10-Hydroxycamptothecin

Base Information

• Chemical Name: 10-Hydroxycamptothecin
• CAS No.: 64439-81-2
• Molecular Formula: C₂₀H₁₆N₂O₅
• Molecular Weight: 364.357
• Hs Code.: 2934999090
• European Community (EC) Number: 613-598-9,805-668-4
• DSSTox Substance ID: DTXSID501125515
• Wikidata: Q105025113
• Metabolomics Workbench ID: 143540
• ChEMBL ID: CHEMBL90124
• Mol file: 64439-81-2.mol

Synonyms:(+/-)-4-Ethyl-4,9-dihydroxy-1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione;

Chemical Property of 10-Hydroxycamptothecin

Chemical Property:

• Vapor Pressure: 1.67E-28mmHg at 25°C
• Melting Point: 230-237 °C
• Refractive Index: 1.776
• Boiling Point: 820.7 °C at 760 mmHg
• PKA: 8.93±0.40(Predicted)
• Flash Point: 450.1 °C
• PSA: 101.65000
• Density: 1.60 g/cm³
• LogP: 1.78520
• Storage Temp.: −20°C
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 364.10592162
• Heavy Atom Count: 27
• Complexity: 774

Purity/Quality:

99% ^*data from raw suppliers

Camptothecin, 10-Hydroxy-, A cell-permeable powerful DNA topoisomerase I inhibitor. ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,T
• Statements: 36/37/38-25
• Safety Statements: 26-36-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1(C2=C(COC1=O)C(=O)N3CC4=C(C3=C2)N=C5C=CC(=CC5=C4)O)O
• Uses: therapeutic effects for liver cancer, stomach, and neck cancer and leukemia. Topoisomerase inhibitor

Technology Process of 10-Hydroxycamptothecin

There total 92 articles about 10-Hydroxycamptothecin 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: 98.5%

10-hydroxycamptothecin → (S)-10-hydroxycamptothecin (19685-09-7,64439-81-2)

Guidance literature:

In 1,4-dioxane; acetonitrile; for 0.75h; UV-irradiation;

Reference yield: 82.0%

10-methoxycamptothecin (19685-10-0) → (S)-10-hydroxycamptothecin (19685-09-7,64439-81-2)

Guidance literature:

With hydrogen bromide; at 110 ℃; for 72h;

DOI:10.1002/(SICI)1521-3765(199801)4:1<67::AID-CHEM67>3.0.CO;2-F

Reference yield: 58.0%

Camptothecin 1-oxide (86639-48-7) + ethyl 2-sulfanylacetate (623-51-8) → (S)-10-hydroxycamptothecin (19685-09-7,64439-81-2) + ((S)-4-Ethyl-4-hydroxy-3,13-dioxo-3,4,12,13-tetrahydro-1H-2-oxa-6,12a-diaza-dibenzo[b,h]fluoren-9-ylsulfanyl)-acetic acid ethyl ester (86639-49-8)

Guidance literature:

With sulfuric acid; In 1,4-dioxane; for 0.5h; Irradiation;

DOI:10.1248/cpb.39.3183

upstream raw materials:

methanol

Camptothecin 1-oxide

acetic acid

1,2,6,7-tetrahydrocamptothecin

Downstream raw materials:

10-hydroxycamptothecin-20-acetate

10-[4-(1-piperidino)-1-piperidino]carbonyloxycamptothecin

Refernces

• 1、 -. "Chemical semi-synthesis process of 10-hydroxycamptothecine". Paragraph 0006; 0007. . Retrieved 2016/10/10.
• 2、 Yu, Shanbao,Huang, Qing-Qing,Luo, Yu,Lu, Wei. "Total synthesis of camptothecin and SN-38". experimental part. p. 713 - 717. Retrieved 2012/03/11.