Tetracycline supplier | CasNO.60-54-8

Name
Tetracycline
EINECS 200-481-9
CAS No. 60-54-8
Article Data14
CAS DataBase
Density 1.644 g/cm³
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
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;
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

: 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

: 60-54-8
TETRACYCLINE

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 80 percent / formic acid / 1 h / 80 °C 2: 88 percent / BBr3 / CH2Cl2 / 15 h / 0 - 20 °C 3: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation 4: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr View Scheme

: 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

: 60-54-8
TETRACYCLINE

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1.1: 85 percent / Br2; (Bu3Sn)2O; MS-4A / CH2Cl2 / 0.25 h / -78 °C 2.1: 91 percent / Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h 3.1: Zn / acetic acid / 0.03 h 4.1: Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h 4.2: 60 percent / dimethyldioxirane; (R,R)-(PhCH-NTs)2BCl; TEA / CH2Cl2 / 0.5 h / -78 °C 5.1: NH2OH*HCl; TEA / methanol / 0.5 h 6.1: CDI / tetrahydrofuran / 0.75 h 7.1: 68 percent / polyposphoric acid / 0.75 h / 100 °C 8.1: 80 percent / formic acid / 1 h / 80 °C 9.1: 88 percent / BBr3 / CH2Cl2 / 15 h / 0 - 20 °C 10.1: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation 11.1: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr View Scheme

Yield

Multi-step reaction with 11 steps
1.1: 85 percent / Br2; (Bu3Sn)2O; MS-4A / CH2Cl2 / 0.25 h / -78 °C
2.1: 91 percent / Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h
3.1: Zn / acetic acid / 0.03 h
4.1: Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h
4.2: 60 percent / dimethyldioxirane; (R,R)-(PhCH-NTs)2BCl; TEA / CH2Cl2 / 0.5 h / -78 °C
5.1: NH2OH*HCl; TEA / methanol / 0.5 h
6.1: CDI / tetrahydrofuran / 0.75 h
7.1: 68 percent / polyposphoric acid / 0.75 h / 100 °C
8.1: 80 percent / formic acid / 1 h / 80 °C
9.1: 88 percent / BBr3 / CH2Cl2 / 15 h / 0 - 20 °C
10.1: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation
11.1: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr
View Scheme

: 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

: 60-54-8
TETRACYCLINE

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h 1.2: 60 percent / dimethyldioxirane; (R,R)-(PhCH-NTs)2BCl; TEA / CH2Cl2 / 0.5 h / -78 °C 2.1: NH2OH*HCl; TEA / methanol / 0.5 h 3.1: CDI / tetrahydrofuran / 0.75 h 4.1: 68 percent / polyposphoric acid / 0.75 h / 100 °C 5.1: 80 percent / formic acid / 1 h / 80 °C 6.1: 88 percent / BBr3 / CH2Cl2 / 15 h / 0 - 20 °C 7.1: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation 8.1: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr View Scheme

Yield

Multi-step reaction with 8 steps
1.1: Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h
1.2: 60 percent / dimethyldioxirane; (R,R)-(PhCH-NTs)2BCl; TEA / CH2Cl2 / 0.5 h / -78 °C
2.1: NH2OH*HCl; TEA / methanol / 0.5 h
3.1: CDI / tetrahydrofuran / 0.75 h
4.1: 68 percent / polyposphoric acid / 0.75 h / 100 °C
5.1: 80 percent / formic acid / 1 h / 80 °C
6.1: 88 percent / BBr3 / CH2Cl2 / 15 h / 0 - 20 °C
7.1: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation
8.1: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr
View Scheme

: 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

: 60-54-8
TETRACYCLINE

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: NH2OH*HCl; TEA / methanol / 0.5 h 2: CDI / tetrahydrofuran / 0.75 h 3: 68 percent / polyposphoric acid / 0.75 h / 100 °C 4: 80 percent / formic acid / 1 h / 80 °C 5: 88 percent / BBr3 / CH2Cl2 / 15 h / 0 - 20 °C 6: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation 7: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr View Scheme

