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| CAS No.: | 19685-09-7 |
|---|---|
| Name: | 10-Hydroxycamptothecin |
| Molecular Structure: | |
|
|
|
| Formula: | C20H16N2O5 |
| Molecular Weight: | 364.357 |
| Synonyms: | 10-Hydroxy-CPT;Camptothecin, hydroxy-;1H-Pyrano(3,4:6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4-ethyl-4,9-dihydroxy-, hydrate, (S)-;(4S)-4-Ethyl-4,9-dihydroxy-1H-pyrano[3,4:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione;Camptothecine, 10-hydroxy- (8CI);Hydroxycamptothecine;1H-Pyrano(3,4:6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione-,4-ethyl-4,9-dihydroxy-, (S)- (9CI); |
| EINECS: | 805-668-4 |
| Density: | 1.6 g/cm3 |
| Melting Point: | 265-270 °C |
| Boiling Point: | 820.7 °C at 760 mmHg |
| Flash Point: | 450.1 °C |
| Appearance: | Yellow solid |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 36/37/38 |
| Safety: | 26-36 |
| PSA: | 101.65000 |
| LogP: | 1.78520 |
- 483366-12-7(2S,4R)-1-Boc-2-cyano-4-hydroxypyrrolidine
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- 5156-58-1N-(1-Benzyl-4-pipperidinyl)-N-phenylpropanamide HCl
- 81281-59-67-Benzylideneaminotheophylline
- 50288-62-5threo-Phenyl-2-piperidyl acetamide
- 82993-81-5D-threo-Ritalinic acid hydrochloride
- 47087-37-6Z-D-Glu-OMe
- 73441-42-6METHYL-5-CHLORO-2,2-DIMETHYLVALERATE
- 211914-50-0N-[[2-[[[4-(Aminoiminomethyl)phenyl]amino]methyl]-1-methyl-1H-benzimidazol-5-yl]carbonyl]-N-(2-pyridinyl)-beta-alanine ethyl ester hydrochloride
- 240444-70-62,3,5,6-Tetrafluor-4-(methoxymethyl)benzyl-2,2-dimethyl-3-(prop-1-en-1-yl)cyclopropancarboxylat
- 7689-03-4
camptothecin
- 19685-09-7
(S)-10-hydroxycamptothecin
| Conditions | Yield |
|---|---|
| Stage #1: camptothecin With hydrogen; acetic acid; platinum(IV) oxide Stage #2: With lead(IV) acetate; acetic acid | 51% |
| Yield given. Multistep reaction; | |
| With sulfuric acid; dihydrogen peroxide; acetic acid 2) irradiation; Yield given. Multistep reaction; |
- 19685-10-0
10-methoxycamptothecin
- 19685-09-7
(S)-10-hydroxycamptothecin
| Conditions | Yield |
|---|---|
| With hydrogen bromide at 110℃; for 72h; | 82% |
| With hydrogen bromide In water at 110℃; for 7h; Inert atmosphere; optical yield given as %ee; | 80% |
| With hydrogen bromide In water at 100℃; Sealed tube; | 80% |
| With hydrogen bromide | 72% |
| With hydrogen bromide In water for 2h; Reflux; |
- 7689-03-4
camptothecin
A
- 19685-09-7
(S)-10-hydroxycamptothecin
B
- 19685-11-1
(S)-9-acetoxy-4-ethyl-4-hydroxy-1,12-dihydro-4H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione
| Conditions | Yield |
|---|---|
| Stage #1: camptothecin With hydrogen; acetic acid; platinum under 760.051 Torr; for 8.5h; Stage #2: With lead(IV) acetate In acetic acid Heating / reflux; |
- 870527-52-9
1,2,6,7-tetrahydro-(20S)-camphthotecine
- 19685-09-7
(S)-10-hydroxycamptothecin
| Conditions | Yield |
|---|---|
| With [bis(acetoxy)iodo]benzene; water In acetic acid Yield given; | |
| With [bis(acetoxy)iodo]benzene; acetic acid | |
| In acetic acid at 20℃; | |
