Taxodione | CAS#19026-31-4 | anti-tumor

MedKoo Cat#: 585020 | Name: Taxodione

Description:

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

Taxodione is an abietane diterpenoid isolated from Salvia austriaca and is known to have antibacterial, cytotoxic and anti-tumor properties.

Chemical Structure

Taxodione

CAS#19026-31-4

Theoretical Analysis

MedKoo Cat#: 585020

Name: Taxodione

CAS#: 19026-31-4

Chemical Formula: C20H26O3

Exact Mass: 314.1882

Molecular Weight: 314.43

Elemental Analysis: C, 76.40; H, 8.34; O, 15.27

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

Taxodione; Taxodion; Taxodione, (+)-

IUPAC/Chemical Name

Podocarpa-7,9(11),13-triene-6,12-dione, 11-hydroxy-13-isopropyl- (8CI)

InChi Key

FNNZMRSRVYUVQT-AZUAARDMSA-N

InChi Code

InChI=1S/C20H26O3/c1-11(2)13-9-12-10-14(21)18-19(3,4)7-6-8-20(18,5)15(12)17(23)16(13)22/h9-11,18,23H,6-8H2,1-5H3/t18-,20+/m0/s1

SMILES Code

CC(C)([C@](C(C=C1C=C2C(C)C)=O)3[H])CCC[C@]3(C)C1=C(O)C2=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

>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

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 314.43 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

