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

MedKoo CAT#: 471011

CAS#: 14259-46-2

Description: Narirutin has anti-inflammatory and antidepressant-like activities


Price and Availability

Size
Price

10mg
USD 320
100mg
USD 1650
Size
Price

25mg
USD 580
Size
Price

50mg
USD 990

Narirutin, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 471011
Name: Narirutin
CAS#: 14259-46-2
Chemical Formula: C27H32O14
Exact Mass: 580.179
Molecular Weight: 580.539
Elemental Analysis: C, 55.86; H, 5.56; O, 38.58


Synonym: Narirutin, Isonaringenin, Isonaringin, Naringenin 7-beta-rutinoside, Naringenin 7-O-rutinoside, (2S)-Narirutin

IUPAC/Chemical Name: (S)-5-hydroxy-2-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)chroman-4-one

InChi Key: HXTFHSYLYXVTHC-AJHDJQPGSA-N

InChi Code: InChI=1S/C27H32O14/c1-10-20(31)22(33)24(35)26(38-10)37-9-18-21(32)23(34)25(36)27(41-18)39-13-6-14(29)19-15(30)8-16(40-17(19)7-13)11-2-4-12(28)5-3-11/h2-7,10,16,18,20-29,31-36H,8-9H2,1H3/t10-,16-,18+,20-,21+,22+,23-,24+,25+,26+,27+/m0/s1

SMILES Code: C[C@@H]1O[C@H]([C@@H]([C@@H]([C@H]1O)O)O)OC[C@H]2O[C@H]([C@@H]([C@H]([C@@H]2O)O)O)Oc3cc4c(C(C[C@@H](c5ccc(O)cc5)O4)=O)c(O)c3


Technical Data

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).

Harmonized System Code:
2934.99.03.00


References

1: Li Y, Du Y, Yang J, Xiu Z, Yang N, Zhang J, Gao Y, Li B, Shi H. Narirutin produces antidepressant-like effects in a chronic unpredictable mild stress mouse model. Neuroreport. 2018 Jul 18. doi: 10.1097/WNR.0000000000001102. [Epub ahead of print] PubMed PMID: 30028378.

2: Chakraborty S, Basu S. Multi-functional activities of citrus flavonoid narirutin in Alzheimer's disease therapeutics: An integrated screening approach and in vitro validation. Int J Biol Macromol. 2017 Oct;103:733-743. doi: 10.1016/j.ijbiomac.2017.05.110. Epub 2017 May 19. PubMed PMID: 28528948.

3: Liu LN, Wang Y, Jin HY, Ma SC, Liu JP. Application of immunoaffinity purification technology as the pretreatment technology for traditional Chinese medicine: Its application to analysis of hesperidin and narirutin in traditional Chinese medicine preparations containing Citri reticulatae Pericarpium. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 May 15;1021:122-128. doi: 10.1016/j.jchromb.2015.10.005. Epub 2015 Oct 22. PubMed PMID: 26526495.

4: Park HY, Ha SK, Eom H, Choi I. Narirutin fraction from citrus peels attenuates alcoholic liver disease in mice. Food Chem Toxicol. 2013 May;55:637-44. doi: 10.1016/j.fct.2013.01.060. Epub 2013 Feb 13. PubMed PMID: 23416143.

5: Ha SK, Park HY, Eom H, Kim Y, Choi I. Narirutin fraction from citrus peels attenuates LPS-stimulated inflammatory response through inhibition of NF-κB and MAPKs activation. Food Chem Toxicol. 2012 Oct;50(10):3498-504. doi: 10.1016/j.fct.2012.07.007. Epub 2012 Jul 17. PubMed PMID: 22813871.

6: Lee S, Khoo CS, Pearson JL, Hennell JR, Bensoussan A. Liquid chromatographic determination of narirutin and hesperidin in Zhi Ke (Citrus aurantium L.) in the form of the raw herb and of the dried aqueous extract. J AOAC Int. 2009 May-Jun;92(3):789-96. PubMed PMID: 19610369.

7: Funaguchi N, Ohno Y, La BL, Asai T, Yuhgetsu H, Sawada M, Takemura G, Minatoguchi S, Fujiwara T, Fujiwara H. Narirutin inhibits airway inflammation in an allergic mouse model. Clin Exp Pharmacol Physiol. 2007 Aug;34(8):766-70. PubMed PMID: 17600554.

8: Zhang J, Brodbelt JS. Screening flavonoid metabolites of naringin and narirutin in urine after human consumption of grapefruit juice by LC-MS and LC-MS/MS. Analyst. 2004 Dec;129(12):1227-33. Epub 2004 Oct 26. PubMed PMID: 15565223.

9: Manach C, Morand C, Gil-Izquierdo A, Bouteloup-Demange C, Rémésy C. Bioavailability in humans of the flavanones hesperidin and narirutin after the ingestion of two doses of orange juice. Eur J Clin Nutr. 2003 Feb;57(2):235-42. PubMed PMID: 12571654.

10: Puig DG, Pérez ML, Fuster MD, Ortuño A, Sabater F, Porras I, Lidón AG, Del Río JA. Effect of ethylene on naringin, narirutin and nootkatone accumulation in grapefruit. Planta Med. 1995 Jun;61(3):283-5. PubMed PMID: 17238080.