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Tetracycline

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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 Molecular Structure of 60-54-8 (Tetracycline) Hazard Symbols HarmfulXn, IrritantXi
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

Tetracycline Synthetic route

102851-25-2

6-deoxy-6-hydroperoxy-5a,11a-dehydrotetracycline

60-54-8

TETRACYCLINE

Conditions
ConditionsYield
With hydrogen; platinum In 1,4-dioxane under 2280 Torr; for 8h; Catalytic hydrogenation;62%
57-62-5

Chlortetracycline

60-54-8

TETRACYCLINE

Conditions
ConditionsYield
With palladium on activated charcoal; 2-methoxy-ethanol; triethylamine Hydrogenation;
With 1,4-dioxane; methanol; palladium on activated charcoal Hydrogenation;

rolitetracycline

60-54-8

TETRACYCLINE

Conditions
ConditionsYield
With water at 19.85℃; Kinetics; Further Variations:; Temperatures;

3,7-bis-benzyloxy-13-dimethylamino-11-hydroperoxy-4a-hydroxy-11-methyl-12a,13-dihydro-4aH,11H,12H-1-oxa-2-aza-cyclopenta[b]naphthacene-4,5,6-trione

60-54-8

TETRACYCLINE

Conditions
ConditionsYield
With hydrogen; palladium In 1,4-dioxane at 23℃; under 760 Torr; for 2h;16.0 mg

3,7-bis-benzyloxy-13-dimethylamino-4a-hydroxy-11-methyl-5a-phenylsulfanyl-11a,12,12a,13-tetrahydro-4aH,5aH,11H-1-oxa-2-aza-cyclopenta[b]naphthacene-4,5,6-trione

60-54-8

TETRACYCLINE

Conditions
ConditionsYield
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

(4aR,5aR,6R,11R,11aS,12aS)-3,7-Bis-benzyloxy-13-dimethylamino-4a,6-dihydroxy-11-methyl-5a-phenylsulfanyl-6,11,11a,12,12a,13-hexahydro-4aH,5aH-1-oxa-2-aza-cyclopenta[b]naphthacene-4,5-dione

60-54-8

TETRACYCLINE

Conditions
ConditionsYield
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

(4aR,5aR,6R,11R,11aS,12aS,13S)-3,7-Bis-benzyloxy-13-dimethylamino-4a-hydroxy-11-methyl-5a-phenylsulfanyl-6-triethylsilanyloxy-6,11,11a,12,12a,13-hexahydro-4aH,5aH-1-oxa-2-aza-cyclopenta[b]naphthacene-4,5-dione

60-54-8

TETRACYCLINE

Conditions
ConditionsYield
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
4938-06-1

7-Methoxy-3-methylphthalide

60-54-8

TETRACYCLINE

Conditions
ConditionsYield
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
1665-56-1, 7518-17-4

anhydrotetracycline

60-54-8

TETRACYCLINE

Conditions
ConditionsYield
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
286961-75-9

(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

60-54-8

TETRACYCLINE

Conditions
ConditionsYield
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

Tetracycline History

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.

Tetracycline Consensus Reports

EPA Genetic Toxicology Program.

Tetracycline Specification

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%.

Tetracycline is prepared by reaction of 6-deoxy-6-hydroperoxy-5a,11a-dehydrotetracycline.

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.

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