Ovatodiolide | CAS#3484-37-5 | anticancer agent

MedKoo Cat#: 562166 | Name: Ovatodiolide

Description:

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

Ovatodiolide is a broad anticancer agent. It acts by upregulating hsa-miR-155, suppressing the BCR-ABL fusion gene and dysregulating the PI3K/AKT/mTOR pathway.

Chemical Structure

Ovatodiolide

CAS#3484-37-5

Theoretical Analysis

MedKoo Cat#: 562166

Name: Ovatodiolide

CAS#: 3484-37-5

Chemical Formula: C20H24O4

Exact Mass: 328.1675

Molecular Weight: 328.40

Elemental Analysis: C, 73.15; H, 7.37; O, 19.49

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

Ovatodiolide; NSC 156130; NSC-156130; NSC156130; Melampodin;

IUPAC/Chemical Name

3,7,11,15(17)-Cembratetraene-16,2:19,6-diolide; (3E,12E)-3,12-Dimethyl-8-methylene-6,18-dioxa-tricyclo(14.2.1.0.5,9)nonadeca-3,12,16(19)-triene-7,17-dione

InChi Key

KTYZKXFERQUCPX-XGKXUXTPSA-N

InChi Code

InChI=1S/C20H24O4/c1-12-5-4-6-15-11-16(23-20(15)22)9-13(2)10-18-17(8-7-12)14(3)19(21)24-18/h5,10-11,16-18H,3-4,6-9H2,1-2H3/b12-5+,13-10+/t16-,17-,18+/m1/s1

SMILES Code

O=C1O[C@@H]2[C@H](CC/C(C)=C/CCC(C(O3)=O)=C[C@H]3C/C(C)=C/2)C1=C

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 328.40 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.

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

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PubMed PMID: 28666799. 4: Huang YJ, Yang CK, Wei PL, Huynh TT, Whang-Peng J, Meng TC, Hsiao M, Tzeng YM, Wu AT, Yen Y. Ovatodiolide suppresses colon tumorigenesis and prevents polarization of M2 tumor-associated macrophages through YAP oncogenic pathways. J Hematol Oncol. 2017 Feb 28;10(1):60. doi: 10.1186/s13045-017-0421-3. PubMed PMID: 28241877; PubMed Central PMCID: PMC5329923. 5: Hsieh YJ, Tseng SP, Kuo YH, Cheng TL, Chiang CY, Tzeng YM, Tsai WC. Ovatodiolide of Anisomeles indica Exerts the Anticancer Potential on Pancreatic Cancer Cell Lines through STAT3 and NF-κB Regulation. Evid Based Complement Alternat Med. 2016;2016:8680372. doi: 10.1155/2016/8680372. Epub 2016 May 8. PubMed PMID: 27242913; PubMed Central PMCID: PMC4875986. 6: Lu KT, Wang BY, Chi WY, Chang-Chien J, Yang JJ, Lee HT, Tzeng YM, Chang WW. Ovatodiolide Inhibits Breast Cancer Stem/Progenitor Cells through SMURF2-Mediated Downregulation of Hsp27. Toxins (Basel). 2016 Apr 28;8(5). pii: E127. doi: 10.3390/toxins8050127. PubMed PMID: 27136586; PubMed Central PMCID: PMC4885042. 7: Bamodu OA, Huang WC, Tzeng DT, Wu A, Wang LS, Yeh CT, Chao TY. Ovatodiolide sensitizes aggressive breast cancer cells to doxorubicin, eliminates their cancer stem cell-like phenotype, and reduces doxorubicin-associated toxicity. Cancer Lett. 2015 Aug 10;364(2):125-34. doi: 10.1016/j.canlet.2015.05.006. Epub 2015 May 11. PubMed PMID: 25976769. 8: Rao YK, Chen YC, Fang SH, Lai CH, Geethangili M, Lee CC, Tzeng YM. Ovatodiolide inhibits the maturation of allergen-induced bone marrow-derived dendritic cells and induction of Th2 cell differentiation. Int Immunopharmacol. 2013 Nov;17(3):617-24. doi: 10.1016/j.intimp.2013.08.002. Epub 2013 Aug 31. PubMed PMID: 24001794. 9: Ho JY, Hsu RJ, Wu CL, Chang WL, Cha TL, Yu DS, Yu CP. Ovatodiolide Targets β -Catenin Signaling in Suppressing Tumorigenesis and Overcoming Drug Resistance in Renal Cell Carcinoma. Evid Based Complement Alternat Med. 2013;2013:161628. doi: 10.1155/2013/161628. Epub 2013 May 26. PubMed PMID: 23781255; PubMed Central PMCID: PMC3677612. 10: Lien HM, Wang CY, Chang HY, Huang CL, Peng MT, Sing YT, Chen CC, Lai CH. Bioevaluation of Anisomeles indica extracts and their inhibitory effects on Helicobacter pylori-mediated inflammation. J Ethnopharmacol. 2013 Jan 9;145(1):397-401. doi: 10.1016/j.jep.2012.11.015. Epub 2012 Nov 21. PubMed PMID: 23178270. 11: Kulkarni RR, Shurpali K, Gawde RL, Sarkar D, Puranik VG, Joshi SP. Phyllocladane diterpenes from Anisomeles heyneana. J Asian Nat Prod Res. 2012;14(12):1162-8. doi: 10.1080/10286020.2012.738672. Epub 2012 Nov 19. PubMed PMID: 23157282. 12: Huang HC, Lien HM, Ke HJ, Chang LL, Chen CC, Chang TM. Antioxidative characteristics of Anisomeles indica extract and inhibitory effect of ovatodiolide on melanogenesis. Int J Mol Sci. 2012;13(5):6220-35. doi: 10.3390/ijms13056220. Epub 2012 May 21. PubMed PMID: 22754360; PubMed Central PMCID: PMC3382824. 13: Liao YF, Rao YK, Tzeng YM. Aqueous extract of Anisomeles indica and its purified compound exerts anti-metastatic activity through inhibition of NF-κB/AP-1-dependent MMP-9 activation in human breast cancer MCF-7 cells. Food Chem Toxicol. 2012 Aug;50(8):2930-6. doi: 10.1016/j.fct.2012.05.033. Epub 2012 May 23. PubMed PMID: 22634262. 14: Lin KL, Tsai PC, Hsieh CY, Chang LS, Lin SR. Antimetastatic effect and mechanism of ovatodiolide in MDA-MB-231 human breast cancer cells. Chem Biol Interact. 2011 Nov 15;194(2-3):148-58. doi: 10.1016/j.cbi.2011.10.002. Epub 2011 Oct 19. PubMed PMID: 22033475. 15: Hou YY, Wu ML, Hwang YC, Chang FR, Wu YC, Wu CC. The natural diterpenoid ovatodiolide induces cell cycle arrest and apoptosis in human oral squamous cell carcinoma Ca9-22 cells. Life Sci. 2009 Jul 3;85(1-2):26-32. doi: 10.1016/j.lfs.2009.04.013. Epub 2009 May 3. PubMed PMID: 19409917. 16: Rao YK, Fang SH, Hsieh SC, Yeh TH, Tzeng YM. 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