109664-02-0

Basic information

• Product Name: Neocryptotanshinone
• Synonyms: Neocryptotanshinone;5,6,7,8-Tetrahydro-3-hydroxy-2-[(1R)-2-hydroxy-1-methylethyl]-8,8-dimethyl-1,4-phenanthrenedione
• CAS NO: 109664-02-0
• Molecular Formula: C19H22O4
• Molecular Weight: 314.37558
• Mol File: 109664-02-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 505.3°C at 760 mmHg
• Flash Point: 273.5°C
• Appearance: /
• Density: 1.255g/cm³
• Vapor Pressure: 4.93E-11mmHg at 25°C
• Refractive Index: 1.602
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: Neocryptotanshinone(CAS DataBase Reference)
• NIST Chemistry Reference: Neocryptotanshinone(109664-02-0)
• EPA Substance Registry System: Neocryptotanshinone(109664-02-0)

Safety Data

• Hazardous Substances Data: 109664-02-0(Hazardous Substances Data)

Usage

General Description

Neocryptotanshinone is a natural chemical compound derived from the root of the traditional Chinese medicinal herb Salvia miltiorrhiza, also known as red sage. It belongs to a class of compounds called tanshinones, which have been investigated for their potential medicinal properties, including anti-inflammatory, antioxidant, and anticancer effects. Neocryptotanshinone has been found to exhibit anti-inflammatory and anticancer activities in various preclinical studies, making it a promising candidate for further research and development as a potential therapeutic agent. Its mechanisms of action involve modulation of various signaling pathways involved in inflammation and cancer progression, and it has been shown to inhibit the growth and proliferation of cancer cells in laboratory studies. Additionally, neocryptotanshinone has demonstrated potential for reducing oxidative stress and protecting cells from damage caused by free radicals. Overall, neocryptotanshinone shows promise as a natural compound with potential medicinal benefits, but further research is needed to fully understand its therapeutic potential and safety for human use.

InChI:InChI=1/C19H22O4/c1-10(9-20)14-16(21)12-6-7-13-11(5-4-8-19(13,2)3)15(12)18(23)17(14)22/h6-7,10,20-21H,4-5,8-9H2,1-3H3

Upstream product

• 35825-57-1 Cryptotanshinone 
• 171979-71-8 1,1-dimethyl-5-tetralyl trifluoromethanesulfonate 
• 171979-67-2 2-diazo-1-(5,5-dimethyl-5,6,7,8-tetrahydro-1-naphthyl)-1-ethanone 
• 171979-68-3 1-(5,5-dimethyl-5,6,7,8-tetrahydro-1-naphthyl)ethan-1-one 
• 171979-70-7 1-methoxy-2-(4-methylpent-3-en-1-yl)benzene 
• 100-66-3 methoxybenzene 
• 33214-70-9 1,1-dimethyl-5-methoxytetralin 
• 171979-69-4 5,5-dimethyl-5,6,7,8-tetrahydronaphthalen-1-ol 
• 578-57-4 2-bromoanisole 
• 2270-59-9 1-bromo-4-methylpent-3-ene 
• 446024-79-9 12,16-epoxycarnosol 
• 149697-32-5 16-hydroxycarnosol 
• 879000-51-8 16-(tert-butyldimethylsilyloxy)-11,12-O-didehydrocarnosol 
• 879000-44-9 11,14-dioxo-12,16-epoxy-8,12-abietadien-20,7β-olide 

Downstream Products

• 568-72-9 tanshinone-IIA 
• 35825-57-1 Cryptotanshinone 

Related news

Neocryptotanshinone (cas 109664-02-0) inhibits lipopolysaccharide-induced inflammation in RAW264.7 macrophages by suppression of NF-κB and iNOS signaling pathways07/22/2019

Neocryptotanshinone (NCTS) is a natural product isolated from traditional Chinese herb Salvia miltiorrhiza Bunge. In this study, we investigated its anti-inflammatory effects in lipopolysaccharide (LPS)-stimulated mouse macrophage (RAW264.7) cells. MTT results showed that NCTS partly reversed LP...detailed

Relevant articles and documents

Quinone derivatives by chemical transformations of 16-hydroxycarnosol from Salvia species

The known diterpenes 12,16-epoxycarnosol (2), isotanshinone II (6), and (+)-neocryptotanshinone (8) were obtained by partial synthesis from 16-hydroxycarnosol (1), a C-16 hydroxylated abietatriene diterpene isolated in relative abundance from the aerial part of Salvia mellifera GREENE. The physical and spectroscopic data of these semisynthetic diterpenes were identical to those given for the natural ones in the literature. These abietane diterpenes have very interesting biological activities and the semisynthetic approach described here represents an alternative to obtain them from other major diterpenes isolated from Salvia species. Additionally, seven new semisynthetic diterpene analogues, 11,14-dioxo-12,16-epoxy-8,12-abietadien-20,7β-olide (3), 11,14-dioxo-12,16-epoxy-8,12,15(16)-abietatrien-20,7β-olide (4), 15,16-didehydro-12,16-epoxycarnosol (5), 1-oxoisotanshinone II (7), 16-hydroxycolumbaridione (9), 12,16-diacetoxycolumbaridione (10), and 14-methoxy-12,16-epoxycarnosol (13), were obtained from 1. The structures of the new compounds were established based on their spectroscopic data.

Atomatic Annulation Strategy for the Synthesis of Angularly-Fused Diterpenoid Quinones. Total Synthesis of (+)-Neocryptotanshinone, (-)-Cryptotanshinone, Tanshinone IIA, and (+/-)-Royleanone

The application of a photochemical aromatic annulation strategy in highly efficient total syntheses of several diterpenoid quinones isolated from the traditional Chinese medicine Dan Chen is reported.The pivotal step in each synthesis involves the assembly of the key tricyclic intermediate via the application of a recently developed "second generation" photochemical aromatic annulation method for the construction of highly substituted aromatic systems.In the total synthesis of neocryptotanchinone, the synthesis of the requisite diazo ketone anulation substrate 7 was achieved using paladium-mediated coupling reactions and an intramolecular Friedel-Crafts cyclization to form key carbon-carbon bonds.The pivotal aromatic annulation reaction was then accomplished by irradiating a solution of the diazo ketone 7 and the readily availabe siloxyalkyne 6 in benzene at room temperature.The desired tricyclic phenol 16 was produced in 58-65percent yield and was then converted to (+)-neocryptotanshinone (1) by treatment with tetra-n-butylammonium fluoride in the presence of oxygen.Cyclization to generate (-)-cryptotanshinone (2) was accomplished in high yield by brief exposure of 1 to an ethanolic solution of concentrated sulfuric acid, and dehydrogenation of 2 with DDQ furnished tanshinone IIA (3).As a further demonstration of the utility of the photochemical aromatic annulation strategy in the construction of angularly-fused diterpenes, the total synthesis of (+/-)-royleanone (4) was also investigated.Irradiation of a solution of the diazo ketone 18 and siloxyalkyne 25 produced the tricyclic intermediate 26, which was converted in two steps to royleanone by desilylation and oxidation.