3301-61-9

Basic information

• Product Name: ent-16beta,17-Dihydroxy-19-kauraic acid
• Synonyms: ent-16beta,17-Dihydroxy-19-kauraic acid;ent-16beta,17-Dihydroxy-19-kauranoic acid;ent-16β,17-Dihydroxy-19-kauranoic acid;ent-16beta,17-Dihydroxykauran-19-oic acid;Diterpenoid SP-II
• CAS NO: 3301-61-9
• Molecular Formula: C20H32O4
• Molecular Weight: 336.46568
• Mol File: 3301-61-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 505.6 °C at 760 mmHg
• Flash Point: 273.6 °C
• Appearance: /
• Density: 1.22 g/cm³
• Vapor Pressure: 2.44E-12mmHg at 25°C
• Refractive Index: 1.577
• CAS DataBase Reference: ent-16beta,17-Dihydroxy-19-kauraic acid(CAS DataBase Reference)
• NIST Chemistry Reference: ent-16beta,17-Dihydroxy-19-kauraic acid(3301-61-9)
• EPA Substance Registry System: ent-16beta,17-Dihydroxy-19-kauraic acid(3301-61-9)

Safety Data

• Hazardous Substances Data: 3301-61-9(Hazardous Substances Data)

Usage

General Description

Ent-16β,17-dihydroxy-19-kauraic acid is a diterpenoid compound that is found in plants such as Sphagneticola trilobata. This chemical has been shown to exhibit various biological activities, including anti-inflammatory, anti-angiogenic, and anti-tumor properties. It has also been reported to have potential therapeutic effects on cardiovascular diseases, diabetes, and neurological disorders. Additionally, ent-16β,17-dihydroxy-19-kauraic acid has been identified as a modulator of the endocannabinoid system, which plays a crucial role in regulating various physiological processes in the body. Therefore, this compound has attracted attention as a potential therapeutic agent for the treatment of various health conditions.

InChI:InChI=1/C20H32O4/c1-17-7-3-8-18(2,16(22)23)14(17)6-9-19-10-13(4-5-15(17)19)20(24,11-19)12-21/h13-15,21,24H,3-12H2,1-2H3,(H,22,23)/t13-,14+,15+,17-,18-,19+,20+/m1/s1

Upstream product

• 22338-67-6 grandiflorenic acid 
• 5095-09-0 kaurenoic acid 
• 55483-24-4 ent-16β,17-dihydroxy-9(11)-kauren-19-oic acid 
• 80442-69-9 (2R,4'R,4a'S,6a'S,9'R,11a'R,11b'S)-4',11b'-dimethyldodecahydro-7'H-spiro[oxirane-2,8'-[6a,9]methanocyclohepta[a]naphthalene]-4'-carboxylic acid 

Relevant articles and documents

A straightforward synthesis of natural oxygenated ent-kaurenoic acid derivatives

The paper presents the synthesis of some natural diterpenoids of ent-kauranic structure, starting from ent-kaur-16-en-19-oic acid, a natural diterpenoid readily available from the dried wastes of sunflower (Helianthus annuus L.). The reported ent-16α,17-dihydroxykauran-19-oic, ent-16α-hydroxy-17-acetoxykauran-19-oic and ent-16α,17-diacetoxykauran-19-oic acids have been previously isolated from different plant sources and showed diverse biological activities, including anti-HIV, anti-cancer and anti-Alzheimer properties. Their chemical synthesis has not been disclosed so far. Additional cytotoxicity studies of the obtained compounds revealed a remarkable cell proliferative effect of parent ent-kaur-16-en-19-oic acid and two of its synthetic derivatives, which is in line with recent pioneering studies in this area.

A new ent-kaurane diterpene derivative from the stems of Eurya chinensis R.Br

One new ent-kaurane diterpene derivative (1), along with four known diterpenes, was isolated from the stems of Eurya chinensis R.Br. The structure of the new compound was established by extensive analysis of mass spectrometric and 1D and 2D NMR spectroscopic data. Compound 1 showed moderate anti-inflammatory activities with IC50 value of 8.12?μM. This is the first example of diterpenoids with 4-hydroxy-4-(2-hydroxyethyl)-1-hydroxyl-cyclohexanoyl substituent.

Oxyfunctionalization products of terpenoids with dimethyldioxirane and their biological activity

Oxyfunctionalization of the bioactive terpenoids, ursolic acid acetate (1), oleanolic acid acetate (5), lupeol acetate (12), and kaurenic acid (17), with dimethyldioxirane (DMDO) was investigated. Treatment of the terpenoids with DMDO under mild conditions afforded a variety of oxidation and oxydegradation products to yield naturally occurring and/or novel compounds in one step. After chromatographic separation, the structures of the individual isolated products were determined using spectroscopic methods including several homonuclear ( 1H-1H) and heteronuclear (1H-13C) shift-correlated 2D-NMR techniques. The inhibitory activity of the terpenoid derivatives against α-glucosidase was investigated and compounds 1, 3, 7, and 9 were found to exhibit potent activity.