1: Kuźma Ł, Wysokińska H, Sikora J, Olszewska P, Mikiciuk-Olasik E, Szymański P. Taxodione and Extracts from Salvia austriaca Roots as Human Cholinesterase Inhibitors. Phytother Res. 2016 Feb;30(2):234-42. doi: 10.1002/ptr.5521. Epub 2015 Dec 1. PubMed PMID: 26621777. 2: Uchihara Y, Tago K, Taguchi H, Narukawa Y, Kiuchi F, Tamura H, Funakoshi-Tago M. Taxodione induces apoptosis in BCR-ABL-positive cells through ROS generation. Biochem Pharmacol. 2018 Aug;154:357-372. doi: 10.1016/j.bcp.2018.05.018. Epub 2018 Jun 1. PubMed PMID: 29859988. 3: Uchihara Y, Tago K, Funakoshi-Tago M. [The mechanisms of taxodione-induced apoptosis in BCR-ABL-positive leukemia cells]. Nihon Yakurigaku Zasshi. 2019;153(4):147-154. doi: 10.1254/fpj.153.147. Japanese. PubMed PMID: 30971653. 4: Shafaei-Bajestani N, Emami SA, Asili J, Tayarani-Najaran Z. Anti-apoptotic effect of taxodione on serum/glucose deprivation-induced PC12 cells death. Cell Mol Neurobiol. 2014 Nov;34(8):1103-9. doi: 10.1007/s10571-014-0085-2. Epub 2014 Sep 4. PubMed PMID: 25187359. 5: Liu YL, Lindert S, Zhu W, Wang K, McCammon JA, Oldfield E. Taxodione and arenarone inhibit farnesyl diphosphate synthase by binding to the isopentenyl diphosphate site. Proc Natl Acad Sci U S A. 2014 Jun 24;111(25):E2530-9. doi: 10.1073/pnas.1409061111. Epub 2014 Jun 9. PubMed PMID: 24927548; PubMed Central PMCID: PMC4078810. 6: Kuźma L, Wysokińska H, Różalski M, Budzyńska A, Więckowska-Szakiel M, Sadowska B, Paszkiewicz M, Kisiel W, Różalska B. Antimicrobial and anti-biofilm properties of new taxodione derivative from hairy roots of Salvia austriaca. Phytomedicine. 2012 Nov 15;19(14):1285-7. doi: 10.1016/j.phymed.2012.07.016. Epub 2012 Aug 27. PubMed PMID: 22951394. 7: Ke RF, Xu SC, Song P, Deng SH, Ma XH, Yang XZ. Crystal structure of taxodione isolated from Taxodium ascendens (B.). Acta Crystallogr E Crystallogr Commun. 2017 Jun 30;73(Pt 7):1102-1104. doi: 10.1107/S205698901700946X. eCollection 2017 Jul 1. PubMed PMID: 28775892; PubMed Central PMCID: PMC5499300. 8: Kuźma Ł, Kaiser M, Wysokińska H. The production and antiprotozoal activity of abietane diterpenes in Salvia austriaca hairy roots grown in shake flasks and bioreactor. Prep Biochem Biotechnol. 2017 Jan 2;47(1):58-66. doi: 10.1080/10826068.2016.1168745. Epub 2016 Apr 12. PubMed PMID: 27070932. 9: Rodríguez B. Structural and spectral assignment by two-dimensional NMR of two new derivatives of the abietane diterpenoid taxodione. Magn Reson Chem. 2005 Jan;43(1):97-9. PubMed PMID: 15505819. 10: Kuźma L, Wysokińska H, Różalski M, Krajewska U, Kisiel W. An unusual taxodione derivative from hairy roots of Salvia austriaca. Fitoterapia. 2012 Jun;83(4):770-3. doi: 10.1016/j.fitote.2012.03.006. Epub 2012 Mar 13. PubMed PMID: 22445553. 11: Zaghloul AM, Gohar AA, Naiem ZA, Abdel Bar FM. Taxodione, a DNA-binding compound from Taxodium distichum L. (Rich.). Z Naturforsch C. 2008 May-Jun;63(5-6):355-60. PubMed PMID: 18669020. 12: Kupchan SM, Karim A, Marcks C. Taxodione and taxodone, two novel diterpenoid quinone methide tumor inhibitors from Taxodium distichum. J Am Chem Soc. 1968 Oct 9;90(21):5923-4. PubMed PMID: 5679178. 13: Mori K, Matsui M. Diterpenoid total synthesis. 13. Taxodione, a quinone methide tumor inhibitor. Tetrahedron. 1970 Jul;26(14):3467-73. PubMed PMID: 5449327. 14: Kupchan SM, Karim A, Marcks C. Tumor inhibitors. 48. Taxodione and taxodone, two novel diterpenoid quinone methide tumor inhibitors from Taxodium distichum. J Org Chem. 1969 Dec;34(12):3912-8. PubMed PMID: 5357534. 15: Tayarani-Najaran Z, Mousavi SH, Tajfard F, Asili J, Soltani S, Hatamipour M, Emami SA. Cytotoxic and apoptogenic properties of three isolated diterpenoids from Salvia chorassanica through bioassay-guided fractionation. Food Chem Toxicol. 2013 Jul;57:346-51. doi: 10.1016/j.fct.2013.03.037. Epub 2013 Apr 9. PubMed PMID: 23583484. 16: Búfalo J, Cantrell CL, Jacob MR, Schrader KK, Tekwani BL, Kustova TS, Ali A, Boaro CS. Antimicrobial and Antileishmanial Activities of Diterpenoids Isolated from the Roots of Salvia deserta. Planta Med. 2016 Jan;82(1-2):131-7. doi: 10.1055/s-0035-1557875. Epub 2015 Aug 26. PubMed PMID: 26308356. 17: Hanson RL, Lardy HA, Kupchan SM. Inhibition of phosphofructokinase by quinone methide and alpha-methylene lactone tumor inhibitors. Science. 1970 Apr 17;168(3929):378-80. PubMed PMID: 4244949. 18: Yang Z, Kitano Y, Chiba K, Shibata N, Kurokawa H, Doi Y, Arakawa Y, Tada M. Synthesis of variously oxidized abietane diterpenes and their antibacterial activities against MRSA and VRE. Bioorg Med Chem. 2001 Feb;9(2):347-56. PubMed PMID: 11249127. 19: Li M, Zhang JS, Ye YM, Fang JN. Constituents of the roots of Salvia prionitis. J Nat Prod. 2000 Jan;63(1):139-41. PubMed PMID: 10650097. 20: Borrás-Linares I, Pérez-Sánchez A, Lozano-Sánchez J, Barrajón-Catalán E, Arráez-Román D, Cifuentes A, Micol V, Carretero AS. A bioguided identification of the active compounds that contribute to the antiproliferative/cytotoxic effects of rosemary extract on colon cancer cells. Food Chem Toxicol. 2015 Jun;80:215-222. doi: 10.1016/j.fct.2015.03.013. Epub 2015 Mar 20. PubMed PMID: 25801906.