Repin | CAS#11024-67-2 | sesquiterpene lactone

MedKoo Cat#: 461223 | Name: Repin

Description:

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

Repin is the principal sesquiterpene lactone isolated from Russian knapweed, a plant responsible for Parkinson-like disease in horses.

Chemical Structure

Repin

CAS#11024-67-2

Theoretical Analysis

MedKoo Cat#: 461223

Name: Repin

CAS#: 11024-67-2

Chemical Formula: C19H22O7

Exact Mass: 362.1366

Molecular Weight: 362.37

Elemental Analysis: C, 62.98; H, 6.12; O, 30.91

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

Repin;

IUPAC/Chemical Name

(3aS,4R,6aS,8R,9S,9aR,9bR)-8-hydroxy-3,6-dimethylene-2-oxodecahydro-2H-spiro[azuleno[4,5-b]furan-9,2'-oxiran]-4-yl (S)-2-methyloxirane-2-carboxylate

InChi Key

HQZJODBJOBTCPI-OGTAOXHGSA-N

InChi Code

InChI=1S/C19H22O7/c1-8-4-11(25-17(22)18(3)6-23-18)13-9(2)16(21)26-15(13)14-10(8)5-12(20)19(14)7-24-19/h10-15,20H,1-2,4-7H2,3H3/t10-,11-,12-,13+,14-,15-,18+,19+/m1/s1

SMILES Code

C[C@]1(C(O[C@@H]([C@@](C2=C)([H])[C@@]([C@]3([H])[C@@]4(OC4)[C@H](O)C[C@]53[H])([H])OC2=O)CC5=C)=O)OC1

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 362.37 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: Best JB. What would Repin do? The daily grind was not restricted to coffee. Med J Aust. 2014 Jun 2;200(10):601-2. PubMed PMID: 24882494. 2: Robles M, Wang N, Kim R, Choi BH. Cytotoxic effects of repin, a principal sesquiterpene lactone of Russian knapweed. J Neurosci Res. 1997 Jan 1;47(1):90-7. PubMed PMID: 8981242. 3: Akbar S, Fries DS, Malone MH. Effect of various pretreatments on the hypothermic activity of repin in naive rats. J Ethnopharmacol. 1995 Dec 1;49(2):91-9. PubMed PMID: 8847889. 4: Robles M, Choi BH, Han B, Santa Cruz K, Kim RC. Repin-induced neurotoxicity in rodents. Exp Neurol. 1998 Jul;152(1):129-36. PubMed PMID: 9682020. 5: Tukov FF, Anand S, Gadepalli RS, Gunatilaka AA, Matthews JC, Rimoldi JM. Inactivation of the cytotoxic activity of repin, a sesquiterpene lactone from Centaurea repens. Chem Res Toxicol. 2004 Sep;17(9):1170-6. PubMed PMID: 15377150. 6: Tukov FF, Rimoldi JM, Matthews JC. Characterization of the role of glutathione in repin-induced mitochondrial dysfunction, oxidative stress and dopaminergic neurotoxicity in rat pheochromocytoma (PC12) cells. Neurotoxicology. 2004 Dec;25(6):989-99. PubMed PMID: 15474617. 7: MacKay RJ, Wyer S, Gilmour A, Kongara K, Harding DR, Clark S, Mayhew IG, Thomson CE. Cytotoxic activity of extracts from Hypochaeris radicata. Toxicon. 2013 Aug;70:194-203. doi: 10.1016/j.toxicon.2013.04.023. Epub 2013 May 9. PubMed PMID: 23665449. 8: Stevens KL, Riopelle RJ, Wong RY. Repin, a sesquiterpene lactone from Acroptilon repens possessing exceptional biological activity. J Nat Prod. 1990 Jan-Feb;53(1):218-21. PubMed PMID: 2348202. 9: Slivka T, Novotný M, Potuzníková B. [Antimicrobial action of a repin bandage in periodontology]. Prakt Zubn Lek. 1990 Jul;38(6):161-4. Czech. PubMed PMID: 2103618. 10: BOGOLEPOVA ES. [N. I. Pirogov in painting of I. E. Repin]. Khirurgiia (Mosk). 1950 Dec;12:22-4. Russian. PubMed PMID: 14804811. 11: NEUMANN J. [The expression of mimicry with Il'ia lefimovich Repin]. Psychiatr Neurol Med Psychol (Leipz). 1961 Oct;13:377-85. German. PubMed PMID: 14479233. 12: Bertels F, Rainey PB. Curiosities of REPINs and RAYTs. Mob Genet Elements. 2011 Nov 1;1(4):262-268. PubMed PMID: 22545236; PubMed Central PMCID: PMC3337134. 13: DOVINER DG. [Anatomical sketches of I. E. REPIN]. Arkh Anat Gistol Embriol. 1962 Feb;42:98-105. Russian. PubMed PMID: 13887598. 14: George Dimitri Repin. Med J Aust. 1977 Jul 23;2(4):112. PubMed PMID: 331048. 15: Nonka TG, Repin AN. [CARDIAC AMYLOIDOSIS. DIAGNOSTICS AND TREATMENT OF AMYLOID CARDIOMYOPATHY. CASE REPORT]. Klin Med (Mosk). 2015;93(4):66-73. Russian. PubMed PMID: 26155713. 16: Bartáková V, Dufek Z, Fingerland A, Kovár J. [Aspiration of a part of zincoxid-eugenol paste, "Repin" during dental prosthesis fitting]. Cesk Stomatol. 1977 Jun;77(3):220-4. Czech. PubMed PMID: 268241. 17: Kozovenko MN. [Portraits of N.I Pirogov in fine arts of I.E. Repin (on 130 years of creation "the portrait of surgeon N.I.Pirogov"]. Vestn Khir Im I I Grek. 2011;170(6):82-9. Russian. PubMed PMID: 22416417. 18: Shchekotov VV, Kravtsova TY, Barlamov PN, Aleeva NG, Repin VN. [Cardiovascular disorders in case of acute gastrointestinal bleeding in patients with arterial hypertension]. Khirurgiia (Mosk). 2015;(9):28-34. doi: 10.17116/hirurgia2015928-34. Russian. PubMed PMID: 26762075. 19: Kosheleva NV, Saburina IN, Zurina IM, Gorkun AA, Borzenok SA, Nikishin DA, Kolokoltsova TD, Ustinova EE, Repin VS. The technology of obtaining multipotent spheroids from limbal mesenchymal stromal cells for reparation of injured eye tissues. Patol Fiziol Eksp Ter. 2016 Oct-Dec;60(4):160-7. PubMed PMID: 29244939. 20: Palatova LF, Nechaev OI. [[Development of Surgical Gastroenterology in Prikamye].]. Eksp Klin Gastroenterol. 2016;(5):88-92. Russian. PubMed PMID: 28614650.