1665-56-1

Basic information

• Product Name: (2Z,4S,4aS,12aS)-2-(amino-hydroxy-methylidene)-4-dimethylamino-10,11,1 2a-trihydroxy-6-methyl-4a,5-dihydro-4H-tetracene-1,3,12-trione
• Synonyms: (2Z,4S,4aS,12aS)-2-(amino-hydroxy-methylidene)-4-dimethylamino-10,11,1 2a-trihydroxy-6-methyl-4a,5-dihydro-4H-tetracene-1,3,12-trione;5a,6-anhydrotetracycline;(1S)-1α-(Dimethylamino)-2,4aα,6,7-tetrahydroxy-4,5-dioxo-11-methyl-1,4a,12,12aα-tetrahydronaphthacene-3-carboxamide;(4S)-4β-Dimethylamino-1,4,4aβ,5,12,12a-hexahydro-3,10,11,12aβ-tetrahydroxy-6-methyl-1,12-dioxo-2-naphthacenecarboxamide;(4S)-Anhydrotetracycline;3,10,11,12aβ-Tetrahydroxy-4β-(dimethylamino)-6-methyl-1,12-dioxo-1,4,4aβ,5,12,12a-hexahydronaphthacene-2-carboxamide;(4R)-4α-Dimethylamino-1,4,4aβ,5,12,12a-hexahydro-3,10,11,12aβ-tetrahydroxy-6-methyl-1,12-dioxo-2-naphthacenecarboxamide;4-Epianhydrotetracycline
• CAS NO: 1665-56-1
• Molecular Formula: C₂₂H₂₂N₂O₇
• Molecular Weight: 426.423
• Mol File: 1665-56-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 221-222 °C (decomp)(Solv: ethyl acetate (141-78-6))
• Boiling Point: 618.6 °C at 760 mmHg
• Flash Point: 327.9 °C
• Appearance: /
• Density: 1.6 g/cm³
• Vapor Pressure: 3.66E-16mmHg at 25°C
• Refractive Index: 1.76
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: (2Z,4S,4aS,12aS)-2-(amino-hydroxy-methylidene)-4-dimethylamino-10,11,1 2a-trihydroxy-6-methyl-4a,5-dihydro-4H-tetracene-1,3,12-trione(CAS DataBase Reference)
• NIST Chemistry Reference: (2Z,4S,4aS,12aS)-2-(amino-hydroxy-methylidene)-4-dimethylamino-10,11,1 2a-trihydroxy-6-methyl-4a,5-dihydro-4H-tetracene-1,3,12-trione(1665-56-1)
• EPA Substance Registry System: (2Z,4S,4aS,12aS)-2-(amino-hydroxy-methylidene)-4-dimethylamino-10,11,1 2a-trihydroxy-6-methyl-4a,5-dihydro-4H-tetracene-1,3,12-trione(1665-56-1)

Safety Data

• Hazardous Substances Data: 1665-56-1(Hazardous Substances Data)

Usage

General Description

The chemical "(2Z,4S,4aS,12aS)-2-(amino-hydroxy-methylidene)-4-dimethylamino-10,11,12a-trihydroxy-6-methyl-4a,5-dihydro-4H-tetracene-1,3,12-trione" is a compound with a tetracycline-like structure. It contains a tetracene ring system with multiple hydroxyl and amino groups attached. The compound is characterized by its potent antibacterial and antibiotic properties, making it a commonly used medication for treating various infections caused by bacteria. Additionally, its unique chemical structure allows for specific interactions with bacterial ribosomes, leading to inhibition of protein synthesis and ultimately bacteriostatic activity. However, due to its complex and potentially toxic nature, this compound should be used with caution and under the guidance of a healthcare professional.

InChI:InChI=1/C22H22N2O7/c1-8-9-5-4-6-12(25)13(9)17(26)14-10(8)7-11-16(24(2)3)18(27)15(21(23)30)20(29)22(11,31)19(14)28/h4-6,11,16,25-26,30-31H,7,23H2,1-3H3/b21-15-/t11-,16-,22-/m0/s1

