Keracyanin | CAS#18719-76-1 | cyanidine chloride derivative

MedKoo Cat#: 558347 | Name: Keracyanin

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Description:

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

Keracyanin is a cyanidine chloride derivative found in pigments in the fire-red blooms of Canna generalis.

Chemical Structure

Keracyanin

CAS#18719-76-1

Theoretical Analysis

MedKoo Cat#: 558347

Name: Keracyanin

CAS#: 18719-76-1

Chemical Formula: C27H31ClO15

Exact Mass: 630.1351

Molecular Weight: 630.98

Elemental Analysis: C, 51.40; H, 4.95; Cl, 5.62; O, 38.03

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 250.00	2 Weeks
5mg	USD 550.00	2 Weeks

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Related CAS #

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Synonym

Keracyanin; Meralop; Prunicyanin; Rutinosyl-3-cyanidine;

IUPAC/Chemical Name

1-Benzopyrylium, 3-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-, chloride

InChi Key

ADZHXBNWNZIHIX-XYGAWYNKSA-N

InChi Code

InChI=1S/C27H30O15.ClH/c1-9-19(32)21(34)23(36)26(39-9)38-8-18-20(33)22(35)24(37)27(42-18)41-17-7-12-14(30)5-11(28)6-16(12)40-25(17)10-2-3-13(29)15(31)4-10;/h2-7,9,18-24,26-27,32-37H,8H2,1H3,(H3-,28,29,30,31);1H/t9-,18+,19-,20+,21+,22-,23+,24+,26+,27+;/m0./s1

SMILES Code

OC1=CC2=[O+]C(C3=CC=C(O)C(O)=C3)=C(O[C@H]4[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]5[C@@H]([C@@H]([C@H]([C@H](C)O5)O)O)O)O4)O)O)O)C=C2C(O)=C1.[Cl-]

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Keracyanin chloride (Cyanidin 3-rutinoside chloride), an anthocyanin, has antioxidant activity.

In vitro activity:

OA (oleic acid), AC (keracyanin), and OAAC (combination) decreased pNFκBp65, PPARγ, IκBα, TNF-α, IL-1β, IL-6, and MCP-1 and increased IL-10. In summary, OA and AC have anti-inflammatory effects individually but their combination (OAAC) exerts a greater effect. Reference: Food Funct. 2021 Sep 7;12(17):7909-7922. https://pubmed.ncbi.nlm.nih.gov/34250536/

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	DMF	20.0	31.70
	DMSO	25.0	39.62
	Ethanol	1.0	1.58
	PBS (pH 7.2)	2.0	3.17

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 630.98 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

Formulation protocol:

1. Santamarina AB , Pisani LP , Baker EJ , Marat AD , Valenzuela CA , Miles EA , Calder PC . Anti-inflammatory effects of oleic acid and the anthocyanin keracyanin alone and in combination: effects on monocyte and macrophage responses and the NF-κB pathway. Food Funct. 2021 Sep 7;12(17):7909-7922. doi: 10.1039/d1fo01304a. Epub 2021 Jul 12. PMID: 34250536.

In vitro protocol:

In vivo protocol:

