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Name |
Tetracycline |
EINECS | 200-481-9 |
CAS No. | 60-54-8 | Density | 1.644 g/cm3 |
PSA | 181.62000 | LogP | 0.48590 |
Solubility | 1.7mg/mlL (28 °C) in water | Melting Point |
172-174 °C |
Formula | C22H24N2O8 | Boiling Point | 790.622 °C at 760 mmHg |
Molecular Weight | 444.441 | Flash Point | 431.953 °C |
Transport Information | N/A | Appearance | Light yellow crystal |
Safety | 22-36-26 | Risk Codes | 22-36/37/38 |
Molecular Structure | Hazard Symbols | Xn, Xi | |
Synonyms |
2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-(7CI,8CI);Abramycin;Achromycin;Acromicina;Actisite;Agromicina;Ambramicina;Arcanacycline;Bio-Tetra;Biocycline;Ciclibion;Cyclomycin;Deschlorobiomycin;Florocycline;Gammatet;Ibicyn;Kinciclina;Latycin;Medocycline;Mericycline;Micycline;NSC 108579;Omegamycin;Orlycycline;Panmycin;Resteclin;Retet;Robitet Robicaps;Tetra-Co;Tetra-Proter;Tetracycline;Tetralan;Tetralen;Tetramig; |
Article Data | 14 |
6-deoxy-6-hydroperoxy-5a,11a-dehydrotetracycline
TETRACYCLINE
Conditions | Yield |
---|---|
With hydrogen; platinum In 1,4-dioxane under 2280 Torr; for 8h; Catalytic hydrogenation; | 62% |
Conditions | Yield |
---|---|
With palladium on activated charcoal; 2-methoxy-ethanol; triethylamine Hydrogenation; | |
With 1,4-dioxane; methanol; palladium on activated charcoal Hydrogenation; |
TETRACYCLINE
Conditions | Yield |
---|---|
With water at 19.85℃; Kinetics; Further Variations:; Temperatures; |
TETRACYCLINE
Conditions | Yield |
---|---|
With hydrogen; palladium In 1,4-dioxane at 23℃; under 760 Torr; for 2h; | 16.0 mg |
TETRACYCLINE
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: m-chloroperoxybenzoic acid / CH2Cl2 / -78 - 0 °C 1.2: air / CHCl3 2.1: 16.0 mg / H2 / Pd / dioxane / 2 h / 23 °C / 760 Torr View Scheme |
TETRACYCLINE
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 77 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 18 h / 35 °C 2.1: m-chloroperoxybenzoic acid / CH2Cl2 / -78 - 0 °C 2.2: air / CHCl3 3.1: 16.0 mg / H2 / Pd / dioxane / 2 h / 23 °C / 760 Torr View Scheme |
TETRACYCLINE
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: 76 percent / triethylamine trihydrofluoride / tetrahydrofuran / 12 h / 23 °C 2.1: 77 percent / o-iodoxybenzoic acid / dimethylsulfoxide / 18 h / 35 °C 3.1: m-chloroperoxybenzoic acid / CH2Cl2 / -78 - 0 °C 3.2: air / CHCl3 4.1: 16.0 mg / H2 / Pd / dioxane / 2 h / 23 °C / 760 Torr View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 16 steps 1.1: 80 percent / LDA / tetrahydrofuran / 0.25 h / -40 °C 2.1: 90 percent / SOCl2; TEA / CH2Cl2 / 0.17 h / -30 °C 3.1: BBr3 / CH2Cl2 / 0.25 h / -78 °C 4.1: H2; TEA / Pd-black / dioxane; H2O / 1 h 5.1: 72 percent / i-Pr2NEt / tetrahydrofuran; methanol / 2 h 6.1: 85 percent / Br2; (Bu3Sn)2O; MS-4A / CH2Cl2 / 0.25 h / -78 °C 7.1: 91 percent / Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h 8.1: Zn / acetic acid / 0.03 h 9.1: Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h 9.2: 60 percent / dimethyldioxirane; (R,R)-(PhCH-NTs)2BCl; TEA / CH2Cl2 / 0.5 h / -78 °C 10.1: NH2OH*HCl; TEA / methanol / 0.5 h 11.1: CDI / tetrahydrofuran / 0.75 h 12.1: 68 percent / polyposphoric acid / 0.75 h / 100 °C 13.1: 80 percent / formic acid / 1 h / 80 °C 14.1: 88 percent / BBr3 / CH2Cl2 / 15 h / 0 - 20 °C 15.1: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation 16.1: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr View Scheme |
anhydrotetracycline
TETRACYCLINE
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation 2: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr View Scheme |
(4S,4aS,12aS)-4-Dimethylamino-3,11,12a-trihydroxy-10-methoxy-6-methyl-1,12-dioxo-1,4,4a,5,12,12a-hexahydro-naphthacene-2-carboxylic acid amide
TETRACYCLINE
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 88 percent / BBr3 / CH2Cl2 / 15 h / 0 - 20 °C 2: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation 3: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr View Scheme |
The Tetracycline (CAS NO.60-54-8) are a large family of antibiotics that were discovered as natural products by Benjamin Minge Duggar and first described in 1948. Tetracycline was then discovered by Lloyd Conover in the research departments of Pfizer. The patent for tetracycline, U.S. Patent 2,699,054, was first issued in 1950. However, Nubian mummies have been studied in the 1990s and were found to contain significant levels of tetracycline; there is evidence that the beer brewed at the time could have been the source. Tetracycline sparked the development of many chemically altered antibiotics and in doing so has proved to be one of the most important discoveries made in the field of antibiotics.
