4496-85-9

Basic information

• Product Name: (2E,4S,4aS,12aS)-2-[amino(hydroxy)methylidene]-4-(dimethylamino)-10,11,12a-trihydroxy-4a,12a-dihydrotetracene-1,3,12(2H,4H,5H)-trione
• CAS NO: 4496-85-9
• Molecular Formula: C₂₁H₂₀N₂O₇
• Molecular Weight: 412.3927
• Mol File: 4496-85-9.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 618.6°C at 760 mmHg
• Flash Point: 327.9°C
• Density: 1.65g/cm³
• Vapor Pressure: 3.69E-16mmHg at 25°C
• Refractive Index: 1.778
• CAS DataBase Reference: (2E,4S,4aS,12aS)-2-[amino(hydroxy)methylidene]-4-(dimethylamino)-10,11,12a-trihydroxy-4a,12a-dihydrotetracene-1,3,12(2H,4H,5H)-trione(CAS DataBase Reference)
• NIST Chemistry Reference: (2E,4S,4aS,12aS)-2-[amino(hydroxy)methylidene]-4-(dimethylamino)-10,11,12a-trihydroxy-4a,12a-dihydrotetracene-1,3,12(2H,4H,5H)-trione(4496-85-9)
• EPA Substance Registry System: (2E,4S,4aS,12aS)-2-[amino(hydroxy)methylidene]-4-(dimethylamino)-10,11,12a-trihydroxy-4a,12a-dihydrotetracene-1,3,12(2H,4H,5H)-trione(4496-85-9)

Safety Data

• Hazardous Substances Data: 4496-85-9(Hazardous Substances Data)

Usage

Description

(2E,4S,4aS,12aS)-2-[amino(hydroxy)methylidene]-4-(dimethylamino)-10,11,12a-trihydroxy-4a,12a-dihydrotetracene-1,3,12(2H,4H,5H)-trione, commonly known as demeclocycline, is a tetracycline antibiotic that features a tetracycline core structure. It is a broad-spectrum antibiotic effective against a wide range of bacterial infections.
Used in Pharmaceutical Industry:
(2E,4S,4aS,12aS)-2-[amino(hydroxy)methylidene]-4-(dimethylamino)-10,11,12a-trihydroxy-4a,12a-dihydrotetracene-1,3,12(2H,4H,5H)-trione is used as an antibiotic for treating various bacterial infections such as respiratory, urinary tract, skin, and sexually transmitted infections. It functions by inhibiting bacterial protein synthesis, which in turn prevents bacterial growth and reproduction. The medication is typically administered orally and is available in tablet form.

Upstream product

• 127-33-3 Demeclocycline 
• 524-14-1 S-(hydrogen malonyl)coenzyme A 

Relevant articles and documents

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