67895-86-7

Basic information

• Product Name: HYDROXYFRIEDELAN-2-ONE, 3-A-(RG)
• Synonyms: HYDROXYFRIEDELAN-2-ONE, 3-A-(RG)
• CAS NO: 67895-86-7
• Molecular Formula: C₃₀H₅₀O₂
• Molecular Weight: 442.73
• Mol File: 67895-86-7.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: HYDROXYFRIEDELAN-2-ONE, 3-A-(RG)(CAS DataBase Reference)
• NIST Chemistry Reference: HYDROXYFRIEDELAN-2-ONE, 3-A-(RG)(67895-86-7)
• EPA Substance Registry System: HYDROXYFRIEDELAN-2-ONE, 3-A-(RG)(67895-86-7)

Safety Data

• Hazardous Substances Data: 67895-86-7(Hazardous Substances Data)

Upstream product

• 67895-85-6 cerin 
• 161739-59-9 3-trimethylsiloxyfriedel-2-ene 

Relevant articles and documents

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.

Terpenoids and Related Compounds: Part XXIII - Mechanism of Some Transformation Reactions of Friedelin and Its Derivatives

DDQ dehydrogenation of friedelin (I) affords friedel-1-ene-3-one (III) in a very low yield (9percent).Treatment of 2α-bromofriedel-3-one (IV) with LiBr and Li2CO3 furnishes (III) (20percent) along with I (15percent).Reaction of IV with AgOAc and glacial HOAc leads to the formation of 3-hydroxyfriedel-3-ene-2-one (V) (66percent).Baeyer-Villiger oxidation of I with p-nitroperbenzoic acid produces the ε-lactone (IX) (41percent) while NiO2 oxidation of cerin (II) affords (V) (20percent) and 3α-hydroxyfriedel-2-one (VI) (15percent).The mechanism of these reactions are discussed.