EPA Genetic Toxicology Program.
The Tetracycline with CAS registry number of 60-54-8 is also known as Abramycin. The IUPAC name is (2Z,4S,4aS,5aS,6S,12aS)-2-[amino(hydroxy)methylidene]-4-(dimethylamino)-6,10,11,12a-tetrahydroxy-6-methyl-4,4a,5,5a-tetrahydrotetracene-1,3,12-trione. It belongs to product categories of Antibiotic Explorer; Intermediates & Fine Chemicals; Pharmaceuticals; Antibacterial; Antibiotics; Antibiotics A to; Antibiotics by Application; Antibiotics T-ZAntibiotics; Chemical Structure Class; Genetic Marker SelectionAntibiotics; Interferes with Protein SynthesisSpectrum of Activity; L-ZAntibiotics; Mechanism of Action; Tetracyclines; Peptide Synthesis/Antibiotics. Its EINECS registry number is 200-481-9. In addition, the formula is C22H24N2O8 and the molecular weight is 444.43. This chemical is a light yellow crystal and should be sealed in dry, dark place under 0 °C.
Physical properties about Tetracycline are: (1)ACD/LogP: 0.62; (2)# of Rule of 5 Violations: 2 ; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 10; (8)#H bond donors: 7; (9)#Freely Rotating Bonds: 7; (10)Index of Refraction: 1.741; (11)Molar Refractivity: 109.088 cm3; (12)Molar Volume: 270.304 cm3; (13)Surface Tension: 100.608 dyne/cm; (14)Density: 1.644 g/cm3; (15)Flash Point: 431.953 °C; (16)Enthalpy of Vaporization: 120.61 kJ/mol; (17)Boiling Point: 790.622 °C at 760 mmHg.
Preparation of Tetracycline: it is prepared by reaction of 6-deoxy-6-hydroperoxy-5a,11a-dehydrotetracycline. The reaction needs reagent H2, catalyst Pt-black and solvent dioxane at the pressure of 2280 for 8 hours. The yield is about 62%.
Uses of Tetracycline: it is first-line therapy for Rocky Mountain spotted fever, Q fever, psittacosis and lymphogranuloma venereum, and to eradicate nasal carriage of meningococci. What's more, it is used as a marker of bone growth for biopsies in humans. It is also used as a biomarker in wildlife and in transcriptional activation.
When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. And it is harmful if swallowed. During using it, wear suitable protective clothing. Do not breathe dust. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
1. Canonical SMILES: CC1(C2CC3C(C(=O)C(=C(N)O)C(=O)C3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)N(C)C)O
2. Isomeric SMILES: C[C@@]1([C@H]2C[C@H]3[C@@H](C(=O)/C(=C(\N)/O)/C(=O)[C@]3(C(=O)C2=C(C4=C1C=CC=C4O)O)O)N(C)C)O
3. InChI: InChI=1S/C22H24N2O8/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28/h4-6,9-10,15,25-26,30-32H,7,23H2,1-3H3/b20-14-/t9-,10-,15-,21+,22-/m0/s1
4. InChIKey: JYHCQVWYCGHXGP-BPPSBWQWSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
guinea pig | LD50 | oral | 1875mg/kg (1875mg/kg) | "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 109, 1982. | |
mouse | LD50 | intraperitoneal | 120mg/kg (120mg/kg) | "Index of Antibiotics from Actinomycetes," Umezawa, H. et al., eds., Tokyo, Univ. of Tokyo Press, 1967Vol. -, Pg. 134, 1967. | |
mouse | LD50 | intravenous | 157mg/kg (157mg/kg) | Farmaco, Edizione Scientifica. Vol. 10, Pg. 346, 1955. | |
mouse | LD50 | oral | 678mg/kg (678mg/kg) | American Journal of Tropical Medicine and Hygiene. Vol. 2, Pg. 254, 1953. | |
mouse | LD50 | subcutaneous | 400mg/kg (400mg/kg) | "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 3, Pg. 42, 1980. | |
rat | LD50 | intraperitoneal | 310mg/kg (310mg/kg) | Drugs in Japan Vol. 6, Pg. 493, 1982. | |
rat | LD50 | intravenous | 129mg/kg (129mg/kg) | Antibiotics and Chemotherapy Vol. 4, Pg. 411, 1954. | |
rat | LD50 | oral | 807mg/kg (807mg/kg) | Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971. | |
women | LDLo | multiple routes | 310mg/kg (310mg/kg) | GASTROINTESTINAL: NAUSEA OR VOMITING LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED" | New England Journal of Medicine. Vol. 270, Pg. 157, 1964. |
women | TDLo | oral | 600mg/kg/15D (600mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) GASTROINTESTINAL: DECREASED MOTILITY OR CONSTIPATION KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED | Southern Medical Journal. Vol. 71, Pg. 961, 1978. |