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(+)-Camptothecin
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  • Name (+)-Camptothecin
  • EINECS444-280-6
  • CAS No. 7689-03-4
  • Density1.513 g/cm3
  • PSA81.42000
  • LogP2.07960
  • Solubilityinsoluble in water
  • Melting Point260 °C (dec.)(lit.)
  • FormulaC20H16N2O4
  • Boiling Point757.01 °C at 760 mmHg
  • Molecular Weight348.358
  • Flash Point411.625 °C
  • Transport InformationUN 1544 6.1/PG 3
  • Appearancelight yellow crystal powder
  • Safety45-36/37/39-26
  • Risk Codes36/37/38-25-20/21/22
  • Molecular Structure
    Molecular Structure of 7689-03-4 ((+)-Camptothecin)
  • Hazard SymbolsToxicT, HarmfulXn, IrritantXi
  • SynonymsToxicT, HarmfulXn, IrritantXi
  • Article Data78

(+)-Camptothecin Synthetic route

1085755-35-6

C29H39N3O3Si2

7689-03-4

camptothecin

Conditions
ConditionsYield
With hydrogenchloride In diethyl ether; ethanol Pinner reaction; Heating;92%
935761-84-5

camptothecin 20-(2-bromo)-n-butyrate

7689-03-4

camptothecin

Conditions
ConditionsYield
With methanol; ammonia In tetrahydrofuran for 12h; Product distribution / selectivity;89%
55857-35-7

(E)-N-(2-aminobenzylidene)-4-methylaniline

110351-94-5

(4S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione

7689-03-4

camptothecin

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene Heating; 1) 30 min, 2) 3 h;84.4%
With toluene-4-sulfonic acid In toluene Heating; 1.) 30 min, 2.) 3 h with Dean-Stark trap;84%
With toluene-4-sulfonic acid In toluene73%
With toluene-4-sulfonic acid 1.) toluene, reflux, 30 min, 2.) toluene, reflux, 3 h; Yield given. Multistep reaction;
841276-70-8

4-ethyl-1,12-dihydro-14H-pyrano[3',4':6,7indolizino[1,2-b]]quinolin-14-one

7689-03-4

camptothecin

Conditions
ConditionsYield
Stage #1: 4-ethyl-1,12-dihydro-14H-pyrano[3',4':6,7indolizino[1,2-b]]quinolin-14-one With potassium osmate; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III) In water; tert-butyl alcohol at 0℃;
Stage #2: With iodine; calcium carbonate In methanol; water at 40℃;		83%
Multi-step reaction with 2 steps
1: K2CO3; MeSO2NH2; K3Fe(CN)6 / OsO4; (DHQD)2-Py / 2-methyl-propan-2-ol; H2O / 7 h / 0 °C
2: I2; CaCO3 / methanol; H2O / 24 h / 20 °C
View Scheme
With methanol; iodine; calcium carbonate In water Sharpless Dihydroxylation;
Multi-step reaction with 2 steps
1: potassium carbonate; hydroquinidine (2,5-diphenyl-4,6-pyrimidinediyl) diether; potassium hexacyanoferrate(III); potassium osmate(VI) dihydrate; methanesulfonamide / water; tert-butyl alcohol / 72 h / 0 °C / Inert atmosphere
2: iodine; calcium carbonate / methanol; water / 20 h / 40 °C / Inert atmosphere
View Scheme
916236-87-8

(S)-O-methylcamptothecin

7689-03-4

camptothecin

Conditions
ConditionsYield
With hydrogen bromide for 0.416667h; Heating;81%
PHF-succinate

PHF-succinate

20-O-(glycyl)camptothecin trifluoroacetic acid salt

A

672333-51-6

camptothecin-20-(N-succinamidoglycinate)

B

camptothecin-PHF conjugate

camptothecin-PHF conjugate

C

847928-87-4

camptothecin-20-(N-succinimidoglycinate)

D

7689-03-4

camptothecin

Conditions
ConditionsYield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In water; N,N-dimethyl-formamide; acetonitrile at -2 - 20℃; for 3.5h; pH=5.9 - 6.0;A n/a
B 80%
C n/a
D n/a
...Expand
50-00-0

formaldehyd

7-((2R,4S)-2-tert-butyl-4-ethyl-5-oxo-1,3-dioxolan-4-yl)indolizino[1,2-b]quinolin-9(11H)-one

7689-03-4

camptothecin

Conditions
ConditionsYield
With hydrogenchloride; acetic acid In 1,4-dioxane; water at 90℃; for 19h;80%
110351-94-5

(4S)-4-ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione

529-23-7

2-aminobenzaldehyde

7689-03-4

camptothecin

Conditions
ConditionsYield
With chloro-trimethyl-silane In N,N-dimethyl-formamide at 100℃; Friedlaender Quinoline Synthesis;78%
With toluene-4-sulfonic acid In toluene for 2h; Heating;57%
86639-48-7

Camptothecin 1-oxide

A

19685-09-7

(S)-10-hydroxycamptothecin

B

7689-03-4

camptothecin

Conditions
ConditionsYield
With sulfuric acid In 1,4-dioxane for 0.5h; Irradiation;A 75%
B 11.5%
53544-22-2, 142696-57-9, 142696-58-0