Upstream product

• 57-62-5 Chlortetracycline 
• 60-54-8 TETRACYCLINE 
• 2602-31-5 6-methylpretetramide 
• 485-80-3 S-adenosyl-L-methionine 
• 3593-53-1 4-amino-anhydrotetracycline 
• 286961-67-9 ((1S,2S,3S,12aR)-2-Benzyloxy-3-benzyloxymethyl-4,6,11-trihydroxy-7-methoxy-11-methyl-5-oxo-1,2,3,5,11,11a,12,12a-octahydro-naphthacen-1-yl)-carbamic acid benzyl ester 
• 286961-68-0 ((1S,2S,3S,12aR)-2-Benzyloxy-3-benzyloxymethyl-4,6-dihydroxy-7-methoxy-11-methyl-5-oxo-1,2,3,5,12,12a-hexahydro-naphthacen-1-yl)-carbamic acid benzyl ester 
• 286961-70-4 C₂₇H₃₂BrNO₈ 
• 286961-74-8 ((1S,4aS,12aS)-3-Cyano-2,4a,6-trihydroxy-7-methoxy-11-methyl-4,5-dioxo-1,4,4a,5,12,12a-hexahydro-naphthacen-1-yl)-carbamic acid tert-butyl ester 
• 286961-82-8 ((1S,2S,3S,12aR)-2,4,6-Trihydroxy-3-hydroxymethyl-7-methoxy-11-methyl-5-oxo-1,2,3,5,12,12a-hexahydro-naphthacen-1-yl)-carbamic acid tert-butyl ester 
• 286961-73-7 ((1S,4aS,12aS)-3-Formyl-2,4a,6-trihydroxy-7-methoxy-11-methyl-4,5-dioxo-1,4,4a,5,12,12a-hexahydro-naphthacen-1-yl)-carbamic acid tert-butyl ester 
• 286961-71-5 ((1S,4aS,12aR)-6-Hydroxy-3-hydroxymethyl-4,7-dimethoxy-11-methyl-2,5-dioxo-1,2,4a,5,12,12a-hexahydro-naphthacen-1-yl)-carbamic acid tert-butyl ester 
• 286961-69-1 ((1S,2S,3S,12aR)-2,6-Dihydroxy-3-hydroxymethyl-4,7-dimethoxy-11-methyl-5-oxo-1,2,3,5,12,12a-hexahydro-naphthacen-1-yl)-carbamic acid tert-butyl ester 
• 286961-84-0 (4S,4aS,12aS)-4-Amino-3,11,12a-trihydroxy-10-methoxy-6-methyl-1,12-dioxo-1,4,4a,5,12,12a-hexahydro-naphthacene-2-carboxylic acid amide 

Downstream Products

• 60-54-8 TETRACYCLINE 

Relevant articles and documents

Accelerated Forced Degradation of Pharmaceuticals in Levitated Microdroplet Reactors

Forced degradation is a method of studying the stability of pharmaceuticals in order to design stable formulations and predict drug product shelf life. Traditional methods of reaction and analysis usually take multiple days, and include LC-UV and LC-MS product analysis. In this study, the reaction/analysis sequence was accelerated to be completed within minutes using Leidenfrost droplets as reactors (acceleration factor: 23–188) and nanoelectrospray ionization MS analysis. The Leidenfrost droplets underwent the same reactions as seen in traditional bulk solution experiments for three chemical degradations studied. This combined method of accelerated reaction and analysis has the potential to be extended to forced degradation of other pharmaceuticals and to drug formulations. Control of reaction rate and yield is achieved by manipulating droplet size, levitation time and whether or not make-up solvent is added. Evidence is provided that interfacial effects contribute to rate acceleration.

Identifying the minimal enzymes required for anhydrotetracycline biosynthesis

The cyclohexenone ring A of tetracyclines exhibits unique structural features not observed among other aromatic polyketides. These substitutions include the C2 primary amide, C4 dimethylamine, and the C12a tertiary alcohol. Here we report the identification and reconstitution of the minimum set of enzymes required for the biosynthesis of anhydrotetracycline (ATC, 5), the first intermediate in the tetracycline biosynthetic pathway that contains the fully functionalized ring A. Using a combination of in vivo and in vitro approaches, we confirmed OxyL, OxyQ, and OxyT to be the only enzymes required to convert 6-methylpretetramid 1 into 5. OxyL is a NADPH-dependent dioxygenase that introduces two oxygen atoms into 1 to yield the unstable intermediate 4-keto-ATC 2. The aminotransferase OxyQ catalyzes the reductive amination of C4-keto of 2, yielding 4-amino-ATC 3. Furthermore, the N,N-dimethyltransferase OxyT catalyzes the formation of 5 from 3 in a (S)-adenosylmethionine (SAM)-dependent manner. Finally, a non-natural anhydrotetracycline derivative was generated, demonstrating that our heterologous host/vector pair can be a useful platform toward the engineered biosynthesis of tetracycline analogues. Copyright

Dehydration of tetracycline

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