Cynarin | CAS#30964-13-7

MedKoo Cat#: 330147 | Name: Cynarin

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Description:

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

Cynarin is a hydroxycinnamic acid and a biologically active chemical constituent of artichoke (Cynara cardunculus). Chemically, it is an ester formed from quinic acid and two units of caffeic acid. It is an ingredient of the drug Sulfad.

Chemical Structure

Cynarin

CAS#30964-13-7

Theoretical Analysis

MedKoo Cat#: 330147

Name: Cynarin

CAS#: 30964-13-7

Chemical Formula: C25H24O12

Exact Mass: 516.1268

Molecular Weight: 516.46

Elemental Analysis: C, 58.14; H, 4.68; O, 37.17

Price and Availability

Size	Price	Availability
10mg	USD 350.00	2 Weeks
25mg	USD 650.00	2 Weeks
50mg	USD 950.00	2 Weeks

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Related CAS #

30964-13-7 212891-05-9 1182-34-9 1884-24-8

Synonym

1,3-Dicaffeoylquinic acid, 1,5-DQA, 1,5-Dicaffeoylquinic acid, Cynarin, Cynarine; Cinarin; Cinarine; Cynarine;

IUPAC/Chemical Name

(1R,3R,4S,5R)-1,3-Bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-4,5-dihydroxycyclohexanecarboxylic acid

InChi Key

YDDUMTOHNYZQPO-RVXRWRFUSA-N

InChi Code

InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1

SMILES Code

O=C([C@]1(OC(/C=C/C2=CC=C(O)C(O)=C2)=O)C[C@@H](OC(/C=C/C3=CC=C(O)C(O)=C3)=O)[C@@H](O)[C@H](O)C1)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 516.46 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: Hakkou Z, Maciuk A, Leblais V, Bouanani NE, Mekhfi H, Bnouham M, Aziz M, Ziyyat A, Rauf A, Hadda TB, Shaheen U, Patel S, Fischmeister R, Legssyer A. Antihypertensive and vasodilator effects of methanolic extract of Inula viscosa: Biological evaluation and POM analysis of cynarin, chlorogenic acid as potential hypertensive. Biomed Pharmacother. 2017 Sep;93:62-69. doi: 10.1016/j.biopha.2017.06.015. Epub 2017 Jun 15. PubMed PMID: 28623784. 2: Tong J, Mo QG, Ma BX, Ge LL, Zhou G, Wang YW. The protective effects of Cichorium glandulosum seed and cynarin against cyclophosphamide and its metabolite acrolein-induced hepatotoxicity in vivo and in vitro. Food Funct. 2017 Jan 25;8(1):209-219. doi: 10.1039/c6fo01531j. PubMed PMID: 27966724. 3: Topal M, Gocer H, Topal F, Kalin P, Köse LP, Gülçin İ, Çakmak KC, Küçük M, Durmaz L, Gören AC, Alwasel SH. Antioxidant, antiradical, and anticholinergic properties of cynarin purified from the Illyrian thistle (Onopordum illyricum L.). J Enzyme Inhib Med Chem. 2016;31(2):266-75. doi: 10.3109/14756366.2015.1018244. Epub 2015 Mar 20. PubMed PMID: 25792498. 4: Xia N, Pautz A, Wollscheid U, Reifenberg G, Förstermann U, Li H. Artichoke, cynarin and cyanidin downregulate the expression of inducible nitric oxide synthase in human coronary smooth muscle cells. Molecules. 2014 Mar 24;19(3):3654-68. doi: 10.3390/molecules19033654. PubMed PMID: 24662080. 5: Kulza M, Malinowska K, Woźniak A, Seńczuk-Przybyłowska M, Nowak G, Florek E. [Development and validation of method for the determination of cynarin, luteolin in plasma]. Przegl Lek. 2012;69(10):987-91. Polish. PubMed PMID: 23421076. 6: Angelini A, Di Pietro R, Centurione L, Castellani ML, Conti P, Porreca E, Cuccurullo F. Inhibition of P-glycoprotein-mediated transport by S-adenosylmethionine and cynarin in multidrug-resistant human uterine sarcoma MES-SA/Dx5 cells. J Biol Regul Homeost Agents. 2012 Jul-Sep;26(3):495-504. PubMed PMID: 23034269. 7: Sun Z, Chen J, Ma J, Jiang Y, Wang M, Ren G, Chen F. Cynarin-rich sunflower (Helianthus annuus) sprouts possess both antiglycative and antioxidant activities. J Agric Food Chem. 2012 Mar 28;60(12):3260-5. doi: 10.1021/jf300737y. Epub 2012 Mar 19. PubMed PMID: 22394088. 8: Dong GC, Chuang PH, Chang KC, Jan PS, Hwang PI, Wu HB, Yi M, Zhou HX, Chen HM. Blocking effect of an immuno-suppressive agent, cynarin, on CD28 of T-cell receptor. Pharm Res. 2009 Feb;26(2):375-81. doi: 10.1007/s11095-008-9754-5. Epub 2008 Nov 7. PubMed PMID: 18989760; PubMed Central PMCID: PMC2701378. 9: Bettero A. [Determination of cynarin by HPLC in pharmaceutical dosage forms]. Boll Chim Farm. 1981 Jan;120(1):49-54. Italian. PubMed PMID: 6894541. 10: Wójcicki J, Pieczyl-Mróz J, Ilnicka-Madry M, Cwajda H. [Cynarin and hyperlipidemia]. Wiad Lek. 1977 Oct 1;30(19):1539-41. Polish. PubMed PMID: 579267. 11: Heckers H, Dittmar K, Schmahl FW, Huth K. Inefficiency of cynarin as therapeutic regimen in familial type II hyperlipoproteinaemia. Atherosclerosis. 1977 Feb;26(2):249-53. PubMed PMID: 576409. 12: Pristautz H. [Cynarin in the modern management of hyperlipemia]. Wien Med Wochenschr. 1975 Dec 5;125(49):705-9. German. PubMed PMID: 820084. 13: Montini M, Levoni P, Ongaro A, Pagani G. [Controlled application of cynarin in the treatment of hyperlipemic syndrome. Observations in 60 cases]. Arzneimittelforschung. 1975 Aug;25(8):1311-4. German. PubMed PMID: 170949. 14: Hammerl H, Kindler K, Kränzl C, Nebosis G, Pichler O, Studlar M. [Effect of Cynarin on hyperlipidemia with special reference to type II (hypercholesterinemia)]. Wien Med Wochenschr. 1973 Oct 13;123(41):601-5. German. PubMed PMID: 4583824. 15: Bobnis W, Szmatloch E, Wesolowska T, Wójcicki J, Zieliński T. [Case of primary hyperlipemia treated with cynarin]. Wiad Lek. 1973 Jul 1;26(13):1267-70. Polish. PubMed PMID: 4728844. 16: Eberhardt G. [Effect of cynarin on fatty liver]. Z Gastroenterol. 1973 Apr;11(3):183-6. German. PubMed PMID: 4803418. 17: Grogan JL, Honigberg IL. Potential hypocholesterolemic agents: dicinnamoykl esters as analogs of cynarin. J Pharm Sci. 1972 May;61(5):802-3. PubMed PMID: 5035795. 18: Dranik LI. [Quantitative analysis of cynarin in the leaves of the artichoke (Cynara scolymus L.)]. Farm Zh. 1965;20(5):56-9. Ukrainian. PubMed PMID: 5888688.