1,2,6,7-tetrahydrocamptothecin

A

19685-09-7

(S)-10-hydroxycamptothecin

B

7689-03-4

camptothecin

Conditions
ConditionsYield
With lead(IV) acetate; trifluoroacetic acid for 0.25h; Ambient temperature;A 73.5%
B 12%

(+)-Camptothecin Chemical Properties

Following is the structure of Camptothecine (CAS NO.7689-03-4):
      
IUPAC Name: 4(S)-Ethyl-4-hydroxy-1H-pyrano-[3',4':6,7]indolizino[1,2-b]quinoline-3,14 (4H,12H)-dione
Molecular formula: C20H16N2O4
Molar mass: 348.35
EINECS: 444-280-6
Melting point: 260 °C
storage temp.: 2-8 °C
Index of Refraction: 1.746
Molar Refractivity: 93.44 cm3
Molar Volume: 230.2 cm3
Density: 1.51 g/cm3
Flash Point: 411.6 °C
Water Solubility: insoluble
Surface Tension: 80.1 dyne/cm
Enthalpy of Vaporization: 115.72 kJ/mol
Boiling Point: 757 °C at 760 mmHg
Vapour Pressure: 4.39E-24 mmHg at 25 °C
Appearance: Light yellow needle crystal
Solubility of Camptothecine (CAS NO.7689-03-4): chloroform/methanol (4:1): 4 mg/mL
Product Categories of Camptothecine (CAS NO.7689-03-4): Alkaloids; Antineoplastic; Camptothecin series; Antitumors for Research and Experimental Use; Biochemistry; Quinoline Alkaloids; Natural Plant Extract; Chiral Reagents; Heterocycles; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals; Natural Anti-cancer Medical Materials and It's Derivatives; Antibiotics; Antibiotics A to; Antibiotics A-FAntibiotics; Antibiotics by Application; Antineoplastic and Immunosuppressive AntibioticsAntibiotics; Inhibits an EnzymeAntibiotics; Interferes with DNA Synthesis; Mechanism of Action;Antitumour; Signalling
Canonical SMILES: CCC1(C2=C(COC1=O)C(=O)N3CC4=CC5=CC=CC=C5N=C4C3=C2)O
Isomeric SMILES: CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=CC5=CC=CC=C5N=C4C3=C2)O
InChI: InChI=1S/C20H16N2O4/c1-2-20(25)14-8-16-17-12(7-11-5-3-4-6-15(11)21-17)9-22(16)18(23)13(14)10-26-19(20)24/h3-8,25H,2,9-10H2,1H3/t20-/m0/s1
InChIKey: VSJKWCGYPAHWDS-FQEVSTJZSA-N

(+)-Camptothecin Uses

 Camptothecine (CAS NO.7689-03-4) is used as Antitumor alkaloid. Italso can be used in the treatment of stomach cancer, colon cancer,ect.

(+)-Camptothecin Toxicity Data With Reference

1.    

dnd-omi 100 mg/L/30M

     NATUAS    Nature. 248 (1974),226.
2.    

dnd-hmn:hla 20 µmol/L

     CNREA8    Cancer Research. 33 (1973),2834.
3.    

dni-hmn:hla 5 µmol/L

     HXPHAU    Handbuch der Experimentellen Pharmakologie. 38 (Pt 2),(1975),649.
4.    

oms-hmn:hla 5 µmol/L

     HXPHAU    Handbuch der Experimentellen Pharmakologie. 38 (Pt 2),(1975),649.
5.    

oms-mus:lym 1 mg/L

     BCPCA6    Biochemical Pharmacology. 21 (1972),1977.
6.    

dni-ckn:emb 500 µg/L

     CJBIAE    Canadian Journal of Biochemistry. 55 (1977),1180.
7.    

ipr-mus LD50:64 mg/kg

     CNREA8    Cancer Research. 39 (1979),2204.
8.    

ivn-mus LD50:38 mg/kg

     NCISP*    National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program, Bethesda, MD 20205 JAN86 .

(+)-Camptothecin Safety Profile

Safety Information of Camptothecine (CAS NO.7689-03-4):
Hazard Codes: ToxicT,IrritantXi,HarmfulXn
Risk Statements:36/37/38-25-20/21/22
36/37/38:Irritating to eyes, respiratory system and skin 
25:Toxic if swallowed 
20/21/22:Harmful by inhalation, in contact with skin and if swallowed
Safety Statements:45-36/37/39-26-36
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) 
36/37/39:Wear suitable protective clothing, gloves and eye/face protection 
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
36:Wear suitable protective clothing 
RIDADR:UN 1544 6.1/PG 3
WGK Germany:3
RTECS Note:UQ0492000
Hazard Note:Irritant
Poison by intravenous and intraperitoneal routes. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also CAMPTOTHECIN, SODIUM SALT.

(+)-Camptothecin Specification

 Camptothecine , its cas register number is 7689-03-4. It also can be called (+)-Camptothecin ; 4-Ethyl-4-hydroxy-1H-pyrano-[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione .

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