559-74-0

Basic information

• Product Name: FRIEDELIN
• Synonyms: FRIEDELAN-3-ONE;FRIEDELIN;DA-FRIEDOOLEANAN-3-ONE;FRIEDELIN, TECH.;FRIEDELIN hplc;FRIEDELIN WITH HPLC;DA-friedooleanan-3-one, Friedelan-3-one;D:A-Friedooleanan-3-one (van) (8ci)(9ci)
• CAS NO: 559-74-0
• Molecular Formula: C30H50O
• Molecular Weight: 426.72
• EINECS: 209-205-1
• Product Categories: Tri-Terpenoids
• Mol File: 559-74-0.mol

Chemical Properties

• Melting Point: 262-265 °C(lit.)
• Boiling Point: 477.2 °C at 760 mmHg
• Flash Point: 233.9 °C
• Appearance: /
• Density: 0.963 g/cm³
• Vapor Pressure: 2.86E-09mmHg at 25°C
• Refractive Index: 1.502
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Merck: 13,4293
• BRN: 1916451
• CAS DataBase Reference: FRIEDELIN(CAS DataBase Reference)
• NIST Chemistry Reference: FRIEDELIN(559-74-0)
• EPA Substance Registry System: FRIEDELIN(559-74-0)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 559-74-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
FRIEDELIN is used as a starting material in the synthesis of various compounds for medicinal purposes. It is used as a precursor for the production of Friedel-3-enol acetate, Friedel-2-oxo-3-enol acetate, Friedel-2-ene derivatives, and Friedelin ketoxime. These synthesized compounds have potential applications in the development of new drugs.
Used in DNA Topoisomerase Inhibition:
Oxygenated FRIEDELIN derivatives are used as potent DNA topoisomerase IIα inhibitors. These inhibitors play a crucial role in controlling the activity of the enzyme, which is essential for DNA replication and transcription. The inhibition of this enzyme can lead to the development of new cancer therapies.
Used in Antimicrobial Applications:
The 1,4-pyrazine derivatives of FRIEDELIN are used as potent antimicrobial agents. These compounds exhibit strong activity against various microorganisms, making them valuable in the development of new antibiotics and antimicrobial treatments.

InChI:InChI=1/C30H50O/c1-20-21(31)9-10-22-27(20,5)12-11-23-28(22,6)16-18-30(8)24-19-25(2,3)13-14-26(24,4)15-17-29(23,30)7/h20,22-24H,9-19H2,1-8H3/t20-,22?,23?,24?,26+,27+,28-,29+,30-/m0/s1

Upstream product

• 5085-72-3 epifriedelanol 
• 17947-01-2 friedelan-3-oxo-2α-acetate 
• 19865-96-4 4-epi-friedelin 
• 7505-10-4 2α-bromofriedel-3-one 
• 72154-51-9 zeylanol thiobenzoate 
• 72154-54-2 zeylandiol dithiobenzoate 
• 88530-45-4 zeylanol acetate 
• 105370-95-4 4α-methyl-3β-hydroxylfriedelan 
• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 302-01-2 hydrazine 
• 161739-59-9 3-trimethylsiloxyfriedel-2-ene 
• 59995-80-1 21α-hydroxy-D:A-friedo-oleanan-3-one 
• 72173-97-8 6β-hydroxyfriedelan-3-one 

Downstream Products

• 7506-18-5 friedelinol 
• 5085-72-3 epifriedelanol 
• 559-73-9 D:A-friedo-oleanane 
• 471-56-7 4-oxa-3,4-secofriedelan-3-oic acid 
• 29621-75-8 3,4-secofriedelan-3 <*> 4-olide 
• 6960-62-9 3-benzoyloxy-friedel-2-ene 
• 7770-59-4 Friedelin-(2.4-dinitro-phenylhydrazon) 
• 7599-27-1 3-(3-phenyl-propionyloxy)-friedelene-⁽²⁾ 
• 28290-47-3 3,3-Diphenyl-3,4-seco-friedelan-3-ol 
• 33710-40-6 maytensifolin B 
• 40768-66-9 3-Benzylthiofriedel-3-en 
• 17947-01-2 friedelan-3-oxo-2α-acetate 
• 127211-74-9 friedel-3-oxo-4α-acetate 
• 127158-59-2 2β,4α-diacetoxyfriedelin 

Relevant articles and documents

Terpenoids of Syzygium formosanum

A new natural product, 4-epifriedelin (1), and 12 known terpenoids have been isolated from the leaves of Syzygium formosanum. The known compounds include caryophyllene oxide, friedelin, canophyllal, glutinol, α-terpineol, phytol, betulinic acid, uvaol, lupeol, betulin, ursolic acid, and oleanolic acid. All of these compounds are reported for the first time from S. formosanum.

FRIEDELIN, D:A-FRIEDO-OLEAN-3,21-DONE AND 21α-HYDROXY-D:A-FREDO-OLEAN-3-ONE FROM KOKOONA ZEYLANICA

Three triterpenes obtained from inner bark of Kokoona zeylanica have been identified as friedelin, D:A-friedo-olean-3,21-dione and 21α-hydroxy-D:A-friedo-olean-3-one by spectroscopic propertiesand chemical interconversions.Their chemotaxanomic significance is emphasized.Key Word Index - Kokoona zeylanica; Celastraceae; friedelin; D:A-friedo-olean-3,21-dione; 21α-hydroxy-D:A-friedo-olean-3-one; structure elucidation; triterpenoids; chemotaxonomy.