| With [bis(acetoxy)iodo]benzene; acetic acid In water at 20℃; for 18h; Large scale reaction; | 1.36 kg |
- 19685-09-7
(S)-10-hydroxycamptothecin
| Conditions | Yield |
|---|---|
| Stage #1: tetrahydrocamptothecin acetate With [bis(acetoxy)iodo]benzene In water; acetic acid at 27.5℃; for 18h; Stage #2: With methanol In N,N-dimethyl-formamide at 27.5 - 76.5℃; for 6h; |
- 19685-09-7
(S)-10-hydroxycamptothecin
| Conditions | Yield |
|---|---|
| In 1,4-dioxane; acetonitrile for 0.75h; UV-irradiation; | 98.5% |
- 9-<(dimethylamino)methyl>-10-hydroxy-(20S)-camptothecin acetate salt
- 123948-88-9
9-<(dimethylamino)methyl>-10-hydroxy-(20S)-camptothecin acetate salt
A
- 942429-91-6
(S)-10-[(dimethylamino)methyl]-4-ethyl-4,9-dihydroxy-12-methylene-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione
B
- 19685-09-7
(S)-10-hydroxycamptothecin
C
- 119413-54-6, 123949-07-5
Topotecan hydrochloride
D
- 7689-03-4
camptothecin
| Conditions | Yield |
|---|---|
| With hydrogenchloride In water for 0.25h; | A < 0.04 %Chromat. B < 0.001 %Chromat. C 99.65 %Chromat. D < 0.009 %Chromat. |
- 53544-22-2, 142696-57-9, 142696-58-0
1,2,6,7-tetrahydrocamptothecin
- 19685-09-7
(S)-10-hydroxycamptothecin
| Conditions | Yield |
|---|---|
| Multi-step reaction with 6 steps 1: 98 percent / pyridine / 1 h / 70 °C 2: 96.3 percent / H2SO4, conc. aq. HNO3 / 1 h 3: 82.3 percent / 20percent aq. H2SO4 / 2 h / Heating 4: 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) / dioxane / 2 h / Heating 5: 96.2 percent / H2 / PtO2 / ethanol; dioxane / 2 h / 760 Torr 6: 1.) 20percent aq. H2SO4, aq. NaNO2, 2.) H2O / 1.) 0-5 deg C, 15 min, 2.) reflux, 1 h View Scheme | |
| Multi-step reaction with 3 steps 1: 12 percent / Pb(OAc)4, trifluoroacetic acid / 0.25 h / Ambient temperature 2: 90.6 percent / 30percent aq. H2O2, acetic acid / 3.5 h / 70 - 80 °C 3: 22.5 percent / 1 N H2SO4 / dioxane / 0.5 h / Irradiation View Scheme | |
| Multi-step reaction with 3 steps 1: 12 percent / Pb(OAc)4, trifluoroacetic acid / 0.25 h / Ambient temperature 2: 90.6 percent / 30percent aq. H2O2, acetic acid / 3.5 h / 70 - 80 °C 3: 25 percent / 1 N aq. H2SO4 / dioxane / 0.5 h / Irradiation View Scheme | |
| Multi-step reaction with 3 steps 1: 12 percent / Pb(OAc)4, trifluoroacetic acid / 0.25 h / Ambient temperature 2: 90.6 percent / 30percent aq. H2O2, acetic acid / 3.5 h / 70 - 80 °C 3: 58 percent / 1 N aq. H2SO4 / dioxane / 0.5 h / Irradiation View Scheme |
- 161681-84-1
2-[2,2-Dimethoxy-eth-(Z)-ylidene]-malonic acid benzyl ester methyl ester
- 19685-09-7
(S)-10-hydroxycamptothecin
| Conditions | Yield |
|---|---|
| Multi-step reaction with 8 steps 1: LDA / tetrahydrofuran / -78 up to -20 deg C 2: H2 / 5percent Pd/C / methanol 3: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran 4: TFA / H2O; toluene 5: DDQ 6: diisobutylaluminum hydride (DIBAH) / CH2Cl2 7: 1.) NaBH4; 2.) aq. NaOH / 1.) MeOH 8: 72 percent / 48percent HBr View Scheme | |
| Multi-step reaction with 8 steps 1: LDA / tetrahydrofuran / -78 up to -20 deg C 2: H2 / 5percent Pd/C / methanol 3: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran 4: TFA / H2O; toluene 5: DDQ 6: diisobutylaluminum hydride (DIBAH) / CH2Cl2 7: NaBH4 / methanol 8: 72 percent / 48percent HBr View Scheme |