: 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

: 60-54-8
TETRACYCLINE

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1.1: 72 percent / i-Pr2NEt / tetrahydrofuran; methanol / 2 h 2.1: 85 percent / Br2; (Bu3Sn)2O; MS-4A / CH2Cl2 / 0.25 h / -78 °C 3.1: 91 percent / Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h 4.1: Zn / acetic acid / 0.03 h 5.1: Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h 5.2: 60 percent / dimethyldioxirane; (R,R)-(PhCH-NTs)2BCl; TEA / CH2Cl2 / 0.5 h / -78 °C 6.1: NH2OH*HCl; TEA / methanol / 0.5 h 7.1: CDI / tetrahydrofuran / 0.75 h 8.1: 68 percent / polyposphoric acid / 0.75 h / 100 °C 9.1: 80 percent / formic acid / 1 h / 80 °C 10.1: 88 percent / BBr3 / CH2Cl2 / 15 h / 0 - 20 °C 11.1: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation 12.1: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr View Scheme

Yield

Multi-step reaction with 12 steps
1.1: 72 percent / i-Pr2NEt / tetrahydrofuran; methanol / 2 h
2.1: 85 percent / Br2; (Bu3Sn)2O; MS-4A / CH2Cl2 / 0.25 h / -78 °C
3.1: 91 percent / Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h
4.1: Zn / acetic acid / 0.03 h
5.1: Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h
5.2: 60 percent / dimethyldioxirane; (R,R)-(PhCH-NTs)2BCl; TEA / CH2Cl2 / 0.5 h / -78 °C
6.1: NH2OH*HCl; TEA / methanol / 0.5 h
7.1: CDI / tetrahydrofuran / 0.75 h
8.1: 68 percent / polyposphoric acid / 0.75 h / 100 °C
9.1: 80 percent / formic acid / 1 h / 80 °C
10.1: 88 percent / BBr3 / CH2Cl2 / 15 h / 0 - 20 °C
11.1: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation
12.1: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr
View Scheme

: C27H30BrNO8

: 60-54-8
TETRACYCLINE

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: Zn / acetic acid / 0.03 h 2.1: Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h 2.2: 60 percent / dimethyldioxirane; (R,R)-(PhCH-NTs)2BCl; TEA / CH2Cl2 / 0.5 h / -78 °C 3.1: NH2OH*HCl; TEA / methanol / 0.5 h 4.1: CDI / tetrahydrofuran / 0.75 h 5.1: 68 percent / polyposphoric acid / 0.75 h / 100 °C 6.1: 80 percent / formic acid / 1 h / 80 °C 7.1: 88 percent / BBr3 / CH2Cl2 / 15 h / 0 - 20 °C 8.1: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation 9.1: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr View Scheme

Yield

Multi-step reaction with 9 steps
1.1: Zn / acetic acid / 0.03 h
2.1: Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h
2.2: 60 percent / dimethyldioxirane; (R,R)-(PhCH-NTs)2BCl; TEA / CH2Cl2 / 0.5 h / -78 °C
3.1: NH2OH*HCl; TEA / methanol / 0.5 h
4.1: CDI / tetrahydrofuran / 0.75 h
5.1: 68 percent / polyposphoric acid / 0.75 h / 100 °C
6.1: 80 percent / formic acid / 1 h / 80 °C
7.1: 88 percent / BBr3 / CH2Cl2 / 15 h / 0 - 20 °C
8.1: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation
9.1: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr
View Scheme

: 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

: 60-54-8
TETRACYCLINE

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 68 percent / polyposphoric acid / 0.75 h / 100 °C 2: 80 percent / formic acid / 1 h / 80 °C 3: 88 percent / BBr3 / CH2Cl2 / 15 h / 0 - 20 °C 4: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation 5: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr View Scheme

: [(1S,4aS,12aS)-2,4a,6-Trihydroxy-3-(hydroxyimino-methyl)-7-methoxy-11-methyl-4,5-dioxo-1,4,4a,5,12,12a-hexahydro-naphthacen-1-yl]-carbamic acid tert-butyl ester

