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MedKoo Cat#: 584212 | Name: Bigelovin

Description:

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

Bigelovin has been shown to cause cell cycle arrest and subsequently induce apoptosis in cancer cells. It is also known as a potent cytotoxic sesquiterpene lactone from Inula sp.

Chemical Structure

Bigelovin
Bigelovin
CAS#3668-14-2

Theoretical Analysis

MedKoo Cat#: 584212

Name: Bigelovin

CAS#: 3668-14-2

Chemical Formula: C17H20O5

Exact Mass: 304.1311

Molecular Weight: 304.34

Elemental Analysis: C, 67.09; H, 6.62; O, 26.28

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 #
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Synonym
Bigelovin
IUPAC/Chemical Name
Ambrosa-2,11(13)-dien-12-oic acid, 6alpha,8alpha-dihydroxy-4-oxo-, 12,8-lactone, acetate
InChi Key
DCNRYQODUSSOKC-AJYLEYFFSA-N
InChi Code
InChI=1S/C17H20O5/c1-8-7-12-14(9(2)16(20)22-12)15(21-10(3)18)17(4)11(8)5-6-13(17)19/h5-6,8,11-12,14-15H,2,7H2,1,3-4H3/t8-,11-,12+,14+,15-,17-/m0/s1
SMILES Code
C[C@@]12C(C=C[C@]([H])1[C@@H](C)C[C@]3([H])[C@@H](C(C(O3)=O)=C)[C@@H]2OC(C)=O)=O
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
>2 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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 304.34 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: Wang Q, Zhou BN, Zhang RW, Lin YY, Lin LZ, Gil RR, Cordell GA. Cytotoxicity and NMR spectral assignments of ergolide and bigelovin. Planta Med. 1996 Apr;62(2):166-8. PubMed PMID: 8657753. 2: Zhang H, Li L, Chen L, Hu L, Jiang H, Shen X. Structure basis of bigelovin as a selective RXR agonist with a distinct binding mode. J Mol Biol. 2011 Mar 18;407(1):13-20. doi: 10.1016/j.jmb.2011.01.032. Epub 2011 Jan 22. PubMed PMID: 21262235. 3: Lee HT, Yang SW, Kim KH, Seo EK, Mar W. Pseudoguaianolides isolated from Inula britannica var. chinenis as inhibitory constituents against inducible nitric oxide synthase. Arch Pharm Res. 2002 Apr;25(2):151-3. PubMed PMID: 12009027. 4: Zhang HH, Kuang S, Wang Y, Sun XX, Gu Y, Hu LH, Yu Q. Bigelovin inhibits STAT3 signaling by inactivating JAK2 and induces apoptosis in human cancer cells. Acta Pharmacol Sin. 2015 Apr;36(4):507-16. doi: 10.1038/aps.2014.143. Epub 2015 Jan 26. PubMed PMID: 25619393; PubMed Central PMCID: PMC4387296. 5: Yue GG, Chan BC, Kwok HF, Wong YL, Leung HW, Ji CJ, Fung KP, Leung PC, Tan NH, Lau CB. Anti-angiogenesis and immunomodulatory activities of an anti-tumor sesquiterpene bigelovin isolated from Inula helianthus-aquatica. Eur J Med Chem. 2013 Jan;59:243-52. doi: 10.1016/j.ejmech.2012.11.029. Epub 2012 Nov 24. PubMed PMID: 23231968. 6: Liu JL, Zeng GZ, Liu XL, Liu YQ, Hu ZG, Liu Y, Tan NH, Zhou GB. Small compound bigelovin exerts inhibitory effects and triggers proteolysis of E2F1 in multiple myeloma cells. Cancer Sci. 2013 Dec;104(12):1697-704. doi: 10.1111/cas.12295. Epub 2013 Nov 8. PubMed PMID: 24118350. 7: Zeng GZ, Tan NH, Ji CJ, Fan JT, Huang HQ, Han HJ, Zhou GB. Apoptosis inducement of bigelovin from Inula helianthus-aquatica on human Leukemia U937 cells. Phytother Res. 2009 Jun;23(6):885-91. doi: 10.1002/ptr.2671. PubMed PMID: 19107858. 8: Nam KW, Oh GT, Seo EK, Kim KH, Koo U, Lee SJ, Mar W. Nuclear factor kappaB-mediated down-regulation of adhesion molecules: possible mechanism for inhibitory activity of bigelovin against inflammatory monocytes adhesion to endothelial cells. J Ethnopharmacol. 2009 Jun 22;123(2):250-6. doi: 10.1016/j.jep.2009.03.017. Epub 2009 Mar 26. PubMed PMID: 19429369. 9: Wang X, Li X, Guo Y, Qi J, Su L, Fu Y. [Simultaneous determination of three sesquiterpene lactones in Inula hupehensis by RP-HPLC]. Zhongguo Zhong Yao Za Zhi. 2011 Sep;36(18):2520-4. Chinese. PubMed PMID: 22256758. 10: Park EJ, Kim J. Cytotoxic sesquiterpene lactones from Inula britannica. Planta Med. 1998 Dec;64(8):752-4. PubMed PMID: 9933993. 11: Kinoshita K, Kawai T, Imaizumi T, Akita Y, Koyama K, Takahashi K. Anti-emetic principles of Inula linariaefolia flowers and Forsythia suspensa fruits. Phytomedicine. 1996 May;3(1):51-8. doi: 10.1016/S0944-7113(96)80010-9. PubMed PMID: 23194861. 12: Abou-Douh AM. New eudesmane derivatives and other sesquiterpenes from the epigeal parts of Dittrichia graveolens. Chem Pharm Bull (Tokyo). 2008 Nov;56(11):1535-45. PubMed PMID: 18981602. 13: Li M, Song LH, Yue GG, Lee JK, Zhao LM, Li L, Zhou X, Tsui SK, Ng SS, Fung KP, Tan NH, Lau CB. Bigelovin triggered apoptosis in colorectal cancer in vitro and in vivo via upregulating death receptor 5 and reactive oxidative species. Sci Rep. 2017 Feb 9;7:42176. doi: 10.1038/srep42176. PubMed PMID: 28181527; PubMed Central PMCID: PMC5299840.