6184-16-3

Basic information

• Product Name: (2S,4aR,6aS,6aS,6bR,8aS,12aS,14bS)-2,4a,6a,6b,9,9,12a-heptamethyl-10,1 3-dioxo-1,3,4,5,6,6a,7,8,8a,11,12,14b-dodecahydropicene-2-carboxylic a cid
• Synonyms: (2S,4aR,6aS,6aS,6bR,8aS,12aS,14bS)-2,4a,6a,6b,9,9,12a-heptamethyl-10,1 3-dioxo-1,3,4,5,6,6a,7,8,8a,11,12,14b-dodecahydropicene-2-carboxylic a cid
• CAS NO: 6184-16-3
• Molecular Formula: C₃₀H₄₄O₄
• Molecular Weight: 468.66796
• Mol File: 6184-16-3.mol
• Article Data: 38

Chemical Properties

• Boiling Point: 586.8°C at 760 mmHg
• Flash Point: 322.7°C
• Appearance: /
• Density: 1.14g/cm³
• Vapor Pressure: 2.72E-15mmHg at 25°C
• Refractive Index: 1.557
• CAS DataBase Reference: (2S,4aR,6aS,6aS,6bR,8aS,12aS,14bS)-2,4a,6a,6b,9,9,12a-heptamethyl-10,1 3-dioxo-1,3,4,5,6,6a,7,8,8a,11,12,14b-dodecahydropicene-2-carboxylic a cid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4aR,6aS,6aS,6bR,8aS,12aS,14bS)-2,4a,6a,6b,9,9,12a-heptamethyl-10,1 3-dioxo-1,3,4,5,6,6a,7,8,8a,11,12,14b-dodecahydropicene-2-carboxylic a cid(6184-16-3)
• EPA Substance Registry System: (2S,4aR,6aS,6aS,6bR,8aS,12aS,14bS)-2,4a,6a,6b,9,9,12a-heptamethyl-10,1 3-dioxo-1,3,4,5,6,6a,7,8,8a,11,12,14b-dodecahydropicene-2-carboxylic a cid(6184-16-3)

Safety Data

• Hazardous Substances Data: 6184-16-3(Hazardous Substances Data)

Usage

General Description

The chemical compound "(2S,4aR,6aS,6aS,6bR,8aS,12aS,14bS)-2,4a,6a,6b,9,9,12a-heptamethyl-10,13-dioxo-1,3,4,5,6,6a,7,8,8a,11,12,14b-dodecahydropicene-2-carboxylic acid" is a complex molecule with a long name, indicating its intricate structure. It contains a dodecahydropicene core with a carboxylic acid substituent, and features a total of 30 carbon atoms, 2 oxygen atoms, and 2 hydrogen atoms. The presence of multiple methyl groups and a dioxo moiety adds to its complexity. (2S,4aR,6aS,6aS,6bR,8aS,12aS,14bS)-2,4a,6a,6b,9,9,12a-heptamethyl-10,1 3-dioxo-1,3,4,5,6,6a,7,8,8a,11,12,14b-dodecahydropicene-2-carboxylic a cid likely possesses unique chemical and biological properties due to its intricate structure, and it could potentially be used in various scientific and industrial applications.

InChI:InChI=1/C30H44O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21,23H,8-15,17H2,1-7H3,(H,33,34)/t19-,21+,23-,26-,27+,28+,29-,30-/m1/s1

Upstream product

• 471-53-4 3β-hydroxy-18α-GA 
• 1405-86-3 glycyrrhizin 
• 410097-37-9 18β-glycyrrhetinic acid 
• 471-53-4 enoxolone 
• 1449-05-4 3β-hydroxy-18β-GA 