: 60-54-8
TETRACYCLINE

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: CDI / tetrahydrofuran / 0.75 h 2: 68 percent / polyposphoric acid / 0.75 h / 100 °C 3: 80 percent / formic acid / 1 h / 80 °C 4: 88 percent / BBr3 / CH2Cl2 / 15 h / 0 - 20 °C 5: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation 6: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr View Scheme

: 286961-70-4
C27H32BrNO8

: 60-54-8
TETRACYCLINE

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1.1: 91 percent / Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h 2.1: Zn / acetic acid / 0.03 h 3.1: Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h 3.2: 60 percent / dimethyldioxirane; (R,R)-(PhCH-NTs)2BCl; TEA / CH2Cl2 / 0.5 h / -78 °C 4.1: NH2OH*HCl; TEA / methanol / 0.5 h 5.1: CDI / tetrahydrofuran / 0.75 h 6.1: 68 percent / polyposphoric acid / 0.75 h / 100 °C 7.1: 80 percent / formic acid / 1 h / 80 °C 8.1: 88 percent / BBr3 / CH2Cl2 / 15 h / 0 - 20 °C 9.1: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation 10.1: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr View Scheme

Yield

Multi-step reaction with 10 steps
1.1: 91 percent / Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h
2.1: Zn / acetic acid / 0.03 h
3.1: Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h
3.2: 60 percent / dimethyldioxirane; (R,R)-(PhCH-NTs)2BCl; TEA / CH2Cl2 / 0.5 h / -78 °C
4.1: NH2OH*HCl; TEA / methanol / 0.5 h
5.1: CDI / tetrahydrofuran / 0.75 h
6.1: 68 percent / polyposphoric acid / 0.75 h / 100 °C
7.1: 80 percent / formic acid / 1 h / 80 °C
8.1: 88 percent / BBr3 / CH2Cl2 / 15 h / 0 - 20 °C
9.1: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation
10.1: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr
View Scheme

: ((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 benzyl ester

: 60-54-8
TETRACYCLINE

Conditions

Conditions	Yield
Multi-step reaction with 13 steps 1.1: H2; TEA / Pd-black / dioxane; H2O / 1 h 2.1: 72 percent / i-Pr2NEt / tetrahydrofuran; methanol / 2 h 3.1: 85 percent / Br2; (Bu3Sn)2O; MS-4A / CH2Cl2 / 0.25 h / -78 °C 4.1: 91 percent / Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h 5.1: Zn / acetic acid / 0.03 h 6.1: Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h 6.2: 60 percent / dimethyldioxirane; (R,R)-(PhCH-NTs)2BCl; TEA / CH2Cl2 / 0.5 h / -78 °C 7.1: NH2OH*HCl; TEA / methanol / 0.5 h 8.1: CDI / tetrahydrofuran / 0.75 h 9.1: 68 percent / polyposphoric acid / 0.75 h / 100 °C 10.1: 80 percent / formic acid / 1 h / 80 °C 11.1: 88 percent / BBr3 / CH2Cl2 / 15 h / 0 - 20 °C 12.1: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation 13.1: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr View Scheme

Yield

Multi-step reaction with 13 steps
1.1: H2; TEA / Pd-black / dioxane; H2O / 1 h
2.1: 72 percent / i-Pr2NEt / tetrahydrofuran; methanol / 2 h
3.1: 85 percent / Br2; (Bu3Sn)2O; MS-4A / CH2Cl2 / 0.25 h / -78 °C
4.1: 91 percent / Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h
5.1: Zn / acetic acid / 0.03 h
6.1: Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h
6.2: 60 percent / dimethyldioxirane; (R,R)-(PhCH-NTs)2BCl; TEA / CH2Cl2 / 0.5 h / -78 °C
7.1: NH2OH*HCl; TEA / methanol / 0.5 h
8.1: CDI / tetrahydrofuran / 0.75 h
9.1: 68 percent / polyposphoric acid / 0.75 h / 100 °C
10.1: 80 percent / formic acid / 1 h / 80 °C
11.1: 88 percent / BBr3 / CH2Cl2 / 15 h / 0 - 20 °C
12.1: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation
13.1: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr
View Scheme