- 19685-09-7
(S)-10-hydroxycamptothecin
| Conditions | Yield |
|---|---|
| Multi-step reaction with 7 steps 1: H2 / 5percent Pd/C / methanol 2: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran 3: TFA / H2O; toluene 4: DDQ 5: diisobutylaluminum hydride (DIBAH) / CH2Cl2 6: 1.) NaBH4; 2.) aq. NaOH / 1.) MeOH 7: 72 percent / 48percent HBr View Scheme | |
| Multi-step reaction with 7 steps 1: H2 / 5percent Pd/C / methanol 2: 89 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole (HOBT), Et3N / tetrahydrofuran 3: TFA / H2O; toluene 4: DDQ 5: diisobutylaluminum hydride (DIBAH) / CH2Cl2 6: NaBH4 / methanol 7: 72 percent / 48percent HBr View Scheme |
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Chemistry
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Product Name: 10-Hydroxycamptothecin
Molecular Weight: 364.35144 [g/mol]
Molecular Formula: C20H16N2O5
XLogP3-AA: 0.6
H-Bond Donor: 2
H-Bond Acceptor: 6
Index of Refraction: 1.776
Molar Refractivity: 94.97 cm3
Molar Volume: 227 cm3
Surface Tension: 92.4 dyne/cm
Density: 1.6 g/cm3
Flash Point: 450.1 °C
Enthalpy of Vaporization: 125.05 kJ/mol
Boiling Point: 820.7 °C at 760 mmHg
Vapour Pressure: 1.67E-28 mmHg at 25 °C
Appearance: Yellow Solid
Melting Point: 265-270 °C
Classification Code of (S)-10-Hydroxycamptothecin (CAS NO.19685-09-7): Drug / Therapeutic Agent; Mutation data; Natural Product
Product Categories: Alkaloids; INTERMEDIATESOFIRINOTECANHCLTRIHYDRATE; Camptothecin series; Natural Plant Extract; Chiral Reagents; Intermediates & Fine Chemicals; Pharmaceuticals; Natural Anti-cancer Medical Materials and It's Derivatives
Uses
(S)-10-Hydroxycamptothecin (CAS NO.19685-09-7) is used in the treatment of cancer. It is used to synthesis 7-Ethyl-10-Hydroxy-CPT,SN-38 .
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | intraperitoneal | 104mg/kg (104mg/kg) | Drugs of the Future. Vol. 7, Pg. 629, 1982. | |
| rat | LD | intravenous | > 10mg/kg (10mg/kg) | KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED KIDNEY, URETER, AND BLADDER: HEMATURIA | Cancer Chemotherapy and Pharmacology. Vol. 41, Pg. 257, 1998. |
Safety Profile
Safety Information of (S)-10-Hydroxycamptothecin (CAS NO.19685-09-7):
Hazard Codes:Xi 
Risk Statements:36/37/38
36/37/38:Irritating to eyes, respiratory system and skin
Safety Statements:26-36
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:Wear suitable protective clothing
WGK Germany:3
Specification
(S)-10-Hydroxycamptothecin (CAS NO.19685-09-7), its Synonyms are (S)-10-Hydroxycamptothecin hydrate ; 10-Hydroxycamptothecin ; 10-Hydroxycamptothecine ; Camptothecin, 10-hydroxy- ; Camptothecin, hydroxy- ; Hydroxycamptothecin ; Hydroxycamptothecine ; 1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione, 4-ethyl-4,9-dihydroxy-, hydrate, (S)- ; 1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dione-,4-ethyl-4,9-dihydroxy-, (S)- (9CI) ; Camptothecine, 10-hydroxy- (8CI) .