Tormentic acid

Base Information

• Chemical Name: Tormentic acid
• CAS No.: 13850-16-3
• Molecular Formula: C₃₀H₄₈O₅
• Molecular Weight: 488.708
• Hs Code.: 2918199890
• NSC Number: 720893
• UNII: 9WL8LH7U78
• DSSTox Substance ID: DTXSID40930135
• Nikkaji Number: J126.654C
• Wikipedia: Tormentic_acid
• Wikidata: Q15634134
• Metabolomics Workbench ID: 128769
• ChEMBL ID: CHEMBL239077
• Mol file: 13850-16-3.mol

Synonyms:tormentic acid

Chemical Property of Tormentic acid

Chemical Property:

• Vapor Pressure: 4.86E-17mmHg at 25°C
• Melting Point: 273 °C
• Refractive Index: 1.579
• Boiling Point: 602.7 °C at 760 mmHg
• PKA: 4.47±0.70(Predicted)
• Flash Point: 332.3 °C
• PSA: 97.99000
• Density: 1.19g/cm³
• LogP: 5.17520
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Pyridine (Sparingly)
• XLogP3: 5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 488.35017463
• Heavy Atom Count: 35
• Complexity: 956

Purity/Quality:

99% ^*data from raw suppliers

Tormentic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CC(C(C5(C)C)O)O)C)C)C2C1(C)O)C)C(=O)O
• Isomeric SMILES: C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(C[C@H]([C@@H](C5(C)C)O)O)C)C)[C@@H]2[C@]1(C)O)C)C(=O)O
• Uses: Tormentic Acid is isolated from Tormentil rhizomes and has inhibitory effect on carcinognenesis. In addition, Tormentic Acid has been implicated to be a potential therapeutic candidate for the prevention of APAP-induced liver injury by inhibiting oxidative stress and inflammation.

Technology Process of Tormentic acid

There total 11 articles about Tormentic 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: 68.2%

2α,19α-dihydroxy-5α,9α-urs-12-en-3-one-28-oic acid-28-O-β-D-glucopyranosyl ester (1309589-79-4) → tormentic acid (53155-25-2,119725-19-8,13850-16-3) + rosamultin (95298-47-8,146356-82-3,88515-58-6)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 1h;

DOI:10.1016/j.phytochem.2014.03.002

Reference yield:

3-O-p-coumaroyltormentic acid → tormentic acid (53155-25-2,119725-19-8,13850-16-3)

Guidance literature:

3-O-p-coumaroyltormentic acid; With water; sodium hydroxide; at 20 ℃; for 15h;

With sulfuric acid; In water;

DOI:10.1016/j.bmc.2010.01.010

Reference yield:

serratolide → tormentic acid (53155-25-2,119725-19-8,13850-16-3)

Guidance literature:

With potassium hydroxide; In methanol; Heating;

DOI:10.1016/S0031-9422(98)00292-1

upstream raw materials:

3-O-trans-p-coumaroyltormentic acid

2α,19α-dihydroxy-5α,9α-urs-12-en-3-one-28-oic acid-28-O-β-D-glucopyranosyl ester

2α,3α,19α-trihydroxyurs-12-en-28-oic acid 28-β-D-glucopyranosyl ester

2α,3α-diacetoxy-19α-hydroxyurs-12-en-28-oic acid

Downstream raw materials:

methyl 2α,3β,19-trihydroxyurs-12-en-28-oate

polnolic acid

(2R,19R)-methyl 2-acetyloxy-19-hydroxy-3-oxours-12-en-28-carboxylate

(2R,3R,19R)-3-acetyloxy-2,19-dihydroxyurs-12-en-28-carboxylic acid

Refernces

• 1、 Woo, Kyeong Wan,Choi, Sang Un,Kim, Ki Hyun,Lee, Kang Ro. "Ursane saponins from the stems of Firmiana simplex and their cytotoxic activity". . p. 1450 - 1456. Retrieved 2015/07/15.
• 2、 Rollinger, Judith M.,Kratschmar, Denise V.,Schuster, Daniela,Pfisterer, Petra H.,Gumy, Christel,Aubry, Evelyne M.,Brandst?tter, Sarah,Stuppner, Hermann,Wolber, Gerhard,Odermatt, Alex. "11β-Hydroxysteroid dehydrogenase 1 inhibiting constituents from Eriobotrya japonica revealed by bioactivity-guided isolation and computational approaches". experimental part. p. 1507 - 1515. Retrieved 2010/05/18.