TBD

1: Sheng F, Wang Y, Zhao X, Tian N, Hu H, Li P. Separation and identification of anthocyanin extracted from mulberry fruit and the pigment binding properties toward human serum albumin. J Agric Food Chem. 2014 Jul 16;62(28):6813-9. doi: 10.1021/jf500705s. Epub 2014 Jul 7. PubMed PMID: 24930424. 2: HAYASHI K, NOGUCHI T, ABE Y. [Studies on anthocyanins. XXIV. Keracyanin, a pigment in the fire-red blooms of Canna generalis]. Pharm Bull. 1954 Mar;2(1):41-5. Undetermined Language. PubMed PMID: 13177118. 3: Ayranci E, Erkan N. Radical scavenging capacity of methanolic Phillyrea latifolia L. extract: anthocyanin and phenolic acids composition of fruits. Molecules. 2013 Jan 30;18(2):1798-810. doi: 10.3390/molecules18021798. PubMed PMID: 23364751. 4: Wang Y, Yang C, Liu C, Xu M, Li S, Yang L, Wang Y. Effects of bagging on volatiles and polyphenols in "Wanmi" peaches during endocarp hardening and final fruit rapid growth stages. J Food Sci. 2010 Nov-Dec;75(9):S455-60. doi: 10.1111/j.1750-3841.2010.01817.x. Epub 2010 Oct 7. PubMed PMID: 21535618. 5: Kano E, Miyakoshi J, Ikebuchi M, Yamagata K, Sugahara T. Dose-modifying effect of a cyanidine chloride derivative, keracyanin, for uv irradiation of murine L fibroblasts cultured in vitro. Radiat Res. 1979 Mar;77(3):547-60. PubMed PMID: 441258. 6: Hariri BM, Payne SJ, Chen B, Mansfield C, Doghramji LJ, Adappa ND, Palmer JN, Kennedy DW, Niv MY, Lee RJ. In vitro effects of anthocyanidins on sinonasal epithelial nitric oxide production and bacterial physiology. Am J Rhinol Allergy. 2016 Jul;30(4):261-8. doi: 10.2500/ajra.2016.30.4331. PubMed PMID: 27456596; PubMed Central PMCID: PMC4953345. 7: Mazzaracchio P, Tozzi S, Boga C, Forlani L, Pifferi PG, Barbiroli G. Interaction between gliadins and anthocyan derivatives. Food Chem. 2011 Dec 1;129(3):1100-7. doi: 10.1016/j.foodchem.2011.05.084. Epub 2011 May 25. PubMed PMID: 25212343. 8: Zhang G, Zhu B, Nakamura Y, Shimoishi Y, Murata Y. Structure-dependent photodegradation of carotenoids accelerated by dimethyl tetrasulfide under UVA irradiation. Biosci Biotechnol Biochem. 2008 Aug;72(8):2176-83. Epub 2008 Aug 7. PubMed PMID: 18685214. 9: Matsufuji H, Shibamoto T. Inhibition of malonaldehyde formation in oxidized calf thymus DNA with synthetic and natural antioxidants. J Agric Food Chem. 2004 Sep 8;52(18):5759-63. PubMed PMID: 15373421. 10: Miskulin M, Godeau G, Tixier AM, Robert AM. [Experimental study of the effects of cyaninoside chloride on collagen, and its potential value in ophthalmology]. J Fr Ophtalmol. 1984;7(11):737-43. French. PubMed PMID: 6085333. 11: Solé P, Rigal D, Peyresblanques J. [Effects of cyaninoside chloride and Heleniene on mesopic and scotopic vision in myopia and night blindness]. J Fr Ophtalmol. 1984;7(1):35-9. French. PubMed PMID: 6381579. 12: Márquez R, Santángelo G, Sastre J, Goldschmidt P, Luyckx J, Pallardó FV, Viña J. Cyanoside chloride and chromocarbe diethylamine are more effective than vitamin C against exercise-induced oxidative stress. Pharmacol Toxicol. 2001 Nov;89(5):255-8. PubMed PMID: 11881979. 13: Łata E, Fulczyk A, Kowalska T, Sajewicz M. Novel thin-layer chromatographic method of screening the anthocyanes containing alimentary products and precautions taken at the method development step. J Chromatogr A. 2017 Dec 29;1530:211-218. doi: 10.1016/j.chroma.2017.11.043. Epub 2017 Nov 21. PubMed PMID: 29173954. 14: Manzanas L, Jesús del Nozal M, Marcos MA, Cordero Y, Bernal JL, Goldschmidt P, Pastor JC. Oral flavonoids, chromocarb diethylamine salt and cyaninosides chloride, to eliminate lipoperoxidation postvitrectomy. Exp Eye Res. 2002 Jan;74(1):23-8. PubMed PMID: 11878815. 15: Deluc L, Barrieu F, Marchive C, Lauvergeat V, Decendit A, Richard T, Carde JP, Mérillon JM, Hamdi S. Characterization of a grapevine R2R3-MYB transcription factor that regulates the phenylpropanoid pathway. Plant Physiol. 2006 Feb;140(2):499-511. Epub 2005 Dec 29. PubMed PMID: 16384897; PubMed Central PMCID: PMC1361319. 16: Matsufuji H, Ochi H, Shibamoto T. Formation and inhibition of genotoxic malonaldehyde from DNA oxidation controlled with EDTA. Food Chem Toxicol. 2006 Feb;44(2):236-41. Epub 2005 Aug 24. PubMed PMID: 16122862. 17: Vieira GS, Marques ASF, Machado MTC, Silva VM, Hubinger MD. Determination of anthocyanins and non-anthocyanin polyphenols by ultra performance liquid chromatography/electrospray ionization mass spectrometry (UPLC/ESI-MS) in jussara (Euterpe edulis) extracts. J Food Sci Technol. 2017 Jun;54(7):2135-2144. doi: 10.1007/s13197-017-2653-1. Epub 2017 Apr 28. PubMed PMID: 28720971; PubMed Central PMCID: PMC5495742.