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MedKoo Cat#: 564374 | Name: Fumagillol

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Fumagillol is a direct precursor of the potent angiogenesis inhibitors TNP-470 and fumagillin.

Chemical Structure

Fumagillol
Fumagillol
CAS#108102-51-8

Theoretical Analysis

MedKoo Cat#: 564374

Name: Fumagillol

CAS#: 108102-51-8

Chemical Formula: C16H26O4

Exact Mass: 282.1831

Molecular Weight: 282.38

Elemental Analysis: C, 68.06; H, 9.28; O, 22.66

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Gelcohol; NSC-9665; NSC 9665; NSC9665; Fumagillol
IUPAC/Chemical Name
(3R,4S,5S,6R)-5-Methoxy-4-[(2R,3R)-2-methyl-3-(3-methylbut-2-enyl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-ol
InChi Key
CEVCTNCUIVEQOY-JQOWZUPLSA-N
InChi Code
InChI=1S/C16H26O4/c1-10(2)5-6-12-15(3,20-12)14-13(18-4)11(17)7-8-16(14)9-19-16/h5,11-14,17H,6-9H2,1-4H3/t11-,12-,13-,14-,15+,16+/m1/s1
SMILES Code
O[C@H](CC1)[C@@H](OC)[C@H]([C@@]2(C)O[C@@H]2C/C=C(C)\C)[C@]31CO3
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 282.38 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Grenning AJ, Snyder JK, Porco JA Jr. Remodeling of fumagillol: discovery of an oxygen-directed oxidative Mannich reaction. Org Lett. 2014 Feb 7;16(3):792-5. doi: 10.1021/ol4035269. Epub 2014 Jan 10. PubMed PMID: 24410175; PubMed Central PMCID: PMC3927640. 2: Balthaser BR, Maloney MC, Beeler AB, Porco JA Jr, Snyder JK. Remodelling of the natural product fumagillol employing a reaction discovery approach. Nat Chem. 2011 Dec;3(12):969-73. PubMed PMID: 22213919; PubMed Central PMCID: PMC3254213. 3: Yamaguchi J, Toyoshima M, Shoji M, Kakeya H, Osada H, Hayashi Y. Concise enantio- and diastereoselective total syntheses of fumagillol, RK-805, FR65814, ovalicin, and 5-demethylovalicin. Angew Chem Int Ed Engl. 2006 Jan 23;45(5):789-93. PubMed PMID: 16365904. 4: Wang XH, Wang Z, Duan BC, Song JT, He JB, Ou LW, Zhang P. [Inhibitory effect of fumagillol combined with cyclophosphamide on metastasis of lung adenocarcinoma cell line LA795 xenograft in mice]. Ai Zheng. 2005 Dec;24(12):1448-52. Chinese. PubMed PMID: 16351790. 5: Jeong BS, Choi NS, Ahn SK, Bae H, Kim HS, Kim D. Total synthesis and antiangiogenic activity of cyclopentane analogues of fumagillol. Bioorg Med Chem Lett. 2005 Aug 1;15(15):3580-3. PubMed PMID: 15978809. 6: Kim D, Ahn SK, Bae H, Kim HS. A stereoselective asymmetric synthesis of antibiotic (-)-fumagillol using claisen rearrangement and intramolecular ester enolate alkylation as key steps. Arch Pharm Res. 2005 Feb;28(2):129-41. PubMed PMID: 15789740. 7: Koyanagi S, Nakagawa H, Kuramoto Y, Ohdo S, Soeda S, Shimeno H. Optimizing the dosing schedule of TNP-470 [O-(chloroacetyl-carbamoyl) fumagillol] enhances its antitumor and antiangiogenic efficacies. J Pharmacol Exp Ther. 2003 Feb;304(2):669-74. PubMed PMID: 12538820. 8: Vosburg DA, Weiler S, Sorensen EJ. Concise stereocontrolled routes to fumagillol, fumagillin, and TNP-470. Chirality. 2003 Feb;15(2):156-66. PubMed PMID: 12520508. 9: Boiteau JG, Van de Weghe P, Eustache J. A new, ring closing metathesis-based synthesis of (-)-fumagillol. Org Lett. 2001 Aug 23;3(17):2737-40. PubMed PMID: 11506622. 10: Singh Y, Morimoto J, Shikata N, Uemura Y, Hioki K, Tsubura A. Inhibitory Effect of the Angiogenesis Inhibitor O-(Chloroacetyl-carbamoyl)fumagillol(TNP-470) on Tumor Growth and Metastasis of Murine Mammary Tumor Cell Line (JYG-B)Inoculated in Female Nude Mice. Breast Cancer. 1996 Jun 28;3(2):105-110. PubMed PMID: 11091561.