: 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

: 60-54-8
TETRACYCLINE

Conditions

Conditions	Yield
Multi-step reaction with 14 steps 1.1: BBr3 / CH2Cl2 / 0.25 h / -78 °C 2.1: H2; TEA / Pd-black / dioxane; H2O / 1 h 3.1: 72 percent / i-Pr2NEt / tetrahydrofuran; methanol / 2 h 4.1: 85 percent / Br2; (Bu3Sn)2O; MS-4A / CH2Cl2 / 0.25 h / -78 °C 5.1: 91 percent / Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h 6.1: Zn / acetic acid / 0.03 h 7.1: Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h 7.2: 60 percent / dimethyldioxirane; (R,R)-(PhCH-NTs)2BCl; TEA / CH2Cl2 / 0.5 h / -78 °C 8.1: NH2OH*HCl; TEA / methanol / 0.5 h 9.1: CDI / tetrahydrofuran / 0.75 h 10.1: 68 percent / polyposphoric acid / 0.75 h / 100 °C 11.1: 80 percent / formic acid / 1 h / 80 °C 12.1: 88 percent / BBr3 / CH2Cl2 / 15 h / 0 - 20 °C 13.1: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation 14.1: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr View Scheme

Yield

Multi-step reaction with 14 steps
1.1: BBr3 / CH2Cl2 / 0.25 h / -78 °C
2.1: H2; TEA / Pd-black / dioxane; H2O / 1 h
3.1: 72 percent / i-Pr2NEt / tetrahydrofuran; methanol / 2 h
4.1: 85 percent / Br2; (Bu3Sn)2O; MS-4A / CH2Cl2 / 0.25 h / -78 °C
5.1: 91 percent / Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h
6.1: Zn / acetic acid / 0.03 h
7.1: Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h
7.2: 60 percent / dimethyldioxirane; (R,R)-(PhCH-NTs)2BCl; TEA / CH2Cl2 / 0.5 h / -78 °C
8.1: NH2OH*HCl; TEA / methanol / 0.5 h
9.1: CDI / tetrahydrofuran / 0.75 h
10.1: 68 percent / polyposphoric acid / 0.75 h / 100 °C
11.1: 80 percent / formic acid / 1 h / 80 °C
12.1: 88 percent / BBr3 / CH2Cl2 / 15 h / 0 - 20 °C
13.1: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation
14.1: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr
View Scheme

: 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

: 60-54-8
TETRACYCLINE

Conditions

Conditions	Yield
Multi-step reaction with 15 steps 1.1: 90 percent / SOCl2; TEA / CH2Cl2 / 0.17 h / -30 °C 2.1: BBr3 / CH2Cl2 / 0.25 h / -78 °C 3.1: H2; TEA / Pd-black / dioxane; H2O / 1 h 4.1: 72 percent / i-Pr2NEt / tetrahydrofuran; methanol / 2 h 5.1: 85 percent / Br2; (Bu3Sn)2O; MS-4A / CH2Cl2 / 0.25 h / -78 °C 6.1: 91 percent / Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h 7.1: Zn / acetic acid / 0.03 h 8.1: Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h 8.2: 60 percent / dimethyldioxirane; (R,R)-(PhCH-NTs)2BCl; TEA / CH2Cl2 / 0.5 h / -78 °C 9.1: NH2OH*HCl; TEA / methanol / 0.5 h 10.1: CDI / tetrahydrofuran / 0.75 h 11.1: 68 percent / polyposphoric acid / 0.75 h / 100 °C 12.1: 80 percent / formic acid / 1 h / 80 °C 13.1: 88 percent / BBr3 / CH2Cl2 / 15 h / 0 - 20 °C 14.1: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation 15.1: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr View Scheme

