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(S)-10-Hydroxycamptothecin
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Name

(S)-10-Hydroxycamptothecin

 EINECS 805-668-4
CAS No. 19685-09-7 Density 1.6 g/cm3
PSA 101.65000 LogP 1.78520
Solubility N/A Melting Point 265-270 °C
Formula C20H16N2O5 Boiling Point 820.7 °C at 760 mmHg
Molecular Weight 364.357 Flash Point 450.1 °C
Transport Information N/A Appearance Yellow solid
Safety 26-36 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 19685-09-7 (10-Hydroxycamptothecin) Hazard Symbols IrritantXi
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);

Article Data 22

(S)-10-Hydroxycamptothecin Synthetic route

7689-03-4

camptothecin

19685-09-7

(S)-10-hydroxycamptothecin

Conditions
ConditionsYield
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
ConditionsYield
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 bromide72%
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
ConditionsYield
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
ConditionsYield
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

tetrahydrocamptothecin acetate

19685-09-7

(S)-10-hydroxycamptothecin

Conditions
ConditionsYield
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;
10-hydroxycamptothecin

10-hydroxycamptothecin

19685-09-7

(S)-10-hydroxycamptothecin

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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

2-[1-((2R,4S)-2-tert-Butyl-4-ethyl-5-oxo-[1,3]dioxolan-4-yl)-2,2-dimethoxy-ethyl]-malonic acid benzyl ester methyl ester

19685-09-7

(S)-10-hydroxycamptothecin

Conditions
ConditionsYield
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

(S)-10-Hydroxycamptothecin Chemical Properties


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

(S)-10-Hydroxycamptothecin 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 .

(S)-10-Hydroxycamptothecin 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.

(S)-10-Hydroxycamptothecin 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

(S)-10-Hydroxycamptothecin 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) .

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