(+)-Camptothecin

Base Information

• Chemical Name: (+)-Camptothecin
• CAS No.: 31456-25-4
• Deprecated CAS: 154380-13-9
• Molecular Formula: C20H16 N2 O4
• Molecular Weight: 348.35
• NSC Number: 302991
• DSSTox Substance ID: DTXSID30274373
• Nikkaji Number: J442.006C
• Wikidata: Q27163449
• Metabolomics Workbench ID: 144232
• ChEMBL ID: CHEMBL276820
• Mol file: 31456-25-4.mol

Synonyms:31456-25-4;(+)-Camptothecin;CHEMBL276820;(S)-(+)-Camptothecin-d5;(+/-)Campathecin;NSC302991;19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione;4-ETHYL-4-HYDROXY-3,4,12,14-TETRAHYDRO-1H-PYRANO[3'4':6,7]INDOLIZINO[1,2-B]QUINOLINE-3,14-DIONE;4-ETHYL-4-HYDROXY-3,4,12,14-TETRAHYDRO-1H-PYRANO[3'4';1329616-37-6;(+/-)-Camptothecine;20(RS)-Camptothecin;dl-Camptothecin;TNP00113;()Campathecin;4-Ethyl-4-hydroxy-1H-pyrano-[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione;(+/-)-Camptothecin;Camptothecine, (+)-;(.+-.)-Camptothecin;Camptothecine, (+-)-;Maybridge1_007381;Neuro_000041;CAMPTOTHECIN (+)-;Oprea1_815005;SCHEMBL2298909;CHEBI:91620;HMS562H11;DTXSID30274373;VSJKWCGYPAHWDS-UHFFFAOYSA-N;HMS3267I18;4-ETHYL-4-HYDROXY-1,12-DIHYDRO-4H-2-OXA-6,12A-DIAZA-DIBENZO[B,H]FLUORENE-3,13-DIONE;LSM-1442;BDBM50045363;AKOS015895425;BCP9000476;NSC-302991;SMP2_000016;4-ethyl-4-hydroxy-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione;NCI60_002559;FT-0618395;FT-0623436;FT-0664215;Camptothecin, Camptotheca acuminata - CAS 2114454;()-Camptothecine;BRD-A30437061-001-01-9;BRD-A30437061-001-04-3;Q27163449;4-Ethyl-4-hydroxy-1H,12H-6,12a-diaza-2-oxa-13H-dibenzo[b,h]fluorene-3,13(4H)-dione;4-ethyl-4-hydroxy-1H-pyrano[3',4':6,7]-indolizino[1,2-b]quinolin-3,14(4H,12H)-dione;(20R)-4-Ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione;(20RS)-4-Ethyl-4-hydroxy-1,12-dihydro-4H-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione;1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione-, 4-ethyl-4-hydroxy-, (+)-;1H-Pyrano[3',7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione-, 4-ethyl-4-hydroxy-, (+-)-;4-Ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, AldrichCPR;4-ethyl-4-hydroxy-3,4,12,14-tetrahydro-1H-pyrano[3'',4'':6,7]indolizino[1,2-b]quinoline-3,14-dione

Chemical Property of (+)-Camptothecin

Chemical Property:

• Melting Point: 264-265 °C (decomp)
• Boiling Point: 757°Cat760mmHg
• PKA: 11.24±0.20(Predicted)
• Flash Point: 411.6°C
• PSA: 81.42000
• Density: 1.51g/cm³
• LogP: 2.07960
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 348.11100700
• Heavy Atom Count: 26
• Complexity: 742

Purity/Quality:

4-ETHYL-4-HYDROXY-3,4,12,14-TETRAHYDRO-1H-PYRANO[3'4':6,7]INDOLIZINO[1,2-B]QUINOLINE-3,14-DIONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1(C2=C(COC1=O)C(=O)N3CC4=CC5=CC=CC=C5N=C4C3=C2)O

Technology Process of (+)-Camptothecin

There total 116 articles about (+)-Camptothecin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

4-ethyl-1,12-dihydro-14-H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-(4H)-dione (34141-35-0) → camptothecin (31456-25-4,91926-09-9)

Guidance literature:

With oxygen; dimethyl amine; copper dichloride; for 20h;

DOI:10.1016/S0040-4039(98)01415-4

Reference yield: 86.0%

O-methylcamptothecin (859849-95-9) → camptothecin (31456-25-4,91926-09-9)

Guidance literature:

With hydrogen bromide; at 140 ℃; for 0.833333h;

DOI:10.1021/ol0509641

Reference yield: 80.0%

4-Ethyl-7,8-dihydro-4-hydroxy-1H-pyrano[3,4-f]indolizine-3,6,10(4H)-trione (102978-40-5) → camptothecin (31456-25-4,91926-09-9)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; for 3.5h; Heating;

DOI:10.1021/jo00055a012

upstream raw materials:

3-ethyl-1,13-dioxo-3a,4,4a,11,13,13a-hexahydro-1H,3H-furo[3',4':6,7]indolizino[1,2-b]quinoline-3-carboxylic acid amide

4-ethyl-6-formyl-1,5b,6,11,11a,12-hexahydro-4H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-dione

4-ethyl-1,12-dihydro-14-H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-(4H)-dione

formaldehyd

Downstream raw materials:

8-methyl-7-propionylindolizino[1,2-b]quinoline-9(11H)-one