10-Hydroxycamptothecin

• CAS: 19685-09-7
• Catalog Number: ACM19685097
• Category: Other Products
• Molecular Weight: 364.35
• Molecular Formula: C20H16N2O5
• Synonyms: (4S)-4,9-Dihydroxy-4-ethyl-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
• IUPAC Name: (19S)-19-ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione
• SMILES: CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=C(C3=C2)N=C5C=CC(=CC5=C4)O)O
• InChI: InChI=1S/C20H16N2O5/c1-2-20(26)14-7-16-17-11(5-10-6-12(23)3-4-15(10)21-17)8-22(16)18(24)13(14)9-27-19(20)25/h3-7,23,26H,2,8-9H2,1H3/t20-/m0/s1
• InChI Key: HAWSQZCWOQZXHI-FQEVSTJZSA-N
• Boiling Point: 820.7±65.0 °C
• Melting Point: 265-270 °C
• Density: 1.6 g/ml
• Appearance: Powder
• Complexity: 774
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 1
• Exact Mass: 364.10592162
• Heavy Atom Count: 27
• Hydrogen Bond Acceptor Count: 6
• Hydrogen Bond Donor Count: 2
• Isomeric SMILES: CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=C(C3=C2)N=C5C=CC(=CC5=C4)O)O
• Monoisotopic Mass: 364.10592162
• Physical State: Solid
• pKa: 8.93±0.40
• Rotatable Bond Count: 1
• Topological Polar Surface Area: 100

Custom Q&A

What is the molecular formula of 10-Hydroxycamptothecin?

The molecular formula of 10-Hydroxycamptothecin is C20H16N2O5.

What is the melting point of 10-Hydroxycamptothecin?

The melting point of 10-Hydroxycamptothecin is 230-237°C.

What are some synonyms for 10-Hydroxycamptothecin?

Some synonyms for 10-Hydroxycamptothecin are 10-HYDROXYCAMPTOTHECIN ACETATE, 7-ETHYL-10-HYDROXY CAMPTHOTECIN, and Hydroxy Camptothecine.

What is the storage temperature recommended for 10-Hydroxycamptothecin?

The recommended storage temperature for 10-Hydroxycamptothecin is under -20°C.

What is the solubility of 10-Hydroxycamptothecin in DMSO?

The solubility of 10-Hydroxycamptothecin in DMSO is ≥ 37.5 mg/mL.

What are the hazard codes for 10-Hydroxycamptothecin?

The hazard codes for 10-Hydroxycamptothecin are Xi and T.

What are the risk statements associated with 10-Hydroxycamptothecin?

The risk statements associated with 10-Hydroxycamptothecin are 36/37/38-25.

What is the primary usage of 10-Hydroxycamptothecin?

The primary usage of 10-Hydroxycamptothecin is as a Topoisomerase inhibitor.

What are the safety statements for handling 10-Hydroxycamptothecin?

The safety statements for handling 10-Hydroxycamptothecin are 26-36-45.

What are some of the chemical properties of 10-Hydroxycamptothecin?

Some of the chemical properties of 10-Hydroxycamptothecin include its mp of 268-270°C and a loss on drying of less than 1%.

Synthetic Use

Upstream Synthesis Route 1

• 7689-03-4

• 19685-09-7

Reference: [1]Gao, Mingzhang; Miller, Kathy D.; Sledge, George W.; Zheng, Qi-Huang
[Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 17, p. 3865 - 3869]

Downstream Synthesis Route 1

• 50-00-0
• 19685-09-7
• 124-40-3

• 123948-87-8

Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 17, p. 3865 - 3869
[2] Anti-Cancer Drugs, 2014, vol. 25, # 6, p. 614 - 623

Downstream Synthesis Route 2

• 19685-09-7

• 91421-43-1

Reference: [1] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 6, p. 671 - 674

Downstream Synthesis Route 3

• 19685-09-7
• 30354-18-8

• 123948-87-8

Reference: [1] Patent: WO2008/127606, 2008, A1, . Location in patent: Page/Page column 5-7

Downstream Synthesis Route 4

• 37595-74-7
• 19685-09-7

• 123949-09-7

Reference: [1]Furuya, Takeru; Strom, Alexandra E.; Ritter, Tobias
[Journal of the American Chemical Society, 2009, vol. 131, p. 1662 - 1663]
[2]Current Patent Assignee: HARVARD UNIVERSITY - WO2010/59943, 2010, A2
Location in patent: Page/Page column 41; 42
[3]Location in patent: scheme or table
Jiao, Yu; Liu, Hongchun; Geng, Meiyu; Duan, Wenhu
[Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 7, p. 2071 - 2074]
[4]Kingsburgy; Boehm; Jakas; Holden; Hecht; Gallagher; Caranfa; McCabe; Faucette; Johnson; Hertzberg
[Journal of Medicinal Chemistry, 1991, vol. 34, # 1, p. 98 - 107]
[5]Yang, Cheng-Jie; Song, Zi-Long; Goto, Masuo; Hsu, Pei-Ling; Zhang, Xiao-Shuai; Yang, Qian-Ru; Liu, Ying-Qian; Wang, Mei-Juan; Morris-Natschke, Susan L.; Shang, Xiao-Fei; Lee, Kuo-Hsiung
[Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 20, p. 4694 - 4697]

Downstream Synthesis Route 5

• 19685-09-7
• 105-36-2

• 73427-87-9

Reference: [1]Wani; Ronman; Lindley; Wall
[Journal of Medicinal Chemistry, 1980, vol. 23, # 5, p. 554 - 560]
[2]Wang; Dervan
[Journal of the American Chemical Society, 2001, vol. 123, # 36, p. 8657 - 8661]
[3]Location in patent: scheme or table
Li; Gao; Qiu; Zu; Su; He; Deng
[Letters in drug design and discovery, 2011, vol. 8, # 9, p. 698 - 703]
[4]Location in patent: scheme or table
Li; Gao; Qiu; Zu; Su; He; Deng
[Letters in drug design and discovery, 2011, vol. 8, # 9, p. 698 - 703]
[5]Attiogbe, Mawusse K. I.; Cao, Lei; Cao, Yong-Xiao; Du, Shuai-Shuai; Fan, Shu; Hei, Yuan-Yuan; Lei, Hao; Li, Guang-Yan; Liu, Yan-Jie; Yang, Xue-Yan; Yao, Jing-Chun; Zhang, Gui-Min; Zhang, Hao; Zhang, San-Qi; Zhang, Xiao-Yan
[European Journal of Medicinal Chemistry, 2020, vol. 202]

* For details of the synthesis route, please refer to the original source to ensure accuracy.