproteinase-9 expression. Pachymic acid has antioxidant activity, affects the removal effect of reactive oxygen species formation as did N-acetyl-L-cysteine and inhibits nuclear factor-κB translocation, it can mitigate the unfavorable conditions induced by AH Plus stimuli, therefore, the use of pachymic acid is suggested to prevent the complications of oral diseases such as inflammation and alveolar destruction of the oral cavity. Pachymic Acid is a natural triterpene extract which suppresses invasiveness of pancreatic cancer cells through the downregulation of MMP-7.

Technology Process of Pachymic acid

There total 1 articles about Pachymic 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:

pachymic acid phthalimidomethyl ester → pachimic acid (29070-92-6)

Guidance literature:

With sodium hydroxide; In ethanol; chloroform; Ambient temperature;

DOI:10.1016/0031-9422(95)00182-7

Refernces