Onopordopicrin

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

MedKoo CAT#: 584912

CAS#: 19889-00-0

Description: Onopordopicrin is isolated from Centaurea sonchifolia and has antibacterial and cytotoxic properties.


Chemical Structure

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Onopordopicrin
CAS# 19889-00-0

Theoretical Analysis

MedKoo Cat#: 584912
Name: Onopordopicrin
CAS#: 19889-00-0
Chemical Formula: C19H24O6
Exact Mass: 348.16
Molecular Weight: 348.395
Elemental Analysis: C, 65.50; H, 6.94; O, 27.55

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Onopordopicrin

IUPAC/Chemical Name: 2-Propenoic acid, 2-(hydroxymethyl)-, 2,3,3a,4,5,8,9,11a-octahydro-10-(hydroxymethyl)-6-methyl-3-methylene-2-oxocyclodeca(b)furan-4-yl ester, (3aR-(3aR*,4S*,6E,10Z,11aR*))-

InChi Key: NOZAJYKZMCFNFG-WULVTUHRSA-N

InChi Code: InChI=1S/C19H24O6/c1-11-5-4-6-14(10-21)8-16-17(13(3)19(23)25-16)15(7-11)24-18(22)12(2)9-20/h5,8,15-17,20-21H,2-4,6-7,9-10H2,1H3/b11-5+,14-8-/t15-,16+,17+/m0/s1

SMILES Code: C=C(CO)C(O[C@H]1C/C(C)=C/CC/C(CO)=C/[C@@]([C@]1([H])C2=C)([H])OC2=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: >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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 348.40 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.

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Móricz ÁM, Krüzselyi D, Alberti Á, Darcsi A, Horváth G, Csontos P, Béni S, Ott PG. Layer chromatography-bioassays directed screening and identification of antibacterial compounds from Scotch thistle. J Chromatogr A. 2017 Nov 17;1524:266-272. doi: 10.1016/j.chroma.2017.09.062. Epub 2017 Sep 28. PubMed PMID: 28989030.

2: Bordignon A, Frédérich M, Ledoux A, Campos PE, Clerc P, Hermann T, Quetin-Leclercq J, Cieckiewicz E. In vitro antiplasmodial and cytotoxic activities of sesquiterpene lactones from Vernonia fimbrillifera Less. (Asteraceae). Nat Prod Res. 2018 Jun;32(12):1463-1466. doi: 10.1080/14786419.2017.1350665. Epub 2017 Jul 10. PubMed PMID: 28693338.

3: Chain FE, Romano E, Leyton P, Paipa C, Catalán CA, Fortuna M, Brandán SA. Vibrational and structural study of onopordopicrin based on the FTIR spectrum and DFT calculations. Spectrochim Acta A Mol Biomol Spectrosc. 2015;150:381-9. doi: 10.1016/j.saa.2015.05.072. Epub 2015 May 29. PubMed PMID: 26057092.

4: Tundis R, Statti G, Menichini F, Delle Monache F. Arctiin and onopordopicrin from Carduus micropterus ssp. perspinosus. Fitoterapia. 2000 Sep;71(5):600-1. PubMed PMID: 11449521.

5: de Almeida AB, Luiz-Ferreira A, Cola M, Di Pietro Magri L, Batista LM, de Paiva JA, Trigo JR, Souza-Brito AR. Anti-ulcerogenic mechanisms of the sesquiterpene lactone onopordopicrin-enriched fraction from Arctium lappa L. (Asteraceae): role of somatostatin, gastrin, and endogenous sulfhydryls and nitric oxide. J Med Food. 2012 Apr;15(4):378-83. doi: 10.1089/jmf.2011.0025. Epub 2011 Dec 22. PubMed PMID: 22191571.

6: Lonergan G, Routsi E, Georgiadis T, Agelis G, Hondrelis J, Matsoukas J, Larsen LK, Caplan FR. Isolation, NMR studies, and biological activities of onopordopicrin from Centaurea sonchifolia. J Nat Prod. 1992 Feb;55(2):225-8. PubMed PMID: 1624943.

7: Bach SM, Fortuna MA, Attarian R, de Trimarco JT, Catalán CA, Av-Gay Y, Bach H. Antibacterial and cytotoxic activities of the sesquiterpene lactones cnicin and onopordopicrin. Nat Prod Commun. 2011 Feb;6(2):163-6. PubMed PMID: 21425665.

8: Formisano C, Sanna C, Ballero M, Chianese G, Sirignano C, Rigano D, Millán E, Muñoz E, Taglialatela-Scafati O. Anti-inflammatory sesquiterpene lactones from Onopordum illyricum L. (Asteraceae), an Italian medicinal plant. Fitoterapia. 2017 Jan;116:61-65. doi: 10.1016/j.fitote.2016.11.006. Epub 2016 Nov 19. PubMed PMID: 27871974.

9: Marco JA, Sanz-Cervera JF, Yuste A, Sancenón F, Carda M. Sesquiterpenes from Centaurea aspera. Phytochemistry. 2005 Jul;66(14):1644-50. PubMed PMID: 16024055.

10: de Almeida AB, Sánchez-Hidalgo M, Martín AR, Luiz-Ferreira A, Trigo JR, Vilegas W, dos Santos LC, Souza-Brito AR, de la Lastra CA. Anti-inflammatory intestinal activity of Arctium lappa L. (Asteraceae) in TNBS colitis model. J Ethnopharmacol. 2013 Mar 7;146(1):300-10. doi: 10.1016/j.jep.2012.12.048. Epub 2013 Jan 10. PubMed PMID: 23313393.

11: Machado FB, Yamamoto RE, Zanoli K, Nocchi SR, Novello CR, Schuquel IT, Sakuragui CM, Luftmann H, Ueda-Nakamura T, Nakamura CV, de Mello JC. Evaluation of the antiproliferative activity of the leaves from Arctium lappa by a bioassay-guided fractionation. Molecules. 2012 Feb 14;17(2):1852-9. doi: 10.3390/molecules17021852. PubMed PMID: 22334063; PubMed Central PMCID: PMC6268082.

12: Zimmermann S, Thomi S, Kaiser M, Hamburger M, Adams M. Screening and HPLC-Based Activity Profiling for New Antiprotozoal Leads from European Plants. Sci Pharm. 2012 Jan-Mar;80(1):205-13. doi: 10.3797/scipharm.1111-13. Epub 2011 Dec 23. PubMed PMID: 22396915; PubMed Central PMCID: PMC3293357.

13: Esmaeili A, Moazami N, Rustaiyan A. Biotransformation of germacranolide from Onopordon leptolepies by Aspergillus niger. Pak J Pharm Sci. 2012 Jan;25(1):155-9. PubMed PMID: 22186324.

14: Fortuna AM, de Riscala EC, Catalan CA, Gedris TE, Herz W. Sesquiterpene lactones from Centaurea tweediei. Biochem Syst Ecol. 2001 Oct;29(9):967-971. PubMed PMID: 11445298.