Denomination of 2-bromo-3-keto triterpenoids using N,N-dimethylaniline

Reflux of 2α-bromo/2,2-dibromolupanone (1/1a), methyl 2α-bromo/2,2-dibromodihydrobetulonate (2/2a) and 2/4α-bromofriedelin (3/3a) with N,N-dimethylaniline (DMA) resulted in the formation of lupanone, methyl dihydrobetulonate and friedelin, respectively in very good yields. The products have been characterized by spectroscopic analysis [IR, NMR ( 1H and 13C) and MS] and optical rotation as well as by comparison with the data reported in literature.

Extraction and purification of friedelin

Friedelin is a natural compound with promising proprieties. On its own or with chemical modification it is possible to introduce relevant biological activities, e.g. anti-cancer, anti-aging and agrochemical. Its availability in significant amounts has been a major drawback on its regular use and in the pursuit of different applications. Cork and cork-derived materials (e.g. black condensate) are the most relevant sources of Friedelin in nature (up to 10% in concentration). The present invention reports straightforward procedures to extract and purify Friedelin from cork and cork-derived materials (e.g. black condensate). It uses solvent extraction and (re)crystallization techniques easy to scale up to an industrial level, with a low solvent and low time consumption, high yields, up to 2.9%, and high purity degrees, up to 96%.

Aqueous hydrogen peroxide activated by ammonium heptamolybdate catalyst - A mild clean effective reagent system for the deprotection of oximes, semicarbazones and phenylhydrazones at room temperature

Oximes, phenylhydrazones and semicarbazones of a wide variety of aldehydes and ketones are cleanly cleaved to the corresponding carbonyl compounds in good to acceptable yields using environmentally safe and convenient oxidizer, 30% hydrogen peroxide in catalytic combination with 20 mol% ammonium heptamolybdate in aqueous acetic acid or tetrahydrofuran at room temperature. Absence of overoxidized by-products in case of oxidation-prone aromatic aldehydes, α,β-unsaturated aldehydes and compatibility with various common functional groups such as hydroxy, methoxy, epoxy, amino, methylenedioxy, conjugated and unconjugated C=C bonds are some of the key advantageous features of the method.

Biovalorization of friedelane triterpenes derived from cork processing industry byproducts

Here, we describe the synthesis, bioactivity screening, and structure-activity relationships of various synthetic triterpenoids prepared from the cork processing byproducts friedelin (1) and 3-hydroxyfriedel-3-en-2- one (2) via oxidative procedures. The synthesis of compounds 2α-trimethylsiloxyfriedelan-3-one (17), friedelin-2,3-lactone (18), friedelin-3-oxime (19), and friedelin-3,4-lactam (20) is also described. We have studied the insecticidal and phytotoxic potential of these compounds, their selective cytotoxic effects on insect and mammalian cells, and their antiparasitic effects. Structural modifications of the A-ring of friedelin (1) improved its insecticidal activity with derivatives 5, 2,3-secofriedelan-2-al-3- oic acid (6), its acetylated derivative 6a, 3β- and 3α- hydroxyfriedelane (9 and 10), 3α-hydroxyfriedel-2-one (11), 4β-hydroxyfriedel-3-one (16), the acetylated 10a, 3,4-secofriedelan-4-oxo- 3-oic-acid (14), lactone 18, and the oxime 19 being stronger insecticides than the parent compound. Methyl-3-nor-2,4-secofriedelan-4-oxo-2-oic acid (12) and its acetylated derivative 12a also showed insecticidal activity in contrast to their inactive parent compound 2. The postingestive effects and cytotoxicity of these compounds suggest a multifaceted insecticidal mode of action. These structural modifications did not result in better phytotoxic agents than the parent compounds except for lactam 20 and yielded several moderately active antiparasite derivatives (seco acids 6, 12, 14, and 4β -hydroxyfriedel-3- one 16) with cytotoxic effects on mammalian cells.

Process for extraction and purification of friedelin from cork smoker wash solids

This invention concerns a method for the extraction and separation of friedelin from the different components smoker wash solids, by means of simple mechanical, physical and chemical treatments. These treatments consist in the fragmentation of the resinous residue, percolation with organic solvents or mixtures of organic solvents at temperatures between room temperature and the boiling point of solvents or mixtures and percolation with alkaline salt solutions, followed by distillation and drying of the extracts. These methods are characterized by a final friedelin yield, that may vary beteween 1% and 3%, with a putity degree (HPLC) within the range of 87%-101%.

The Reaction of Lupane and Friedo-Oleanane Type Triterpenes with m-Chloroperbenzoic Acid

Lupane-3β,28-diol, lupan-3β-ol, and friedelan-3β-ol were treated with m-chloroperbenzoic acid (mCPBA) in refluxing chloroform to afford corresponding lactones in one step, while lupane-3β,28-diyl, diacetate, lupan-3β-yl acetate, and friedelan-3β-yl acetate to give hydroxylated or keto derivatives.Similar reaction of dendropanoxide with mCPBA yielded 6β-, 7β-, 21α-, and 22β-hydroxylated compounds.

OXIDATION OF UNACTIVATED CARBON ATOMS OF LUPANE AND FRIEDELANE-TYPE TRITERPENES WITH m-CHLOROPERBENZOIC ACID

The reaction of lupan-3β,28-diyl diacetate, lupan-3β-yl acetate, and friedelan-3β-yl acetate with m-chloroperbenzoic acid gave their hydroxy or keto derivatives upon oxidation of unactivated carbon atoms.

Reductive Ring-opening of Triterpenoid Epoxides with Lithium and Ethylenediamine

The reactions of lithium and ethylenediamine with 3α,4α-(I, III) and 3β,4β-epoxides (VIII, IX) of friedel-3-ene afford the hydroxy derivatives via epoxide ring-opening.