151561-88-5

Basic information

• Product Name: ent-3-Oxokauran-17-oic acid
• Synonyms: ent-3-Oxokauran-17-oic acid;3-Oxokauran-17-oic acid
• CAS NO: 151561-88-5
• Molecular Formula: C20H30O3
• Molecular Weight: 318.45
• Mol File: 151561-88-5.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ent-3-Oxokauran-17-oic acid(CAS DataBase Reference)
• NIST Chemistry Reference: ent-3-Oxokauran-17-oic acid(151561-88-5)
• EPA Substance Registry System: ent-3-Oxokauran-17-oic acid(151561-88-5)

Safety Data

• Hazardous Substances Data: 151561-88-5(Hazardous Substances Data)

Usage

General Description

Ent-3-Oxokauran-17-oic acid is a natural diterpenoid compound found in plants of the Lamiaceae family, such as Salvia and Vitex. It is derived from the ent-kaurenoic acid, and has been found to exhibit various biological activities, including anti-inflammatory, anticancer, and antimicrobial properties. Research has shown that ent-3-Oxokauran-17-oic acid has potential therapeutic applications in the treatment of inflammatory and infectious diseases, as well as in cancer therapy. Its chemical structure makes it a promising candidate for further exploration in drug development and medicinal chemistry.

Upstream product

• 548486-42-6 (16R)-16,17-(isopropylidenedioxy)-19-{[(4-methylphenyl)sulfonyl]oxy}phyllocladan-3-one 
• 544476-39-3 (2R,3S,16R)-16,17-(isopropylidenedioxy)phyllocladane-2,3-diol 2-(4-methylbenzenesulfonate) 
• 548486-39-1 (2R,3S,16R)-16,17-(isopropylidenedioxy)phyllocladane-2,3-diol 3-acetate 2-(3-methylbut-2-enoate) 
• 548486-44-8 (2R,3S,16R)-16,17-(isopropylidenedioxy)phyllocladane-2,3-diol 2,3-bis(methanesulfonate) 
• 544476-38-2 (2R,3S,16R)-16,17-(isopropylidenedioxy)phyllocladane-2,3-diol 
• 548486-40-4 (16R)-16,17,19-trihydroxyphyllocladan-3-one 
• 548486-41-5 (16R)-19-hydroxy-16,17-(isopropylidenedioxy)phyllocladan-3-one 
• 544476-40-6 (3S,16R)-16,17-(isopropylidenedioxy)phyllocladane-3-ol 
• 548776-81-4 (16R)-16,17-epoxyphyllocladan-3-one 
• 246857-15-8 (16R)-16-hydroxy-17-{[(4-methylphenyl)sulfonyl]oxy}phyllocladan-3-one 
• 49817-37-0 (16R)-16,17-(isopropylidenedioxy)phyllocladan-3-one 
• 548776-84-7 (16R)-3-oxophyllocladan-17-al 

Relevant articles and documents

Chemical transformations of phyllocladane (=13β-kaurane) diterpenoids

Earlier phytochemical work on Plectranthus ambiguus (Lamiaceae) afforded a series of tetracyclic phyllocladane-type (=13β-kaurane) diterpenoids (see 1a-f). In the course of investigations concerning the reaction behavior of this rare natural-products, a new constituent of P. ambiguus was isolated, (2S,3R,16R)-phyllocladane-2,3,16,17-tetrol 2,3-diacetate (1g), and another eighteen new phyllocladanes were prepared by chemical transformations and characterized. The main constituent 1b of P. ambiguus was chemically transformed to the known natural diterpenoid calliterpenone (=(16R)-16,17-dihydroxyphyllocladan-3-one; 2) thus unambiguously establishing its structure (Scheme 1). Epimerization at C(16) via the epoxy derivative 20 yielded 16-epicalliterpenone (21), 17-hydroxyphylloclad-15-ene-3-one (22), and (16R)-3-oxophyllocladan-17-al (23) (Scheme 6). Comparing this reaction sequence with the corresponding one starting from diastereoisomeric (16R)-16,17-dihydroxy-ent-kauran-3-one (=abbeokutone; 27) showed basically the same outcome (Scheme 7). Furthermore, three new C(16)-substituted ent-kauran-3-ones were characterized. Reliable spectroscopic arguments for the determination of the configuration at C(16) in phyllocladanes and kauranes as well as for the differentiation of the diastereoisomeric skeletons are presented.