Downstream Products

• 157519-07-8 (4aS,6S,8aS)-6-(tert-Butyl-diphenyl-silanyloxy)-2,5,5,8a-tetramethyl-4a,5,6,7,8,8a-hexahydro-4H-naphthalen-1-one 
• 157519-05-6 tert-Butyl-diphenyl-((1aR,3aS,5S,7aS,7bS)-1a,4,4,7a-tetramethyl-decahydro-1-oxa-cyclopropa[a]naphthalen-5-yloxy)-silane 
• 157519-06-7 (1R,4aS,6S,8aS)-6-(tert-Butyl-diphenyl-silanyloxy)-2,5,5,8a-tetramethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalen-1-ol 
• 157519-03-4 tert-Butyl-diphenyl-((2S,4aR,8aR)-1,1,4a,6-tetramethyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-2-yloxy)-silane 
• 151702-18-0 (4aS,6S,8aS)-6-Benzyloxy-2,5,5,8a-tetramethyl-octahydro-naphthalen-1-one 
• 157519-04-5 (3S,8aR)-3-(benzyloxy)-4,4,7,8a-tetramethyl-1,2,3,4,4a,5,6,8a-octahydro naphthalene 

Relevant articles and documents

Synthesis and biological evaluation of pentacyclic triterpenoid derivatives as potential novel antibacterial agents

A series of ursolic acid (UA), oleanolic acid (OA) and 18β-glycyrrhetinic acid (GA) derivatives were synthesized by introducing a range of substituted aromatic side-chains at the C-2 position after the hydroxyl group at C-3 position was oxidized. Their antibacterial activities were evaluated in vitro against a panel of four Staphylococcus spp. The results revealed that the introduction of aromatic side-chains at the C-2 position of GA led to the discovery of potent triterpenoid derivatives for inhibition of both drug sensitive and resistant S. aureus, while the other two series derivatives of UA and OA showed no significant antibacterial activity even at high concentrations. In particular, GA derivative 33 showed good potency against all four Staphylococcus spp. (MIC = 1.25–5 μmol/L) with acceptable pharmacokinetics properties and low cytotoxicity in vitro. Molecular docking was also performed using S. aureus DNA gyrase to rationalize the observed antibacterial activity. This series of GA derivatives has strong potential for the development of a new type of triterpenoid antibacterial agent.

Glycyrrhetinic acid derivative Z-type isomer and preparation method thereof

The invention discloses a glycyrrhetinic acid derivative Z-type isomer and a preparation method thereof. The method comprises the following steps: dissolving a glycyrrhetinic acid derivative E-type isomer in a mixed solvent of an organic solvent and water, and stirring under 254-380nm light to obtain the glycyrrhetinic acid derivative Z-type isomer. According to the method, through a green and healthy mode, no catalyst is used, and isomerization from the glycyrrhetinic acid derivative E-type isomer to the glycyrrhetinic acid derivative Z-type isomer is caused only in the mixed solution of the organic solvent and water by utilizing distortion and relaxation of a central double bond of the isomer under induction of a clean light energy source. The glycyrrhetinic acid derivative E-type isomer provided by the invention has relatively good stability and antibacterial property.

A versatile tailoring tool for pentacyclic triterpenes of Penicillium griseofulvum CICC 40293

In the biosynthetic pathway of pentacyclic triterpenes (PTs), tailoring reactions can produce a wide range of end products from a small number of common scaffolds and the microbial transformation has also been established as an alternative technique for this purpose. In this study, we explored the tailoring reactions involved in the microbial transformation of pentacyclic triterpenes by Penicillium griseofulvum CICC 40293. Preparative biotransformation of eight different PTs from three scaffolds resulted in the isolation of thirteen metabolites. The structures of metabolites were elucidated by HR-ESI-MS, 1D, and 2D NMR spectroscopy. We discovered the highly efficient regio- and stereo-selective hydroxylation of inactivated sp3 CH2 and CH3 on the position of 2α, 7β, 15α, 21β, 23(angular methyl), and 30?COOH glycosylation, this versatile tailoring system for PTs would provide an effective method for expanding their structural diversities. In addition, all compounds were subjected to the bioassay on the model of lipopolysaccharide (LPS)-stimulated RAW 264.7 cells to evaluate their anti-inflammatory activity through nitric oxide (NO) inhibition activity. Compounds 2a and 5a exhibited excellent NO inhibitory activity with IC50 values of 8.35 ± 2.81 μM and 19.60 ± 4.25 μM, respectively.