Yield

Multi-step reaction with 15 steps
1.1: 90 percent / SOCl2; TEA / CH2Cl2 / 0.17 h / -30 °C
2.1: BBr3 / CH2Cl2 / 0.25 h / -78 °C
3.1: H2; TEA / Pd-black / dioxane; H2O / 1 h
4.1: 72 percent / i-Pr2NEt / tetrahydrofuran; methanol / 2 h
5.1: 85 percent / Br2; (Bu3Sn)2O; MS-4A / CH2Cl2 / 0.25 h / -78 °C
6.1: 91 percent / Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h
7.1: Zn / acetic acid / 0.03 h
8.1: Dess-Martin periodinane / acetonitrile; CH2Cl2 / 0.25 h
8.2: 60 percent / dimethyldioxirane; (R,R)-(PhCH-NTs)2BCl; TEA / CH2Cl2 / 0.5 h / -78 °C
9.1: NH2OH*HCl; TEA / methanol / 0.5 h
10.1: CDI / tetrahydrofuran / 0.75 h
11.1: 68 percent / polyposphoric acid / 0.75 h / 100 °C
12.1: 80 percent / formic acid / 1 h / 80 °C
13.1: 88 percent / BBr3 / CH2Cl2 / 15 h / 0 - 20 °C
14.1: 75 percent / O2; TPP / CHCl3 / 0.17 h / 20 - 40 °C / Irradiation
15.1: 62 percent / H2 / Pt-black / dioxane / 8 h / 2280 Torr
View Scheme

: C36H32N2O9

: 60-54-8
TETRACYCLINE

Conditions

Conditions	Yield
With hydrogen; palladium In 1,4-dioxane at 23℃; under 760.051 Torr; for 2.08333h;

: 73590-58-6
omeprazole

: 60-54-8
TETRACYCLINE

: 64-75-5
tetracycline hydrochloride

: 60-54-8
TETRACYCLINE

Conditions

Conditions	Yield
In water pH=9; pH-value; Cooling;

: 50-00-0
formaldehyd

: 60-54-8
TETRACYCLINE

: 70458-96-7
1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxylic acid

: 7-(4-{[(4-dimethylamino-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carbonyl)-amino]-methyl}-piperazin-1-yl)-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Conditions

Conditions	Yield
In ethanol for 0.05h; Mannich reaction; microwave irradiation;	78%

...Expand

: 60-54-8
TETRACYCLINE

: C20H17NO9

Conditions

Conditions	Yield
With hydrogenchloride; N-chloro-succinimide In water at 25℃; for 0.5h;	74.4%

: 50-00-0
formaldehyd

: 60-54-8
TETRACYCLINE

: 160738-57-8, 112811-59-3
gatifloxacin

: 1-cyclopropyl-7-(4-{[(4-dimethylamino-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carbonyl)-amino]-methyl}-3-methyl-piperazin-1-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Conditions

Conditions	Yield
In ethanol for 0.05h; Mannich reaction; microwave irradiation;	69%

...Expand

: 50-00-0
formaldehyd

: 60-54-8
TETRACYCLINE

: 85721-33-1
ciprofloxacin

: 1-cyclopropyl-7-(4-{[(4-dimethylamino-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carbonyl)-amino]-methyl}-piperazin-1-yl)-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Conditions

Conditions	Yield
In ethanol for 0.05h; Mannich reaction; microwave irradiation;	61%

...Expand

: 60-54-8
TETRACYCLINE

: 74-88-4
methyl iodide

: 6602-90-0
1,4,4a,5,5a,6,11,12a-octahydro-2-aminocarbonyl-3,6,10,12,12a-hexahydroxy-6-methyl-1,11-dioxonaphthacene-4-trimethylammonium iodide

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 96h;	57%
In tetrahydrofuran at 20℃; for 144h;

: 50-00-0
formaldehyd

: 60-54-8
TETRACYCLINE

: 98079-51-7
lomefloxacin

: 7-(4-{[(4-dimethylamino-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carbonyl)-amino]-methyl}-3-methyl-piperazin-1-yl)-1-ethyl-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Conditions

