CAS No.60-54-8,Tetracycline Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	60-54-8
Name:	Tetracycline
Article Data:	14

Formula:	C₂₂H₂₄N₂O₈
Molecular Weight:	444.441
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;
EINECS:	200-481-9
Density:	1.644 g/cm³
Melting Point:	172-174 °C
Boiling Point:	790.622 °C at 760 mmHg
Flash Point:	431.953 °C
Solubility:	1.7mg/mlL (28 °C) in water
Appearance:	Light yellow crystal
Hazard Symbols:	Xn, Xi
Risk Codes:	22-36/37/38
Safety:	22-36-26
PSA:	181.62000
LogP:	0.48590

Synthetic route

: 102851-25-2
6-deoxy-6-hydroperoxy-5a,11a-dehydrotetracycline

: 60-54-8
TETRACYCLINE

Conditions

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

: 57-62-5
Chlortetracycline

: 60-54-8
TETRACYCLINE

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

: (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

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

: (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

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

: 4938-06-1
7-Methoxy-3-methylphthalide

: 60-54-8
TETRACYCLINE

Conditions

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

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

: 1665-56-1, 7518-17-4
anhydrotetracycline

: 60-54-8
TETRACYCLINE

Conditions

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

: 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

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

Raw Materials

57-62-5

1665-56-1

64-75-5

73590-58-6

Downstream Products

64-75-5

Total:126 Page 1 of 4 1 2 3 4 Next>>

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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.

Consensus Reports

EPA Genetic Toxicology Program.

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.