114394-01-3

Basic information

• Product Name: urodiolenone
• Synonyms: urodiolenone
• CAS NO: 114394-01-3
• Molecular Formula: C15H24O3
• Molecular Weight: 252.34926
• Mol File: 114394-01-3.mol

Chemical Properties

• Boiling Point: 423.1°Cat760mmHg
• Flash Point: 223.8°C
• Appearance: /
• Density: 1.11g/cm³
• Vapor Pressure: 6.25E-09mmHg at 25°C
• Refractive Index: 1.534
• PKA: 14.28±0.29(Predicted)
• CAS DataBase Reference: urodiolenone(CAS DataBase Reference)
• NIST Chemistry Reference: urodiolenone(114394-01-3)
• EPA Substance Registry System: urodiolenone(114394-01-3)

Safety Data

• Hazardous Substances Data: 114394-01-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H24O3/c1-10-6-13(17)7-11-4-5-12(8-14(10,11)2)15(3,18)9-16/h7,10,12,16,18H,4-6,8-9H2,1-3H3/t10-,12?,14+,15+/m1/s1

Upstream product

• 4674-50-4 (+)-nootkatone 
• 50763-67-2 4α,4aα-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2α-ol 
• 4674-50-4 (+)-nootkatone 

Relevant articles and documents

Urodiolenone from grapefruit juice, a urinary metabolite found in hypertensive subjects

Urodiolenone, a compound isolated from the urine of hypertensive subjects, is a 1:1 epimeric mixture of two dihydroxy derivatives of nookatone, a constituent of grapefruit. The structure of urodiolenone was suggested by NMR spectroscopy and confirmed by partial synthesis from nootkatone, a sesquiterpenoid ketone with a valencene skeleton. In addition, we show that urodiolenone itself is also present in the grapefruit in free form and possibly also as a glucuronide. The question whether urodiolenone is produced exogenously or endogenously is discussed.

Microbial transformation of (+)-nootkatone and the antiproliferative activity of its metabolites

Six metabolites were obtained as a result of microbial transformation of (+)-nootkatone (1) by the fungal strains: Botrytis, Didymosphaeria, Aspergillus, Chaetomium and Fusarium. Their structure were established as (+)-(4R,5S,7R,9R)-9α-hydroxynootkatone (2), (+)-(4R,5S,7R)-13- hydroxynootkatone (3) and (+)-(4R,5S,7R,9R,11S)-11,12-epoxy-9α- hydroxynootkatone (4), (+)-(4R,5S,7R,11S)-11,12-epoksynootkatone (5), (+)-(4R,5S,7R)-11,12-dihydroxynootkatone (6) and (+)-(4R,5S,7R)-7,11,12- trihydroxynootkatone (7) on the basis of their spectral data. Two products: (4) and (7) were not previously reported in the literature. The antiproliferative activity of (+)-nootkatone (1) and isolated metabolites (2-7) of its biotransformation has been evaluated.

Biotransformation of citrus aromatics nootkatone and valencene by microorganisms

Biotransformations of the sesquiterpene ketone nootkatone (1) from the crude drug Alpiniae Fructus and grapefruit oil, and the sesquiterpene hydrocarbon valencene (2) from Valencia orange oil were carried out with microorganisms such as Aspergillus niger, Botryosphaeria dothidea, and Fusarium culmorum to afford structurally interesting metabolites. Their stereostructures were established by a combination of high-resolution NMR spectral and X-ray crystallographic analysis and chemical reaction. Metabolic pathways of compounds 1 and 2 by A. niger are proposed.

The Preparation and Microbiological Hydroxylation of the Sesquiterpenoid Nootkatone

The sesquiterpenoid nootkatone has been prepared from valencene by copper(I) iodide catalysed oxidation with t-butylhydroperoxide and hydroxylated at C-9 by Mucor plumbeus and Cephalosporium aphidicola.