Conditions	Yield
In ethanol for 0.05h; Mannich reaction; microwave irradiation;	54%

...Expand

: manganese(II) perchlorate hydrate

: 60-54-8
TETRACYCLINE

: Mn(C22H24O8N2)2(OClO3)(1+)*ClO4(1-)=[Mn(C22H24O8N2)2(OClO3)]ClO4

Conditions

Conditions	Yield
In further solvent(s) the soln. of salt in ethanol/triethyl orthoformate was heated at 40-50°C, added tetracycline, refluxed for 24-48 h, concn. by heating under reduced prdssure, cooled to room temp.; filtered, washed with cold EtOH, dried in vac. over anhyd. CaCl2;	42%

: 60-54-8
TETRACYCLINE

A: C20H17NO9

B: 3764-23-6
4-Oxo-4-dedimethylaminotetracyclin-hemiketal-(4.6)

Conditions

Conditions	Yield
Stage #1: TETRACYCLINE With ethylenediaminetetraacetic acid; silver carbonate In N,N-dimethyl-formamide at 37℃; for 48h; Molecular sieve; Stage #2: With dipotassium hydrogenphosphate; water; edetate disodium In N,N-dimethyl-formamide; acetonitrile at 0 - 20℃; for 8h; pH=5.5; Stage #3: In chloroform at 0 - 5℃; for 168h;	A n/a B 42%

: 50-00-0
formaldehyd

: 60-54-8
TETRACYCLINE

: 104963-85-1
4-nitrooxypiperidine

: amido-N-[4-nitrooxypiperidinomethyl]-tetracycline

Conditions

Conditions	Yield
In tetrahydrofuran for 4h; Inert atmosphere; Reflux;	36%
In tetrahydrofuran for 4h; Reflux; Inert atmosphere;	36%

...Expand

: 50-00-0
formaldehyd

: 60-54-8
TETRACYCLINE

: 56-12-2
4-amino-n-butyric acid

: C27H33N3O10

Conditions

Conditions	Yield
With acetic acid In ethanol at 20℃; for 12h; Mannich Aminomethylation;	31%

...Expand

: 60-54-8
TETRACYCLINE

A: 2,5-dihydroxy-4-(((1S,4R,10S)-6-hydroxy-1-methyl-3,5-dioxo-1,3,4,5-tetrahydro-1,4-methanobenzo[c]oxepin-10-yl)methyl)-3,6-dioxocyclohexa-1,4-dienecarboxamide

B: 2,3,5,6-tetrahydroxy-4-(((1S,4R,10S)-6-hydroxy-1-methyl-3,5-dioxo-1,3,4,5-tetrahydro-1,4-methanobenzo[c]oxepin-10-yl)methyl)benzamide

Conditions

Conditions	Yield
With mercury(II) diacetate; acetic acid at 50℃; for 48h;	A 30% B 10%

: zinc(II) perchlorate hydrate

: 60-54-8
TETRACYCLINE

: Zn(C22H24O8N2)2(OClO3)(1+)*ClO4(1-)=[Zn(C22H24O8N2)2(OClO3)]ClO4

Conditions

Conditions	Yield
In further solvent(s) the soln. of salt in ethanol/triethyl orthoformate was heated 40-50°C, added tetracycline, refluxed for 24-48 h, concn. by heating underreduced pressure, cooled to room temp.; filtered, washed with cold EtOH, dried in vac. over anhyd. CaCl2;	28%

: 60-54-8
TETRACYCLINE

: C22H24N2O9

Conditions

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In methanol for 0.0833333h; Solvent; Inert atmosphere; Cooling with ice;	27%

: 60-54-8
TETRACYCLINE

: 2,5-dihydroxy-4-(((1S,4R,10S)-6-hydroxy-1-methyl-3,5-dioxo-1,3,4,5-tetrahydro-1,4-methanobenzo[c]oxepin-10-yl)methyl)-3,6-dioxocyclohexa-1,4-dienecarboxamide

