Cynaropikrin - CAS 35730-78-0
Catalog number: B0005-479861
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Molecular Formula:
C19H22O6
Molecular Weight:
346.37
COA:
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Chemical Family:
Sesquiterpenoids
Description:
Cynaropikrin, a polyphenolic compound, is a sesquiterpene lactone in C. scolymus. Cynaropikrin is the bitter principle in artichoke and is, therefore, an important compound in the chemical profiling of the plant. Cynara scolymus L. (Asteraceae), commonly found in southern Europe and the USA, is cultivated as a vegetable and medicinal plant artichoke leaves are traditionally used for treatment of bile and liver diseases. Pharmacological studies have shown that extracts of the plant significantly increase choleresis (C. scolymus is used for treatment of dyspeptic syndrome) and reduce blood cholesterol, mainly because of inhibition of hepatocellular de novo cholesterol biosynthesis.
Ordering Information
Catalog Number Size Price Stock Quantity
B0005-479861 10mg $199 In stock
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Purity:
> 98%
Appearance:
Solid powder
Synonyms:
2-Propenoic acid, 2-(hydroxymethyl)-, dodecahydro-8-hydroxy-3,6,9-tris(methylene)-2-oxoazuleno[4,5-b]furan-4-yl ester, [3aR-(3aα,4α,6aα,8β,9aα,9bβ)]-; Cynaropicrin (6CI); Azuleno[4,5-b]furan, 2-propenoic acid deriv.
Solubility:
Soluble in DMSO
Storage:
Store in a cool and dry place and at 0 - 4℃ for short term (days to weeks) or -42℃ for long term (months to years).
MSDS:
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Quality Standard:
Enterprise Standard
Quantity:
Milligrams-Grams
Boiling Point:
566.2±50.0 °C | Condition: Press: 760 Torr
Density:
1.28±0.1 g/cm3
1.Synthesis of cynaropicrin-d(4).
Sato T;Hara S;Sato M;Ogawa K;Adams M;Usuki T Bioorg Med Chem Lett. 2015 Dec 1;25(23):5504-7. doi: 10.1016/j.bmcl.2015.10.065. Epub 2015 Oct 23.
Cynaropicrin is a guaianolide sesquiterpene lactone, which has potent in vitro and in vivo inhibitory activity against Trypanosoma brucei, the protozoan parasite that causes human African trypanosomiasis (HAT; sleeping sickness). Herein, we describe the synthesis of cynaropicrin's deuterated derivative, cynaropicrin-d4, by the replacement of the side chain of natural cynaropicrin. The synthesized cynaropicrin-d4 could be employed as an internal standard for liquid chromatography-mass spectrometry (LC-MS) analysis, in the pharmacokinetic study of cynaropicrin. This could potentially advance the study of this therapeutic lead.
2.New cytotoxic guaianolides and derivatives from Grosheimia macrocephala.
Barbetti P;Fardella G;Chiappini I;Scarcia V;Candiani AF Farmaco Sci. 1985 Oct;40(10):755-69.
Grosheimia macrocephala (Compositae) proved to be a very interesting natural source, not only of grosheimin (I), but also of cynaropicrin (III). Some derivatives from these two natural sesquiterpene gamma-lactones were prepared (Schemes 2 and 3) and two new natural guaianolides: 4'-deoxy-cynaropicrin (V) and 4'-nor-2'-metoxy-cynaropicrin (VI) were isolated and structurally identified. A series of these compounds were submitted to in vitro preliminary testing of cytostatic activity against KB cell lines and relationships between bioactivity and chemical features were investigated.
3.Supercritical fluid extraction of cynaropicrin and 20-hydroxyecdysone from Leuzea carthamoides DC.
Sovová H;Opletal L;Sajfrtová M;Bártlová M J Sep Sci. 2008 May;31(8):1387-92. doi: 10.1002/jssc.200700496.
Leuzea carthamoides is an adaptogenic plant containing biologically active compounds as ecdysteroids and guaianolide-type sesquiterpene lactones, conventionally extracted from the plant with ethanol. It may be a potential source of the mentioned natural compounds. Ethanol-modified near-critical CO(2) was used as selective solvent with the aim to increase the level of 20-hydroxyecdysone in the extract from L. carthamoides roots and to remove selectively cynaropicrin, a sesquiterpene lactone of bitter taste, from the leaves. The extraction conditions were varied (pressure 20-28 MPa, temperature 40-60 degrees C, ethanol concentration in the solvent 0-7.1%) and the extraction yield and extract composition were compared with the results of ethanolic extraction. The supercritical fluid extraction (SFE) from finely powdered plant was controlled by phase equilibrium. Cynaropicrin was quantitatively removed from the leaves where 89% of 20-hydroxyecdysone was retained. The extraction yield of 20-hydroxyecdysone from roots with ethanol-modified CO(2 )was lower by 30% than with ethanol but its concentration in the extract was higher by 67%.
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CAS 35730-78-0 Cynaropikrin

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