20547-99-3

Basic information

• Product Name: 3,5,5-Trimethylcyclohexane-1,4-dione
• Synonyms: 2,2,6-Trimethyl-1,4-cyclohexanedione;2,2,6-Trimethylcyclohexane-1,4-dione;2,6,6-Trimethyl-1,4-cyclohexadione;2,6,6-Trimethylcyclohexane-1,4-dione;3,5,5-Trimethylcyclohexane-1,4-dione;1,4-Dioxo-3,3,5-trimethylcyclohexane;2,6,6-Trimethyl-1,4-cyclohexanedione;3,5,5-Trimethyl-1,4-cyclohexanedione
• CAS NO: 20547-99-3
• Molecular Formula: C₉H₁₄O₂
• Molecular Weight: 154.21
• Mol File: 20547-99-3.mol
• Article Data: 17

Chemical Properties

• Melting Point: 63-65℃
• Boiling Point: 236℃
• Flash Point: 86℃
• Appearance: /
• Density: 0.976
• Vapor Pressure: 0.0474mmHg at 25°C
• Refractive Index: 1.444
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 3,5,5-Trimethylcyclohexane-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5,5-Trimethylcyclohexane-1,4-dione(20547-99-3)
• EPA Substance Registry System: 3,5,5-Trimethylcyclohexane-1,4-dione(20547-99-3)

Safety Data

• Hazardous Substances Data: 20547-99-3(Hazardous Substances Data)

Usage

General Description

3,5,5-Trimethylcyclohexane-1,4-dione, also known as triketohydrindene hydrate, is a chemical compound with a molecular formula C9H14O2. It is a cyclic ketone containing a cyclohexane ring with three methyl groups and two carbonyl groups attached to adjacent carbon atoms. 3,5,5-Trimethylcyclohexane-1,4-dione is commonly used in organic synthesis and as a building block for the construction of more complex molecules. It is also used as a fragrance ingredient in perfumes and colognes. 3,5,5-Trimethylcyclohexane-1,4-dione is a colorless crystalline solid at room temperature and has a characteristic odor. It is considered to be a stable compound and is not known to pose significant health risks when handled and used according to proper safety guidelines.

InChI:InChI=1/C9H14O2/c1-6-4-7(10)5-9(2,3)8(6)11/h6H,4-5H2,1-3H3

Upstream product

• 896107-70-3 9-hydroxymegastigma-4,7-dien-3-one 
• 1125-21-9 2,6,6-trimethyl-2-cyclohexene-1,4-dione 
• 1135-90-6 (-)-4-Oxo-2,6,6-trimethyl-2-cyclohexenessigsaeuremethylester 
• 55057-38-0 2,4-dihydroxy-2,6,6-trimethylcyclohexanone 
• 1133-02-4 (3aS,7aR)-4,4,7a-Trimethyl-hexahydro-benzofuran-2,6-dione 
• 110-87-2 3,4-dihydro-2H-pyran 
• 14203-59-9 4-hydroxy-3,5,5-trimethyl-cyclohex-2-enone 
• 78-59-1 3,5,5-Trimethylcyclohex-2-en-1-one 

Downstream Products

• 1403373-31-8 (2Z)-3-ethyl-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-N-propylpent-2-en-4-ynamide 
• 1403371-98-1 ethyl (2E)-5-[1-hydroxy-4-(methoxyimino)-2,6,6-trimethylcyclohex-2-en-1-yl]-3-(trifluoromethyl)pent-2-en-4-ynoate 
• 1403369-97-0 (2E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-(trifluoromethyl)pent-2-en-4-ynoic acid 
• 1403369-91-4 ethyl (2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-(trifluoromethyl)penta-2,4-dienoate 
• 1403369-90-3 ethyl (2E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-(trifluoromethyl)pent-2-en-4-ynoate 
• 1403369-85-6 ethyl (2Z)-3-[(E)-2-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)vinyl]hex-2-enoate 
• 1403369-84-5 ethyl (2Z)-3-[(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-ethynyl]hex-2-enoate 
• 1402897-13-5 methyl 2-[(E)-2-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)vinyl]-6-methylbenzoate 
• 1402942-17-9 methyl-2 [(E)-2-(8-hydroxy-2,3,7,9,9-pentamethyl-1,4-dioxaspiro[4.5]dec-6-en-8-yl)vinyl]-6-methylbenzoate 
• 1402893-98-4 4-hydroxy-3,5,5-trimethyl-4-{[2-(trifluoromethyl)phenyl]ethynyl}cyclohex-2-en-1-one 
• 1402893-97-3 2,3,7,9,9-pentamethyl-8-{[2-(trifluoromethyl)phenyl]ethynyl}-1,4-dioxaspiro[4.5]-dec-6-en-8-ol 
• 1402904-29-3 ethyl 2-[(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)ethynyl]cyclopent-1-ene-1-carboxylate 
• 1402893-48-4 4-hydroxy-3,5,5-trimethyl-4-[(E)-2-(2-methylphenyl)vinyl]cyclohex-2-en-1-one 
• 1402904-30-6 ethyl 2-[(E)-2-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)vinyl]cyclopent-1-ene-1-carboxylate 

Relevant articles and documents

Better than Nature: Nicotinamide Biomimetics That Outperform Natural Coenzymes

The search for affordable, green biocatalytic processes is a challenge for chemicals manufacture. Redox biotransformations are potentially attractive, but they rely on unstable and expensive nicotinamide coenzymes that have prevented their widespread expl

Engineering a nicotinamide mononucleotide redox cofactor system for biocatalysis

Biological production of chemicals often requires the use of cellular cofactors, such as nicotinamide adenine dinucleotide phosphate (NADP+). These cofactors are expensive to use in vitro and difficult to control in vivo. We demonstrate the development of a noncanonical redox cofactor system based on nicotinamide mononucleotide (NMN+). The key enzyme in the system is a computationally designed glucose dehydrogenase with a 107-fold cofactor specificity switch toward NMN+ over NADP+ based on apparent enzymatic activity. We demonstrate that this system can be used to support diverse redox chemistries in vitro with high total turnover number (~39,000), to channel reducing power in Escherichia coli whole cells specifically from glucose to a pharmaceutical intermediate, levodione, and to sustain the high metabolic flux required for the central carbon metabolism to support growth. Overall, this work demonstrates efficient use of a noncanonical cofactor in biocatalysis and metabolic pathway design.

Synthesis and Biochemical Evaluation of Nicotinamide Derivatives as NADH Analogue Coenzymes in Ene Reductase

Nicotinamide and pyridine-containing conjugates have attracted a lot of attention in research as they have found use in a wide range of applications including as redox flow batteries and calcium channel blockers, in biocatalysis, and in metabolism. The interesting redox character of the compounds’ pyridine/dihydropyridine system allows them to possess very similar characteristics to the natural chiral redox agents NAD+/NADH, even mimicking their functions. There has been considerable interest in designing and synthesizing NAD+/NADH mimetics with similar redox properties. In this research, three nicotinamide conjugates were designed, synthesized, and characterized. Molecular structures obtained through X-ray crystallography were obtained for two of the conjugates, thereby providing more detail on the bonding and structure of the compounds. The compounds were then further evaluated for biochemical properties, and it was found that one of the conjugates possessed similar functions and characteristics to the natural NADH. This compound was evaluated in the active enzyme, enoate reductase; like NADH, it was shown to help reduce the C=C double bond of three substrates and even outperformed the natural coenzyme. Kinetic data are reported.