Conditions

Conditions	Yield
In dimethyl sulfoxide at 30℃; for 48h;	26%

: 50-00-0
formaldehyd

: 60-54-8
TETRACYCLINE

: 56-40-6
glycine

: C25H29N3O10

Conditions

Conditions	Yield
With acetic acid In ethanol at 20℃; for 12h; Mannich Aminomethylation;	24%

...Expand

: 110-91-8
morpholine

: 60-54-8
TETRACYCLINE

: 298-12-4
Glyoxilic acid

: 13729-37-8
(4-dimethylamino-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carbonylamino)-morpholin-4-yl-acetic acid

Conditions

Conditions	Yield
In tert-butyl alcohol Heating;

...Expand

: 75-77-4
chloro-trimethyl-silane

: 60-54-8
TETRACYCLINE

: C31H48N2O8Si3

Conditions

Conditions	Yield
With 1,1,1,3,3,3-hexamethyl-disilazane In pyridine at 20℃; for 0.0166667h;

: 75-77-4
chloro-trimethyl-silane

: 60-54-8
TETRACYCLINE

: C37H64N2O8Si5

Conditions

Conditions	Yield
With 1,1,1,3,3,3-hexamethyl-disilazane In pyridine at 20℃; for 12h;

: 60-54-8
TETRACYCLINE

: 1-Cyclohex-1-enyl-piperidine; compound with perchloric acid

: (4S,4aS,5aS,6S,12aS)-4-Dimethylamino-3,6,10,12,12a-pentahydroxy-6-methyl-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid cyclohex-1-enylamide

Conditions

Conditions	Yield
(i) DMF, (ii) piperidine; Multistep reaction;

: 73-40-5
2-amino-1,9-dihydro-6H-purin-6-one

: 60-54-8
TETRACYCLINE

: 78696-74-9
guanine*tetracycline

Conditions

Conditions	Yield
In water at 23℃; formation constant; further solvents;;

: 63-91-2
L-phenylalanine

: 60-54-8
TETRACYCLINE

: 78696-79-4
phenylalanine*tetracycline

Conditions

Conditions	Yield
In water at 23℃; formation constant; further solvents;;

: 60-54-8
TETRACYCLINE

: 1665-57-2
4-epi-anhydrotetracycline

Conditions

Conditions	Yield
With 2-hydroxyethanethiol at 4℃; Irradiation; Title compound not separated from byproducts;

: 60-54-8
TETRACYCLINE

: 60-18-4
L-tyrosine

: 78696-80-7
tyrosine*tetracycline

Conditions

Conditions	Yield
In water at 23℃; formation constant; further solvents;;

: 60-54-8
TETRACYCLINE

: 66-22-8
uracil

: 78696-78-3
uracil*tetracycline

Conditions

Conditions	Yield
In water at 23℃; formation constant; further solvents;;

: 60-54-8
TETRACYCLINE

: 65-71-4
thymin

: 78696-77-2
thymine*tetracycline

Conditions

Conditions	Yield
In water at 23℃; formation constant; further solvents;;

: 60-54-8
TETRACYCLINE

: 68-94-0
hypoxanthine

: 78696-76-1
hypoxanthine*tetracycline

Conditions

Conditions	Yield
In water at 23℃; formation constant; further solvents;;

: 60-54-8
TETRACYCLINE

: 66224-66-6, 66224-67-7, 66224-68-8, 66224-69-9, 134434-48-3, 134434-49-4, 134454-76-5, 134461-75-9
adenine

: 78696-73-8
adenine*tetracycline

Conditions

Conditions	Yield
In water at 23℃; formation constant; further solvents;;

: 60-54-8
TETRACYCLINE

: 69-89-6
xanthine

: 78696-75-0
xanthine*tetracycline

Conditions

Conditions	Yield
In water at 23℃; formation constant; further solvents;;

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.

Product Name

Tetracycline

Synthetic route

Tetracycline History

Tetracycline Consensus Reports

Tetracycline Specification

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